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A lignan and pyrone and other constituents from Hyptis capitata

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Abstract

Investigation of the aerial parts of the medicinal plant Hyptis capitata led to the isolation of two new compounds: 2,3-di(3′,4′-methylenedioxybenzyl)-2-buten-4-olide, a lignan with a γ-butenolide structure and 10-epi-olguine, a 5,6-dihydro-α-pyrone. The structure of 10-epi-olguine was determined using X-ray diffraction. Also isolated were stigmasterol, 5-hydroxy-4′,7-dimethoxyflavone (apigenin-4′,7-dimethyl ether), oleanolic, ursolic and rosmarinic acids. The crude extracts prepared with petrol, dichloromethane and methanol showed no pronounced fungicidal or insecticidal eitects. The plant contains no alkaloids.

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... yielded two new triterpene acids, named hyptatic acids A (90) and B (91), along with the known ones 2α-hydroxyursolic acid (86), maslinic acid (87) and tormentic acid (92) . Other study led to the isolation of oleanolic acid (75), ursolic acid (78) and stigmasterol (93) from the same species (Almtorp et al., 1991;Kashiwada et al., 1998;Lee et al., 1988). From Hyptis brevipes Poit., three triterpenes, ursolic acid (78), sitosterol-β-D-glucoside (80) and maslinic acid (87) were obtained (Deng et al., 2009) (93), 3β-hydroxy-28-methyl-ursulate (94) and stigmasterol-β-D-glucoside (95) (da Costa et al., 2008). ...
... The bioguided fractionation of the aerial parts of Hyptis rhomboidea M. Martens & Galeotti allowed the identification of seven new lignans named hyprhombin A -E (135 -139), epihyprhombin B (140) and hyprhombin B methyl ester (141) (Tsai and Lee, 2014). In another study, the aerial parts from Hyptis capitata afforded the lignan 2,3-di(3 ′ , 4 ′ -methylenedioxybenzyl)-2-buten-4-olide (142) (Almtorp et al., 1991). The roots of Mesosphaerum suaveolens (syn. ...
... The compound 10-epi-olguine (170) was isolated from the aerial parts of Hyptis capitata. This compound is structurally similar to hypurticin (167) that presents an acetoxy group linked to the lactone pyran ring (Almtorp et al., 1991). Later, a series of chemical studies carried out with Hyptis brevipes led to the identification of fifteen new α-pyrones named brevipolides A -F (171-176) (Deng et al., 2009), G -J (177-180) (Suárez-Ortiz et al., 2013) and K -O (181-185) (Suárez-Ortiz et al., 2017). ...
Article
Ethnopharmacological relevance The subtribe Hyptidinae contains approximately 400 accepted species distributed in 19 genera (Hyptis, Eriope, Condea, Cantinoa, Mesosphaerum, Cyanocephalus, Hypenia, Hyptidendron, Oocephalus, Medusantha, Gymneia, Marsypianthes, Leptohyptis, Martianthus, Asterohyptis, Eplingiella, Physominthe, Eriopidion and Rhaphiodon). This is the Lamiaceae clade with the largest number of species in Brazil and high rates of endemism. Some species have been used in different parts of the world mainly as insecticides/pest repellents, wound healing and pain-relief agents, as well as for the treatment of respiratory and gastrointestinal disorders. Aim of the review This review aims to discuss the current status concerning the taxonomy, ethnobotanical uses, phytochemistry and biological properties of species which compose the subtribe Hyptidinae. Materials and methods The available information was collected from scientific databases (ScienceDirect, Pubmed, Web of Science, Scopus, Google Scholar, ChemSpider, SciFinder ACS Publications, Wiley Online Library), as well as other literature sources (e.g. books, theses). Results The phytochemical investigations of plants of this subtribe have led to the identification of almost 300 chemical constituents of different classes such as diterpenes, triterpenes, lignans, α-pyrones, flavonoids, phenolic acids and monoterpenes and sesquiterpenes, as components of essential oils. Extracts, essential oils and isolated compounds showed a series of biological activities such as insecticide/repellent, antimicrobial and antinociceptive, justifying some of the popular uses of the plants. In addition, a very relevant fact is that several species produce podophyllotoxin and related lignans. Conclusion Several species of Hyptidinae are used in folk medicine for treating many diseases but only a small fraction of the species has been explored and most of the traditional uses have not been validated by current investigations. In addition, the species of the subtribe appears to be very promising, as alternative sources of podophyllotoxin-like lignans which are the lead compounds for the semi-synthesis of teniposide and etoposide, important antineoplastic agents. Thus, there is a wide-open door for future studies, both to support the popular uses of the plants and to find new biologically active compounds in this large number of species not yet explored.
... Hyptis is the largest genus of the neotropical sub-tribe Hyptidinae [(Lamiaceae) tribe Ocimeae] with over 300 species (Raymond and Harley, 1988). Many of its reported species are known for their medicinal use as indigenous drugs (Kuhnt et al., 1994;Almtorp et al., 1991;Raja Rao et al., 1990), however a literature survey revealed that phytochemical analysis of plants belonging to this genus has been limited to a few species. Previous chemical reports include the isolation of a range of triterpenes ( Lee et al., 1988;Yamagishi et al., 1998;Almtorp et al., 1991;Deng et al., 2009;Pereda-Miranda and Delgado, 1990;Pereda-Miranda and Gascon-Figueroa, 1988;Mukherjee et al., 1984), flavonoids ( Almtorp et al., 1991;Deng et al., 2009;Takahiko et al., 2006;Lin et al., 1993;Romo de Vivar et al., 1991;Pereda-Miranda and Delgado, 1990;Messana et al., 1990) lignans (Indane and Chaturvedi, 2007), lactones (Romo de Vivar et al., 1991;Pereda-Miranda and Delgado, 1990;Deng et al., 2009;Fragoso-Serrano et al., 1999;Boalino et al., 2003) and diterpenes, especially of the labdane and abietane-type ( Bakir et al., 2006;Lin et al., 1993;Chukwujekwu et al., 2005;Araujo et al., 2004Araujo et al., , 2005Araujo et al., , 2006Porter Roy et al., 2009;Urones et al., 1998). ...
... Many of its reported species are known for their medicinal use as indigenous drugs (Kuhnt et al., 1994;Almtorp et al., 1991;Raja Rao et al., 1990), however a literature survey revealed that phytochemical analysis of plants belonging to this genus has been limited to a few species. Previous chemical reports include the isolation of a range of triterpenes ( Lee et al., 1988;Yamagishi et al., 1998;Almtorp et al., 1991;Deng et al., 2009;Pereda-Miranda and Delgado, 1990;Pereda-Miranda and Gascon-Figueroa, 1988;Mukherjee et al., 1984), flavonoids ( Almtorp et al., 1991;Deng et al., 2009;Takahiko et al., 2006;Lin et al., 1993;Romo de Vivar et al., 1991;Pereda-Miranda and Delgado, 1990;Messana et al., 1990) lignans (Indane and Chaturvedi, 2007), lactones (Romo de Vivar et al., 1991;Pereda-Miranda and Delgado, 1990;Deng et al., 2009;Fragoso-Serrano et al., 1999;Boalino et al., 2003) and diterpenes, especially of the labdane and abietane-type ( Bakir et al., 2006;Lin et al., 1993;Chukwujekwu et al., 2005;Araujo et al., 2004Araujo et al., , 2005Araujo et al., , 2006Porter Roy et al., 2009;Urones et al., 1998). H. carvalhoi is a subshrub growing to 1 m high, endemic to Bahia that grows in the cerrado region of Central Brazil, and no phytochemical investigation on this species has so far been reported. ...
... Many of its reported species are known for their medicinal use as indigenous drugs (Kuhnt et al., 1994;Almtorp et al., 1991;Raja Rao et al., 1990), however a literature survey revealed that phytochemical analysis of plants belonging to this genus has been limited to a few species. Previous chemical reports include the isolation of a range of triterpenes ( Lee et al., 1988;Yamagishi et al., 1998;Almtorp et al., 1991;Deng et al., 2009;Pereda-Miranda and Delgado, 1990;Pereda-Miranda and Gascon-Figueroa, 1988;Mukherjee et al., 1984), flavonoids ( Almtorp et al., 1991;Deng et al., 2009;Takahiko et al., 2006;Lin et al., 1993;Romo de Vivar et al., 1991;Pereda-Miranda and Delgado, 1990;Messana et al., 1990) lignans (Indane and Chaturvedi, 2007), lactones (Romo de Vivar et al., 1991;Pereda-Miranda and Delgado, 1990;Deng et al., 2009;Fragoso-Serrano et al., 1999;Boalino et al., 2003) and diterpenes, especially of the labdane and abietane-type ( Bakir et al., 2006;Lin et al., 1993;Chukwujekwu et al., 2005;Araujo et al., 2004Araujo et al., , 2005Araujo et al., , 2006Porter Roy et al., 2009;Urones et al., 1998). H. carvalhoi is a subshrub growing to 1 m high, endemic to Bahia that grows in the cerrado region of Central Brazil, and no phytochemical investigation on this species has so far been reported. ...
Article
Highlights ► We presented the phytochemical studie of Hyptis carvalhoi. ► Abietane diterpenes were isolated and charactherized from the leaves. ► We suggested abietane diterpenes as chemomarkers of the Lamiaceae.
... Hyptis spp. have shown spasmolytic effect, such as Hyptis capitata, which is used in folk medicine for asthma treatment (Almtorp et al., 1991) and Hyptis suaveolens that is used to treat dysmenorrhoea (Agra et al., 2007). ...
... In folk medicine, some species of Hyptis (e.g. H. capitata) (Almtorp et al., 1991) as well as H. macrostachys Benth., were used for asthma treatment (Agra et al., 2008). A possible activity of HM-EtOH PA on guinea pig trachea contracted by CCh in both functional epithelium absence and presence were evaluated. ...
... Until now, hydroxy-7,49-dimethoxy flavone was not described to occur in any of the Eucalyptus species, although it is reported in leaves of other plants [24][25][26][27][28]. Mabry et al. [24] confirmed its occurrence in rosemary and presented its APCI mass spectrum as well as the HPLC retention time on an RP18 phase. ...
... Hyun et al. [28] described its occurrence in leaves of Biota orientalis. The spectral data (UV, 1 H NMR, IR and EI-MS) cited in the literature [24][25][26][27][28] are in good agreement with our findings which supports our assignment. ...
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Leaves from Eucalvptus camaldulensis var. brevirostris trees, planted in the Nile delta in Egypt, were examined for the antioxidant activity of their nonvolatile compounds. The extracts obtained by ethanol digestion and by supercritical fluid extraction (SFE; CO2 with 15% ethanol) showed the most promising antioxidative activities. In order to identify the most active compounds, both extracts were subjected to a semipreparative reversed-phase HPLC separation, the main fractions were collected, tested for antioxidative activity and analysed by different chromatographical and spectroscopical methods for identification of the most relevant compounds. Gallic and ellagic acid were found to be the prevailing antioxidants in the ethanolic extract. The main two compounds of the SFE extract with antioxidative activity revealed to be flavones. To a high degree of probability they were identified as 5-hydroxy-7,4'-dimethoxy flavone and 5-hydroxy-7,4'-dimethoxy-8-methyl flavone, respectively. The extracts obtained by ethanoldigestion were dried and administered to rats for toxicity evaluation (up to 3 g/kg body weight). No mortality was observed which indicates a very low lethality of the tested extract.
... This genus has different species that have therapeutic potential such as antifungal (Rocha et al., 2019), antinociceptive, anti-inflammatory (Anjos et al., 2017;Figueiredo et al., 2019), antiedematogenic (Barbosa et al., 2017), antibacterial (Andrade et al., 2017), among others. In addition, several Hyptis species have shown spasmolytic and antidiarrheal effects, such as H. fruticosa, H. pectinata, H. martiusii (Agra et al., 2008), H. suavelons (Agra et al., 2008;Attah et al., 2012;Shaikat et al., 2012), H. capitata (Almtorp et al., 1991), and H. macrostachys (Souza et al., 2013;Costa et al., 2014). ...
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Leptohyptis macrostachys, previously known as Hyptis macrostachys Benth., is used in folk medicine to relieve the symptoms of asthma, cough, and bronchitis. Recently, we showed that the ethanol extract obtained from Leptohyptis macrostachys has selective spasmolytic activity on guinea pig ileum. Therefore, the aim of this study was to characterize the spasmolytic mechanism of this extract, investigated whether it presents toxicological and antidiarrheal activities. Therefore, the crude ethanolic extract of Leptohyptis macrostachys was analyzed by high-performance liquid chromatographic-diode array detection (HPLC–DAD). The spasmolytic effect was evaluated on guinea pig ileum, toxicological activity using rats and antidiarrheal activity using male and female mice. In HPLC-DAD analysis, Rosmarinic acid (5.44%) was the most abundant phenolic compound, being considered as a chemical marker. The spasmolytic potency of the extract on histamine-induced contraction was reduced in the presence of 1 mM TEA+, a selective big–conductance K+ channels blocker (BKCa). The extract produces a dose–dependent antidiarrheal activity, inhibiting equipotently defecation frequency and liquid stool formation. In addition, the extract has inhibited in a dose–dependent manner both castor oil–induced intestinal transit and intestinal fluid content. Thus, the spasmolytic activity of the extract involves positive modulation of BKCa and its antidiarrheal activity is related to inhibition of intestinal motility and secretion.
... PENDAHULUAN Hyptis capitata Jacq. atau yang dikenal di daerah Palolo, Sulawesi Tengah dengan nama baka-baka merupakan tumbuhan herba daerah tropis dari famili Lamiaceae yang telah dimanfaatkan secara luas sebagai tumbuhan obat, misalnya oleh masyarakat Taiwan (Almtorp et al., 1991), Cina (Xu et al., 2013) ...
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Hyptis capitata Jacq. plant has been using for traditional medicine. Utilization of medicinal plant must always consider to given dose because of toxic effect when too much medicine is taken. The aim of this study was to measure the liver damage in rats caused by H. capitata Jacq. leave extract. Either 300 (P1), 600 (P2) or 900 (P3) µg/kgBW H. capitata Jacq. leave extract was given orally to rats every 24 hours during 14 days. Zero point five ml ethanol 96% was given daily (K-) and without given anything (K+) was also conducted as a control. Both macroscopic and microscopic of liver damage were assessed. The result showed that rats given P3 treatment had the highest liver damage. The liver damage in rats was not statistically significant difference between P3 and K-treatments. The lowest liver damage was in rats given K+ treatment. There was no significant difference between P1 and P2 treatments on rats liver damage. Utilization of medicinal plant as traditional medicine should always be consider to doses. ABSTRAK Tumbuhan Hyptis capitata Jacq. telah lama digunakan sebagai obat tradisional. Pemanfaatan tumbuhan obat harus tetap memperhatikan dosis karena bila melebihi akan menimbulkan efek toksik. Tujuan dari penelitian ini adalah untuk mengetahui kerusakan hati pada tikus karena diberi ekstrak daun H. capitata. Penelitian dilakukan dengan memberikan 300 (P1), 600 (P2) atau 900 (P3) µg/kgBB ekstrak daun H. capitata Jacq. setiap hari secara oral kepada tikus selama 14 hari dengan durasi pemberian 24 jam. Pemberian 0,5 ml etanol 96% perhari (K-) dan tanpa pemberian perlakuan (K+) juga dilakukan sebagai pembanding. Parameter penilaian adalah kerusakan hati secara makroskopik dan mikroskopik. Hasil penelitian menunjukkan bahwa kerusakan sel hati tertinggi diperoleh pada tikus yang diberi perlakuan P3 yang nilainya tidak berbeda nyata dengan kerusakan hati tikus yang diberi perlakuan K-. Kerusakan sel hati terendah terdapat pada tikus yang diberi perlakuan K+. Tidak ada perbedaan yang nyata antara kerusakan hati tikus yang disebabkan perlakuan P1 dan P2. Penggunaan tumbuhan obat sebagai obat tradisional sebaiknya tetap memperhatikan dosisnya.
... From the chemical point of view, the genus Hyptis shows a wide variety of chemical constituents, including flavonoids (Abedini et al. 2013), monoterpenes (Abedini et al. 2013;Tafurt-García et al. 2014), diterpenes (Urones et al. 1998;Alvarez et al. 2015), triterpenes (Lee et al. 1988;Kashiwada et al. 1998;Deng et al. 2009), brevipolides (Suárez-Ortiz et al. 2017, lactones (Almtorp et al. 1991), and steroids (Costa et al. 2014;Tang et al. 2014). Hyptis is commonly used in the treatment of gastrointestinal infections, skin infections, pain, headache, cramps, stomach discomfort, menstrual pain, treatment of flu/fever (Rocha et al. 2009;McNeil et al. 2011), for antiulcer and anti-inflammatory problems (de Jesus et al. 2009), as antiparasitic and insect repellent (Cudd et al. 2014;Limachi et al. 2019), in the treatment of snakebites and scorpion stings (da . ...
Article
Hyptis Jacq. (Lamiaceae) has been used in traditional medicine for the treatment of many diseases around the world. However, Harley and Pastore in 2012 proposed a new circumscription for this large genus, reducing its number of species, but supporting its monophyly. Hyptis and Peltodon were used as keywords, and triage of articles was performed using genus delimitation sensu Harley and Pastore. Only 29 species have some type of record in the literature for their medicinal use and chemical description, corresponding to 20% of the 148 species. Most cited biological activities were the antioxidant activity, reported for 9% of the species, and the antifungal activity reported for 5% of the species. For 11% of the species was described the essential oil composition, while non-volatile compounds were reported for only 6% of them. Terpenes, flavonoids, and caffeic acid derivatives are the most reported compounds for this genus. Only 8% of the species are reported as medicinal, with potential as antibacterial and antiparasitic, pointing to relevance of Hyptis to bioprospecting studies, especially in South America and Africa. However, there is a lack of studies regarding isolated compounds concerning their toxicology and efficacy, important information to achieve the production and the effective use of Hyptis as a herbal medicine.
... After successive chromatographic procedures on the acetone extract from A. orbicularis roots, 32 compounds were isolated, of which six (compounds 1−6) have not been reported previously. The 26 known compounds were identified as (4S,8R)-p-menth-1-en-9-ol, 8 caryophyllene β-oxide, 9 madoline R, 10 3β-acetyl-Δ 7 -sitosterol, 11,12 syringic acid, 13 squalene, 3,5-dimethoxysalicilic acid, β-amyrin, 14 α-caryophyllenol, 15 transtriacontyl-4-hydroxy-3-methoxycinnamate, 16 β-sitosterol, 17 stigmasterol, 17 2-(4-hydroxyphenyl)-1-nitroethane, 18,19 ferulic acid, 20 the lignans savinin, 21 hinokinin, and pluviatolide, previously isolated from Aristolochia constricta, 22 dehydrohinokinin, 23 an inseparable diastereomeric mixture of 7′S-parabenzlactone and 7′R-parabenzlactone, 24 an inseparable diastereomeric mixture of 8R,8′R,9S-cubebin and 8R,8′R,9R-cubebin, also previously isolated from A. lagesiana and A. pubescens, 25 6αhydroxy-β-eudesmol (β-chenopodiol), 26 4(15)-eudesmene-1β,6α-diol, 27 ursolic acid, 28 and the aristolochic acid derivatives aristololactam AII, 29 aristololactam BI (taliscanine), 30 and aristololactam BIII. 31 The structures of all these compounds were identified based on a comparison of their physical and spectroscopic data with literature values. ...
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Six new compounds, aristoloxazine A (1), aristoloxazine B (2), 7-methoxytaliscanine (3), humul-7-en-1,4,11-triol (4), 8-hydroxy-β-logipinene (5), and 1β-hydroxy-4(14)-eudesmene (6), corresponding to two sulfur-containing aristoloxazines (1 and 2), an aristolactam (3), and three sesquiterpenes (4-6) were isolated, along with 26 known compounds, from the roots of Aristolochia orbicularis. The structures of the new compounds were established based on their spectroscopic and spectrometric data and in the case of aristoloxazine A (1) by single-crystal X-ray crystallography. This is the first report of sulfur-containing aristoloxazines from a natural source. Furthermore, aristoloxazine A (1) was found to possess potent in vitro antimicrobial activity against all resistant Staphylococcus aureus and several fungal strains in which it was evaluated.
... Hyptis capitata aerial part [193] guayadequiene [194] *Basic structures (BS) of DBLs marked with A-Q are shown in Fig. (3); **Chirality was not determined; ***DBLs contain an additional hydroxyl at position C2; #For the occurrence of DBLs in the Linum genus see [195]; ##The occurrence of DBLs in the Centaurea genus has been reviewed: [68,196,197,198]. Only those Centaurea species are listed in the Table which were not involved in these papers.; ...
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Objective: Dibenzylbutyrolactone lignans represent a unique group of plant secondary metabolites with increasing significance in medicine. This review summarizes their structural characteristics and classification, as well as the biosynthesis starting in the chloroplast, and their supposed biological activity associated with plant defense mechanisms are also discussed. Over 85 natural dibenzylbutyrolactone lignans known to date and their corresponding plant sources are summarized herein for the first time, highlighting a taxon- and organ-specific accumulation of these compounds. Conclusion: The isolation strategies, applied analytical methods and pharmacological activities of dibenzylbutyrolactone lignans are also thoroughly reviewed.
... The majority of Hyptis experimental studies involved testing the essential oil and these species were reported to have activities such as insecticidal, fungicidal, anti-HIV and antiplasmodial, although there are Hyptis species for which these effects were not confirmed by these experiments (Almtorp et al., 1991;Antoun et al., 1999;Bourdy et al., 2004). This factor could be due to genotype and the environmental condition that plays a very important role in the type and quantity of compounds found in the plant essential oil (Pino et al., 2002;Martins et al., 2006;Koba et al., 2007;Ngassoum et al., 2007;Sales et al., 2007;Silva et al., 2007;Grassi et al., 2008). ...
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The chemical profile and medicinal effects of H. crenata on two mouse models were evaluated in order to quantify pharmacological effects caused by bioactive compounds. A survey was conducted regarding traditional preparation and use of H. crenata in Brazil (20 regular users). The extraction methods reported were: (i) decoction (boiling in water); (ii) infusion (tea); (iii) cold extraction (water); (iv) cold extraction (15% alcohol); and (v) cold extraction (40% alcohol). The decoction extract (i) showed the highest concentration of dry matter (4.55 g/L). The traditional uses most frequently reported were for forms of mild pain (11/20 - headache, stomach discomfort, menstrual pain) or treatment of flu/fever (6/20). Based on this traditional use, a study was conducted on the antinociceptive effects of the decoction extract (i) in 8 C57/BL6 mice per treatment. Orally administered doses of 15 and 150 mg/kg b.w. were compared with water and Indomethacin 10 mg/kg b.w in models of phasic pain (Hargreaves test) and tonic pain (acetic acid-induced writhing). In both models the treatment effects were significantly different from the water control treatment, but not from the positive control Indomethacin. HPLC analysis of the decoction extract compared with an authentic standard of salicylic acid showed that salicylic acid was not detectable in the extract.
... Interest in carrying out this work was based on the biological activity of Hyptis species employed in popular medicine, such as H. suaveolens, H. capitata and H. fruticosa (Agra et al., 2008;Almtorp et al., 1991), which are utilized for respiratory diseases treatment, and also the species H. pectinata and H. macrostachy Benth., which possess activity in the respiratory system (Mukherjee et al., 1984). The use of Hyptis species in the treatment of gastrointestinal disorders has been reported for the species H. suaveolens, H. martiusii, H. umbrosa and H. verticillata (Agra et al., 2008;Mukherjee et al., 1984;Rojas et al., 1992). ...
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A new alpha-pyrone was isolated from aerial parts of Hyptis macrostachys Benth. Its structure was determined as 6R-[( 5'S, 6'S-diacetoxy)-1'Z,3'E-heptenyl]-5,6-dihydro-2H-pyran-2-one, named hyptenolide based on a combination of 1D and 2D NMR techniques and CD data. Hyptenolide inhibited the contractions induced by CCh ( IC50 = 1.7 +/- 0.3 x 10 (4) M) or histamine ( IC50 = 0.9 +/- 0.05 x 10 (4) M) in guinea pig ileum, demonstrating for the first time a pharmacological activity for the pyrone. Crown Copyright
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Hyptis capitata is one of the important traditional medicinal plants, in which different parts of the plant are used in various countries in treating several diseases. This review was conducted to present a comprehensive overview of distribution, taxonomic characters, ethnobotany and the various pharmacological properties of H. capitata This review presents scientific information about pharmacological potentials of H. capitata as a medicinal ingredient and its opportunities to be developed and utilized more broadly. The literature review was carried out on both abstracts and full articles, further analyzed and included in this review. H. capitata is used to treat various diseases such as fever, digestive disorders and open wounds. The pharmacological study of H. capitata showed that this plant has the potential to be developed as an antioxidant, antibacterial, antiviral and anticancer. Due to being widely used by the community, further studies regarding the pharmacological potential and the safety parameters of H. capitata are needed.
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Objective: To study the chemical constituents of Acanthopanax senticosus. Methods: A. senticosus was extracted with 75% EtOH and separated with petroleum ether and EtOAc, successively. The EtOAc-soluble fraction was isolated by column chromatography and RP-preparative HPLC. Their structures were identified by spectroscopic method (MS, 1H-NMR, and 13C-NMR). Results: Nineteen compounds were isolated from the EtOAc fraction of A. senticosus and identified as quercetin (1), quercitrin (2), kaempferol (3), hyperoside (4), rutin (5), acacetin (6), daidzin (7), 3'-methoxydaidzin (8), puerarin (9), 3'-methoxypuerarin (10), 4'-methoxypuerarin (11), syringaldehyde (12), syringic acid (13), glucosyringic acid (14), isofraxidin (15), 2, 3-di(3', 4'-methyl-endioxy-benzyl)-2-buten-4-olide (16), l-sesamin (17), methylpluviatolide (18), and 4'-hydroxy-2'-methoxycinnamaldehyde (19). Conclusion: Compounds 6-11, 14, 16, 18, and 19 are isolated from the plants in Acanthopanax (Deche et Planch.) Miq. for the first time.
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Chemical investigations by chromatography and CC-MS analyses of the root and stem extracts of Zanthoxylum lemairie resulted in the detection and isolation of nine aliphatic and aromatic amides, four alkaloids, five coumarins and ten lignans. The structure of some constituents were confirmed by synthesis and in particular the lignan structures were elucidated by extensive spectroscopic methods. The isolation of a carbazole alkaloid and the accumulation of a large number of lignans by Z. lemairie is of chemotaxonomic and biogenetic significance. This is the first report of glycozoline, piperlonguminine and six lignans in the genus Zanthoxylum.
Article
The essential oils from leaves and inflorescences of Hyptis martiusii Benth were analyzed by GC-MS. Twenty-six compounds representing 93.2% of the essential oil of leaves were characterized; Delta-3-carene (22.5%),1,8-cineole (24.27%), beta-caryophyllene (6.15%), and bicyclogermacrene (6.32%) were found as the major components. In the essential oil of inflorescences 27 compounds representing 87.7% of the oil were identified. The major components were Delta-3-carene (13.5%), alpha-pinene (5.78%), beta-caryophyllene (6.59%), viridiflorene (8.25%), and germacrene B (5.21%). The essential oil of leaves and 1,8-cineole showed pronounced insecticidal effect against Aedes aegypti larvae and Bemisia argentifolii, the vectors of dengue fever and white fly fruit plague, respectively.
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In this paper we analysis the relation between of ownership structure and performance of the city commercial banks in China. In the analysis method and chooses data, we attention the comparability to the existing research literature. It is found that the higher the proportion of government shareholding and the proportion of the largest shareholder proportion, the poorer performance of the city commercial bank is, which is consistent to the existing majority literature search conclusion. We also found that foreign capital shareholding will reduce non-performing loans ratio of city commercial bank, but the proportion of shareholding did not have remarkable influence to the performance. Therefore, the city commercial bank do not have to introduce foreign strategic investors, may also introduce the high quality domestic strategic investor. In the end, The size of banks and ROE has a positive relationship, but the size of banks and non-performing loans ratio has a negative relationship, this indicates that under the existing environment, the city commercial bank should expand their own assets scale, and reduce the non-performing loan rate simultaneously.
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Three pyrones and a 2(5H)-furanone, designated pectinolides D–G, have been isolated from the dichloromethane extract of Hyptis pectinata. The metabolites were characterized on the basis of 1D and 2D NMR spectroscopic techniques. The pyrones were identified as 6S-[3S,6S-(diacetoxy)-5R-hydroxy-1Z-heptenyl]-5S-hydroxy-5,6-dihydro-2H-pyran-2-one (1)- pectinolide D, 6S-[3S,5R,6S-(triacetoxy)-1Z-heptenyl]-5S-acetoxy-5,6-dihydro-2H-pyran-2-one (2)- pectinolide E and 6S-[3S,5R,6S-(triacetoxy)-1Z-heptenyl]-5S-acetoxy-4R-methoxy-3,4,5,6-tetrahydro-4H pyran-2-one (3)- pectinolide F. The furanone was identified as [2′Z,5(1′)Z] 5-(4′S,6′R,7′S-triacetoxy-2-octenylidene)-2(5H)-furanone (4)-pectinolide G.
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The species Hyptis fasciculata Benth. is a shrub that is still unknown by the chemical point of view. This species has been studied in our group using their aerial parts. After many cromatographic processes over silica gel column, it was possible to isolate free triterpene (betulinic acid) and triterpenes in mixture (ursolic acid with betulinic acid and ursolic acid with oleanolic acid), one steroid mixture (sitosterol and stigmasterol) and a mixture of steroid with cafeic acid (stigmasterol and cafeic acid) and with lignan (sitosterol and sesamin). These compounds were identified by nuclear magnetic ressonance 1H and 13C.
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Three new abietane diterpenes 19-oxo-inuroyleanol, 11,14-dihydroxy-12-methoxy-7-oxo-8,11,13-abietatrien-19,20 b-olide and 19,20-epoxy-12-methoxy-11,14,19-trihydroxy-7-oxo-8,11,13 -abietatriene, in addition to inuroyleanol, and coulterone were isolated from roots of Hyptis platanifolia. Investigation of the aerial parts yielded a mixture of the steroids stigmasterol and b-sitosterol, and the triterpenes betulinic and ursolic acids. Structural characterization of all compounds was established on the basis of spectroscopic methods, particularly 1D and 2D NMR, and comparison with data from literature.
Article
An efficient regioselective synthesis of pyronyl pendant ethyl methylthiocarbonylalkanoates 5 has been delineated from the base catalyzed reaction of suitably functionalized 2-pyranone 1 and 2-carbethoxycycloalkanones 2, 6 through successive substitution and regioselective ring opening by in situ generated mercaptide ion. To assess the effect of C-4 substituent on regioselectivity, reactions of 6-aryl-3-cyano-4-(piperidin-1-yl)-2-oxopyran 8 with 2-carbethoxycyclohexanone 6a and 2-carbethoxy-2-methylcyclohexanone 6b were carried out separately under analogous reaction conditions but the compounds isolated were identical and characterized as 4-aryl-8-methyl-2-piperidin-1-yl-5,6,7,8-tetrahydronaphthalene-1-carbonitriles 9. Ethyl 2-(5-amino-4′-bromo-4,6-dicyanobiphenyl-3-yl)-5-methylsulfanylcarbonylpentanoate 10 has also been prepared through base catalyzed ring transformation of ethyl 2-[6-(4-bromophenyl)-3-cyano-2-oxo-2H-pyran-4-yl]-5-methylsulfanylcarbonylpentanoate 5d by malononitrile in DMF.
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A number of 3-acylamino-6-polyfluoroalkyl-2H-pyran-2-ones 3 were synthesized from beta-alkoxyvinyl polyfluoroalkyl ketones 1 and N-acylglycines 2 in acetic anhydride in high yield. The reactions of trifluoromethyl-containing 2H-pyran-2-one 3b with O- and N-nucleophiles were studied and 3-N-benzoylamino-6-hydroxy-6-trifluoromethyl-5,6-dihydro-2H-pyran-2-one (13) 3-N-benzoylamino-6-hydroxy-6-trifluoromethyl-5,6-dihydro-2H-pyridin-2-one (14a), and N- and O-substituted 3-(N-benzoylamino)-6-trifluoromethyl-2H-pyridin-2-ones (15c,e, and 16) were synthesized.
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Cultivation of the fungal strain Annulohypoxylon ilanense, an endophytic fungus isolated from the wood of medicinal plant Cinnamomum species, resulted in the isolation of one new furanoid derivative, ilanefuranone (1), one new pyrrole alkaloid, ilanepyrrolal (2), and one new biarylpropanoid derivative, ilanenoid (3), together with 22 known compounds, of which one α-tetralone analog, (-)-(4R)-3,4-dihydro-4,6-dihydroxynaphthalen-1(2H)-one (4) was isolated for the first time from a natural source. The structures were elucidated on the basis of physicochemical evidence, in-depth NMR spectroscopic analysis, and high-resolution mass spectrometry, and the antimycobacterial activities were also evaluated.
Article
A short, versatile and stereospecific synthesis of two lignans 1 and 2, was achieved in 40% overall yield. Our strategy was based in the use of amino acids as chiral and readily available starting materials. Stereocontroled transformation of amino acids to chiral organic phosphonates gave the key intermediate of the synthetic sequence. A Homer-Wadsworth-Emmons (HWE) reaction followed by selective reduction and stereospecific hydrogenation in the last step resulted in the title compounds with the desired absolute stereochemistry.
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Bioactivity-directed fractionation of the crude extract prepared from the medicinal Mexican plant Hyptis spicigera (Lamiaceae) tested on KB cells led to the isolation of spicigerolide (1). The structure for this novel cytotoxic compound was elucidated as 6R-[3S,4S,5S,6S-tetraacetyloxy-1Z-heptenyl]-5,6-dihydro-2H-pyran-2-one. The relative stereochemistry of this flexible molecule was determined by a combination of molecular mechanics calculations and 1H–1H coupling constant data, while the absolute configuration was established according to CD measurements. The MM/3JH–H calculations, as applied to 1, was validated with model linear compounds prepared from l-rhamnose: 2,3,4,5-tetra-O-acetyl-6-deoxy-l-mannose (5) and tetra-O-acetyl-1,6-dideoxy-l-mannitol (8). Both compounds possess the same stereochemistry predicted to be present in the acyclic moiety of spicigerolide (1) but lacking the stereochemical influence of the chiral pyrone.
Article
Phytochemical investigation of the aerial parts of Eriope blanchetii and E. latifolia (Lamiaceae) yielded podophyllotoxin, as well as the aryltetralin lignans α- and β-peltatin and yatein. Oleanolic, ursolic and epikatonic acids were also isolated. This is the first occurrence of podophyllotoxin in the family.
Article
A dihydrobenzo[c]phenanthridine alkaloid, epizanthocadinanine A (1), together with 27 known compounds, including eight benzo[c]phenanthridines, i.e., oxynitidine (2), oxyavicine (3), oxychelerythrine (4), dihydrochelerythrine (5), 6-acetonyldihydrochelerythrine (6), norchelerythrine (7), decarine (8), and arnottianamide (9); two 2-quinolones, i.e., flindersine (10) and 4-methoxy-1-methyl-2-quinolone (11); two furoquinolines, i.e., skimmianine (12) and gamma-fagarine (13); three aporphines, i.e., liriodenine (14), N-acetyldehydroanonaine (15), and N-acetylanonaine (16); six lignans, i.e., sesamin (17), episesamin (18), piperitol-3,3-dimethylallyl ether (19), xanthoxylol-3,3-dimethylallyl ether (20), savinin (21), and 2,3-bis(3,4-methylenedioxybenzyl)but-2-en-4-olide (22); three terpenoids, i.e., alpha-cadinol (23), anticopalol (24), and spathulenol (25); one coumarin, i.e., aesculetin dimethyl ether (26); and two steroids, i.e., beta-sitosterol (27) and beta-sitostenone (28) were isolated from the stem bark of Zanthoxylum nitidum. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR as well as MS analyses. Moreover, the recently reported structures 2'-4' of rhoifolines B and A, and '8-methoxynorchelerythrine', resp., isolated as new compounds from Z. rhoifolium and Z. nitidum, resp., could be assigned the revised structures 2-4 by reinvestigation of the spectroscopic data. In addition, the cytotoxicity of the isolates was evaluated on the MCF-7, NCI-H460, and SF-268 cell lines. Among these isolates, liriodenine (14) was the most active compound against the MCF-7, NCI-H460, and SF-268 cell lines with IC(50) values of 2.19, 2.38, and 3.19 microg/ml, resp.
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As most anticancer drugs are derived from natural sources, the screening of local medicinal flora should be considered a primary step in the search for new sources for antineoplastic agents. In Mexico, more than 6000 medicinal plant species are used for the treatment of various diseases, including cancer. A multifactorial plant selection method, employing various criteria was designed and applied in order to select alternative sources of podophyllotoxin lignan analogues. For each criterion (chemotaxonomy, traditional medical uses and published scientific data), an arbitrary score system was ascribed to the species and the sum of these enabled us to compare potential candidates. The resulting selected plants were tested for cytotoxic activity and the compounds responsible for this activity were evaluated by liquid chromatography-mass spectroscopy (LC-MS). Around 50 species from the Mexican flora were initially considered. From these, six species were selected by referring to the results from the scoring system and these were then collected. Three extracts were evaluated as being highly cytotoxic against three different cancer cell lines. Finally, podophyllotoxin-like lignans could be identified by observing the fragmentation pattern on mass spectra, obtained from the LC-MS in two species: Linum scabrellum and Hyptis suaveolens.
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The essential oils from leaves and inflorescences of Hyptis martiusii Benth were analyzed by GC-MS. Twenty-six compounds representing 93.2% of the essential oil of leaves were characterized; Delta-3-carene (22.5%), 1,8-cineole (24.27%), beta-caryophyllene (6.15%), and bicyclogermacrene (6.32%) were found as the major components. In the essential oil of inflorescences 27 compounds representing 87.7% of the oil were identified. The major components were Delta-3-carene (13.5%), alpha-pinene (5.78%), beta-caryophyllene (6.59%), viridiflorene (8.25%), and germacrene B (5.21%). The essential oil of leaves and 1,8-cineole showed pronounced insecticidal effect against Aedes aegypti larvae and Bemisia argentifolii, the vectors of dengue fever and white fly fruit plague, respectively.
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The structure (including absolute stereochemistry) of anamarine, a new unsaturated lactone isolated from an unclassified species, has been established.
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The structure (including absolute stereochemistry) of olguine, an unsaturated lactone isolated from an unclassified species, has been established by spectroscopic and X-ray analysis.
Article
Three new lignans, 2β-hydroxy-2α-3′,4′-dimethoxybenzyl-3α-3″,4″-methylenedioxybenzyl-γ-butyrolactone, 2β-acetyl-2α-3′,4′-dimethoxybenzyl-3α-3″,4″-methylenedioxybenzyl-γ-butyrolactone and 3′,4′-dimethoxybenzyl-3-3″,4″-methylenedioxybenzyl-2,3-dehydro-γ-butyrolactone, were isolated from the leaves of Bupleurum salicifolium. Three other lignans were identified as 2β-3′,4′-dimethoxybenzyl-3α-3″,4″-methylene-dioxybenzyl-γ-butyrolactone, 2β,3α-bis(3′,4′-dimethoxybenzyl)-γ-butyrolactone and 1-3′,4′-dimethoxyphenyl-2,3-naphthalide-γ-butyrolactone. The triterpene betulin was also obtained.
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The bitter principle hyptolide, C18.H24O8, is an unsaturated lactone (II).
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The absolute stereochemistry of 4-deacetoxy-10-epi-olguine, a six-membered α,β-unsaturated C12-lactone isolated from Hyptis oblongifolia, has been established as 6R-[5R,6S-(diacetyloxy)-1R,2S-(epoxy)-3E-heptenyl]-5,6-dihydro-2H-pyran-2-one. The structural elucidation of three new bioactive α-pyrones, minor constituents of the aerial parts of this species, has been performed. Their structures were elucidated as 6R-[5R,6S-(diacetyloxy)-1R-(hydroxy)-2R-(methoxy)-3E-heptenyl]-5,6-dihydro-2H-pyran-2-one, 6R-[5R,6S-(diacetyloxy)-1S,2R-(dihydroxy)-3E-heptenyl]-5,6-dihydro-2H-pyran-2-one and its corresponding diacetylated product, 6R-[1R,2R,5R,6S-(tetracetyloxy)-3E-heptenyl]-5,6-dihydro-2H-pyran-2-one, based on spectral, chiroptical and chemical evidence. Five known triterpenoids were also identified: ursolic, maslinic, 2α-hydroxyursolic, pomolic and 2α,3α-dihydroxy oleanolic acids.
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Bioassay-directed fractionation of the cytotoxic antileukemic extracts of Prunella vulgaris, Psychotria serpens, and Hyptis capitata has led to the isolation of ursolic acid as one of the active principles. Ursolic acid showed significant cytotoxicity in the lymphocytic leukemia cells P-388 and L-1210 as well as the human lung carcinoma cell A-549. It also demonstrated marginal cytotoxicity in the KB and the human colon (HCT-8) and mammary (MCF-7) tumor cells. Esterification of the hydroxyl group at C-3 and the carboxyl group at C-17 led to compounds with decreased cytotoxicity in the human tumor cell lines, but with equivalent or slightly increased activity against the growth of L-1210 and P-388 leukemic cells.
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Der Petrolätherextrakt der Blätter von Rosmarin enthält 5-Hydroxy-7,4′-dimethoxyflavon (Genkwanin-4′-methyläther).
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Bioassay-directed fractionation of a methanolic extract of Hyptis capitata has led to the isolation and characterization of five triterpene acids which include the new hyptatic acids -A and -B in addition to the known 2α-hydroxyursolic acid, tormentic acid and maslinic acid. Spectral data in conjunction with X-ray analysis of the methanol solvate of hyptatic acid-A established the structures of these compounds. Hyptatic acid-A and 2α-hydroxyursolic acid demonstrated significant in vitro cytotoxicity in human colon HCT-8 tumour cells.
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Seven caffeic acid derivatives were tested for their activity against two plant-pathogenic fungi and seven plantpathogenic bacteria. A determination of minimum inhibitory concentration (MIC) in solid media was used for the fungi, and for the bacteria agar diffusion, as well as determintion of the MIC in liquid media, were used. A distinct concentration related activity was seen for most of the compounds. The molar activity of the caffeoyl esters against the bacteria was similar to that of tartaric acid, higher than that of phenol, but much lower than that of streptomycin. For most host plants, their ‘own’ compounds were less active against their pathogens than foreign ones. Of the tested compounds, ferulic acid, caffeic acid, esculine, esculetin and orobanchoside were the most active against the two fungi, and similarly, ferulic acid and esculetin were the most active against the bacteria.
Article
Rosmarinic acid (RA) is a naturally occurring compound, isolated from Rosmarinus officinalis or Melissa officinalis which inhibits the in vitro immunohaemolysis of antibody-coated sheep erythrocytes by guinea pig serum. In further experiments this reduced immunohaemolysis was found to be due to inhibition of the C3-convertase of the classical complement pathway. The threshold concentration for inhibition of C3-convertase was 10(-6) mol/l. RA with an optimal inhibitory concentration between 5 and 10 mumol/l., resulting in about 70% inhibition of haemolysis. However, higher concentrations of RA were less effective at inhibiting C3-convertase. The inhibition may not be specific for C3-convertase, since another serine protease, elastase, was also weakly inhibited by RA in vitro. RA also exhibited inhibitory activity in three in vivo models in which complement activation plays a role. Thus, RA (0.316-3.16 mg/kg i.m.) reduced paw oedema induced by cobra venom factor (CVF) in the rat, and at 1-100 mg/kg p.o. inhibited passive cutaneous anaphylaxis in the rat. In addition, at 10 mg/kg i.m. RA impaired in vivo activation by heat-killed Corynebacterium parvum (i.p.) of mouse macrophages, as measured by the decreased capacity of the activated macrophages to undergo the oxidative burst. RA (0.1-10 mg/kg i.m.) did not inhibit t-butyl hydroperoxide-induced paw oedema in the rat, indicating selectivity for complement-dependent processes.