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Rapid Screening and Quantitative Determination of Bioactive Compounds from Fruit Extracts of Myristica Species and Their In vitro Antiproliferative Activity

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... Due to the diverse chemical properties of natural products, these are being used as therapeutic regimens against various human diseases [2,5]. Many phytochemicals have demonstrated biological properties such as anti-inflammatory and antioxidant activity and minimizing the risk of cardiovascular disease, cancer, type 2 diabetes, liver diseases, cataracts, and progression in Alzheimer's disease [1,[6][7][8]. ...
... The characterization of metabolites is essential to understand the chemical properties of the components present in the extracts. Liquid chromatography/gas chromatography-mass spectrometry (LC/GC-MS), nuclear magnetic resonance (NMR) spectroscopy, and X-ray crystallography are the techniques most widely used to determine the chemical structures of molecules [7,22,23]. NMR spectroscopy is a widely utilized and well-explored technique for the elucidation of the structures of secondary metabolites [24], and NMR results are unbiased as they do not depend on ionization, as is the case in mass spectrometry [25]. Additionally, NMR can be used to characterize unprecedented compounds [26] and complex secondary metabolites in complex plant extracts [7,27], but the low resolution in proton NMR spectroscopy demands high magnetic field instrumentation and 2D NMR experiments. ...
... NMR spectroscopy is a widely utilized and well-explored technique for the elucidation of the structures of secondary metabolites [24], and NMR results are unbiased as they do not depend on ionization, as is the case in mass spectrometry [25]. Additionally, NMR can be used to characterize unprecedented compounds [26] and complex secondary metabolites in complex plant extracts [7,27], but the low resolution in proton NMR spectroscopy demands high magnetic field instrumentation and 2D NMR experiments. X-ray crystallography is one of the best techniques for absolute structure elucidation but the crystallization of several classes of compounds is tedious work [28], whereas NMR requires samples in a solution state, which is an advantage over X-ray crystallography for the analysis of organic samples. ...
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Secondary metabolites are essential components for the survival of plants. Secondary metabolites in complex mixtures from plants have been adopted and documented by different traditional medicinal systems worldwide for the treatment of various human diseases. The extraction strategies are the key components for therapeutic development from natural sources. Polarity-dependent solvent-selective extraction, acidic and basic solution-based extraction, and microwave- and ultrasound-assisted extraction are some of the most important strategies for the extraction of natural products from plants. The method needs to be optimized to isolate a specific class of compounds. Therefore, to establish the mechanism of action, the characterization of the secondary metabolites, in a mixture or in their pure forms, is equally important. LC-MS, GC-MS, and extensive NMR spectroscopic strategies are established techniques for the profiling of metabolites in crude extracts. Various protocols for the extraction and characterization of a wide range of classes of compounds have been developed by various research groups and are described in this review. Additionally, the possible means of characterizing the compounds in the mixture and their uniqueness are also discussed. Hyphenated techniques are crucial for profiling because of their ability to analyze a vast range of compounds. In contrast, inherent chemical shifts make NMR an indispensable tool for structure elucidation in complex mixtures.
... Myristica species have received considerable attention from the scientific world and resulted in the isolation of several interesting structures such as acylphenols, dimeric acylphenols, diarylpropanoids, phenylpropanoid ethers, lignins, benzofuranoid neolignans and fatty acids (Cao et al. 2015;Abourashed and El-Alfy 2016;Pandey et al. 2016). The characteristic metabolites of nutmeg have demonstrated potential biological activities and that may support its use in traditional medicines. ...
... Compounds belonging to phenylpropanoid ether and their dimers, acyl phenols and their dimers, fatty acid and their ester were detected in seed, mace and pericarp of M. malabarica by qualitative screening through HPLC-QTOF-MS/MS and NMR analysis (Pandey et al. 2016). ...
... magnifica (Bedd.) has resulted in the identification of 16 components for the first time from, belonging to, phenylpropanoid ether and their dimers, acyl phenols and their dimers, fatty acid and their ester (Pandey et al. 2016). ...
... Next, three flavonoids were labeled in the nutmeg extracts. Catechin − ) was tentatively identified as 5-(6,7-dimethoxy-3-methyl-5propenyl-2,3-dihydro-benzofuran-2-yl)-3-methoxy-benzene-1,2-diol, a lignan previously reported by Pandey et al. [23]. The cleavage of the furan ring gave the fragment ion at m/z 193.0860, whereas the removal of a CH 2 O group from this ion yielded the fragment at m/z 163.0752 [23]. ...
... Catechin − ) was tentatively identified as 5-(6,7-dimethoxy-3-methyl-5propenyl-2,3-dihydro-benzofuran-2-yl)-3-methoxy-benzene-1,2-diol, a lignan previously reported by Pandey et al. [23]. The cleavage of the furan ring gave the fragment ion at m/z 193.0860, whereas the removal of a CH 2 O group from this ion yielded the fragment at m/z 163.0752 [23]. ...
... Peaks 10, 11, and 13 were provisionally annotated as the diarylnonanoids malabaricone C, malabaricone B, and malabaricone A, respectively [23]. The fragment ions at m/z at 247.1325 for malabaricone C, 231.1387 for malabaricone A, and 215.1394 for malabaricone A resulted from the neutral loss of resorcinol. ...
Article
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The essential oil of Myristica fragrans Hutt. (nutmeg) is an important commodity used as a flavoring agent in the food, pharmaceutical, and cosmetic fields. Hydrodistillation is chiefly employed at the industrial scale for nutmeg essential oil isolation, but such a technique generates large quantities of post-distillation by-products (e.g., spent plant material and residual distillation water). Therefore, our work aimed to propose a novel strategy for the valorization of nutmeg wastes, with beneficial economic and ecological advantages. Thus, the current study assessed the phytochemical (GC-MS, LC-HRMS/MS) and biological (antioxidant, enzyme inhibitory, antimicrobial) profile of nutmeg crude materials (essential oil and total extract) and post-distillation by-products (residual water and spent material extract). Identified in these were 43 volatile compounds, with sabinene (21.71%), α-pinene (15.81%), myristicin (13.39%), and β-pinene (12.70%) as the main constituents. LC-HRMS/MS analysis of the nutmeg extracts noted fifteen metabolites (e.g., organic acids, flavonoids, phenolic acids, lignans, and diarylnonanoids). Among the investigated nutmeg samples, the spent material extract was highlighted as an important source of bioactive compounds, with a total phenolic and flavonoid content of 63.31 ± 0.72 mg GAE/g and 8.31 ± 0.06 mg RE/g, respectively. Moreover, it showed prominent radical-scavenging and metal-reducing properties and significantly inhibited butyrylcholinesterase (4.78 ± 0.03 mg GALAE/g). Further, the spent material extract displayed strong antimicrobial effects against Streptococcus pneumoniae, Micrococcus luteus, and Bacillus cereus (minimum inhibitory concentrations of 62.5 mg/L). Overall, our study brings evidence on the health-promoting (antioxidant, anti-enzymatic, antimicrobial) potential of nutmeg post-distillation by-products with future reference to their valorization in the pharmaceutical, cosmeceutical, and food industries.
... Myristica species have received considerable attention from the scientific world and resulted in the isolation of several interesting structures such as acylphenols, dimeric acylphenols, diarylpropanoids, phenylpropanoid ethers, lignins, benzofuranoid neolignans and fatty acids (Cao et al. 2015;Abourashed and El-Alfy 2016;Pandey et al. 2016). The characteristic metabolites of nutmeg have demonstrated potential biological activities and that may support its use in traditional medicines. ...
... Compounds belonging to phenylpropanoid ether and their dimers, acyl phenols and their dimers, fatty acid and their ester were detected in seed, mace and pericarp of M. malabarica by qualitative screening through HPLC-QTOF-MS/MS and NMR analysis (Pandey et al. 2016). ...
... magnifica (Bedd.) has resulted in the identification of 16 components for the first time from, belonging to, phenylpropanoid ether and their dimers, acyl phenols and their dimers, fatty acid and their ester (Pandey et al. 2016). ...
Chapter
The plant kingdom represents an extraordinary reservoir of molecules with a variety of astonishingly diverse structural features derived from complex biosynthetic steps. Medicinal plants are a rich bioresource of drugs for traditional systems of medicine and modern medicines, nutraceuticals and food supplements. Threatened medicinal plants have an important role in traditional herbal medicinal practices and are being widely exploited, leading to near extinction. The phytochemical profiling of threatened medicinal plants has potential application in identifying novel sources of bioactive compounds, identification of authentic plant material, in excluding the adulterants, in maintaining the quality and consistency of the herbal drug and in evolving suitable conservation strategies. Chemical profiling of the secondary metabolites can be achieved by conventional approaches involving extraction, separation and identification; by chromatographic and spectroscopic profiling such as HPLC, HPTLC, GC, UV-Vis, IR, NMR and MS; or by online separation, identification and quantitative evaluation using modern hyphenated techniques such as LC-MS, LC-MS/MS, LC-NMR and LC-MS/NMR. The Western Ghats hosts a number of medicinal plants and their wild relatives, mostly coming under threatened category, and the present chapter gives a brief outlook into the phytochemistry of selected threatened species belonging to Garcinia, Myristica, Rauwolfia and Coscinium from the Western Ghats.
... An in-house library of different metabolites was created through a literature search of previously reported metabolites from different species of the Myristicaceae family such as M. fragrans, Myristica malabarica, Myristica beddomei [12,[22][23][24]. The structural and spectral information of metabolites were retrieved from different online metabolites databases like Metlin (https://metlin.scripps. ...
... Among genus Myristica, there is overwhelming research on understanding the chemistry of Myristica fragrans, common name "nutmug," due to its innumerable medicinal and bioactive applications [12]. [12,[22][23][24] used with a mass accuracy of 10 ppm. Similarly, other databases like bio-molecules provided by the Waters Corporation also was used for the identification. ...
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Untargeted profiling of phytochemicals from plant extracts would aid in the exploration of various groups of compounds and assist in the identification of new bioactive compounds, reducing the redundancy in compound identification. The potential bioactive phytochemicals present in Myristica dactyloides, an endemic ethnomedicinal plant widely used in traditional treatment practices, were explored and cataloged in this study. The untargeted phytochemical profile of active methanolic leaves and bark extracts was assessed by Ultra high-performance liquid chromatography coupled to electrospray ionization and quadrupole time-offlight mass spectrometry. Preliminary screening results highlighted the high efficiency of methanolic extract as an effective antioxidant and anti-inflammatory agent, along with a remarkable amount of total phenolics and flavonoid content. Thus, the methanolic extracts of leaves and bark samples were further subjected to catalog its chemical constituents through untargeted metabolite profiling. Analysis of high-resolution liquid chromatography-mass spectrometer spectra, exhibited 3,813 and 1,797 molecular features in the ESI+ mode with clean retention time-exact mass, resulted in identifying 35 major therapeutically important common compounds for the first time in both leaves and bark extracts of M. dactyloides, fitting to major groups like lignans, neolignans, phenylpropanoids, diarylnonanoid, flavonoids, and others. Our results prove the presence of Myoinositol, Malabaricone B, Malabaricone C, Malabaricone D, and 1-(2,6-dihydroxyphenyl)- 9-(4-hydroxy-3-methoxyphenyl) nonan-1-one previously reported from M. dactyloides, along with promising chemical signatures like Monotropein, Austrobailignan 7, Fragransol B, Guaiacin, Myricanone, Nectandrin A, Argenteane, and Epicatechin to the phytochemical catalog of M. dactyloides. Furthermore, our research not only confirms the existence of previously known molecules and adds new phytochemicals, but it also sheds light on the wide application of M. dactyloides for possible bio-prospecting for a new chemical entity.
... It is extensively utilized as a substituent or adulterant of nutmeg products in South India. [12][13][14] There are very few reports on the phytochemistry and pharmacological activities of M. beddomei. [15,16] The pericarp of Myristica beddomei ssp. ...
... [39,40] M. beddomei has shown antiproliferative activity against human cancer cell lines A549, DLD-1, DU145, FaDu, and MCF-7 too. [14] An earlier study has shown the highest antiproliferative activity with > 96 % growth inhibition was found for the extracts of pericarp and seed of M. beddomei at 100 μg mL -1 concentration. However, in the present study >200 μg mL -1 has been required for 50 % of inhibition of L929 cell line. ...
Article
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Plants are traditionally used for pharmacological activities because of its ability to produce bioactive compounds. Myristica beddomei King ssp. ustulata W.J. de Wilde is an ethnomedicinal plant and it is seen in South Western Ghats of Kerala, India. The present study assessed the phenolic content, flavonoid concentration, in vitro antioxidant and cytotoxic effect of different parts of Myristica beddomei King. The total phenolic contents in the extracts ranged from 96.29 (pericarp) to 314.47 (bark) mg g-1 gallic acid equivalent. The concentration of flavonoids in different plant part extracts ranged from 1.81 to 2.76 mg g-1 equivalent to quercetin. All the parts exhibited potential antioxidant activity with an IC50 value of 2.87 to 9.67 μg ml-1 when compared to the standard ascorbic acid with an IC50 value of 2 μg ml-1 in 1,1-diphenyl-2- picryl-hidrasil (DPPH) method. Bark showed highest activity in terms of DPPH radical scavenging (IC50 value of 2.87 µg ml-1), phosphomolybdenum test (2261.33 ± 1.65 mg g-1 trolox equivalent) and ferric ion reducing antioxidant power (FRAP) (113.1 ± 0.28 µmol Fe2+ µg-1) while pericarp showed low antioxidant activity. The in vitro screening results revealed that the seeds exhibited promising anticancer activity compared to PA1 (Ovarian Cancer) cells (50 % inhibition) were observed at a concentration 100.68 µg ml-1. In cytotoxicity test L929 (Fibroblast) cell line compared to the other parts pericarp, mace and seed needed higher concentration (>240 µg ml-1) for LC50 value. It is a promising plant for further development of antioxidant agent as it got high content of phenolic compounds and potential antioxidant and anticancer activity.
... As these wild nutmeg species are botanically close to the cultivated nutmeg, they must be studied in detail to explore the possibility of using them for industrial purposes (Pandey et al. 2016;Bohra et al. 2019). The present investigation was, therefore, carried out to study the variation amongst species of three genera of Myristicaceae in terms of their seed morphology, fatty acid composition and total phenolic content. ...
... As all the studied species belong to the family Myristicaceae, dominance of this compound is expected (Spencer et al. 1980). The presence of this compound has also been reported from cultivated and wild nutmeg species from other tropical countries (Pandey et al. 2016;Essumang et al. 2008). Methyl myristate and methyl palmitate have been reported to have repellant properties against Musca domestica and Sarcophaga bullata (Henderson et al. 1991). ...
Article
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Myristicaceae is a tropical family, the members of which are utilized for medicinal properties in their native regions. Myristica fragrans is a species commercially exploited as a spice and medicine worldwide, while most of its allied species are yet to be studied in detail. In present study, three species viz. Horsfieldia glabra, Knema andamanica and Myristica andamanica were compared with the commercial nutmeg morphologically and biochemically to identify their utilization potential. Distinct variations were observed for seed morphological parameters among these species and seed dimensions were found to be the maximum in seeds of M. andamanica. Extraction yield varied significantly with solvent in H. glabra, K. andamanica and M. fragrans. Higher total phenolic content was recorded in methanolic extracts than acetone extracts in all the species and methanolic extract of M. andamanica had the highest total phenolic content (6.54 mg/g GAE). Seeds of all species were rich in saturated fats that varied between 59.4% (H. glabra) and 83.4% (M. andamanica). Methyl tetradecanoate was the most dominant compound in all the species, the content of which varied between 46.87 and 68.84%, while (Z)-9-octadecenoic acid methyl ester and methyl hexadecanoate were the other dominant compounds. Higher quantities of methyl dodecanoate (27.02%) and methyl cis -13-docosenoate (16.97%) were obtained from M. andamanica and H. glabra, respectively, while these compounds were present in minute quantities in other species.
... The LC-MS/MS is a useful technique to conduct structural identification of flavonol aglycone type [35,50,51]. The LC-MS/MS method has been developed for the rapid screening and determination of bioactive compounds in fruit efficiently and sensitively [52]. Singh et al. [51] identified quercetin-o-pentohexoside, quercetin-3-diglucoside, quercetin-o-xylo-pentoside and kaempferol-o-glucoside using LC-MS/MS and found some molecular ions in the full scan mass spectra, such as m/z 625, m/z 595, m/z 579, and some other ion fragments, including m/z 301, m/z 285 [51]. ...
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Actinidia arguta (Sieb. et Zucc.) is abundant of vitamin C and bioactive compounds with high antioxidant activities. In this study, eight wild A. arguta accessions from different areas in Northeast China were collected. Some bioactive compounds were extracted from leaves, petioles and fruits of different germplasms for constituent analysis and non-enzymatic antioxidant assay. Liquid chromatography with tandem mass spectrometry (LC–MS/MS) was used to detect the flavonoid compounds. The results showed that the highest vitamin C content was found in young apical leaves of ‘CBS-6’ (7.47 mg/g fresh weight), and the highest soluble sugar content was in fruits of ‘CJ-1’ (196.52 mg/g fresh weight) and the highest total phenolic content and total flavonoids content were in young apical leaves of ‘CBS-11’ (3.48 mg/g fresh weight) and of ‘CBS-3’ (2.00 mg/g fresh weight), respectively. Ten flavonoid compounds including kaempferol, isorhamnetin and quercetin were detected in leaves, petioles and fruits. The total content of flavonoids was highest in young apical leaves (10219.84 µg/g) and the lowest in fruits (78.75 µg/g). Based on the comparison of the contents of several bioactive compounds, the two accessions ‘CJ-1’ and ‘CBS-8’ stood out; the young leaves had the strongest antioxidant activity among different tissues based on the non-enzymatic antioxidant assay. These results highlighted the radical-scavenging potential in vitro of A. arguta leaves as a major source of phenolics and vitamin C as well as flavonoids. It provided a theoretical basis for the utilization of leaves of A. arguta. Supplemental data for this article is available online at https://doi.org/10.1080/13102818.2021.1908166 . Supplemental data for this article can be accessed online at https://doi.org/10.1080/13102818.2021.1908166.
... Nevertheless, several analytical data have been previously published on the chemistry of other species within the Myristica genus. Similar to M. hypargyraea extracts in this study, malabaricone A was detected as a major constituent of M. malabarica seed, and malabaricone B and C were abundant in M. beddomeii and M. fatua (Pandey et al., 2016). The lignan otobain was previously isolated from the fruit of M. otoba, and its two stereochemical isomers ( §) have been previously reported (Klyne et al., 1966). ...
Article
Hexane extracts derived from the arils and seeds of two Samoan indigenous plant species, Myristica hypargyraea A. Gray and Myristica inutilis Rich ex A. Gray, were assessed for their in vitro anti-staphylococcal effect using a broth microdilution assay. Additionally, their cytotoxic activity against human colon cancer and normal intestinal cell lines was determined. In this study, all plant extracts tested showed a certain degree of growth-inhibitory effect against various strains of Staphylococcus aureus with minimum inhibitory concentrations (MICs) ranging from 8 to 1,024 µg/mL. The aril extract of M. hypargyraea possessed the highest antibacterial activity with MIC value 8 µg/mL against one standard strain and three clinical isolates of S. aureus, the effective concentrations of this extract were found to be safe for the intestinal cells. The aril extract of M. inutilis showed the highest selective antiproliferative effect on intestinal cancer cells with a lower toxicity to normal cell lines. Using gas chromatography-mass spectrometry analysis, malabaricone A, otobain, licarin A, and licarin B were identified as the major components of both the aril and seed extracts of M. hypargyraea and M. inutilis.
... Myristicin (27) Cancer chemopreventive agent [51], anti-inflammatory [52], antimicrobial against B. subtilis, E. coli, S. aureus [110], hepatoprotective [111], cytoprotective against hypoxia-induced apoptosis and endoplasmic reticulum stress [112], down-regulates expression of pro-inflammatory cytokines [113], cytotoxic against SK-N-SH (human neuroblastoma) cancer cell line [114], acetylcholinesterase inhibitor [115], antiproliferative [116], insecticidal against Culex pipiens and Aedes aegypti [117]. ...
Article
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Silphion was an ancient medicinal gum-resin; most likely obtained from a Ferula species growing in the Cyrene region of Libya ca. 2500 years ago. Due to its therapeutic properties and culinary value, silphion became the main economic commodity of the Cyrene region. It is generally believed that the source of silphion became extinct in the first century AD. However, there are a few references in the literature about the cultivated silphion plant and its existence up to the fifth century. Recently, a rare and endemic Ferula species that produces a pleasant-smelling gum-resin was found in three locations near formerly Greek villages in Anatolia. Morphologic features of this species closely resemble silphion, as it appears in the numismatic figures of antique Cyrenaic coins, and conform to descriptions by ancient authors. Initial chemical and pharmacological investigations of this species have confirmed the medicinal and spice-like quality of its gum-resin supporting a connection with the long-lost silphion. A preliminary conservation study has been initiated at the growth site of this rare endemic Ferula species. The results of this study and their implications on the regional extinction event, and future development of this species will be discussed.
... Nutmeg has carminative, aromatic, narcotic, stimulant, astringent, aphrodisiac, anti-inflammatory, antioxidant, hypolipidemic, antidysenteric, anti-platelet aggregation, and antithrombotic activities. It is used as a remedy for dietary habits, rheumatism, vomiting in pregnancy, and stomach ache, as both a herb and a spice (Pandey et al., 2016;Tisserand & Young, 2013). Dorman and Deans (2000) evaluated the antioxidant activity of nutmeg and its main components by modified TBARD assay, and their results showed that nutmeg oil was able to inhibit the oxidative bleaching of β-carotene. ...
Article
Background Biodegradable packaging from natural biopolymers can be further enhanced with antimicrobial and antioxidant agents to form active packaging. Scope and approach Plant extracts are attractive components for biodegradable food packaging owing to their natural origin and functionality (antimicrobial/antioxidant activity). Here we demonstrate the effect of bioactive contents of tropical plants and their by-products as promising natural ingredients in the fabrication of biopolymer food packaging. Key findings and conclusions Different parts of tropical plants, such as leaves, flowers, seeds, and roots, can potentially be utilized for new and green packaging systems due to their biological nature. In the food industry, lipid oxidation and microbial spoilage are two problems which reduce the shelf life of food products. It seems that the use of potential bioactive agents in biodegradable packaging is a promising strategy to solve this problem, offering a green alternative to traditional packaging and enhancing the shelf-life of food.
... The LC-ESI-MS analyses were performed as done earlier [14]. Detailed procedure is mentioned in supplementary section. ...
Article
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Untreated hyperthyroidism may develop serious complications. This attempt was made to investigate the potential of Aloe vera gel in regulating experimentally induced hyperthyroidism in rats. Female Wistar rats were made hyperthyroid with L-thyroxine (L-T4) at 0.5 mg/kg/day, i.p. for 14 days and the effects of Aloe vera methanolic fraction (AVMF) (50 or 500 mg/kg/day, p.o.,) and a conventional antithyroid drug propylthiouracil (PTU) (10 mg/kg, i.p.) for 30 days were studied in those hyperthyroid rats. At the end, alterations in serum thyroid hormones and thyroid stimulating hormone (TSH); hepatic 5′mono-deiodinase-1(5′D1) activity, oxidative stress markers and antioxidants; serum inflammatory cytokines and the expression of thyrotropin receptor in thyroid gland were evaluated in all experimental animals. Hyperthyroid condition was confirmed by an increase in thyroid hormone levels and hepatic 5′D-1 activity with a decrease in TSH. However, either AVMF or PTU treatment in hyperthyroid rats decreased the levels of thyroid hormones and 5′D1 activity. AVMF administration in T4-induced rats also decreased the oxidative stress markers such as thiobarbituric acid reactive substances and lipid hydroperoxides and increased the antioxidant levels in liver tissues. Levels of liver marker enzymes, cytokines and different lipids were decreased in T4-induced AVMF treated rats. Further, a down regulation in the TSHR expression in thyroid was observed in AVMF or PTU treated groups. All these thyroid inhibiting effects were supported by an improvement in thyroid histology in hyperthyroid rats. It appears, about 15 compounds, as evidenced by LC–MS/MS study, mostly phenolics are involved in this anti-thyroid effects of the test compound.
... Recently, our group reported the antidiabetic potential of phytochemicals from the stem bark of M. fatua (Prabha et al. 2018). In 2016, Pandey et al. reported the LC-MS screening of the different fruit parts of M. fatua and its in vitro antiproliferative activity (Pandey et al. 2016). Beside these, there is no detailed phytochemical and pharmacological evaluation of the seeds of M. fatua. ...
Article
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Promalabaricone B (PMB), an acylphenol was isolated from dichloromethane-soluble extract of the seeds of Myrisitica fatua Houtt. PMB exhibited significant inhibitory activity on α-glucosidase enzyme. The molecular docking and dynamics studies of PMB with human maltase-glucoamylase were performed. PMB exhibited an enhanced glucose uptake in L6 myotubes with 46.3% in 2.5 µM. Encouraged with these results; we investigated the molecular mechanism of PMB through the upregulation of AMPK. The results revealed that PMB promoted the glucose uptake in myocytes by stimulating the translocation and expression of GLUT4. From this, it is clear that PMB can acts as a potential therapeutic option for diabetes treatment, and its hypoglycaemic effect may be mediated by AMPK upregulation and induction of GLUT4 translocation.
... Lignans and acylphenols are the secondary metabolites major compound produced by this family (Nemethy, 1986;Woo, 1987;Cooray, 1987;Kumar, 1988;Hada, 1988;Nakatani, 1988;Herath, 1996;Herath, 1997;Pham, 2000& 2002Talukdar, 2000;Calliste, 2010;Cuong, 2011;Chong, 2011;Manjunatha, 2011;Ragasa, 2013;Cao, 2013;Cao, 2015;Acuna, 2016;Wahab, 2016;Pandey, 2016;. In addition to their activities of antioxidant, antibacterial, antimicrobial, nematocide, and cytotoxic (Pham, 2000;Talukdar, 2000;Pham, 2002), antiinflammatory (Cuong, 2011;Cao, 2013;Cao, 2015), anxiogenic (Sonavane, 2002),antihelmintic (Lopez, 2015), cholinesterase inhibitor (Wahab, 2016), terapeutic (Jangid, 2014), acylphenols also been known to have alpha-glucosidase inhibitor activity . ...
Article
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Myristica fatua Houtt. is one of the endemic plants growth in Wallace region. Isolation of the secondary metabolite compounds from the ethyl acetate fraction of the bark of Myristica fatua Houtt. has been done using some chromatography techniques afforded two resorcinol compounds, malabaricone C (1), and malabaricone B (2). The structures of 1-2 were determined using spectroscopic techniques, including mass spectrometry, 1D-NMR and 2D-NMR. Both compounds showed in vitro cytotoxic activity against the breast carcinoma cancer cell lines MCF-7 using alamar blue assay method, with IC50 of 2.38 and 0.71 μg/mL, respectively.
... The UHPLC-QqQLIT-MS/MS analysis was performed by following the protocol of Pandey et al. [33] with minor modifications. The optimized compound dependent Multiple Reaction Monitoring (MRM) parameters of each analyte are presented in Table 1. ...
Article
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Background Research of natural products from traditionally used medicinal plants to fight against the human ailments is fetching attention of researchers worldwide. Bidens pilosa Linn. var. Radiata (Asteraceae) is well known for its folkloric medicinal use against various diseases from many decades. Mizoram, North East India, has high plant diversity and the use of this plant as herbal medicine is deep rooted in the local tribes. The present study was executed to understand the pharmacological potential of B. pilosa leaves extract. Methods The antimicrobial potential was determined using agar well diffusion and broth microdilution method against bacterial and yeast pathogens. Cytotoxicity was evaluated using MTT and apoptotic DNA fragmentation assays. Further, the antioxidant ability of the extract was analysed using DPPH and ABTS free radical scavenging assay. Mosquitocidal activity was evaluated against third in-star larvae of C. quinquefasciatus using dose response and time response larvicidal bioassay. Additionally, the major phenolic and volatile compounds were determined using UHPLC-QqQLIT-MS/MS and GC/MS respectively. ResultsWe found that the extract showed highest antimicrobial activity against E. coli (MIC 80 μg/mL and IC50 110.04 μg/mL) and showed significant cytotoxicity against human epidermoid carcinoma (KB-3-1) cells with IC50 values of 99.56 μg/mL among the tested cancer cell lines.The IC50 values for scavenging DPPH and ABTS was 80.45 μg/mL and 171.6 μg/mL respectively. The extract also showed the high phenolics (72 μg GAE/mg extract) and flavonoids (123.3 μg Quercetin /mg extract). Lastly, five bioactive and six volatile compounds were detected using UHPLC-QqQLIT-MS/MS and GC-MS respectively which may be responsible for the plant’s bioactivities. An anticancerous compound, Paclitaxel was detected and quantified for the first time from B. pilosa leaves extract, which further showed the anticancerous potential of the tested extract. Conclusion On the basis of the present investigation, we propose that the leaf extract of B. pilosa might be a good candidate for the search of efficient environment friendly natural bioactive agent and pharmaceutically important compounds.
... In our previous report, the n-hexane fraction from methanol extract of M. fatua leaves showed high toxicity against brine shrimp (LC50 153.1 µg/mL), indicating its potential to be developed as an anticancer agent [14]. Antiproliferative activity against MCF-7 cell lines was found in M. fatua [15]. Therefore, the n-hexane further Optical Density (cells+ sample)-Optical Density (negative control) 030087-2 examined against MCF-7 breast cancer cell lines. ...
Conference Paper
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The aims of this research were to determine the chemical constituents of n- hexane fraction from Myristica fatua Houtt leaves by Gas Chromatograpy/Mass Spectrometry (GC/MS) and their cytotoxic activities against MCF-7 cell lines. The results indicated that sesquiterpenes and fatty acids were major compounds of this fraction, there were trans-calamenene (17.75 %), hexadecanoic acid (11.14 %), caryophyllene (7.49 %), α-muurolene (6.99 %), and γ-muurolene (6.60 %). In vitro anticancer activity test against breast cancer MCF-7 cell lines showed potential cytotoxic at IC50 2.19 μg/mL.
... Pharmacological research revealed various activities of nutmeg such as antioxidant, antibacterial, antidiabetic, hypolipidemic, hepatoprotective and analgesic (Gupta et al. 2013). Ethanolic extract of M. fragrans seeds showed low antiproliferative activity (B53 % growth inhibitory effect) against lung, colon, prostate, head and neck and breast human cancer cell lines (Pandey et al. 2016). The flavor and therapeutic action are due to the volatile oil (Leela 2008). ...
Article
This study evaluated the effect of conventional maceration and ultrasound assisted extraction techniques on the extraction yield, chemical composition and sensory characteristics of nutmeg oleoresins. Extraction was performed using material: absolute ethanol ratio 1:4, at room temperature. The volatile components of the oleoresin were identified by gas chromatography–mass spectrometry. The results of the study showed that the yield ranged from 4.55 to 9.63 %. Fifty-three compounds in the nutmeg oleoresin have been identified to account for >90 % of the total oil content. Sabinene, myristicin, elemicin, α-pinene, β-pinene, limonene, terpinen-4-ol and myristic acid were found as major compounds of all the nutmeg oleoresins obtained by different techniques. The sensory characteristics of the oleoresin were strongly influenced by the ultrasonic intensity and duration of extraction. The experimental results showed that ultrasound assisted extraction technique at 40 % of the maximal output power and 10 min produced superior quality nutmeg oleoresin with a remarkable yield.
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Malabaricone A isolated from Myristica malabarica induces apoptosis in triple-negative breast cancer cells through intrinsic and extrinsic pathways, which is validated through in vitro and in silico studies and resembles a potent phyto-entity.
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The Myristicaceae family has 500 species, divided into 3 genera: Myristica, Knema, and Horsfieldia. These species are distributed across tropical Asia, Africa, and America. This plant has active ingredients, including polyketides and lignans, which have a range of biological properties such as anti-inflammatory, anti-cancer, and anti-microbial. This review aims to examine the variety of biological activities and chemical structures of the bioactive chemicals present in the Myristicaceae family from across the globe.
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Introduction Nymphaea rubra belongs to the Nymphaea family and is regarded as a vegetable used in traditional medicine to cure several ailments. These species are rich in phenolic acid, flavonoids, and hydrolysable tannin. Objective This study aimed to assess the biological activities of Nymphaea rubra flowers (NRF) and leaves (NRL) by identifying and quantifying their polyphenolic compounds using ultra‐performance liquid chromatography coupled to quadrupole cyclic ion mobility time‐of‐flight mass spectrometry (UHPLC‐Q‐cIM‐TOF‐MS) and triple quadrupole mass spectrometry (UHPLC‐TQ‐MS). Methodology NRF and NRL powder was extracted with methanol and fractionated using hexane, ethylacetate, and water. Antioxidant and α‐glucosidase, and tyrosinase enzyme inhibitory activities were evaluated. The polyphenolic components of NRF and NRL were identified and quantified using UHPLC‐Q‐cIM‐TOF‐MS and UHPLC‐TQ‐MS. The method was validated using linearity, precision, accuracy, limit of detection (LOD), and lower limit of quantification (LLOQ). Results Bioactive substances and antioxidants were highest in the ethylacetate fraction of flowers and leaves. Principal component analysis showed how solvent and plant components affect N. rubra 's bioactivity and bioactive compound extraction. A total of 67 compounds were identified, and among them 21 significant polyphenols were quantified. Each calibration curve had R ² > 0.998. The LOD and LLOQ varied from 0.007 to 0.09 μg/mL and from 0.01 to 0.1 μg/mL, respectively. NRF contained a significant amount of gallic acid (10.1 mg/g), while NRL contained abundant pentagalloylglucose (2.8 mg/g). Conclusion The developed method is simple, rapid, and selective for the identification and quantification of bioactive molecules. These findings provide a scientific basis for N. rubra 's well‐documented biological effects.
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Alstonia scholaris is a well-known source of alkaloids and widely recognized for therapeutic purposes to treat the ailments in human and livestock. However, the composition and production of alkaloids vary due to tissue specific metabolism and seasonal variation. This study investigated alkaloids in leaves, stems, trunk barks, fruits, and flowers of A. scholaris. The impact of seasonal changes on the production of alkaloids in the leaves of A. scholaris was also investigated. One and two-dimensional Nuclear Magnetic Resonance (NMR) experiments were utilized for the characterization of alkaloids and total eight alkaloids (picrinine, picralinal, akuammidine, 19 S scholaricine, 19,20 E vallesamine, Nb-demethylalstogustine N-Oxide, Nb-demethylalstogustine, and echitamine) were characterized and quantified. Quantitative and multivariate analysis suggested that the alkaloids content is tissue specific, illustrating the effect of plant tissue organization on alkaloidal production in A. scholaris. The results suggest that the best part to obtain alkaloids is trunk barks, since it contains 7 alkaloids. However, the best part for isolating picrinine, picralinal, akuammidine, 19 S scholaricine, and 19,20 E vallesamine is fruit, since it shows highest amount of these alkaloids. Undoubtedly, NMR and statistical methods are very helpful to differentiate the profile of alkaloids in A. scholaris.
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Bioinsecticides are regarded as important alternatives for controlling agricultural pests. However, few studies have determined the persistence of these compounds in stored grains. This study aimed at optimizing and validating a fast and effective method for extraction and quantification of residues of safrole (the main component of Piper hispidinervum essential oil) in cowpea beans. It also sought to assess the persistence of this substance in the grains treated by contact and fumigation. The proposed method used headspace solid-phase microextraction (HS-SPME) and gas chromatography with a flame ionization detector (GC/FID). Factors such as temperature, extraction time and type of fiber were assessed to maximize the performance of the extraction technique. The performance of the method was appraised via the parameters selectivity, linearity, limit of detection (LOD), limit of quantification (LOQ), precision, and accuracy. The LOD and LOQ of safrole were 0.0057 and 0.019 μg kg−1, respectively and the determination coefficient (R2) was >0.99. The relative recovery ranged from 99.26 to 104.85, with a coefficient of variation <15%. The validated method was applied to assess the persistence of safrole residue in grains, where concentrations ranged from 1.095 to 0.052 µg kg−1 (contact) and from 2.16 to 0.12 µg kg −1 (fumigation). The levels measured up from the fifth day represented less than 1% of the initial concentration, proving that safrole have low persistence in cowpea beans, thus being safe for bioinsecticide use. Thus, this work is relevant not only for the extraction method developed, but also for the possible use of a natural insecticide in pest management in stored grains.
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Antioxidant plays an important role in reducing the risk of chronic diseases. By using DPPH radical scavenging assay-guided fractionation, a bioactive compound has been isolated from the methanol extract of the leaves of Myristica fatua Houtt and subsequently identified as methyl 3,4-dihydroxybenzoic (MDB). The structure of MDB was confirmed by UV, FT-IR, MS, 1- and 2-D NMR spectroscopy. This compound exhibit antioxidant activity together with previous compounds i.e (7S,8R,8′S,7′S)-7,7′-bis(3-hydroxy-5-methoxyphenyl)-8,8′-dimethylbuthane-7,7′-diol and 3”-hydroxy demethyldactyloidin with IC 50 values 7.96, 101.1 and 15.4 μg/mL, respectively. These findings demonstrate that MDB can be considered as a natural antioxidant.
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Ethnopharmacological relevance Herbal medicines (HMs) often exert integration effects, including synergistic, additive and antagonistic effects, in such ways that they act on multiple targets and multiple pathways on account of their multiple components. Turmeric, made from the rhizome of Curcuma longa L., is a well-known HM prescribed in the polyherbal formulas for cancer treatment in traditional Chinese medicines (TCMs). However, neither the multiple anticancer compounds of turmeric nor the integration effects of these components are fully known. Aim of the study This work aims to develop a systematic approach to reveal the integration effect mechanisms of multiple anticancer compounds in turmeric against prostate cancer PC3 cells. Materials and methods Combination index and omics technologies were applied to profile the integration effect mechanisms of bioactive compounds in proportions naturally found in turmeric. PC3 cell line (a prostate cancer cell line) fishing and high resolution mass spectrometry were employed to screen and identify the anticancer compounds from turmeric. The combinations which contain different cell-bound compounds in natural proportions were prepared for further evaluation of anti-cancer activity by using cell viability assays, and assessment of cell apoptosis and cell cycle analysis. Combination index analysis was applied to study the integration effects of the anticancer compounds in their natural proportions. Finally, quantitative glycoproteomics/proteomics and Western blot were implemented to reveal the potential synergistic effect mechanisms of the anticancer compounds based on their natural proportions in turmeric. Results Three curcuminoids (curcumin, CUR; demethoxycurcumin, DMC; bisdemethoxycurcumin, BDMC) in turmeric were discovered and shown to possess significant synergistic anticancer activities. Combination index analysis revealed an additive effect of CUR combined with DMC or BDMC and a slight synergistic effect of DMC combined with BDMC in natural proportions in turmeric, while a combination of all three curcuminoids (CUR, DMC and BDMC) at a ratio of 1:1:1 yielded superior synergistic effects. Interestingly, the presence of BDMC and DMC are essential for synergistic effect. Glycoproteomics and proteomics demonstrated that different curcuminoids regulate various protein pathways, such as ribosome, glycolysis/gluconeogenesis, biosynthesis of amino acids, and combination of CUR + DMC + BDMC showed the most powerful effects on down-regulation of protein expression. Conclusions Our analytical approach provides a systematic understanding of the holistic activity and integration effects of the anti-cancer compounds in turmeric and three curcuminoids of turmeric showed a synergistic effect on PC3 cells.
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The pericarp of Myristica fragrans fruit extract was utilized for a low cost, eco-friendly synthesis of silver (AgNPs) and copper oxide (CuONPs) nanoparticles. The aqueous fruit extract of the plant was used as reducing and stabilizing agents for this preparation. Characterization of the biosynthesized nanoparticles was carried out using UV–Vis spectroscopy, FTIR spectroscopy and X-Ray Diffraction studies. Morphology and size of the particles was observed using Field-Emission Scanning Electron Microscopy (FESEM) and High Resolution Transmission Electron Microscopy (HRTEM). The copper and silver nanoparticles show Surface Plasmon Resonance (SPR) band at 360 and 478 nm respectively in the UV–Vis spectrum. It was observed that size of the synthesized copper oxide and silver nanoparticles are in the range 10–50 nm. The presence of copper and silver elements was confirmed from their respective EDS spectrum. Involvement of phytochemicals in the stabilization and reduction of the nanoparticles was confirmed by FTIR spectroscopy. CuONPs exhibited catalytic activity in 1,3-dipolar cycloaddition reaction between azides and terminal alkynes to form 1,2,3-triazoles. Silver nanoparticle possesses good antibacterial activity against multidrug human pathogens Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Bacillus subtilis. The present study focuses on the utilization of the less economic part of Myristica fragrans fruit's pericarp for the preparation of copper oxide and silver nanoparticles which have good catalytic and antibacterial activities.
Chapter
Myristica fragrans is a fragrant tree, known for its commercial spicy products, namely, the nutmeg, mace, and essential oil, which are predominantly used in flavor, fragrance, and pharmaceutical industries. Being one of the popular spices in the culinary sector, the plant products are traditionally used in folk medicines for treating various human ailments. Its therapeutic potentials include antioxidant, anti-inflammatory, chemopreventive, anti-obesity, antiangiogenic, neuroprotective, analgesic, antithrombotic, antifeedant, hepatoprotective, insecticidal, aphrodisiac, radioprotective properties, and many more. Also, the plant is noted for its hallucinogenic or narcotic-like properties. The clinical evidences have suggested about the intoxication, poisonings, and adverse effects of M. fragrans. The present chapter provides a comprehensive information on the botanical, pharmacological, and toxicological aspects of M. fragrans products.
Article
Ethnopharmacological relevance: Plant materials used in this study were selected based on the ethnobotanical literature. Plants have either been utilized by Thai practitioners as alternative treatments for cancer or identified to exhibit anti-cancer properties. Aim of the study: To screen ethnomedicinal plants using a yeast cell-based assay for synthetic lethal interactions with cells deleted for RAD1, the yeast homologue of human ERCC4 (XPF) MATERIALS AND METHODS: Ethanolic extracts from thirty-two species of medicinal plants utilized in Thai traditional medicine were screened for synthetic lethal/sick interactions using a yeast cell-based assay. Cell growth was compared between the parental strain and rad1∆ yeast following exposure to select for specific toxicity of plant extracts. Candidate extracts were further examined for the mode of action using genetic and biochemical approaches. Results: Screening a library of ethanolic extracts from medicinal plants identified Bacopa monnieri and Colubrina asiatica as having synthetic lethal effects in the rad1∆ cells but not the parental strain. Synthetic lethal effects for B. monneiri extracts were more apparent and this plant was examined further. Genetic analysis indicates that pro-oxidant activities and defective excision repair pathways do not significantly contribute to enhanced sensitivity to B. monneiri extracts. Exposure to B. monneiri extracts resulted in nuclear fragmentation and elevated levels of ethidium bromide staining in rad1∆ yeast suggesting promotion of an apoptosis-like event. Growth inhibition also observed in the human Caco-2 cell line suggesting the effects of B. monnieri extracts on both yeast and human cells may be similar. Conclusions: B. monneiri extracts may have utility in treatment of colorectal cancers that exhibit deficiency in ERCC4 (XPF).
Chapter
Spices and aromatic herbs have been used since antiquity as preservatives, colorants, and flavor enhancers. Secondary metabolites(SM) are compounds that are not necessary for a cell (organism) to live, but play a role in the interaction of the cell (organism) with its environment. These compounds are often involved in plants protection against biotic or abiotic stresses. Secondary metabolites are mainly responsible for plant defense and have no direct involvement in the growth and development of such plants. Terpenes, alkaloids and phenolics are three main classes of secondary metabolites in plants. Black pepper, cardamom, ginger, turmeric, cinnamon, clove and nutmeg are spices of great commercial importance as it provides flavor and taste to the culinary preparations were it is added. Secondary metabolites of these spices are of great significance in the present era of nutraceuticals as these spices possess antioxidant, anticancerous, numerous other medicinal properties. Detailed information on these spices is very interesting. © Springer International Publishing AG, part of Springer Nature 2018.
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Myrictica fatua Houtt widely used in Indonesian as one of the traditional medicinal plants. Cancer and diabetic mellitus (DM) type 2 are two degenerative diseases caused by the presence of excessive free radicals in the body. Antioxidant and anti-diabetic active compounds were needed to reduce the risk of the diseases. One of the chemical compound groups that can be used as antioxidant and antidiabetic is phenolic compound. Isolation of the methanolic extract of the bark of M. fatua Houtt using chromatography methods led to the isolation of phenolic compound. Methyl 3,4-dihydroxybenzoate showed antioxidant and antidiabetic activities through DPPH free radicals scavenger and α-glucosidase inhibitions activities test showed IC50 value 7.96 and 7.68 ug / mL, respectively
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The fruit (aril) of the endangered genus Taxus plants is an abandoned herbal resource. Traditionally, people enthusiasticly focus on its bark, its renewable, tremendous arils fall into the soil with seeds after they are mature. The present research investigated the fruit of two species from the genus Taxus, Taxus chinensis var. mairei and Taxus media, with regards to their antioxidant and antihyperglycaemic activities, safety, and bioactive constituents. Results showed that T. chinensis var. mairei and T. media both had certain biological activities with T. chinensis var. mairei better in antioxidant activity and T. media better in antihyperglycaemic activity. Correlation analysis revealed that the differences in bioactivities depended on content of their mainly chemical components. The mice acute oral toxicity test indicated that the methanol extracts of the two biotypes of Taxus were safe. And nineteen compounds were tentatively assigned from the two varieties, via tandem mass spectrometry using a LC-ESI-Q-TOF-MS instrument, which included phenols, flavonoids and terpenes. These results indicate a possible application of Taxus fruit extracts in various fields like in food industry, however this still needs further investigations.
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Fatty oil obtained by solvent extraction method using light pet-ether (40°-60°C) of the fruits oil of Myristia fragrans Houtt (Nutmeg) collected from India and Sri Lanka the oil was analyzed by GC. Total seven fatty acids were indentified from the fatty oil of Indian nutmeg. The major constituents were oleic acid (37.73%), arachidic acid (26.97%), palmtic acid (21.97%). On the other hand total six fatty acids were indentified from the fatty oil of Sri Lankan nutmeg. The major constituents were myristic acid (84.60%), palmtic acid (7.38%). Physio-chemical characteristics, such as iodine value, acid value, color, Solubility, moisture, ash, crude fiber, protein of the nutmeg were also determined.
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Background: Nutmeg is the imperative spices having pharmacological importance. Objectives: The objective of this work was to standardize Nutmeg extract by RP-high performance liquid chromatography (HPLC) analysis. Settings and Design: An RP-HPLC method was developed for simultaneous quantification of quercetin (QUE), eugenol (EUG), myristicin (MYRS), and safrole (SAFR) from nutmeg fruit and mace extracts. Materials and Methods: RP-HPLC method was performed with Waters 2695 Alliance system using a 2996 photodiode array detector (PDA). QUE, EUG, MYRS, and SAFR were separated on a reverse-phase 250 × 4.6 mm, 5-m, Zorbax SB C18 column (Agilent). The mobile phase was prepared from 0.1% orthophosphoric acid in water of pH 2.5 (solvent-A) and acetonitrile (solvent-B). The gradient program was selected for separation. The PDA was set at 220 nm, which shows maximum response for all peaks. Statistical Analysis: Percent relative standard deviation (% RSD) and correlation coefficient (r 2 ) were calculated by standard formulas. Results: QUE, EUG, MYRS, and SAFR were satisfactorily resolved with retention time about 3, 7, 19 and 21 min. respectively. The method was validated and results obtained showed accepted values for correlation of coefficient and % RSD. Conclusions: The method was accurate and specific for analysis of nutmeg extract.
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The antioxidant activities of the ethanol extract, its benzene and chloroform fraction from seed aril of Myristica malabarica (Myristicaceae) were assessed in an effort to validate the hepatoprotective potency of this plant. The extract and the fractions showed scavenging of 1, 1-diphenyl-2picrylhydrazyl (DPPH) radical and inhibition of ABTS radical in vitro. Antioxidant activities of the extracts were also demonstrable in vivo by the inhibition of the carbon tetrachloride (CCl) -induced formation of lipid peroxides in the liver of rats by 4 pretreatment with the extracts. CCl -induced hepatotoxicity in rats, as judged by the raised serum enzymes, 4 aspartate transaminase, alanine transaminase and alkaline phosphatases was prevented by pretreatment with the extracts/fractions, demonstrating the hepatoprotective action. Among the tested extracts benzene fraction recorded highest efficiency in protecting liver damage induced by toxic effect of CCl followed by crude 4 ethanolic extract and chloroform fraction. These findings were confirmed by histopathological study of the liver sections of the treated groups.
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The present study was aimed to develop a simple and validated chromatographic method for the estimation of Trimyristin in the API and in poly herbal Ayurvedic formulations by UFLC method, along with stress induced degradation studies of the drug and validate the method as per the ICH guidelines. The analysis was carried out under isocratic conditions using dichloromethane and acetonitrile in the ratio of 95:5 as mobile phase with a flow rate of 1.0 ml/min at 210nm. The method was simple, specific, precise, and accurate with retention times 0.904 and 0.906 minutes for the API and isolated product. The system obeys the Beer's law in the concentration range of 10-90μg/ml. The percentage recovery studies performed showed a percentage recovery of 98.3 -101.6%w/v and found to be linear with a correlation coefficient (r2) of 0.9993. The method was found to be precise with relative standard deviation of less than 2%, detection limit and quantitation limit was estimated to be 4.58μg/ml, 15.27μg/ml respectively. The method was found to be robust even by change in mobile phase ratio of ±5%, change in wavelength and change in flow rate of ±0.1 ml/min. This validated method was sensitive and reproducible enough to be used for routine analysis of Poweromin tablet and Makaradhwaj vatti in time and cost effective manner.
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Jaiswal P, Kumar P, Singh VK, Singh DK. Biological Effects of Myristica fragrans. Annu Rev Biomed Sci 2009;11:21-29. Myristica fragrans is an evergreen tree that produces two spices, nutmeg and mace. Its medicinal uses in the aurvedic system of treatment are based on traditional experience inherited from one generation to other. Scientists from various disciplines are now directing their research towards investigat-ing the effects of M. fragrans on human health. The chemical constituents of M. fragrans have been investigated for hypolipidaemic and hypocholesterolemic effects, antimicrobial, antidepressant, aphrodi-siac, memory enhancing, antioxidant and hepatoprotective properties. Recent studies have revealed strong insecticidal and molluscicidal activities of M. fragrans. Despite some laboratory studies on the insecti-cidal / molluscicidal activity of M. fragrans, more field studies are recommended for effective control of pests. It is clearly evident from the literature review that M. fragrans deserves more attention by scientific community and public health specialists to explore its full range of benefits in the welfare of the society.
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Cross-sections of Myristica malabarica (Lam) seed and mouse brain tissue were imprinted on such ordinary surfaces as printer paper and TLC plates, and successfully imaged by desorption electrospray ionization mass spectrometry (DESI-MS) at 250 μm resolution. Chemical images representing the distribution of the alkaloid malabaricone C in the seed substructures and individual lipids in the substructures of the brain were obtained. Practical implications include analysis of irregular or soft materials, easy recording, transportation and storage of the latent image, and posterior analysis of the samples by different techniques without the requirement of addition of matrices or use of specific types of surfaces.
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Today, there is a tremendous demand of herbal medicine in the global market and the scarcity of data regarding the parameters and methods employed for assessing the quality of medicines. Aril (Mace) of Myristica fragrans Houtt., known as "Javetri," belonging to the Myristicaceae family, plays a foremost role in the Unani system of medicine. It contains Myristicin, an active principle of drug isolated by column chromatography, and its structure was established by spectroscopic methods. Different solvent drug extracts posses pharmacological properties like hypocholesteremic, anti-inflammatory, anti-diarrheal, chemopreventive action, etc. and hence there is a great need to determine the amount of myristicin present in the different extracts. The proposed method employed the High Performance Thin Layer Chromatography (HPTLC) DESAGA Sarstedt Gruppe and pre-coated aluminum sheets of silica gel developed with 100% chloroform to quantitatively determine the myristicin concentrations present in various extracts that are responsible for their different pharmacological actions. An attempt was made through instrumental analysis for quantitative estimations that are widely accepted for the quality assessment of herbal drugs such as TLC and HPTLC studies, etc. Physicochemical parameters, microbial load, aflatoxin and heavy metals and fluorescence studies were also carried out to lay down the standard for genuine drug. HPTLC studies were carried out in petroleum ether, chloroform, ethyl acetate, ethanol and methanol extracts and detected at 254 nm. Estimated high amount of myristicin in the petroleum ether extract w.r.t. the other extracts was confirmed by spectroscopy. The present paper describes the isolation, characterization and quantification of myristicin along with chemical standardization in order to develop standard parameters for the genuine drug.
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Atmospheric pressure chemical ionization liquid chromatography/mass spectrometry was used in the identification of diacylglycerol and triacylglycerol (TAG) molecular species in a sample of a structured lipid. In the study of acylglycerol standards, the most distinctive differences between the diacylglycerol and TAG molecules were found to be the molecular ion and the relative intensity of monoacylglycerol fragment ions. All saturated TAG ranging from tricaproin to tristearin, and unsaturated TAG including triolein, trilinolein, and trilinolenin, had ammonium adduct molecular ions [M+NH4]+. Protonated molecular ions were also produced for TAG containing unsaturated fatty acids and the intensity increased with increasing unsaturation. Diacylglycerol fragment ions were also formed for TAG. The ammonium adduct molecular ion was the base peak for TAG containing polyunsaturated fatty acids, whereas the diacylglycerol fragment ion was the base peak for TAG containing saturated and monounsaturated medium- and long-chain fatty acids; the relative intensities of the ammonium adduct molecular ions were between 14 and 58%. The most abundant ion for diacylglycerols, however, was the molecular ion [M−17]+, and the relative intensity of the monoacylglycerol fragment ion was also higher than that for TAG. These distinctive differences between the diacylglycerol and TAG spectra were utilized for rapid identification of the acylglycerols in the sample of a structured lipid.
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Acylphenols from Myristica crassa were identified based on liquid chromatography high-resolution mass spectrometry and liquid chromatography tandem mass spectrometry (MS/MS) experiments. Two types of compound were found in the extract of the plant: monomeric (malabaricone B and C) and dimeric compounds (C-C bonded biphenyl and C-C bonded phenyl-linear carbon chain). Evidence of formation of covalent dimeric ions during the electrospray ionization and matrix-assisted laser desorption ionization (MALDI) processes was established. [2M-3H](-) dimeric ions were detected on the mass spectra of each monomeric compound during high-performance liquid chromatography separation. The MS/MS spectra of those species were compared to the MS/MS spectra obtained for the dimeric compounds synthesized by the plant. Fragmentation pathways were studied for the two classes of dimer. The dimeric ions formed in the ion source were C-C bonded biphenyl compounds. Further evidence was obtained from MALDI experiments: increase in the extraction delay time leads to an increase of the dimeric ions relative abundance. Their formation is based on the high reactivity of phenols or phenolate ions which are easily oxidized yielding phenoxy radicals.
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Twenty-nine extracts of 18 medicinal plants used in New Caledonia by traditional healers to treat inflammation, fever and in cicatrizing remedies were evaluated in vitro against several parasites (Leishmania donovani, Trypanosoma brucei brucei, Trichomonas vaginalis and Caenorhabditis elegans). Among the selected plants, Scaevola balansae and Premna serratifolia L. were the most active against Leishmania donovani with IC(50) values between 5 and 10microg/ml. The almond and aril extracts from Myristica fatua had an IC(50) value of 0.5-5microg/ml against Trypanosoma brucei brucei. Only Scaevola balansae extract presented a weak activity against Trichomonas vaginalis. The almond extract from Myristica fatua presented significant activity against Caenorhabditis elegans (IC(50) value of 6.6+/-1.2microg/ml).
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The essential oil composition, total phenolic and anthocyanin, antioxidant and nutritional analysis of pericarp of Myristica beddomei ssp. ustulata have been investigated. β-caryophyllene (25.41 %) was identified to be the major constituent of pericarp essential oil. The results revealed that the methanolic extract of pericarp showed higher amount of phenols and polyphenols. The total anthocyanin content was found to be 33.064 mg/100 g. Due to the presence of higher phenolic and anthocyanin compounds, the extract produces higher scavenging ability against radicals. The pericarp was found to be a rich source of nutritional compounds and hence may be used as a functional food. Further exploration in this species, is likely to provide some leads in the direction.
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Two natural dihydrobenzofuran neolignans licarin A(1) and dihydrocarinatin(2) were systhesized from isoeugenol with Ag2O-catalyzed biomimetic oxidative coupling as the key step. Four novel dihydrobenzofuran triazolylglycoside(3–6) were achieved in good yields via Cu(I)-catalyzed azide-alkyne cycloadditions of licarin A terminal alkynes with different azide acetylated sugar and deacetylation with sodium methoxide in anhydrous methanol. The structures of all the compounds synthesized were determined by elemental analysis, MS, 1H NMR and 13C NMR. And the inhibition activity of synthesized compounds on α-glucosidase was determined by in vitro experiments. The results show that triazolyglycosides 3, 4, 5 and 6 show moderate inhibitory activity on α-glucosidase.
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Fruits of Myristica fragrans Houtt., are the source of two valuable spices: nutmeg and mace, traditionally used for its flavoring and medicinal properties and found as an ingredient in many marketed multi-herbal formulations and food products. In this study, a sensitive and efficient ultra high performance liquid chromatography electrospray ionization tandem mass spectrometry method was developed and validated for the rapid determination of 16 bioactive constituents in different parts of the fruit of M. fragrans and its marketed multi-herbal formulations using a polarity switching technique. Chromatographic separation was achieved on an Aquity UPLC BEH C18 column in 9.4 min. Quantitative analysis was performed using multiple reaction monitoring mode with continuous polarity switching in a single analysis. The developed method found to be accurate with overall recovery in the range from 95.95–102.07% (RSD ≤ 1.91%), precise (RSD ≤ 1.98%) and linear (r2 ≥ 0.9992) over the concentration range of 0.1–200 ng/mL. Quantitative analysis indicated that the total content of the 16 bioactive constituents was highest in the mace of M. fragrans. Thus, this rapid and sensitive method could be utilized as a promising reference method for the quality control of M. fragrans and its marketed herbal formulations/food products.This article is protected by copyright. All rights reserved
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Essential oils from the leaves of Myristica malabarica and Gymnacranthera canarica (Myristicaceae) were isolated by hydrodistillation and analyzed by GC/FID and GC/MS. Seventy-six constituents (98.5%) with β-caryophyllene (27.3%), α-humulene (13.8%) and α-copaene (11.5%) as major components were identifed from the leaf oil of M. malabarica. Also, seventy-six constituents (98.1%) with β-caryophyllene (23.4%), linalool (13.4%) and α-humulene (11.3%) as major constituents were identified from the leaf oil of G. canarica. Sesquiterpene hydrocarbons constituted 77.3% in M. malabarica leaf oil and 58.1% in G. canarica leaf oil.
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Methyleugenol is a substance that is possibly carcinogenic to humans, which may occur in foods containing certain herbs and spices. The European Union has set maximum levels for some product groups, but there is a lack of comprehensive market surveys for this compound. In this study, we compare two procedures for methyleugenol determination in foods, namely GC/MS, which is currently seen as gold standard for such an analytical problem, and NMR, which is hypothesized to be suitable as a faster screening. The sample preparation for GC/MS consists of homogenization in ethanol followed by liquid–liquid extraction for fat-free foods or automatic steam distillation for fat-containing foods. The extract or distillate is then measured using GC/MS either in SCAN or SIM mode (dependent on concentration) with cyclodecanone as internal standard. For 1H NMR, the ethanolic solution can be directly measured without further extraction or distillation. Quantification using external standardization is conducted for NMR. Both procedures were validated and fulfilled the requirements for quantitative food analysis. The applicability was demonstrated by analyzing 120 samples including basil, estragon, pimento, nutmeg, several teas, alcoholic beverages, and pesto. GC/MS is more sensitive, precise, and suitable for regulatory purposes but time-consuming and expensive. NMR can be used for a faster screening analysis and appears to be ideal for conducting larger surveys to estimate human exposure.
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Analyses of the essential oil of Myristica fragrans Houttuyn (nutmeg oil), from St. Catherine, Jamaica were compared with the literature data (1976-1997) for West Indian (primarily Grenadian) and East Indian nutmeg oils. GC, GC/MS and RP-HPLC strategies were used to qualitatively and quantitatively assess the Jamaican oil which was found to contain lower quantities (weight percent) of the phenylpropanoids myristicin (0.16%) and safrole (<0.2%), than the East Indian oils. Three isomers of ocimene, namely (E)-β-ocimene, (Z)-β-ocimene and (Z)-α-ocimene where identified in the Jamaican oil. These have not been reported as being present in the other oils under review. The monoterpenoids α-pinene (19.9%), β-pinene (18.8%), and terpinen-4-ol (17.8%) also showed differences in amounts, which could lead to use of these compounds as markers to distinguish between the West Indian oils.
Article
Roots of Piper regnellii (Piperaceae) contain three phenylpropanoids: apiol, dillapiol and myristicin; seven 4′,7-epoxy-8,3′-neolignans; and three 8′,9′-dinor-4′,7-epoxy-8,3′-neolignans. The structures and absolute configurations of the isolates (four new neolignans including regnelline) were established based on analysis of spectroscopic data.
Article
A new aryl alkanone 1-(2,6-dihydroxypheny1)dodecan-1-one, trimyristin, myristic acid, asarinin and horsfieldin were isolated from the methanolicextractofseedsofHorsfieldia irya. Thepetrolextract gave trimyristin and myristic acid. The isolated compounds were characterized using spectral data.
Article
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Article
Microbial Baeyer-Villiger oxidn. of representative prochiral ketones with a cyclobutanone structural motif was investigated using a collection of eight monooxygenases of different bacterial origin. This platform of enzymes is able to perform stereoselective biotransformations on an array of structurally diverse substrates. With several ketone precursors, biooxidns. yielded enantiocomplementary butyrolactones as key intermediates for the synthesis of natural products and bioactive compds. The microbial Baeyer-Villiger oxidn. allows a facile and rapid entry to several compd. classes in a desymmetrization reaction upon de novo generation of chirality. [on SciFinder(R)]
Article
Over the past few years, the applications of liquid chromatography coupled with mass spectrometry (LC-MS) in natural product analysis have been dramatically growing because of the increasingly improved separation and detection capabilities of LC-MS instruments. In particular, novel high-resolution hybrid instruments linked to ultra-high-performance LC and the hyphenations of LC-MS with other separation or analytical techniques greatly aid unequivocal identification and highly sensitive quantification of natural products at trace concentrations in complex matrices. With the aim of providing an up-to-date overview of LC-MS applications on the analysis of plant-derived compounds, papers published within the latest years (2007-2012) involving qualitative and quantitative analysis of phytochemical constituents and their metabolites are summarized in the present review. After briefly describing the general characteristics of natural products analysis, the most remarkable features of LC-MS and sample preparation techniques, the present paper mainly focuses on screening and characterization of phenols (including flavonoids), alkaloids, terpenoids, steroids, coumarins, lignans, and miscellaneous compounds in respective herbs and biological samples, as well as traditional Chinese medicine (TCM) prescriptions using tandem mass spectrometer. Chemical fingerprinting analysis using LC-MS is also described. Meanwhile, instrumental peculiarities and methodological details are accentuated.
Article
The essential oil extracted from Piper betle L. leaf using pilot plant steam distillation was tested against the adult housefly, Musca domestica, for insecticidal activity. LC50 values at the end of 24 and 48 h exposure periods were 10.3 and 8.7 mg/dm3, respectively. Ceylon citronella oil (Cymbopogon nardus) used as a standard showed LC50s of 26.5 and 24.2 mg/dm3 for the same exposure periods. Bioassay-guided fractionation of P. betle leaf oil revealed safrole and eugenol as the active principles against M. domestica, safrole showing LC50 values of 4.8 and 4.7 mg/dm3, and eugenol 7.3 and 6.2 mg/dm3 for the 24 and 48 h exposure periods, respectively, while citronellal (synthetic standard) showed equal LC50 values of 14.3 mg/dm3 for the same exposure periods. Using safrole as the starting compound, eight analogues were prepared to study structure–activity relationships. Among the eight analogues, dihydrosafrole gave almost equal mortality at LC50 4.7 mg/dm3 as that of the parent compound safrole after 24 and 48 h exposure, but isosafrole was twice as active as safrole, showing LC50 values of 2.3 and 2.2 mg/dm3 for the 24 and 48 h exposure periods. Our GC–MS studies on Sri Lankan P. betle leaf oil show that it contains safrole (52.7%), allylpyrocatechol diacetate (15.4%), eugenol (6.4%) and eugenyl acetate (5.8%) as the major components. Here we also present the GC–MS profile of fractions of Sri Lankan P. betle leaf oil. Copyright © 2006 John Wiley & Sons, Ltd.
Article
Three new compounds, prepromalabaricone B (1) and two dimeric acylphenols, giganteones A (2) and B (3) were isolated from EtOAc extract of the fruits of Myristica gigantea (Myristicaceae), together with known promalabaricone C (4), malabaricones A–C (5–7) and maingayone (8). The structures were determined by mass and 2D NMR spectral analysis, and the enzymatic synthesis of giganteones A and B was performed from malabaricone C. Both 2 and 3 possess significant cytotoxic activity in vitro against human nasopharynx KB cells.
Article
Two colorimetric assays, MTT and SRB, were compared as cytotoxicity endpoints. They were evaluated against four anti-cancer drugs and seven human tumour cell lines, results were analyzed by ANOVA. Both assays gave a linear response with respect to cell number. The cell lines exhibited differential cytotoxicity to the cancer drugs. Both assays gave similar dose/response curves with the MTT assay giving generally higher IC50 values than the SRB assay. Similar cytotoxicity profiles were obtained for each drug across the cell line panel with the two assays. Whilst both assays are suitable as cytotoxicity endpoints the SRB assay is recommended.
Article
The 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay of the ether, methanol, and aqueous extracts of the spice Myristica malabarica (rampatri) revealed the methanol extract to possess the best antioxidant activity. Column chromatography of the methanol extract led to the isolation of a new 2-acylresorcinol and four known diarylnonanoids of which the diarylnonanoid, malabaricone C, showed the maximum DPPH scavenging activity. Malabaricone C could prevent both Fe(II)- and 2,2'-azobis(2-amidinopropane)dihydrochloride-induced lipid peroxidation (LPO) of rat liver mitochondria more efficiently than curcumin. The anti-LPO activity of malabaricone C was attributed to its better radical scavenging and Fe(II) chelation capacities. The superior activity of malabaricone C was rationalized by a systematic structure-activity correlation of the results obtained with the structurally related diarylnonanoids and curcumin. Malabaricone C also prevented the gamma-ray-induced damage of pBR322 plasmid DNA in a concentration-dependent manner. The radioprotective activity was found to correlate with its (*)OH radical scavenging property, which matched well with that of d-mannitol.
Article
Four new natural neolignans and lignans, which were given the trivial names odoratisols A-D (1-4), together with (-)-licarin A, kachirachirol B, obovatifol, and machilin-I were isolated from the air-dried bark of the Vietnamese medicinal plant Machilius odoratissima NEES (Lauraceae). Their absolute structures were determined on the basis of spectroscopic analyses including circular dichroism spectra.
Article
Extracts from acacia, chestnut, cherry, mulberry, and oak wood, used in making barrels for aging wine and spirits were studied by GC/MS positive ion chemical ionization (PICI). Wood chips were extracted by a 50% water/ethanol solution and a tartrate buffer pH 3.2-12% ethanol (model wine) solution. The principal compounds identified in extracts were guaiacol-containing aldehydes and alcohols, such as benzaldehyde and derivatives, vanillin and syringaldehyde, cinnamaldehyde and coniferaldehyde, eugenol and methoxyeugenol, guaiacol and methoxyguaiacol derivatives. PICI using methane as reagent gas produced a high yield of the protonated molecular ion of volatile phenols, compound identification was confirmed by collision-induced-dissociation (CID) experiments on [M + H](+) species. MS/MS fragmentation patterns were studied with standard compounds: guaiacol-containing molecules were characterized by neutral methyl and methanol losses, benzaldehyde derivatives by CO loss. Acacia wood extracts contained significant syringaldehyde and anisaldehyde, but no eugenol and methoxyeugenol. Significant syringaldehyde, eugenol and methoxyeugenol, and high vanillin were found in chestnut and oak wood extracts; low presence of volatile benzene compounds was found in mulberry wood extracts. Cherry wood extracts were characterized by the presence of several benzaldehyde derivatives and high trimethoxyphenol.
Article
A versatile route to the synthesis of 2,5-diaryl-3,4-dimethyltetrahydrofuran lignans, (-)-odoratisol C (1), (-)-futokadsurin A (2), (-)-veraguensin (3), (+)-fragransin A2 (4), (+)-galbelgin (5), and (+)-talaumidin (6), is described. Central to the synthesis of the lignans is BF(3) x OEt(2)-promoted deoxygenation/epimerization of the hemiketal 9a followed by stereoselective reduction of the oxocarbenium ion intermediates 8a,b.
Simultaneous determination of eugenol, isoeugenol, myristicin and elemicin in Myristica fragrans Houtt. by GC
  • X S Zhao
  • L B Huang
  • H J Yang
  • S L Ou
  • J D Feng
Zhao, X. S., Huang, L. B., Yang, H. J., Ou, S. L., & Feng, J. D. (2012). Simultaneous determination of eugenol, isoeugenol, myristicin and elemicin in Myristica fragrans Houtt. by GC. Chinese Journal of Pharmaceutical Analysis, 32, 1569-1573.
16 (d, J = 7.1), 3.82 (s), 3
  • Giang
Licarin B 5.83 (s), 5.16 (d, J = 7.1), 3.82 (s), 3.40 (m), 1.41 (d, J = 5.5) 100.9, 92.4, 55.6, 41.2, 18.5 S2, P1 Giang et al. (2006)