Isopentenylated Bibenzyls and Phenolic Compounds from <i>Dendrobium chrysotoxum</i> Lindl

Liu, Ying; Zhang, Jiaqian; Zhan, Rui; Chen, Ye‐Gao

doi:10.1002/cbdv.202200259

Cited by 10 publications

(5 citation statements)

References 26 publications

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“…Research shows that the levels of compounds from different Dendrobium varied greatly. In D. nobile , the major metabolite types were alkaloids, terpenoids, flavonoids and phenanthrenes, however, in D. chrysotoxum , the largest number of metabolite types belonged to bibenzyls, phenanthrenes and phenolic acids, which was consistent with previous studies [ 55 – 57 ]. Notably, D. nobile stem is abundant and diversified in alkaloids, such as dendrobine, N-isopentenyl-dendrobinium and N-methyldendrobinium, in D. chrysotoxum , bibenzyls and phenanthrenes secondary metabolites were significantly accumulated, such as chrysotobibenzyl, chrysotoxin, moscatilin, and chrysotoxene.…”

Section: Discussionsupporting

confidence: 92%

Comprehensive chemical profiling of two Dendrobium species and identification of anti-hepatoma active constituents from Dendrobium chrysotoxum by network pharmacology

Xia

Feng

Jiahao

et al. 2023

BMC Complement Med Ther

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Background Dendrobium nobile and Dendrobium chrysotoxum are important species of the genus Dendrobium and have great economic and medicinal value. However, the medicinal properties of these two plants remain poorly understood. This study aimed to investigate the medical properties of D. nobile and D. chrysotoxum by conducting a comprehensive chemical profiling of the two plants. Additionally, active compounds and predictive targets for anti-hepatoma activity in D. chrysotoxum extracts were identified using Network Pharmacology. Results Chemical profiling showed that altogether 65 phytochemicals were identified from D. nobile and D. chrysotoxum, with major classes as alkaloids, terpenoids, flavonoids, bibenzyls and phenanthrenes. About 18 compounds were identified as the important differential metabolites in D. nobile and D. chrysotoxum. Furtherly, CCK-8 results showed that the extracts of stems and leaves of D. nobile and D. chrysotoxum could inhibit the growth of Huh-7 cells, and the anti-hepatoma activity of extracts were dose-dependent. Among the extracts, the extract of D. chrysotoxum showed significant anti-hepatoma activity. In order to find the potential mechanism of anti-hepatoma activity of D. chrysotoxum, five key compounds and nine key targets were obtained through constructing and analyzing the compound-target-pathway network. The five key compounds were chrysotobibenzyl, chrysotoxin, moscatilin, gigantol and chrysotoxene. Nine key targets, including GAPDH, EGFR, ESR1, HRAS, SRC, CCND1, HIF1A, ERBB2 and MTOR, could be considered as the core targets of the anti-hepatoma activity of D. chrysotoxum. Conclusions In this study, the chemical composition difference and anti-hepatoma activity of stems and leaves of D. nobile and D. chrysotoxum were compared, and the potential anti-hepatoma mechanism of D. chrysotoxum was revealed in a multi-target and multi-pathway manner.

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Section: Discussionsupporting

confidence: 92%

Comprehensive chemical profiling of two Dendrobium species and identification of anti-hepatoma active constituents from Dendrobium chrysotoxum by network pharmacology

Xia

Feng

Jiahao

et al. 2023

BMC Complement Med Ther

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show abstract

“…Research shows that the levels of compounds from different Dendrobium varied greatly. Among them, D. nobile stem is abundant and diversi ed in alkaloids, such as dendrobine, N-isopentenyldendrobinium and N-methyldendrobinium, in D. chrysotoxum, bibenzyls and phenanthrenes secondary metabolites were signi cantly accumulated, such as chrysotobibenzyl, chrysotoxin, moscatilin, and chrysotoxene, which was consistent with previous studies [42][43][44]. In addition, we also found that there was no signi cant difference in the chemical composition of stems and leaves of Dendrobium species, indicating that leaves of Dendrobium species are also essential sources of natural lead compounds [45,46].…”

Section: Quality Oriented Metabolite Ngerprintsupporting

confidence: 91%

Comprehensive chemical profiling of two Dendrobium species and identification of anti-hepatoma active constituents from Dendrobium chrysotoxum by Network Pharmacology

Xia

Jiahao

et al. 2022

Preprint

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Background D. nobile and D. chrysotoxum were important species of the genus Dendrobium and has great economic and medicinal value. The material basis of the medicinal effect of D. nobile and D. chrysotoxum is still unclear, and the biomarkers associated with the anti-cancer are not entirely clear so far. There is no scientific, universal and measurable quality control system, which greatly restricts the development of the Dendrobium industry. This study focused on the comprehensive chemical profiling of two Dendrobium species and identification of anti-hepatoma active constituents from Dendrobium chrysotoxum by Network Pharmacology. Results Chemical profiling showed that altogether 65 phytochemicals were identified from D. nobile and D. chrysotoxum, with major classes as alkaloids, terpenoids, flavonoids, bibenzyls and phenanthrenes. About 18 compounds were identified as the important differential metabolites in D. nobile and D. chrysotoxum. Furtherly, CCK-8 results showed that the extracts of stems and leaves of D. nobile and D. chrysotoxum could inhibit the growth of Huh-7 cells, and the anti-hepatoma activity of extracts were dose-dependent. Among the extracts, the extract of D. chrysotoxum showed significant anti-hepatoma activity. To find the material basis and mechanisms underlying the anti-hepatoma activity of D. chrysotoxum. By constructing and analyzing the compound-target-pathway network, five key compounds and nine key targets were obtained. The five key compounds were chrysotobibenzyl, chrysotoxin, moscatilin, gigantol and chrysotoxene. The nine key targets GAPDH, EGFR, ESR1, HRAS, SRC, CCND1, HIF1A, ERBB2 and MTOR could be considered as the core-targets of the hepatoma activity of D. chrysotoxum to hepatoma. Conclusions In this study, mass spectrometry-based molecular networking and multivariate statistical analysis was conducted to screen 18 differential metabolites in D. nobile and D. chrysotoxum. CCK-8 results showed that D. nobile and D. chrysotoxum extracts could inhibit the growth of Huh-7 cells. The molecular network revealed chrysotobibenzyl, chrysotoxin, moscatilin, gigantol and chrysotoxene were identified as core components of D. chrysotoxum on anti-hepatoma. This study compared the chemical composition differences and anti-hepatoma activities between the whole herbs of D. nobile and D. chrysotoxum, and revealed the anti-hepatoma effects of D. chrysotoxum and its potential underlying therapeutic mechanisms in a multi-target and multi-pathway manner.

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“…However, the investigation on secondary metabolisms of planted D. devonianum was limited. Drived by our continuous interests of finding bioactive components from the cultivated Dendrobium species, [7] in this study, we carried out a phytochemical work on D. devonianum collected from greenhouse cultivation base in Mangshi of Yunnan Province. As a result, two new bibenzyl‐phenylpropane hybrids ( Figure 1, 1 – 2 ) and nine known bibenzyls ( 3 – 11 ) were isolated and identified.…”

Section: Introductionmentioning

confidence: 99%

Immunosuppressive Bibenzyl‐phenylpropane Hybrids from Dendrobium devonianum

Zhan

Zhang

et al. 2023

Chemistry & Biodiversity

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Two new bibenzyl‐phenylpropane hybrids, dendrophenols A and B (1 and 2), along with nine known bibenzyls, were isolated from the aerial part of Dendrobium devonianum Paxt. Their structures were determined by extensive spectroscopic methods and methylation. Bioassays revealed that compounds 1–9 were specifically immunosuppressive to T lymphocytes with IC50 values ranging from 0.41 to 9.4 μM, of which compounds 1 (IC50=1.62 μM) and 2 (IC50=0.41 μM) were promising immunosuppressive agents for T lymphocytes with the selectivity indices of 19.9 and 79.5, respectively.

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Isopentenylated Bibenzyls and Phenolic Compounds from Dendrobium chrysotoxum Lindl

Cited by 10 publications

References 26 publications

Comprehensive chemical profiling of two Dendrobium species and identification of anti-hepatoma active constituents from Dendrobium chrysotoxum by network pharmacology

Comprehensive chemical profiling of two Dendrobium species and identification of anti-hepatoma active constituents from Dendrobium chrysotoxum by network pharmacology

Comprehensive chemical profiling of two Dendrobium species and identification of anti-hepatoma active constituents from Dendrobium chrysotoxum by Network Pharmacology

Immunosuppressive Bibenzyl‐phenylpropane Hybrids from Dendrobium devonianum

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