ABSTRACT
This study aimed to provide a scientific basis for the application of the mycorrhizal planting technology of Dendrobium officinale by investigating the effects of mycorrhizal planting on the fingerprints of D. officinale and the content of six chemical components. Seventeen samples of D. officinale under mycorrhizal and conventional planting were collected from four regions, such as Jinhua of Zhejiang. The HPLC fingerprints were established to evaluate the similarity of the samples. The content of six chemical components of the samples was determined by HPLC. There were 15 common peaks in the fingerprints, and five of them were identified by marker compounds, which were naringenin, 4,4'-dihydroxy-3,5-dimethoxybibenzyl, 3,4'-dihydroxy-5-methoxybibenzyl, 3',4-dihydroxy-3,5'-dimethoxybibenzyl(gigantol), and 3,4-dihydroxy-4',5-dimethoxybibenzyl(DDB-2). The similarities of the fingerprints of mycorrhizal and conventional planting samples and the control fingerprint were in the ranges of 0.733-0.936 and 0.834-0.942, respectively. The influences of mycorrhizal planting on fingerprints were related to planting regions, the germplasm of D. officianle, and the amount of fungal agent. The content of six chemical components in the samples varied greatly, and the content of DDB-2 was the highest, ranging from 69.83 to 488.47 μg·g~(-1). The mycorrhizal planting samples from Chongming of Shanghai and Taizhou of Jiangsu showed an increase in the content of 5-6 components, while samples from Zhangzhou of Fujian and Jinhua of Zhejiang showed an increase in the content of 1-2 components. The results showed that mycorrhizal planting technology did not change the chemical profile of small molecular chemical components of D. officinale, but affected the content of chemical components such as bibenzyls, which has a good application prospect.
Subject(s)
Dendrobium/chemistry , Mycorrhizae , China , Chromatography, High Pressure LiquidABSTRACT
Bibenzyls, a kind of important plant polyphenols, have attracted growing attention for their broad and remarkable pharmacological activities. However, due to the low abundance in nature, uncontrollable and environmentally unfriendly chemical synthesis processes, these compounds are not readily accessible. Herein, one high-yield bibenzyl backbone-producing Escherichia coli strain was constructed by using a highly active and substrate-promiscuous bibenzyl synthase identified from Dendrobium officinale in combination with starter and extender biosynthetic enzymes. Three types of efficiently post-modifying modular strains were engineered by employing methyltransferases, prenyltransferase, and glycosyltransferase with high activity and substrate tolerance together with their corresponding donor biosynthetic modules. Structurally different bibenzyl derivatives were tandemly and/or divergently synthesized by co-culture engineering in various combination modes. Especially, a prenylated bibenzyl derivative ( 12) was found to be an antioxidant that exhibited potent neuroprotective activity in the cellular and rat models of ischemia stroke. RNA-seq, quantitative RT-PCR, and Western-blot analysis demonstrated that 12 could up-regulate the expression level of an apoptosis-inducing factor, mitochondria associated 3 (Aifm3), suggesting that Aifm3 might be a new target in ischemic stroke therapy. This study provides a flexible plug-and-play strategy for the easy-to-implement synthesis of structurally diverse bibenzyls through a modular co-culture engineering pipeline for drug discovery.
ABSTRACT
Fifteen bibenzyls were isolated and purified from the ethyl acetate extract of the stems of Dendrobium officinale by macroporous resin, MCI, silica gel, Sephadex LH-20, and ODS column chromatographies, as well as preparative thin-layer chromatography and preparative HPLC. The structures of compounds were identified according to the spectra data of ~1H-NMR, ~(13)C-NMR, and MS, and the physical and physiochemical properties: dendrocandin X(1), 3,4'-dihydroxy-4,5-dimethoxybibenzyl(2), 6″-de-O-methyldendrofindlaphenol A(3), 3,4-dihydroxy-4',5-dimethoxybibenzyl(4), dendrosinen B(5), 3,4,4'-trihydroxy-5-methoxybibenzyl(6), 3,3'-dihydroxy-4,5-dimethoxybibenzyl(7), 3,4'-dihydroxy-5-methoxybibenzyl(8), moscatilin(9), gigantol(10), 4,4'-dihydroxy-3,5-dimethoxybibenzyl(11), 3,4',5-trihydroxy-3'-methoxybibenzyl(12), 3-O-methylgigantol(13), dendrocandin U(14), and dendrocandin N(15). Compound 1 was a novel compound. Compound 2 was isolated from Dendrobium species for the first time. Compounds 3-7 were isolated from D. officinale for the first time.
Subject(s)
Bibenzyls , Chromatography, High Pressure Liquid , Dendrobium , Magnetic Resonance SpectroscopyABSTRACT
Objective To study the chemical constituents and cytotoxic activity of Dendrobium wardianum. Methods The compounds were separated and purified by various column chromatography techniques and semi-preparative liquid chromatography, and the structures were then identified by NMR, MS and TLC. And the cytotoxic activity of compounds 3, 6, 8, 9, 11, 14, 15 were detected by MTS assay. Results Sixteen compounds were isolated from D. wardianum. They were identified as amotin (1), aduncin (2), E-ferulic acid eicosyl ester (3), E-ferulic acid docosyl ester (4), tetracosyl p-coumarate (5), 4-hydroxy-3-methoxy cinnamaldehyde (6), dihydroconiferyl alcohol (7), 3,7-dimethoxy-5-hydroxy-1,4-phenanthrenequinone (8), 3-ethoxy-5-hydroxy-7- methoxy-1,4-phenanthrenequinone (9), 4-methoxy-9,10-dihydrophilic-2,7-diol (10), 5,7,4’-trihydroxy dihydroflavone (11), 5,7,4’- trihydroxy-3’,5’-dimethoxy dihydroflavone (12), tricin (13), 3,5,4’-trimethoxy-4-hydroxybibenzyl (14), 3,5,3’-trimethoxy-4’- hydroxybibenzyl (15) and 3,3’-dimethoxy-4,5’-dihydroxybibenzyl (16). Compounds 6 and 8 have tumor growth inhibitory activity on tumor growth in vitro. Conclusion Compounds 3, 5, 6 are isolated from Dendrobium for the first time, and 10, 11, 14, 15 are isolated from D. wardianum for the first time. The active components of D. wardianum need to be further explored.
ABSTRACT
Objective: To study the chemical constituents of Dendrobium hercoglossum. Methods: The compounds were isolated and purified by column chromatography and preparative HPLC, and their chemical structures were identified on the basis of spectral analysis. Results: Ten compounds were isolated and identified as 3,4,α-trihydroxy-5,3'-dimethoxybibenzyl (1), 4,α-dihydroxy-3,5,3'- trimethoxybibenzyl (2), 4,5-dihydroxy-3,3',α-trimethoxybibenzyl (3), 4,3'-dihydroxy-3,5-dimethoxybibenzyl (4), 4,4'-dihydroxy- 3,5,3'-trimethoxybibenzyl (5), N-trans-cinnamoyltyramine (6), protocatechuic acid (7), vanillyl alcohol (8), hexadecanoic acid 2,3-dihydroxypropyl ester (9) and syringaresinol (10). Conclusion: Compound 1 is a new compound, named dendhercoine A, compounds 2-10 are isolated from this plant for the first time.
ABSTRACT
Objective: To study the chemical constituents of ethyl acetate extract from the whole herb of Pholidota articulata. Methods: Silica gel and Sephadex LH-20 gel column chromatographic techniques were used to separate and purify the chemical constituents. Their structures were elucidated based on NMR spectroscopic and reported data. Results: A total of 17 compounds were isolated from 78% ethyl acetate extracts of P. articulata and identified as flavidin (1), flaccidin (2), imbricatin (3), coelonin (4), lusianthridin (5), hircinol (6), gigantol (7), batatasin III (8), 5,3'-dihydroxy-3-methoxybibenzyl (9), cirrhopetalidin (10), β-sitosterol (11), stigmasterol (12), glut-5-en-3-ol (13), laurostearic acid (14), 4, 4'-dihydroxydiphenylmethane (15), 3-methoxy-benzaldehyde (16), and trans-cinnamic acid (17). Conclusion: Compounds 3-17 are isolated from this plant for the first time. In addition, compounds 9, 10, 13, and 16 are found in the genus Pholidota for the first time.
ABSTRACT
Objective: To study the chemical constituents from Dendrobium hancockii. Methods: The compounds were isolated and purified by column chromatography and preparative HPLC, and their structures were elucidated by spectral analysis. Results: A total of nine compounds were isolated from D. hancockii and the structures were identified as 3,α-dihydroxy-4,5,3’- trimethoxybibenzyl (1), 3,4’,5-trihydroxy-3-methoxybibenzyl (2), 4,4’-dihydroxy-3,5,3’-trimenthoxybibenzyl (3), 4,3’-dihydroxy- 3,5’-dimethoxybibenzyl (4), 7-hydroxy-2-methoxy-1,4-phenanthrenequinone (5), 2,5-dihydroxy-4-methoxyphenanthrene (6), 2,5-dihydroxy-4,9-dimethoxyphenanthrene (7), nobilone (8), and crepidatuol B (9). Conclusion: Compound 1 is a new compound named dendrohanol A, and compounds 2-9 are isolated from this plant for the first time.
ABSTRACT
ABSTRACT Phytochemical investigation of Bauhinia acuruana Moric., Fabaceae, resulted in the isolation of sixteen constituents, including two new compounds 2'-hydroxy-2,3,5-trimethoxybibenzyl (1), (2R,3S)-2-(3,4'-dihydroxyphenyl)-5-methoxy-6-methylchroman-3,7-diol (2), together with fourteen known ones (3-16). The structures of the compounds were established by spectroscopic analysis including HR-ESI-MS, 1D and 2D NMR data, followed by comparison with previously reported data from the literature. Compounds 1, 2, 6, 7, 8 and 9 were evaluated for their cytotoxicity, which turned out to be marginal in a panel of six human cancer cell lines.
ABSTRACT
Eighteen compounds were isolated from the EtOAc soluble fraction of Bletilla striata by various chromatographic techniques, such as silica gel, ODS, Sephadex LH-20, RP-HPLC. Their structures were identified by spectroscopic methods and physicochemical properties, as 5-hydroxy-2-(p-hydroxybenzyl)- 3- methoxybibenzyl(1), shancigusins B(2), shanciguol(3),arundinan(4), 3',5-dihydroxy-2,4-di(p-hydroxybenzyl)-3-methoxybibenzyl(5), arundin(6), 3,3'-dihydroxy-2-(p-hydroxybenzyl)-5-methoxybibenzyl(7), 3, 3'-dihydroxy-2', 6'-bis(p-hydroxybenzyl)-5-methoxybibenzyl(8), 7-hydroxy-2,4-dimethoxyphenanthrene(9), bleformin B(10),nudol(11), 3,7-dihydroxy-2, 4-dimethoxyphenanthrene(12), 2, 7-dihydroxy-4-methoxy-9,10-dihydrophenathrene(13), bleformin D(14), 4,4'-dimethoxy-9,10-dyhydro-[6,1'-biphenanthrene]-2,2',7,7'-tetraol(15),gymconopin C(16),(2,3-trans)-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-10-methoxy-2,3,4,5-tetrahydro-phenanthro[2,1-b]furan-7-ol(17),shanciol(18). Among them, compound 1 was a new compound, Compounds 2-6,9,15-18 were isolated from this genus for the first time.
ABSTRACT
Phytochemical investigation indicates that plants of Bletilla Rchb. f. have many components with different chemical structures, including bibenzyl, dihydrophenanthrene, stilbene, biphenanthrene, and quinone. These compounds were found to have potent bioactivities, such as hemostasis, antitumor, sterilization and anti-inflammation, healing, and growth promotion of cells. This review focuses on the chemical structures of constituents and medical functions of genus, Bletilla Rchb. f. It would provide a good reference to further utilize this medicinal plant.