Four New Bibenzyl Derivatives from Dendrobium candidum

Li, Yan; Wang, Chunlan; Wang, Yajun; Guo, Shunxing; Yang, Jun‐Shan; Chen, Xiaomei; Xiao, Pei‐Gen

doi:10.1248/cpb.57.997

Cited by 51 publications

(30 citation statements)

References 6 publications

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“…Besides polysaccharides, bibenzyl is relatively common in the genus and has neuro-protective and antitumor activities [8][9][10]. Phytochemical analyses of D. officinale have shown that it contains a wide variety of low molecular weight compounds including bibenzyls, phenanthrenes, and flavanones [11,12]. However, these have not been used to identify D. officinale, or for quality control of Dendrobii Officinalis Caulis.…”

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confidence: 99%

Discrimination of the rare medicinal plant Dendrobium officinale based on naringenin, bibenzyl, and polysaccharides

Chen

Wang

et al. 2012

Sci. China Life Sci.

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The aim of this study was to establish a method for discriminating Dendrobium officinale from four of its close relatives Dendrobium chrysanthum, Dendrobium crystallinum, Dendrobium aphyllum and Dendrobium devonianum based on chemical composition analysis. We analyzed 62 samples of 24 Dendrobium species. High performance liquid chromatography analysis confirmed that the four low molecular weight compounds 4′,5,7-trihydroxyflavanone (naringenin), 3,4-dihydroxy-4′,5-dimethoxybibenzyl (DDB-2), 3′,4-dihydroxy-3,5′-dimethoxybibenzyl (gigantol), and 4,4′-dihydroxy-3,3′,5-trimethoxybibenzyl (moscatilin), were common in the genus. The phenol-sulfuric acid method was used to quantify polysaccharides, and the monosaccharide composition of the polysaccharides was determined by gas chromatography. Stepwise discriminant analysis was used to differentiate among the five closely related species based on the chemical composition analysis. This proved to be a simple and accurate approach for discriminating among these species. The results also showed that the polysaccharide content, the amounts of the four low molecular weight compounds, and the mannose to glucose ratio, were important factors for species discriminant. Therefore, we propose that a chemical analysis based on quantification of naringenin, bibenzyl, and polysaccharides is effective for identifying D. officinale. Dendrobium officinale, naringenin, bibenzyl, polysaccharide, discriminant analysis Citation:Chen X M, Wang F F, Wang Y Q, et al. Discrimination of the rare medicinal plant Dendrobium officinale based on naringenin, bibenzyl, and polysaccharides.

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confidence: 99%

Discrimination of the rare medicinal plant Dendrobium officinale based on naringenin, bibenzyl, and polysaccharides

Chen

Wang

et al. 2012

Sci. China Life Sci.

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“…Furthermore, compound 1 and dendrocandin F have similar 1 H and 13 C NMR spectroscopic data, except for the absence of a methoxyl group signal [4]. The HMBC correlations [1-OMe (d H 3.82)/C-1, 12-OMe (d H 3.64)/ C-12 and 1 0 -OMe (d H 3.75)/C-1 0 ] and the molecular formula of 1 suggested that the methoxyl group at C-12 0 in dendrocandin F is replaced by a hydroxyl group in compound 1.…”

Section: Resultsmentioning

confidence: 86%

“…The relative configurations of the chiral centers of 6 were confirmed as trans from the ROESY cross peak H-6 0 $ H-8 0 and the coupling constant (J 7 0 ,8 0 ¼ 7.8 Hz) between H-7 0 and H-8 0[8- 10].The HR-ESI-MS of dendrocandin P (7) exhibited a pseudomolecular ion peak at m/z 515.1743 [M 2 H] 2 , ascribable to a molecular formula of C 30 H 28 O 8 . The NMR spectroscopic data of compound 7 resembled those of dendrocandin I, except for the absence of two methoxyl group signals[4]. The HMBC correlations[1-OMe (d H 3.70)/C-1 and 1 0 -OMe (d H 3.60)/C-1 0 ] and the molecular formula of 7 indicated that the methoxyl groups at C-12 and C-12 0 in dendrocandin I are replaced by two hydroxyl groups in compound 7.…”

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confidence: 74%

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Eight new bibenzyl derivatives fromDendrobium candidum

Li¹,

Wang²,

Zhao³

et al. 2014

Journal of Asian Natural Products Research

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Eight bibenzyl derivatives, namely dendrocandins J-Q (1-8), were isolated from the stems of Dendrobium candidum. Their structures were elucidated by 1D and 2D NMR experiments and mass spectrometry. Compounds 1-8 were examined for antioxidant activity by 1,1-diphenyl-2-picrylhydrazyl free radical scavenging assay, and the IC50 values were 36.8, 70.2, 45.0, 60.5, 87.6, 50.4, 22.3, and 30.3 μM, respectively.

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“…Several Dendrobium species are used in traditional medicine as tonics to nourish the stomach, promote the production of body fluids and decrease fever (Ng et al, 2012;Xu et al, 2013). They produce a variety of secondary metabolites, such as phenolic compounds (Hu et al, 2010;Li et al, 2009a;Zhao et al, 2003), bibenzyl derivatives (Bi et al, 2004;Chen et al, 2010;Hu et al, 2008;Li et al, 2009bLi et al, , 2009cLi et al, , 2014Majumder et al, 1999;Majumder and Chatterjee, 1989), lignin glycosides and phenanthrenes (Hu et al, 2008), and alkaloids (Elander et al, 1973;Kierkegaard et al, 1970;Li et al, 2008;Venkateswarlu et al, 2002). Such metabolites are responsible for these species' wide variety of medicinal properties (Chand et al, 2016;Paudel et al, 2015Paudel et al, , 2017.…”

Section: Introductionmentioning

confidence: 99%

Antibacterial activity of selected Dendrobium species against clinically isolated multiple drug resistant bacteria

Paudel¹,

Rajbanshi²,

Sah³

et al. 2018

Afr. J. Microbiol. Res.

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Dendrobium species are widely used in traditional medicine as remedies for tonic to nourish the stomach, promote the production of body fluids and decrease fever. In this study, the antibacterial activities of four traditionally used Dendrobium species were tested against clinically isolated multiple drug resistant (MDR) bacteria. Hexane, chloroform, acetone, ethanol and methanol extracts of Dendrobium amoenum, Dendrobium crepidatum, Dendrobium moniliforme and Dendrobium longicornu were tested for antibacterial activity against methicillin-resistant Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Salmonella typhi and Acinetobacter baumannii by using the well diffusion method. Minimum inhibitory concentrations (MICs) and minimum bactericidal concentrations (MBCs) were determined using the serial dilution method. For D. amoenum, hexane, chloroform and acetone extracts showed antibacterial activity against S. aureus (ZOI: 11.33, 12.00 and 11.00 mm respectively), acetone extract against A. baumannii (ZOI: 13.00 mm) and methanol extract against P. aeruginosa (ZOI: 12.00 mm). For D. crepidatum, hexane, chloroform, acetone, ethanol and methanol extracts showed antibacterial activity against S. typhi (ZOI: 10.00, 11.67, 12.00, 9.67 and 12.67 mm respectively), hexane, ethanol and methanol extracts against P. aeruginosa (ZOI: 10.00, 9.67 and 15.00 mm respectively), choloroform and acetone extracts against S. aureus (ZOI: 9.67 mm) and ethanol extract against E. coli (ZOI: 11.00 mm). For D. moniliforme, chloroform extract showed antibacterial activity against K. pneumoniae, P. aeruginosa, S. typhi, A. baumannii (ZOI: 12.67, 12.00, 11.67 and 13.00 mm respectively), acetone extract against S. aureus (ZOI: 11.00 mm) and A. baumannii (ZOI: 12.67 mm). For D. longicornu, chloroform extract showed antibacterial activity against A. baumannii (ZOI: 12.00 mm). MIC and MBC of these extracts of plants showed they have moderate antibacterial activity against the bacterial strains used. In conclusion, these Dendrobium species can be used as antibiotic agents.

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Four New Bibenzyl Derivatives from Dendrobium candidum

Cited by 51 publications

References 6 publications

Discrimination of the rare medicinal plant Dendrobium officinale based on naringenin, bibenzyl, and polysaccharides

Discrimination of the rare medicinal plant Dendrobium officinale based on naringenin, bibenzyl, and polysaccharides

Eight new bibenzyl derivatives fromDendrobium candidum

Antibacterial activity of selected Dendrobium species against clinically isolated multiple drug resistant bacteria

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