Article

Chemistry, bioactivity and quality control of Dendrobium, a commonly used tonic herb in traditional Chinese medicine

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  • Jiangsu Province Academy of Traditional Chinese Medicine and Jiangsu Branch of China Academy of Chinese Medical Sciences, Najing, China
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Abstract

The fresh or dried stems of many Dendrobium species are well known as one of the most expensive tonics in traditional Chinese medicine. Documented as a “superior grade” herbal medicine in the ancient text “Shen Nong’s Herbal Classic”, Dendrobium has been used for thousands of years and is now a popular health food worldwide. The main chemical components of Dendrobium are alkaloids, aromatic compounds, sesquiterpenoids and polysaccharides, with multiple biological activities, including immunomodulatory, neuroprotective and anti-tumor effects, etc. Various qualitative and quantitative methods have been developed for the quality evaluation of Dendrobium. In this review, the research progress since the 1930s relating to the chemistry, bioactivity and quality control of Dendrobium is summarized, existing problems and prospects are also discussed.

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... In light of traditional importance as a medicinal plant, knowledge on the constituents of various Dendrobium species and their pharmacological activities has been growing, and methodologies have been developed for effective propagation [5,6]. Indeed, a large number of pharmacological activities have been assigned to different Dendrobium species, such as anti-inflammatory, antiplatelet aggregation, hepatoprotective, anti-fibrotic, antiviral, antifungal, antimicrobial, antioxidant, antidiabetic, neuroprotective, immunomodulatory, and anticancer [7,8]. ...
... As the Dendrobium species have been used in traditional medicines [2,6], their misidentification and adulteration led to a loss of therapeutic potency and potential intoxication [5]. For decades, fast-developing molecular techniques using DNA fingerprinting, DNA sequencing, and DNA microarray have been applied extensively to authenticate medicinal materials, including various Dendrobium species [5]. ...
... The biological activities and pharmacological actions of all the isolated compounds were investigated [23]. More than 100 compounds from 42 Dendrobium species including 32 alkaloids, 6 coumarins, 30 bibenzyls, 4 fluorenones, 22 phenanthrenes, and 7 sesquiterpenoids have been identified and discussed [6,8,18,24,25]. The active anticancer bibenzyls, 3,4,3 0 -trimethoxy-5,4 0 -dihydroxybibenzyl (1), 3,4-dihydroxy-3 0 ,4 0 -dimethoxybibenzyl (2), 4-(3-hydroxy-4-methoxyphenethyl)-2,6dimethoxylphenol (3), 4,4 0 -dihydroxy-3,5-dimethoxybibenzyl (4), 4,5,4-0 -trihydroxy-3,3 0 -dimethoxybibenzyl (5), 5,3 0 -dihydroxy-3,4-dimethoxy-bibenzyl (6), aloifoll (7), chrysotoxine (8), dendrocandin B (9), dendrocandin I (10), dendrocandin U (11), dendrofalconerol A (12), dendrosignatol (13), dengraols A and B (14) and (15), denofficin (16), erianin (17), fimbriadimerbibenzyl A, B, E, F, and G (18)(19)(20)(21)(22), gigantol (23), longicornuol A (24), moscatilin (25), and tristin (26) (Fig. 2); phenanthrenes, chrysotoxol B (27), confusarin (28), cypripedin (29), denbinobin (30), epheranthol B (31), lusianthrindin (32), moniliformediquinone (33), and moscatin (34) (Fig. 3); and fluorenones, 1,4,5-trihydroxy-7-methoxy-9Hfluoren-9-one (35) and dendroflorin (36) (Fig. 4), have been isolated from different Dendrobium species. ...
Chapter
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Dendrobium represents one of the most important genera of the Orchidaceae family, having medicinal and ornamental value. Dendrobium species have been traditionally used as first-rate medicinal herbs in the treatment of a variety of disorders, such as nourishing the stomach and enhancing the production of body fluids. Many species of this genus are the sources of tonic for astringent, analgesic, anti-pyretic, antioxidant, antimicrobial, antidiabetic, anticancer, anti-inflammatory, anti-metastasis, and antiangiogenesis because they have alkaloids, aromatic compounds, sesquiterpenoids, and polysaccharides as main components. This chapter includes the active constituents, extract and pure isolate, from 23 Dendrobium species and their effect in the anticancer, anti-metastasis, and antiangiogenesis.
... Previous reviews on Dendrobium species have provided a comprehensive overview on their chemical components and bioactivities including anti-cancer, anti-diabetic, antiinflammatory, and neuroprotective effects, without a particular focus on the mechanism of action and active compounds related to diabetes (29)(30)(31). Phytochemicals such as polysaccharides, bibenzyls, and alkaloids have been used in the quality standards of dendrobium monographs although they are used as marker compounds, rather than active compounds. Focused review on the mechanism and active compounds of dendrobiums related to diabetes is still lacking. ...
... The substituents of bibenzyls often take place at the para and/or meta-positions on the benzene ring while the C7 and C8 atoms are rarely substituted. Common substituents include hydroxyl and methoxy but mono-substitution of bibenzyls has not been identified (29). Three main bibenzyl compounds erianin, moscatilin and gigantol are similar in structure but can be differentiated by the positions of methoxy and hydroxyl groups on the phenyl rings. ...
... In contrast to bibenzyls, dendrobine was the first alkaloid identified from D. nobile (50). So far, fourteen alkaloids have been isolated from D. nobile, which are the largest number of alkaloids among Dendrobium species (29). ...
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Background Medicinal dendrobiums are used popularly in traditional Chinese medicine for the treatment of diabetes, while their active compounds and mechanism remain unclear. This review aimed to evaluate the mechanism and active compounds of medicinal dendrobiums in diabetes management through a systematic approach. Methods A systematic approach was conducted to search for the mechanism and active phytochemicals in Dendrobium responsible for anti-diabetic actions using databases PubMed, Embase, and SciFinder. Results Current literature indicates polysaccharides, bibenzyls, phenanthrene, and alkaloids are commonly isolated in Dendrobium genusin which polysaccharides and bibenzyls are most aboundant. Many animal studies have shown that polysaccharides from the species of Dendrobium provide with antidiabetic effects by lowering glucose level and reversing chronic inflammation of T2DM taken orally at 200 mg/kg. Dendrobium polysaccharides protect pancreatic β-cell dysfunction and insulin resistance in liver. Dendrobium polysaccharides up-regulate the abundance of short-chain fatty acid to stimulate GLP-1 secretion through gut microbiota. Bibenzyls also have great potency to inhibit the progression of the chronic inflammation in cellular studies. Conclusion Polysaccharides and bibenzyls are the major active compounds in medicinal dendrobiums for diabetic management through the mechanisms of lowering glucose level and reversing chronic inflammation of T2DM by modulating pancreatic β-cell dysfunction and insulin resistance in liver as a result from gut microbita regulation.
... It was observed that leaf followed by stem and roots methanolic extract having higher scavenging activity that of aqueous leaf extract (table 3). It was found to be that at the concentration of lC 50 6.52 µg mL -1 the methanolic leaf extract possesses the highly significantly (P>0.001; table3) DPPH scavenging activity leaf 8.42 µg mL -1 (84%) and stem IC 50 11.38 µg mL -1 (72.3%). ...
... It was found to be that at the concentration of lC 50 6.52 µg mL -1 the methanolic leaf extract possesses the highly significantly (P>0.001; table3) DPPH scavenging activity leaf 8.42 µg mL -1 (84%) and stem IC 50 11.38 µg mL -1 (72.3%). However, root methanolic extracts registered lesser scavenging activity IC 50 16.57 ...
... table3) DPPH scavenging activity leaf 8.42 µg mL -1 (84%) and stem IC 50 11.38 µg mL -1 (72.3%). However, root methanolic extracts registered lesser scavenging activity IC 50 16.57 µg mL -1 , but its exhibited DPPH activity between 25.3 to 57.0%. ...
Article
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Vanda spathulata is known to be collected from the wild and used in horticulture and Ayurvedic medicine. V. spathulata are thought to have healing properties in treating asthma, depression and some memory enhancing antioxidant and anticancer property. To date, reports on phytochemical analyses were most available on endangered and medicinal orchids. The present study was conducted to determine the total phenolics, total flavonoids, and antioxidant activity of five different extracts prepared from leaves, stem and roots. Among the three plant parts Methanolic Leaf extract contained the highest total phenolics content with a value of 1.52 and total phenols 0.32 mg g-1 which is proved because of bioactive compounds identified by GC-MS. The compound from methanolic extract of leaf has 78 compounds are 5 Hydroxy methyl furfural n-Hexadecanoic acid 4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl 3’5’ Dimethoxyacetophenone Dichloroacetic acid, tridec-2-ynyl ester Hexadecanoic acid, 2-hydroxy-1-(hydroxy methyl) ethyl ester ,12-Octadecadienoic acid (Z,Z) which has the antioxidant property, root methanolic extract the compound l-(+)-Ascorbic acid 2,6-dihexadecanoate used for synthesis of cancer compound. The aqueous extract of leaf, root and stem has 15 compounds were identified. There are four unknown which is not yet identified the compounds are aqueous root 1,1-Dibromo-2-Hexylcyclopropanev. 3-Cyclopentylpropionic acid from Stem aqueous extract, 3-chloroprop-2-enyl ester, 4-Bromo-4-Methyl-5-Oxo-Tetrahydro-Furan-2-Carboxylic Acid. Z,Z-3,13-Octadecedien-1-ol in aqueous leaf. A wide range of fatty acids, heterocyclic compound which are having anti-fungal, anti-inflammatory, antibiotic activity, skin conditioning property were identified so that it can be recommended as a plant of phytopharmaceutical importance. Key Words: Phytochemical analysis, GC-MS analysis, V. spathulata, Antioxidant activity.
... Then, differential markers compounds were screened by T-test; differential marker compounds can be identified when p < 0.01 and fold change (FC) ≥ 2 or FC ≤ 0.5. Combined with the database comparison and reports in the literature [4,[28][29][30], it was confirmed that there were 15 differential markers in the Through the analysis of loading plot and volcano plot, the 3645 and 2344 peaks detected were screened for differential compounds. Then, differential markers compounds were screened by T-test; differential marker compounds can be identified when p < 0.01 and fold change (FC) ≥ 2 or FC ≤ 0.5. ...
... Then, differential markers compounds were screened by T-test; differential marker compounds can be identified when p < 0.01 and fold change (FC) ≥ 2 or FC ≤ 0.5. Combined with the database comparison and reports in the literature [4,[28][29][30], it was confirmed that there were 15 differential markers in the positive ion mode and 17 in the negative ion mode, as shown in Table 1. In the heatmap (Figure 8), the blue part indicates that the relative content of metabolites is low, and the red part indicates that the relative content is high. ...
Article
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In this study, in order to protect the characteristic Dendrobium devonianum Paxt industry in the Longling area, and promote the healthy development of its characteristic Chinese herbal medicines in Yunnan Province, China, the identification of Dendrobium devonianum Paxt and Dendrobium officinale Kimura et Migo from Longling county was discussed using time of flight mass spectrometry. The data of 13 Dendrobium devonianum and 7 Dendrobium officinale in the Longling area were collected by TOF MS-IDA-15 MS/MS mode, and the collected data were analyzed by PCA and T-test using MarkerView software, and the difference markers were searched using the database to confirm their compound structures. In positive and negative ion modes, 3645 and 2344 peaks were detected, respectively; 64 positive ion compounds and 60 negative ion compounds, for a total of 124 compounds were identified, mainly including organic acids, polyphenols, alkaloids, amino acids and their derivatives, benzene and its derivatives, and other compounds. The score plot and loading plot analyzed by PCA show that Dendrobium devonianum and Dendrobium officinale collected in the Longling area can be effectively identified and differentiated by high-resolution mass spectrometry with the 15 different markers in positive ion mode and 17 markers in negative ion mode, respectively. The successful identification of Dendrobium devonianum and Dendrobium officinale fully demonstrates that TOF MS can be effectively used in the identification of Dendrobium and related Chinese herbal medicines with broadly application foreground.
... Takamiya et al. (2014) recorded odorproducing cells in all species of Section Densiflora and the majority of the Section Dendrobium, thus hypothesizing that this character has probably been acquired after the divergence between the Asian and the Australasian Superclades [4]. Despite the great number of studies aimed at optimizing in vitro propagation protocols (i.e., Marting and Madassery, 2006; Teixera da Silva et al., 2015;Calevo et al. 2020; and references therein) [12][13][14], and at characterizing anatomical and chemical traits (Carlsward et al., 1997;Xu et al., 2013;Devadas et al., 2016 and references therein) [15][16][17], the genus Dendrobium has been little investigated from the point of view of the reproductive biology, and even less is known about floral volatilome [18]. To the best of our knowledge, only a few authors had carried out characterizations of floral volatiles from Dendrobium species. ...
... Takamiya et al. (2014) recorded odorproducing cells in all species of Section Densiflora and the majority of the Section Dendrobium, thus hypothesizing that this character has probably been acquired after the divergence between the Asian and the Australasian Superclades [4]. Despite the great number of studies aimed at optimizing in vitro propagation protocols (i.e., Marting and Madassery, 2006; Teixera da Silva et al., 2015;Calevo et al. 2020; and references therein) [12][13][14], and at characterizing anatomical and chemical traits (Carlsward et al., 1997;Xu et al., 2013;Devadas et al., 2016 and references therein) [15][16][17], the genus Dendrobium has been little investigated from the point of view of the reproductive biology, and even less is known about floral volatilome [18]. To the best of our knowledge, only a few authors had carried out characterizations of floral volatiles from Dendrobium species. ...
Article
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A detailed chemical composition of Dendrobium essential oil has been only reported for a few main species. This article is the first to evaluate the essential oil composition, obtained by steam distillation, of five Indian Dendrobium species: Dendrobium chrysotoxum Lindl., Dendrobium har-veyanum Rchb.f., and Dendrobium wardianum R.Warner (section Dendrobium), Dendrobium amabile (Lour.) O’Brien, and Dendrobium chrysanthum Wall. ex Lindl. (section Densiflora). We investigate fresh flower essential oil obtained by steam distillation, by GC/FID and GC/MS. Several com-pounds are identified, with a peculiar distribution in the species: Saturated hydrocarbons (range 2.19–80.20%), organic acids (range 0.45–46.80%), esters (range 1.03–49.33%), and alcohols (range 0.12–22.81%). Organic acids are detected in higher concentrations in D. chrysantum, D. wardianum, and D. harveyanum (46.80%, 26.89%, and 7.84%, respectively). This class is represented by palmitic acid (13.52%, 5.76, and 7.52%) linoleic acid (D. wardianum 17.54%), and (Z)-11-hexadecenoic acid (D. chrysantum 29.22%). Esters are detected especially in species from section Dendrobium, with ethyl linolenate, methyl linoleate, ethyl oleate, and ethyl palmitate as the most abundant compounds. Alcohols are present in higher concentrations in D. chrysantum (2.4-di-tert-butylphenol, 22.81%), D. chrysotoxum (1-octanol, and 2-phenylethanol, 2.80% and 2.36%), and D. wardianum (2-phenylethanol, 4.65%). Coumarin (95.59%) is the dominant compound in D. amabile (section Densiflora) and detected in lower concentrations (range 0.19–0.54%) in other samples. These volatile compounds may represent a particular feature of these plant species, playing a critical role in in-teracting with pollinators.
... The genus Dendrobium contains approximately 1100 species, which is one of the largest genera in the family Orchidacea, and mainly distributed in southwestern Asia, Europe and Australia, such as China, Thailand, Myanmar and Vietnam (Yu et al., 2015). In traditional medicine, several Dendrobium species are used for various diseases or as beverages (Cakova et al., 2017;Xu et al., 2013). Among them, the stems of D. nobile is the most dominant sources of Shihu, a famous traditional Chinese medicine (Chinese Pharmacopoeia Commission, 2020) and used as a tonic to nourish Yin, clear heat, nourish stomach, and replenish body fluid (Cakova et al., 2017;Shin et al., 2017;Xu et al., 2017). ...
... In term of pharmacological effects, D. nobile exhibits effects of regulating lipid metabolism, antioxidant activity, protecting the nervous system, anti-immune activity, antifibrosis, antitumor, and others. Previous phytochemical investigations on D. nobile indicated that diversified compounds, including sesquiterpene glycosides, alkaloids, bibenzyls, plysaccharides and phenanthrenes have been isolated from this plant (Lam et al., 2015;Thanh et al., 2017;Wang et al., 2019;Xu et al., 2013;Xu et al., 2017). Among them, protecting the nervous system, regulating lipid metabolism has been closely related to alkaloids Lv et al., 2020). ...
... The plant has been listed as threatened and endangered in the Convention on International Trade in Endangered Species of Wild Fauna and Flora (Jin et al. 2016). Dendrobium huoshanense harbors a variety of characteristic compounds (polysaccharides, terpenoids, stilbenoids, alkaloids, flavonoids, etc.) with functions in oxidation resistance, immunity, liver protection, and tumor suppression (Xu et al. 2013;Zha et al. 2014;Xie et al. 2016). ...
... Furthermore, we 1A). These findings are consistent with previous experimental studies indicating the importance of polysaccharides in D. huoshanense (Xu et al. 2013;Zha et al. 2014). ...
Article
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Dendrobium huoshanense is used to treat various diseases in traditional Chinese medicine. Recent studies have identified active components. However, the lack of genomic data limits research on the biosynthesis and application of these therapeutic ingredients. To address this issue, we generated the first chromosome-level genome assembly and annotation of D. huoshanense. We integrated PacBio sequencing data, Illumina paired-end sequencing data, and Hi-C sequencing data to assemble a 1.285 Gb genome, with contig and scaffold N50 lengths of 598 kb and 71.79 Mb, respectively. We annotated 21,070 protein-coding genes and 0.96 Gb transposable elements, constituting 74.92% of the whole assembly. In addition, we identified 252 genes responsible for polysac-charide biosynthesis by Kyoto Encyclopedia of Genes and Genomes functional annotation. Our data provide a basis for further functional studies, particularly those focused on genes related to glycan biosynthesis and metabolism, and have implications for both conservation and medicine.
... Sesquiterpenoids are reported in Dendrobium nobile, the type of terpenes that consist of three isoprene units (Wang et al., 2016). The biosynthesis of sesquiterpenoids takes place from a 15-carbon atom compound called farnesyl pyrophosphate (FPP), which is formed from the reaction between isopentenyl pyrophosphate and geranyl pyrophosphate (Xu et al., 2013) (Fig. 2). Another class of alkaloids that are found in D. crepidatum and D. polyanthum is indolizidine alkaloids; structurally characterized by six and five membered ring which is fused to form a planar structure (Wang et al., 2016). ...
Article
Orchidaceae has been considered as the second largest family among the angiosperms. It is commercially important in the cut-flower industry and many of its members also possess medicinal properties to cure innumerable ailments. Among them, Anoectochilus and Dendrobium are the prime genera of medicinally important orchids. A greater number of such orchid species are commercially being used as major sources of main-stream pharmaceutical products. In nature, the population of medicinal orchids is at risk, mainly due to deforestation. In orchid propagation, the conventional methods suffer from several shortcomings such as slow growth, poor germination, susceptibility to pests, and nutritional deficiencies. Therefore, interventions of biotechnological tools and techniques become quite crucial for the improvements in the propagation process and simultaneously, the production of secondary metabolites. In this context, knowledge of biosynthetic pathways of the key secondary metabolites from different medicinal orchid species becomes imperative in order to enhance their production via in vitro biotechnological approaches. This review addresses the availability of secondary metabolites in medicinal orchids, their biosynthetic pathways, pharmacological applications and it is further entwined with the success and shortcomings of the in vitro strategies that have been applied to medicinal orchids in order to enhance their propagation, conservation and secondary metabolites production. Eventually, this in vitro biotechnology-based review will provide a promising platform to construct innovative ideas to harness the commercial production of pharmaceutically important secondary metabolites available in medicinal orchids.
... Dendrobium nobile Lindl., Orchidaceae, is a herbal plant commonly used in Chinese traditional medicine, and it is one of the several Dendrobium species that were specified in the Chinese Pharmacopeia. 1,2 Previous research has shown that Dendrobium has pharmacological activities such as regulating immunity, regulating blood sugar and blood lipids, anticoagulation, and anti-tumor. 3 Many compounds have been extracted and isolated from the Dendrobium species, including alkaloids, 4,5 polysaccharides, 6,7 phenanthrenes, 8 phenolics, 9,10 and bibenzyls. ...
Article
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The quality of Dendrobium nobile Lindl. is related to its endophytic fungi. It has been reported that the mycorrhizal fungus MF23 helps to increase the content of dendrobine in Dendrobium, but few studies have explained the mechanism underlying this phenomenon. In a previous study, we verified the mechanism of symbiosis between MF23 and D. nobile on agar medium. The research carried out in this study on bark medium, similar to the natural environment, is of great importance because of its benefits for wide application. We found a significant effect, especially in the later period of cultivation, in which the highest dendrobine content in the experimental group was 0.147%, which is equivalent to 2.88 times that of the control group, and suggesting that MF23 promoted D. nobile in the natural environment, which verifies the application of the technique in field conditions. This result also implied that post-modification enzyme genes might play an important role in stimulating the biosynthesis of dendrobine.
... The active constituents in Dendrobium are polysaccharides, alkaloids, flavonoids, amino acids, bibenzyls, and several trace elements (He et al., 2020). The polysaccharides from Dendrobium exhibit immunomodulatory and hepatoprotective activities; and the alkaloids are antioxidant, anticancer, and neuroprotective, while other compounds display anti-angiogenesis, anticytotoxicity, and anti-mutagenesis effects (Ng et al., 2012;Xu et al., 2013). Alkaloids are the earliest identified category of compounds in Dendrobium (Chen and Chen, 1935). ...
Article
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Dendrobium is a genus of flowering plants belonging to the Orchidaceae family with more than 1,400 species. Many Dendrobium species have been used as medicinal plants in several Asian countries for thousands of years. Alkaloids were reported as the major biological markers due to their complex chemical compositions and various types. In this review, we summarized the structural types of alkaloids, their pharmacological activities, as well as the mechanisms of biological activities. More than sixty alkaloids were isolated and identified from the Dendrobium genus. Moreover, the pharmacological effects of Dendrobium alkaloids as hepatic lipid and gluconeogenesis regulation, as neuroprotection, and as anti-tumor, anti-inflammatory, anti-diabetes, and anti-virus factors were described. Besides, the total chemical synthesis of dendrobine is provided, while the biosynthetic pathway of dendrobine has been proposed based on the functions of associated genes. For applications of these invaluable herbs, more researches on the extraction of biological markers from compounds are needed. Further confirmation of the proposed biosynthetic pathways is anticipated as well.
... For the convenience of next analysis, the format of files of near spectra of samples were converted '.sp' to '.spc' in OMNIC 9.77 overtone of C-H deformation modes. In polysaccharides, cellulose, alkaloids, and aromatic compounds, they were abundant in C@O, CAOAC, CAH, and NAH bonds [41,42]. The two broad peaks at 5200 to 7000 cm À1 , mainly 5777.69 and 6807.49 ...
Article
Dendrobium Sw., as a traditional herb and function food with over 1500 years of history, shows a significant effect in improving immunity and fatigue resistance. However, due of course the large number of species and the quality fluctuating in different species, a fast and effective discrimination method was in need. Recently, spectroscopic techniques combined with chemometrics have become an effective method for low-cost and fast analysis in food and herb. Nevertheless, chemometrics method which based on one-dimensional spectral dataset still encounter the difficulty that can not effectively extract useful information from the spectra. Different from one-dimensional spectra, the two-dimensional correlation spectroscopy (2DCOS) can reveal more details information of the spectral dataset. Moreover, the appearance of convolutional neural network makes the application of deep learning in image recognition faster and more accurate. In this study, a novel method 2DCOS combined with residual convolutional neural network (ResNet) was used to discriminate the 10 species of Dendrobium. Five feature bands were selected based on spectrum standard deviation (SDD) method in NIR and MIR spectra. Moreover, the models based on full band, total five feature bands, and their fusion-bands had been compared. The results showed that three feature bands 1800-450 cm⁻¹ and 2400-1900 cm⁻¹ displayed 100% accuracy in both training set and test set. And also, the accurate discrimination of 10% external validation showed that these models have good generalization ability. In conclusion, 2DCOS combined with ResNet could be an effective and accurate method for classify different Dendrobium species.
... Previous phytochemical investigations on "Shihu" showed that alkaloids, bibenzyls, phenanthrenes, phenolic acids, and sesquiterpenoids, were the main secondary metabolites. Dendrobium species have the activities of antioxidant, anti-tumor, anti-angiogenesis, anti-inflammatory, anti-aggregation, etc [2][3][4][5][6]. In our continuing endeavor to discover new structures from Dendrobium species [7][8][9][10][11], two new bibenzyl compounds 3-hydroxy-4, 5, 3′-trimethoxybibenzyl (1) and (R)-4-hydroxy-3, 5, 3′, αtetramethoxybibenzyl (2) (Figure 1), along with twelve known compounds were isolated from the stems of Dendrobium hercoglossum Reichb. ...
... In traditional Chinese medicine, Dendrobium nobile Lindl has been used as a medicinal herb to treat a variety of disorders, such as nourishing the stomach, enhancing body fluid production, or replenishing vital essence. A systems pharmacology approach has shown that the active ingredients of Dendrobium nobile Lindl, including alkaloids, glycosides phenanthrenes and bibenzils, have several pharmacological effects, including tonic, astringent, analgesic, anti-pyretic, and anti-inflammatory actions (Xu et al., 2013). ...
Article
At present, treatments for Alzheimer's disease can temporarily relieve symptoms but cannot prevent the decline of cognitive ability and other neurodegenerative changes. Dendrobium nobile Lindl alkaloid is the main active component of Dendrobium nobile Lindl. Dendrobium nobile Lindl alkaloid has been shown to resist aging, prolong life span, and exhibit immunomodulatory effects in animals. This review summarizes the mechanisms behind the neuroprotective effects reported in Alzheimer's disease animal models. The neuroprotective effects of Dendrobium nobile Lindl alkaloid have not been studied in patients. The mechanisms by which Dendrobium nobile Lindl alkaloid has been reported to improve cognitive dysfunction in Alzheimer's disease animal models may be associated with extracellular amyloid plaque production, regulation of tau protein hyperphosphorylation, inhibition of neuroinflammation and neuronal apoptosis, activation of autophagy, and enhanced synaptic connections.
... Dendrobiums are also applied in Indian Ayurveda medicine with D. alpestre as a source of "Jewanti" and D. teretifolium, D. macraei, D. densiflorum, D. fimbriatum, and D. discolor in the management of dysentery, pain, pimples, skin eruption, liver upset, nervous debility, asthma, bronchitis, throat trouble, and fever and is used as an aphrodisiac [33][34][35][36][37][38][39][40][41]. Many Dendrobiums have rich contents of phytochemical compounds such as gigantol, moscatilin, dendrobinae, mucilage, dendrobine, denbinobine, dendroside derivatives, nobilin D, nobilin E and nobilone in D. nobile [31,42,43]; dendromoniliside derivatives, moniliformin, 4-and diabetes and in the treatment of cataracts and fever [1,61]. The grounded pseudobulbs are made into a paste with some water used to treat fractured and dislocated bones [52,62]. ...
... Dendrobium catenatum is a valuable traditional Chinese medical herb, of which alkaloids, amino acids, polysaccharides and phenols are the main active ingredients Xu et al., 2013). It mainly functions on gastro-protective, anti-tumor, hypoglycemic, hepatoprotective, immunomodulatory and so on Liang et al., 2019Liang et al., , 2018Xie et al., 2016;Zhang et al., 2019). ...
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Aromatic compounds in Dendrobium catenatum could affect brewing quality. Methyl jasmonate (MeJA) treatment enhances the content of aromatic compounds in D. catenatum, improving the wine quality in brewing industry and medicinal value. In this study, two D. catenatum genotypes, A6 and B1, were used to investigate the effect of MeJA treatment on aromatic compounds. A total of 52 aromatic metabolites were identified using metabolome technique. Based on RNA-seq, weighted gene co-expression network analysis (WGCNA) of 16, 841 highly expressed transcripts uncovered black, cyan and turquoise modules that are significantly associated with the variation of aromatic compounds. These results reveal the changes of aromatic metabolites during MeJA treatment and provide insight into the biosynthesis mechanism of aromatic compounds in D. catenatum, which could be conducive to the synthesis of active bioactive compounds and their use as industrial by-products.
... "Shi Hu" is a traditional Chinese medicine (TCM) and food since ancient times [4,5]. Polysaccharides, alkaloids, phenanthrenes, sesquiterpenoids, flavonoid, fluorenones and other metabolites have been widely isolated and researched [6]. Dendrobine, the characteristic component of D. nobile, helps in nourishing lungs to treat cough, enhancing body's immunity and reducing blood sugar levels [4]. ...
Article
Emergency of nanoparticulate drug delivery systems has improved the target, bioavailability, and curative effect of traditional Chinese medicine (TCM). However, the application of nano-preparation has been limited owing to the low content of active ingredients in part TCM. MicroRNAs (miRNAs) regulate plant growth, development, and response to environmental stresses at post-transcriptional regulation level by cleavage or translational inhibition. The molecular functions of miRNAs playing a role in synthesizing active comportments at medicinal plants have been widely researched. Dendrobium nobile is a perennial herb in the orchidaceae family. D. nobile protocorm can produce plant-specific metabolites at a short period. Therefore, it is a good substitute for producing metabolites. To understand the functions of miRNAs in D. nobile protocorm, Illumina sequencing of D. nobile protocorm (Dnp), D. officinale protocorm (Dcp), and D. nobile leaf (Dnl) were carried out. A total of 439, 412, and 432 miRNAs were identified from Dnp, Dcp, and Dnl, respectively. Some specific miRNAs were identified among them. Through combing GO and KEGG function annotation, miRNAs mainly involved metabolic pathways, plant hormone signal transduction, biological regulation, and protein binding. Acetyl-CoA acetyltransferase (AACT), mevalonate kinase (MK), 1-deoxy-D-xylulose 5-phosphate reductoisomerase (DXR), and 2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase (HDS), synthesizing basic precursor isoprene pyrophosphate (IPP) in terpenoid backbone biosynthesis pathway, were predicted as potential targets of 6 different miRNAs. Twenty-six miRNAs participated in auxin, cytokinin, abscisic acid, jasmonic acid, and salicylic acid signal transduction pathway. This report provided valuable candidate genes in Dnp involved in terpenoid biosynthesis and plant hormone signal transduction pathway. At the same time, it can help accelerate the use of dendrobine into nano preparation.
... Dendrobium is more susceptible to the effects of precipitation, especially wild Dendrobium, which shows a slow growth and low reproductive rate at low precipitation levels Xu et al. 2013), D. moniliforme can adapt better to the future habitats than the other two Dendrobium species and could be used more widely in the future cultivation. ...
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... Dendrobium is the largest genus of orchidaceae, with 1500-2000 species, and can be eaten as a health food or herbal medicine in China [5]. It has been reported in Shennong's Herbal that Dendrobium is a high-grade drug because the stem of Dendrobium has been used in Chinese medicine for 1500 years in tonics or functional medicines to nourish the stomach, improve immunity and promote fluid production [6]. Among the medicinal and edible species of this genus, Dendrobium officinale has been officially listed in the Pharmacopoeia of the People's Republic of China [7]. ...
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... At present, the chemical components isolated from Dendrobium spp. mainly included polysaccharides, alkaloids, amino acids, bibenzyls, phenanthrenes, sesquiterpenes, fluorenones, flavonoids, phenolic acids, phenylpropanoids, lignans, amides, alkaloids, steroids, etc. (Ng et al., 2012;Xu et al., 2013). Alkaloids were the first chemicals studied and structurally confirmed in Dendrobium. ...
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We synthesized [6,6,6]- and [6,6,7]-tricyclic compounds via intramolecular [4+2] cycloaddition by gold or copper catalysts. Substrates for cyclization were prepared by coupling reactions between eight types of diyne and four types of aromatic moieties. We have successfully synthesized eleven tricyclic compounds.
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A new polysaccharide (cDFP-W1) with high immunostimulatory activities was isolated from the stems of Dendrobium fimbriatum Hook. The analysis of the physicochemical properties showed that cDFP-W1 consisted of mannose and glucose in a molar ratio of 1 : 3.84, and its relative molecular weight was 4.0 × 104 Da. Structural analysis implied that the linear backbone of cDFP-W1 was composed of α-1,4-d-Glcp, β-1,4-d-Manp, 3-O-acetyl-α-1,4-d-Glcp and α-1,4,6-d-Glcp, and its branches were the terminal β-d-Manp that was attached to the C-6 position of α-1,4,6-d-Glcp. An in vivo immunostimulatory assay exhibited that cDFP-W1 at 200 mg kg-1 could significantly increase the proportions of CD4+ T-cell subpopulations, B cells, natural killer cells and dendritic cells, decrease the proportion of CD8+ T-cell subpopulations, and upregulate the percentage of activated macrophages (p < 0.01) in the spleen of mice. An in vitro immunostimulatory assay revealed that cDFP-W1 could effectively promote the proliferation of spleen lymphocytes, enhance the proliferation and phagocytosis of macrophage RAW264.7 cells, and stimulate the mRNA expression and extracellular release of NO, TNF-α and IL-1β of RAW264.7 cells. The western blot experiment suggested that the immunostimulatory activities of cDFP-W1 were closely related to the activation of MAPKs, NF-κB and PI3K/Akt signaling pathways.
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Jasmonate (JA) signaling plays a pivotal role in plant stress responses and secondary metabolism. Many studies have demonstrated that JA effectively induce the expressions of alkaloid biosynthetic genes in various plants, which rendered to the accumulation of alkaloid to counteract stresses. Despite the multiple roles of JA in the regulation of plant growth and different stresses, less studied involved in the regulatory role of JA in Dendrobium officinale alkaloids. A strategy for the rapid identification of alkaloid and the intermediates of D. officinale was established based on a solid-phase extraction coupled with high-performance liquid chromatography tandem mass spectrometry method. By using SPE-LC-MS/MS method, the potential compounds were tentatively identified by aligning the accurate molecular weight with the METLIN and Dictionary of Natural Products databases. The chemical structures and main characteristic fragments of the potential compounds were further confirmed by retrieving the multistage mass spectra from the MassBank and METLIN databases. The Mass Frontier software was used to speculate the fragmentation pathway of the identified compounds. Seven alkaloids were separated and identified from D. officinale, which were mainly classified into five types (tropane alkaloids, tetrahydroisoquinoline alkaloids, quinolizidine alkaloids, piperidine alkaloids, and spermidine alkaloids). Besides the alkaloids, forty-nine chemical substances, including guanidines, nucleotides, dipeptides, sphingolipids and nitrogen-containing glucosides, were concurrently identified. These findings gives the composition of chemicals currently found in D. officinale, which could provide the scientific method for the identification of alkaloids in other Dendrobium plants.
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Plants belonging to the Dendrobium genus occupy a dominant position among the orchids because of their high ornamental and therapeutic values. They are widely popular in the international floriculture trade as they bear stunning flowers with diverse coloration, varied forms, and patterns. The ethnomedicinal uses of these orchids are also prominently found due to the possession of immense medicinal properties. Excessive exploitation through rampant unregulated collection and widespread habitat destruction have dwindled the Dendrobium natural populations at an alarming rate. The fast and reliable micropropagation techniques offer an alternative to the slow conventional methods of Dendrobium propagation. The rapid in vitro regeneration of genetically stable Dendrobiums is essential for effective germplasm conservation and large-scale orchid commercialization. Several genetic stable Dendrobiums have been successfully propagated by ascertaining the clonal fidelity of the regenerants using different molecular markers. This chapter focuses on the uses of Dendrobiums as important ethnomedicine, their in vitro propagation, and clonal assessment for producing genetically stable orchids using DNA markers.
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With the ever-increasing demands for personalized drugs, disease-specific and condition-dependent drug delivery systems, four-dimensional (4D) printing can be used as a new approach to develop drug capsules that display unique advantages of self-changing drug release behavior according to the actual physiological circumstances. Herein, a plant stomata-inspired smart hydrogel capsule was developed using an extrusion-based 4D printing method, which featured with UV cross-linked poly(N-isopropylacrylamide) (PNIPAM) hydrogel as the capsule shell. The lower critical solution temperature (LCST) of the PNIPAM hydrogels was approximately 34.9 °C and macroporous PNIPAM hydrogels were prepared with higher molecular weight polyethylene glycols (PEGs) as the pore-forming agents. Owing to the LCST-induced shrinking/swelling properties, the prepared PNIPAM hydrogel capsules exhibited temperature-responsive drug release along with the microstructure changes in the PNIPAM hydrogels. The in vitro drug release test confirmed that the PNIPAM hydrogel capsules can autonomously control their drug release behaviors on the basis of ambient temperature changes. Moreover, the increased PEG molecular weights in the macroporous PNIPAM hydrogel capsules caused an obvious improvement of drug release rate, distinctly indicating that the drug release profiles can be well programmed by adjusting the internal pore size of the hydrogel capsules. In vitro biocompatibility studies confirmed that the PNIPAM hydrogel capsules have great potential for biomedical applications. The bioinspired 4D printed hydrogel capsules pioneer the paradigm of smart controlled drug release.
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Personalized drugs, as well as disease-specific and condition-dependent drug release, have been highly desired in drug delivery systems for effective and safe therapies. Four-dimensional (4D) printing, as a newly emerging technique to develop drug capsules, displays unique advantages that can autonomously control drug release according to the actual physiological circumstances. Herein, core–shell structured hydrogel capsules were developed using a multimaterial extrusion-based 4D printing method, which consists of a model drug as the core and UV cross-linked poly(N-isopropylacrylamide) (PNIPAM) hydrogel as the shell. Owing to the lower critical solution temperature (LCST)-induced shrinking/swelling properties, the prepared PNIPAM hydrogel capsules showed temperature-responsive drug release along with the topography changes in the cross-linked PNIPAM network. The in vitro drug release test confirmed that the PNIPAM hydrogel capsules can autonomously control their drug release behaviors according to changes in ambient temperature. Moreover, the increased shell thickness of these capsules causes an obvious reduction in drug release rate, distinctly indicating that the drug release behavior can be well adjusted by setting the shell thickness of the capsules. The proposed 4D printing strategy pioneers the paradigm of smart drug release by showing great potential in the smart controlled release of drugs and macromolecular active agents.
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Xylariales are common endophytes of Dendrobium. However, xylarialean species resolution remains difficult without sequence data and poor sporulation on artificial media and asexual descriptions for only several species and old type material. The surface-sterilized and morph-molecular methods were used for fungal isolation and identification. A total of forty-seven strains were identified as twenty-three species belonging to Apiosporaceae, Hypoxylaceae, Induratiaceae, and Xylariaceae. Five new species—Annulohypoxylon moniliformis, Apiospora dendrobii, Hypoxylon endophyticum, H. officinalis and Nemania dendrobii were discovered. Three tentative new species were speculated in Xylaria. Thirteen known fungal species from Hypoxylon, Nemania, Nigrospora, and Xylaria were also identified. Another two strains were only identified at the genus and family level (Induratia sp., Hypoxylaceae sp.). This study recorded 12 new hosts for xylarialean endophytes. This is the first report of Xylariales species as endophytes from Dendrobium aurantiacum var. denneanum, D. cariniferum, D. harveyanum, D. hercoglossum, D. moniliforme, and D. moschatum. Dendrobium is associated with abundant xylarialean taxa, especially species of Hypoxylon and Xylaria. We recommend the use of oat agar with low concentrations to induce sporulation of Xylaria strains.
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Introduction: Alkaloids and glycosides are the active ingredients of the herb Dendrobium nobile, which is used in traditional Chinese medicine. The pharmacological effects of alkaloids include neuroprotective effects and regulatory effects on glucose and lipid metabolism, while glycosides improve the immune system. The pharmacological activities of the above chemical components are significantly different. In practice, the stems of 3-year-old D. nobile are usually used as the main source of Dendrobii Caulis. However, it has not been reported whether this harvesting time is appropriate. Objective: The aim of this study was to compare the chemical characteristics of D. nobile in different growth years (1-3 years). Methods: In this study, ultra-high-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry (UPLC-Q/TOF-MS) was employed to analyze the constituents of D. nobile. The relative abundance of each constituent was analyzed with multivariate statistical analyses to screen the characteristic constituents that contributed to the characterization and classification of D. nobile. Dendrobine, a component of D. nobile that is used for quality control according to the Chinese Pharmacopoeia, was assayed by gas chromatography. Results: As a result, 34 characteristic constituents (VIP > 2) were identified or tentatively identified as alkaloids and glycosides based on MS/MS data. Moreover, the content of alkaloids decreased over time, whereas the content of glycosides showed the opposite trend. The absolute quantification of dendrobine was consistent with the metabolomics results. Conclusion: Our findings provide valuable information to optimize the harvest period and a reference for the clinical application of D. nobile.
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Phytochemical investigation of the stems of Dendrobium nobile Lindl., led to the isolation of six sesquiterpene glycosides, including dendronobiloside E (1), dendronobiloside C (2), dendronobiloside D (3), dendronobiloside A (4), dendromoniliside D (5), dendroside G (6). Their chemical structures were identified on the basis of HR-ESI-MS, NMR spectroscopic analyses and comparison with reported data. Among them, dendronobiloside E (1) was a new compound. The chemotaxonomic significance of these sesquiterpene glycosides was discussed herein.
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A new tetrahydroanthracene, 3,6,9-trihydroxy-3,4-dihydroanthracen-1(2H)-one (1), six phenolics, moscatilin (2), gigantol (3), batatasin (4), moscatin (5), 9,10-dihydromoscatin (6), 10-dihydrophenanthrene-2,4,7-triol (7), and a sesquiterpenoid, corchoionoside C (8), together with two sterols β-sitosterol (9) and daucosterol (10), were isolated from the stems of Dendrobium polyanthum. Compounds 1 and 2 were assessed for cytotoxic activity against two human tumor cell lines (A549 and HL-60).
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A new bibenzyl derivative, moniliformine, along with six known compounds, was isolated from a orchid Dendrobium moniliforme (L.) Sw. The new compound was identified as 3,4-dihydroxy-5,4'-dimethoxy bibenzyl on the basis of 1D and 2D NMR experiments. The six known compounds were determined to be alpha-dihydropicrotoxinin, n-triacontyl p-hydroxy-cis-cinnamate, n-octacostyl ferulate, beta-sitosterol, daucosterol and n-nonacosane, respectively. Among them, alpha-dihydropicrotoxinin was isolated for the first time from the plant kingdom.
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Bibenzyls are biologically active compounds widely found in Dendrobii Caulis. A HPLC method was developed for the determination of two specific bibenzyls, moscatilin and gigantol. Chromatographic separation was performed on a reverse-phase C18 column employing a binary linear gradient elution with acetonitrile and 0. 01% trifluroacetic acid. The linear ranges of moscatilin and gigantol were from 2. 29 (μg/mL to 1 144. 00 μg/mL and 1.79 (μg/mL to 1 196.00 μg/mL respectively with good correlation coefficients greater than 0.999 7. The average recoveries measured at three levels were 102.7% and 99. 1%, respectively. The validated method was applied for 18 different species of Dendrobium plants and 18 batches of Dendrobii Caulis, which proved to be sensitive, reliable and applicable for the quality control.
Article
OBJECTIVE: To characterize the chemical structures of DT2 and DT3, two homogeneous polysaccharides from Dendrobium candidum. METHODS: Molecular weights were estimated by HPLC. Sugar composition, methylation, partial hydrolysis and 13C-NMR were used to elucidate the structural features of DT2 and DT3. RESULTS: The molecular weights were estimated to be 7.4 × 10 5 and 5.4 × 105. Sugar analysis indicated that DT2 and DT3 were mainly composed of glucose, galactose, xylose, arabinose and mannose in molar ratios of 5.9:1.0:1.0:0.8:0.5 and 7.9:1.3:1.0:0.5:0.7, respectively. Methylation analysis and NMR data showed that the main chains of DT2 and DT3 were composed of 1,4 linked α-D-Glc. CONCLUSION: Polysaccharides DT2 and DT3 were isolated from D. candidum for the first time.
Article
To establish a HPLC method for the determination of dendrobin in Dendrobium nobile. METHODS The determination was carried out on a Waters XTerra™RP18 (3.9 mm×150 mm, 5 μm) column with acetonitril-water-triethylamine (21 : 79 : 0.005) as the mobile phase. The UV wavelength was 210 nm . RESULTS The calibration curve was in good linearity over the range of 30.9-618 mg.L-1 with the regression equation Y=3 191.5P+14 191 (r=0.999 9) . The average recovery was 99.11% (RSD=2.61%) . CONCLUSION The method was proved to be simple, accurate, reproducible, and feasible for determining the content of dendrobin in D. nobile.
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A new bibenzyls compound, Isomoniliformine A, 1-{(7-hydroxy-5-methoxy-6- (18-(hydroxylmethyl)oxiranyl)-16,18-dimethoxylphenoxy)-phenyl} -2-(11-methoxyphenyl)ethane, was isolated from stems of Dendrobium gratiosissmum Rchb. f. The structure of this unusual bibenzyl compound was determined by chemical and spectroscopic methods, particularly one- and two-dimensional 1H and 13C NMR.
Article
OBJECTIVE: To investigate the structural feature and immunomodulatory activity of the water-soluble polysaccharide DMP4a-1 from Dendrobium moniliforme (L.) Sw. METHODS: The chemical structure of the polysaccharide DMP4a-1 was elucidated by periodate oxidation, HPGPC, TLC, GC, GC-MS and IR; TNF-α was quantified by sandwich ELISA, the proliferation of spleen lymphocyte was measured by CCK-8 reagent in vitro. RESULTS: DMP4a-1 was composed of Glc-Man-Rha-Ara-Gal in a molar ratios of 2.873:2.850:1.762:1.279:1 with M r 3 049. They were (1→4, 1→3, 1→6) linked with glycosidic residues, in a ratio of 1.194:2.430:1. DMP4a-1 significantly stimulated the secretion of TNF-α in macrophage and promoted the proliferation of lymphocyte from spleen in vitro. CONCLUSION: Polysaccharide DMP4a-1 consists of β-D-pyranyl glycoside with (1→3) glycosidic bond, and markedly enhances immunological activity.
Article
A new picrotoxane type sesquiterpene named dendrodensiflorol has been isolated from the stems of Dendrobium densiflorum. Its structure was identified on the basis of spectroscopic method.
Article
A new bibenzyl glycoside has been isolated from the stems of Dendrobium moniliforme (L.) Sw. (Orchidaceae). Its structure has been identified on the basis of spectroscopic and chemical methods.
Article
OBJECTIVE: To establish qualitative and quantitative methods for the quality evaluation of Dendrobium aurantiacum var. denneanum. METHODS: Two bibenzyls gigantol and moscatilin were identified by TLC. The separation of gigantol was obtained by RP-HPLC (Shim-pack CLC-ODS) using elution systems of acetonitrile-0.2% formic acid (65:35) at 25°C. RESULTS: Calibration curve showed good linear regression (r = 0.9999) within test ranges of 0.196-12.54 μg. Average recovery was 100.6% with RSD of 3.01%. CONCLUSION: The developed methods were proved to be sensitive, reliable and useful by analysis of ten different samples from D. aurantiacum var. denneanum. The samples collected in April, May (Spring) and October, November (Autumn) accumulate much higher amount of gigantol than those of other months.
Article
OBJECTIVE: To study the physical and chemical properties of polysaccharides in Dendrobium officinale protocorm. METHODS: The crude polysaccharides in D. officinal (CDO) and D. officinal protocorm (CDOP) were extracted and purified by consecutive steps of hot-water extraction, alcohol precipitate, deprotein and dialysis. CDOP was then subjected to DEAE cellulose DE-52 and Sephadex G-200 column chromatography to obtain homogeneous polysaccharide. High performance gel permeation chromatography (HPGPC), gas chromatography (GC), and periodate oxidation and Smith degradation were used to analyze the physical and chemical properties of polysaccharide. RESULTS: CDO was mainly composed of Man and Glu in a molar ratio of 4.29:1.00. CDOP was mainly composed of Gal, Ara and Glu in a molar ratio of 2.80:1.00:0.61. Six homogeneous polysaccharides, including DOPW-1 (78 × 103), DOPW-2 (37×103), DOPS1-1 (287 × 103), DOPS1-2 (351×103), DOPS1-3 (335×103) and DOPS1-4 (171×103), were isolated from CDOP, and their monosaccharide composition and molar ratio were similar to that of CDOP. In the primary structure of homogeneous polysaccharides, 1→3 glycosidic linkage was mainly composed of Gal in addition to Ara, Glu and Rha, and no 1→4 glycosidic linkage could be tested except for in DCPS1-4. CONCLUSION: Polysaccarides DOPW-1, DOPW-2, DOPS1-1, DOPS1-2, DOPS1-3 and DOPS14 were isolated from D. officinale protocorm for the first time.
Article
OBJECTIVE: To investigate the chemical structure of DMP2a-1, a polysaccharide isolated from Dendrobium moniliforme (L.) Sw, with molecular weight of 6 kDa determined by high performance gel permeation chromatography. METHODS: Ultraviolet spectrum, infrared spectrum, periodate oxidation, methylation analysis, mass spectrometry and (1H, 13C) NMR spectrometry were used to determine the structure of DMP2a-1. RESULTS: DMP2a-1 was composed of 4-substituted α-D-glucopyranosyl residues. Mannopyranosyl and glucopyranosyl side chains were present as terminal residue on the 6-position of 4-linked glucopyranosyl residues. Approximately one equivalent of substituted groups per six 4-linked glucopyranosyl residue was present. CONCLUSION: DMP2a-1 is a new polysaccharide and is isolated for the first time from this medicinal plant.
Article
Objective: To study the chemical constituents from the 60% ethanol extract of the stems of Dendrobium nobile. Methods: Compounds were isolated through various chromatographic methods and identified by spectroscopic data. Results: Eight sesquiterpenes were obtained. Their structures were characterized as dendronobilin J (I), dendrobane A (II), dendrodensiflorol (III), bullatantirol (IV), dendrobiumane A (V), 6α, 10, 12-trihydroxypicrotoxane (VI), 10, 12-dihydroxypicrotoxane (VII), and 10β, 13, 14-trihydroxyalloaromadendrane (VIII), respectively. Conclusion: Compound I is a new compound named as dendronobilin J. Compound IV is reported for the first isolation from the plants of Dendrobium Sw. Compounds III and V are isolated from this plant for the first time.
Article
OBJECTIVE: To develop a method based on pre-column derivation-HPLC combined with cluster analysis and discriminant analysis to determine the monosaccharide compositions and contents in polysaccharide of Dendrobium officinale and to identify growth years. METHODS: After medicinal Dendrobium was degreazed by ethanol, the polysaccharides were extracted with hot water and hydrolyzed with 3.0 mol · L -1 HQ. Then, the monosaccharides were derivated by PMP. The, monosaccharide derivatives were assayed by HPLC. Cluster analysis and discriminant analysis (DA) were performed by SPSS16.0. RESULTS: The polysaccharide of Dendrobium candidum was composed of mannose and glucose. The ranges of the mannose contents were 19.65%-34.27%, and all met the standard of Chinese Pharmacopoeia. However, the mannose content decreased with growth years. The peak area ratio between mannose and glucose was significandy different. The samples analyzed can be clustered into three classes and the same ages were clustered into one class, meanwhile the recognition function was established and the accuracy of classification testing was 100%. CONCLUSION: The monosaccharide compositions and contents in polysaccharide of Dendrobium officinale, combined with chemometrics, can accurately identify growth year. The study provided experimental evidence for quality evaluation and development of Dendrobium officinale.
Article
A new dendrobine-type alkaloid has been isolated from stems of Dendrobium nobile lindl.. Its structure has been identified on the basis of spectroscopic method.
Article
The methanol extract of the dried stems of Dendrobium sonia was found to contain six stilbenoids denbinobin (1), 3-methylgigantol (2), 3′,4-dihydroxy-5,5′dimethoxybibenzyl (3), nudol (2,7-dihydroxy-3,4-dimethoxyphenanthrene) (4), lusianthridin (5), and confusarin (2,7-dihydroxy-3,4,8-trimethoxyphenanthrene) (6). The structures of these compounds were identified by comparison of their spectral data (EIMS and NMR) with published reports. Compounds 1 and 2 were also established by direct comparison (co-TLC) with the authentic samples.
Article
OBJECTIVE: To isolate and elucidate the constituents from Dendrobium aduncum Hook. METHODS: The chromatography on silica gel was used for the isolation and purification of the constituents. The structures were determined by IR, MS, 1H-NMR, 13C-NMR and HMBC spectral analysis. RESULTS: Nine compounds were obtained and identified as following: n-triacontyl p-hydroxy-cis-cinnamate(I), defuscin (II), β-sitosterol(III), aduncin(IV), dengibsinin(V), dengibsin(VI), chrysotoxone(VII),4-hydroxy-3-methoxy benzoic acid(VIII) and daucosterol (IX). CONCLUSION: The compound of 4-hydroxy-3-methoxy benzoic acid is firstly isolated from Genus Dendrobium and Compound I-III, V-IX are found from this species for the first time, The 13C-NMR data of compound IV and V are reported for the first time.
Article
Aim: To investigate the chemical constituents of Dendrobium trigonopus Rchb. f., Sect. Formosae. Method: Compounds were isolated by silica gel, Sephadex LH-20 and RP-C18 column chromatography and the structures were elucidated on the basis of spectroscopic methods. Result: Nine compounds were isolated and identified as one lignans: (+)-syringaresinol (I); one fluorenones: dendroflorin(II); three bibenzyles: moscatilin (III) , gigantol (IV) , tristin (V); one phenanthrenes: moscatin (VI); one flavanones: naringenin(VII) and phytosterols: β-sitosterol (VIII), daucosterol (IX). Conclusion: All the nine compounds were obtained from this plant for the first time.
Article
AIM: To investigate the chromatographic fingerprints of five kinds of Dendrobium(Shi-Hu). METHOD: Separations were performed on Agilent ZORBAX SB-C18 and Shmadzu Shim-pack VP-ODS C18 analytical columns with the mobile phase consisting of acetonitrile or methanol-water-formic acid as gradient eluent. The UV at varies wavelenth and TIC by an electrospray ionization mass spectrometer were recorded. RESULT: Perfect chromatographic fingerprints of the five species of Dendrobium(Shi-Hu) were obtained and fifteen chemical constituents contained in three species of Dendrobium(Shi-Hu) were confirmed by analyzing their extracted mass spectrum. CONCLUSION: The methods established can be used for the quality control and saved as a reference on the chemical constituents investigation of the five kinds of Dendrobium(Shi-Hu).
Article
Aim: To investigate the chemical constituents of the antiplatelet fraction of Dendrobium chrysanthum Wall. ex Lindl. Method: Various chromatographic techniques were employed for isolation and purification of the active constituents. The structures were elucidated by spectral analyses. Result: Nine compounds were isolated and identified as chrysotobibenzyl(1), crepidatin (2), moscatilin (3), dengibsin (4), dendroflorin (5), emodin (6), physcion (7), chrysophanol (8) and β-sitosterol(9). Conclusion: All of the above compounds were obtained from this plant for the first time except for compound 3.
Article
A new bibenzyl derivative, 3,4-dihydroxy-4′,5-dimethoxy bibenzyl, was isolated from a orchid Dendrobium moniliforme. The structure elucidation and 1 H, 13 C NMR assignments were achieved by spectroscopic method. The chinese crude drug "Shihu", derived from the dried or fresh stems of many plants of Genus Dendrobium, is usually used to clear heat and for the benefit of eyes. In previous communications 1,2,3 we reported the isolation of some phenolic compounds from Dendrobium chrysotoxum Lindl., in this paper, we report the isolation of a new phenolic compound from Dendrobium moniliforme (L.) Sw.. The structure of the new compound 1 was established as 3, 4-dihydroxy-4′,5-dimethoxy bibenzyl (Scheme) from the spectral evidence.
Article
AIM: To study the chemical constituents of Dendrobium chrysotoxum Lindl. METHODS: Compounds were separated by column chromatography on silica gel and their structures were elucidated based on chemical and spectral analyses. RESULTS: Four compounds were isolated from Dendrobium chrysotoxum and identified as 2,4,7-trihydroxy-9, 10-dihydrophenanthrene(I), 2, 7-dihydroxy-3, 4, 6-trimethoxy-phenanthrene (II), 5, 4′-dihydroxy -3,3′- dimethoxydibenzyl(III), 3, 4-dihydroxybenzoic acid(IV). CONCLUSION: Compounds I-IV were obtained from Genus Dendrobium for the first time.
Article
Thirteen compounds were isolated from the stems of Dendrobium moniliforme. They were identified as heptacosane (1), octacosanyl hexadecanoate (2), methyl and ethyl linolenates (3a, 3b), 4-methoxybenzaldehyde (4), alkyl ferulates (5), vanillin (6), alkyl 4′-hydroxy-cis-cinnamates (7), denbinobin (8), alkyl 4′-hydroxy-trans-cinnamates (9), stigmast-4-en-3-one (10), phytosterols (11a, 11b, 11c), linoleic acid (12) and heptatriaconsanoic acid (13). Compounds 2, 3a, 3b, 4, 6 and 12 were isolated from Dendrobium species for the first time.
Article
A new bibenzyl 1 and a new phenanthrenedione 2 were identified from the stems of Dendrobium densiflorum (Orchidaceae).
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Objective: To study the chemical constituents from the stems of Dendrobium nobile. Methods: Compounds were isolated through various chromatographic techniques and identified by spectral data. Results: Twelve phenolic compounds were obtained. Their structures were characterized as dihydroconiferyl dihydro-p-coumarate (I), vanillin (II), apocynin (III), p-hydroxybenzaldehyde (IV), syringaldehyde (V), syringic acid (VI), syringylethanone (VII), α-hydroxypropiosyringone (VIII), coniferyl aldehyde (IX), dihydroconiferyl alcohol (X), 2-hydroxyphenylpropanol (XI), and 3-hydroxy-4-methoxy-phenylethanol (XII), respectively. Conclusion: All above compounds are reported from this plant for the first time. Compounds I and III - XII are reported for the first time from the plants of Dendrobium Sw.
Article
OBJECTIVE: To isolate the water-soluble polysaccharides from Dendrobium moniliforme (L.) Sw. and investigate its structural feature. METHODS: The polysaccharides prepared from Dendrobium moniliforme were purified with column chromatography on DEAE-cellulose, Sephacryl S-400 HR and Sephacryl S-200 HR. The structural feature of the main polysaccharide was elucidated by periodate oxidation, HPGPC, TLC, GC, GC-MS and IR respectively. RESULTS: Eight polysaccharides, DMP1a-1, DMP1a-2, DMP2a-1, DMP3a-1, DMP4a-1, DMP5a-1, DNT6a-1 and DMP7a-1, were obtained from Dendrobium moniliforme. The results indicated that DMP1a-1 was a glucomannan with a 1:4. 798 glucose-mannose ratio and Mr was 28 000. Periodate oxidation analysis indicated DMP1a-1 containing β(1→-3,1→4,1→6) glycosidic bond, appeared in the molar ratio of 8.75:23. 59: 1. CONCLUSION: Eight polysaccharides are isolated from this medicinal plant for the first time. DMP1a-1 is a β-D-pyranyl glucomannan.
Article
OBJECTIVE: To study the chemical constituents of Dendrobium nobile Lindl. METHODS: The constituentes were isolated through column chromatography and identified on the basis of their physiochemical and spectral data. RESULTS: Five monomers and two mixtures were isolated and identified as pimaradiene, n-docosyl ferulate, n-tetracosyl ferulate, stigmasterol, n-triacontyl cis-p-coumarate, the mixture of n-tetracosyl trans-p- coumarate, n- hexacosyl trans-p-coumarate, n-octacosyl trans-p-coumarate and defuscin, respectively, and the mixture of n-hexacosyl alcohol and n-octacosyl alcohol and n-triacontyl alcohol, n-hentriacontyl alcohol, n-dotriacontyl alcohol. CONCLUSION: All these constituentes were isolated from this plant for the first time. Pimaradiene was isolated from Dendrobium genus for the first time.
Article
OBJECTIVE: To study the antioxidant activity of bibenzyls and phenolic components isolated from the 60% EtOH extract of Dendrobium nobile, and discuss the structure-activity relationship. METHODS: Compounds were isolated from the 60% EtOH extract of Dendrobium nobile through various chromatographic techniques and identified by spectral data. The antioxidant activity of 16 compounds was evaluated by DPPH free radical scavenging assay and oxygen radical absorbance capacity assay. RESULTS: Three new bibenzyls and thirteen phenolic compounds were obtained. Their structures were characterized as nobilin A(1), nobilin B(2), nobilin C(3), syringic acid(4), 2-hydroxyphenylpropanol(5), vanillin(6), apocynin(7), coniferyl aldehyde(8), syringaldehyde(9), syringylethanone(10), p-hydroxybenzaldehyde(11), 3-hydroxy-4-methoxyphenylethanol(12), α-hydroxysyringylethanone(13), dihydroxyconiferyl alcohol(14), p-hydroxybenzoic acid(15), and p-hydroxyphenylpropionic acid(16), respectively. In the DPPH assay, compound 4 exhibited significant scavenging activity, compared with vitamin C. Compounds 1, 2, 12 and 14 showed higher activity than BHT and weaker activity than vitamin C. The activity of compounds 3 and 8 was very weak. In the ORAC assay, compound 2-4, 7-10, and 15 displayed stronger peroxyl radical scavenging activity than vitamin C, and compound 12, 14, 16 showed weak activity. CONCLUSION: Most of the bibenzyls and phenolic components exhibited antioxidant activity in different levels, and the relationship between structure and activity was found.
Article
Aim: To investigate the chemical constituents of Dendrobium thyrsiflorum Rchb. f. Method: Compounds were isolated by silic gel, Sephadex LH-20 and RP-C18 column chromatography and identified mainly by spectral data. Result: Nine compounds including fluorenones, bibenzyles, phenanthrenes and flavonoids were isolated and identified as dengibsin (I), dendroflorin (II), denchrysan A (III), denchrysan B (IV), moscatilin (V), gigantol (VI), trisin (VII) and moscatin (VIII), hircinol (IX), tricin (X), chrysoeriol (XI), homoeriodictyol (XII), naringenino (XIII). Conclusion: Compounds IX, X, and XI were firstly isolated from Dendrobium SW. The others were also obtained from this plant for the first time.