Triterpene saponins from Chenopodium quinoa Willd.

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dc.contributor.authorTiwatt Kuljanabhagavad
dc.contributor.authorPiyanut Thongphasuk
dc.contributor.authorWalee Chamulitrat
dc.contributor.authorMichael Wink
dc.contributor.correspondenceM. Wink; Department of Biology, Institute of Pharmacy and Molecular Biotechnology, University of Heidelberg, D-69120 Heidelberg, Im Neuenheimer Feld 364, Germany; email: wink@uni-hd.de
dc.date.accessioned2025-03-10T07:38:07Z
dc.date.available2025-03-10T07:38:07Z
dc.date.issued2008
dc.description.abstractTwenty triterpene saponins (1-20) have been isolated from different parts of Chenopodium quinoa (flowers, fruits, seed coats, and seeds) and their structures have been elucidated by analysis of chemical and spectroscopic data including 1D- and 2D-NMR. Four compounds (1-4) were identified: 3_-[(O-_-d-glucopyranosyl-(1 _ 3)-_-l-arabinopyranosyl)oxy]-23-oxo-olean-12-en-28-oic acid _-d-glucopyranoside (1), 3_-[(O-_-d-glucopyranosyl-(1 _ 3)-_-l-arabinopyranosyl)oxy]-27-oxo-olean-12-en-28-oic acid _-d-glucopyranoside (2), 3-O-_-l-arabinopyranosyl serjanic acid 28-O-_-d-glucopyranosyl ester (3), and 3-O-_-d-glucuronopyranosyl serjanic acid 28-O-_-d-glucopyranosyl ester (4). The following known compounds have not previously been reported as saponin constituents from the flowers and the fruits of this plant: two bidesmosides of serjanic acid (5, 6), four bidesmosides of oleanolic acid (7-10), five bidesmosides of phytolaccagenic acid (11-15), four bidesmosides of hederagenin (16-19), and one bidesmoside of 3_,23,30-trihydroxy olean-12-en-28-oic acid (20). The cytotoxicity of these saponins and their aglycones was tested in HeLa cells. Induction of apoptosis in Caco-2 cells by bidesmosidic saponins 1-4 and their aglycones I-III was determined by flow cytometric DNA analysis. The saponins with an aldehyde group were most active. The relationships between structure and cytotoxic activity of saponins and their aglycones are discussed. © 2008.
dc.identifier.citationPhytochemistry
dc.identifier.doi10.1016/j.phytochem.2008.03.001
dc.identifier.issn319422
dc.identifier.scopus2-s2.0-44549085427
dc.identifier.urihttps://repository.dusit.ac.th//handle/123456789/5051
dc.languageEnglish
dc.rights.holderScopus
dc.subjectApoptosis
dc.subjectBidesmosidic saponins
dc.subjectChemotaxonomy
dc.subjectChenopodium quinoa
dc.subjectCytotoxicity
dc.subjectStructure-activity relationship
dc.titleTriterpene saponins from Chenopodium quinoa Willd.
dc.typeArticle
mods.location.urlhttps://www.scopus.com/inward/record.uri?eid=2-s2.0-44549085427&doi=10.1016%2fj.phytochem.2008.03.001&partnerID=40&md5=42bdd35b373bc02839057cf9e44f032b
oaire.citation.endPage1926
oaire.citation.issue9
oaire.citation.startPage1919
oaire.citation.volume69
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