Phytochemical Constituents from the Flowers of Gymnaster koraiensis and Their Cytotoxic Activities in vitro

Lee, Il Kyun; Kim, Ki‐Hyun; Ryu, Shi Yong; Choi, Sang Un; Lee, Kang Ro

doi:10.5012/bkcs.2010.31.01.227

Cited by 16 publications

(11 citation statements)

References 17 publications

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“…Of the cytotoxic C 17 -polyacetylenes from G. koraiensis, (3S,8S)-dehydrofalcarindiol (73) and gymnasterkoreayne C (75) exhibited significant cytotoxicity against the L1210 tumor cells, with ED 50 values of 2.1 and 0.12 µg/mL, respectively, while compounds 76, 82, 83, 85 and 86 were less potently cytotoxic with ED 50 values of 3.1-10.4 µg/mL [116]. These cytotoxic polyacetylenes also occur in the flowers of the plant [118]. The above results indicates that a terminal double bond (vinyl group) in the vicinity to the diyne moiety is important for the enhancement of the cytotoxicity of G. koraiensis polyacetylenes against L1210 tumor cells, and confirm the results from the structure-activity analysis of other cytotoxic C 17 acetylenic oxylipins described in Section 2.1.…”

Section: Cytotoxic C 17 and C 18 Acetylenic Oxylipins From Other Planmentioning

confidence: 98%

Bioactive C17 and C18 Acetylenic Oxylipins from Terrestrial Plants as Potential Lead Compounds for Anticancer Drug Development

Christensen

2020

Molecules

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Bioactive C17 and C18 acetylenic oxylipins have shown to contribute to the cytotoxic, anti-inflammatory, and potential anticancer properties of terrestrial plants. These acetylenic oxylipins are widely distributed in plants belonging to the families Apiaceae, Araliaceae, and Asteraceae, and have shown to induce cell cycle arrest and/or apoptosis of cancer cells in vitro and to exert a chemopreventive effect on cancer development in vivo. The triple bond functionality of these oxylipins transform them into highly alkylating compounds being reactive to proteins and other biomolecules. This enables them to induce the formation of anti-inflammatory and cytoprotective phase 2 enzymes via activation of the Keap1–Nrf2 signaling pathway, inhibition of proinflammatory peptides and proteins, and/or induction of endoplasmic reticulum stress, which, to some extent, may explain their chemopreventive effects. In addition, these acetylenic oxylipins have shown to act as ligands for the nuclear receptor PPARγ, which play a central role in growth, differentiation, and apoptosis of cancer cells. Bioactive C17 and C18 acetylenic oxylipins appear, therefore, to constitute a group of promising lead compounds for the development of anticancer drugs. In this review, the cytotoxic, anti-inflammatory and anticancer effects of C17 and C18 acetylenic oxylipins from terrestrial plants are presented and their possible mechanisms of action and structural requirements for optimal cytotoxicity are discussed.

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Section: Cytotoxic C 17 and C 18 Acetylenic Oxylipins From Other Planmentioning

confidence: 98%

Bioactive C17 and C18 Acetylenic Oxylipins from Terrestrial Plants as Potential Lead Compounds for Anticancer Drug Development

Christensen

2020

Molecules

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“…Compound (10) presented good results against Escherichia coli due to the presence of bulky groups without substituents with two aromatic rings, such as with diphenylmethyl caffeate (10; diphenylmethyl group); this was compared to benzyl caffeate (15; benzyl group), which presented a better bond to its target. e antimicrobial activity of caffeic acid derivatives has been reported in other studies [43,[60][61][62][63][64][65]. For example, Merkl et al [66] investigated the antibacterial activity of a series of caffeic acid esters (methyl, ethyl, propyl, and butyl caffeate) against E. coli DMF 7503.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Antibacterial Evaluation, and QSAR of Caffeic Acid Derivatives

Araújo

Pêssoa

Lira

et al. 2019

Journal of Chemistry

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The present study evaluates the antibacterial effects of a set of 16 synthesized caffeic acid ester derivatives against strains of Staphylococcus aureus and Escherichia coli, as well as discusses their structure-activity relationship (SAR). The antibacterial assays were performed using microdilution techniques in 96-well microplates to determine minimal inhibitory concentration (MIC). The results revealed that five of the compounds present strong to optimum antibacterial effect. Of the sixteen ester derivatives evaluated, the products with alkyl side chains, as propyl caffeate (3), butyl caffeate (6), and pentyl caffeate (7), presented the best antibacterial activity with MIC values of around 0.20 μM against Escherichia coli and only butyl caffeate (6) showing the same MIC against Staphylococcus aureus. For products with aryl substituents, the best MIC results against the tested strain of Escherichia coli were 0.23 µM for (di-(4-chlorobenzyl)) caffeate (13) and 0.29 µM for diphenylmethyl caffeate (10) and all were less active against the Staphylococcus aureus strain. Preliminary quantitative structure-activity relationship (QSAR) analyses confirmed that certain structural characteristics, such as a median linear carbon chain and the presence of electron withdrawal substituents at the para position of the aromatic ring, help potentiate antibacterial activity.

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“…It has been reported that the extracts of A. koraiensis have a variety of biological activities including anti-proliferative activity on human and mouse tumor cell lines [ 3 , 4 ]. The extracts also exhibited antioxidant and α -glucosidase inhibitory activities [ 5 ].…”

Section: Introductionmentioning

confidence: 99%

New Eudesmane-Type Sesquiterpene Glycosides from the Leaves of Aster koraiensis

Kim

Seo

Lee

et al. 2020

Plants

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Four new eudesmane-type sesquiterpenoids, (1R,5S,6R,7S,9S,10S)-1,6,9-trihydroxy-eudesm-3-ene-1,6-di-O-β-d-glucopyranoside (1), (1R,5S,6S,7R,9S,10S)-1,6,9,11-tetrahydroxy-eudesm-3-ene-1,6-di-O-β-d-glucopyranoside (3), (1R,5S,6R,7S,9S,10R)-9-O-(Z-p-coumaroyl)-1,6,9-trihydroxy-eudesm-3-ene-6-O-β-d-glucopyranoside (6), and (1R,5S,6R,7S,9S,10R)-9-O-(E-feruloyl)-1,6,9-trihydroxy-eudesm-3-ene-6-O-β-d-glucopyranoside (7), were isolated from a 95% EtOH extract of the leaves of Aster koraiensis by repeated chromatography. Moreover, three sesquiterpenoids (2, 4, and 5) and two caffeoylquinic acids (8 and 9) having previously known chemical structures were isolated during the isolation procedure. The four new compounds (1, 3, 6, and 7) were elucidated by spectroscopic data (1D- and 2D-NMR, MS, and ECD) interpretation and hydrolysis. Moreover, the absolute configurations of 2, 4, and 5 were determined for the first time in this study. The compounds isolated were tested for their viability on nitric oxide (NO) and prostaglandin E2 (PGE2) production on LPS-stimulated RAW 264.7 cells. Among them, only 7 presented weak inhibitory effects on both NO and PGE2 production.

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Phytochemical Constituents from the Flowers of Gymnaster koraiensis and Their Cytotoxic Activities in vitro

Cited by 16 publications

References 17 publications

Bioactive C17 and C18 Acetylenic Oxylipins from Terrestrial Plants as Potential Lead Compounds for Anticancer Drug Development

Bioactive C17 and C18 Acetylenic Oxylipins from Terrestrial Plants as Potential Lead Compounds for Anticancer Drug Development

Synthesis, Antibacterial Evaluation, and QSAR of Caffeic Acid Derivatives

New Eudesmane-Type Sesquiterpene Glycosides from the Leaves of Aster koraiensis

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