Phenanthrenes, 9,10-dihydrophenanthrenes, bibenzyls with their derivatives, and malate or tartrate benzyl ester glucosides from tubers of Cremastra appendiculata

Seven 9,10-dihydrophenanthrene derivatives and four malate benzyl ester glucosides, along with 23 known compounds were isolated from tubers of Cremastra appendiculata. Among the compounds obtained, one compound showed moderate while five showed weak cytotoxic activity against the A549 cell line. •Se...

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Bibliographic Details
Published in:Phytochemistry (Oxford) 2013-10, Vol.94, p.268-276
Main Authors: Wang, Yang, Guan, Shu-Hong, Meng, Yu-Hui, Zhang, Yi-Bei, Cheng, Chun-Ru, Shi, Yang-Yang, Feng, Rui-Hong, Zeng, Feng, Wu, Zhi-Yuan, Zhang, Jing-Xian, Yang, Min, Liu, Xuan, Li, Qing, Chen, Xiao-Hui, Bi, Kai-Shun, Guo, De-An
Format: Article
Language:English
Subjects:
2,3,4,5-Tetrahydro-phenanthro[2,1-b]furan
9,10-Dihydrophenanthrene
adenosine
Antineoplastic Agents, Phytogenic - chemistry
Antineoplastic Agents, Phytogenic - isolation & purification
Antineoplastic Agents, Phytogenic - pharmacology
Benzene - chemistry
Bibenzyl
Bibenzyls - chemistry
Bibenzyls - isolation & purification
Bibenzyls - pharmacology
Cell Line, Tumor
Cell Survival - drug effects
Cremastra appendiculata
cytotoxicity
Esters - chemistry
glucosides
Glucosides - chemistry
Glucosides - isolation & purification
Glucosides - pharmacology
Humans
Magnetic Resonance Spectroscopy
Malate benzyl ester glucoside
malates
Malates - chemistry
Orchidaceae
Orchidaceae - chemistry
Phenanthrene
Phenanthrenes - chemistry
Phenanthrenes - isolation & purification
Phenanthrenes - pharmacology
Plant Tubers - chemistry
Spectrometry, Mass, Electrospray Ionization
Spectrophotometry, Infrared
Tartrate benzyl ester glucoside
Tartrates - chemistry
tubers
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Summary:Seven 9,10-dihydrophenanthrene derivatives and four malate benzyl ester glucosides, along with 23 known compounds were isolated from tubers of Cremastra appendiculata. Among the compounds obtained, one compound showed moderate while five showed weak cytotoxic activity against the A549 cell line. •Seven 9,10-dihydrophenanthrene derivatives were isolated and identified.•Four malate benzyl ester glucosides were isolated and identified.•Six of the isolated compounds showed cytotoxic activity against the A549 cell line. Eleven previously unknown compounds and 23 known compounds, including 20 phenanthrene or 9,10-dihydrophenanthrene derivatives, five bibenzyls, seven malate or tartrate benzyl ester glucosides, adenosine and gastrodin were isolated from tubers of Cremastra appendiculata. Among the obtained compounds, two are the first isolated dimers with one phenanthrene or bibenzyl unit connected to C-3 of 2,3,4,5-tetrahydro-phenanthro[2,1-b]furan moiety. In addition, 33 of these compounds were evaluated in vitro for their cytotoxic activity against two cancer cell lines. Among the compounds examined, one compound showed moderate cytotoxic activity, while five showed weak cytotoxic activity against the A549 cell line.
ISSN:0031-9422
1873-3700
DOI:10.1016/j.phytochem.2013.06.001