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Glaucasides A–C, three saikosaponins from Atriplex glauca L. var. ifiniensis (Caball) Maire
Author(s) -
Jabrane Aymen,
Ben Jannet Hichem,
Miyamoto Tomofumi,
Tanaka Chiaki,
Mirjolet JeanFrançois,
Duchamp Olivier,
HarzallahSkhiri Féthia,
LacailleDubois MarieAleth
Publication year - 2011
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.2696
Subject(s) - chemistry , stereochemistry , beta (programming language) , programming language , computer science
From the roots of Atriplex glauca L. var. ifiniensis (Caball) Maire (syn. of Atriplex parvifolia Lowe var. genuina Maire), three new saikosaponins designated as glaucasides A–C ( 1–3 ) were isolated together with the known 3‐ O ‐ $\bf{\beta}$ ‐ D ‐glucopyranosyl‐(1 → 2)‐ $\bf{\beta}$ ‐ D ‐galactopyranosyl‐saikogenin F ( 4 ). The structures of the new compounds were elucidated by extensive analysis of one‐dimensional and two‐dimensional NMR spectroscopy, FABMS, HR‐ESIMS and chemical evidence as 13 $\bf{\beta}$ ,28‐epoxy‐16 $\bf{\beta}$ ,21 $\bf{\beta}$ ‐dihydroxyolean‐11‐en‐3 $\bf{\beta}$ ‐yl O ‐ $\bf{\beta}$ ‐ D ‐[2‐ O ‐sulfate]‐glucopyranosyl‐(1 → 2)‐ $\bf{\alpha}$ ‐ L ‐arabinopyranoside ( 1 ), 13 $\bf{\beta}$ ,28‐epoxy‐16 $\bf{\beta}$ ,21 $\bf{\beta}$ ‐dihydroxyolean‐11‐en‐3 $\bf{\beta}$ ‐yl O ‐ $\bf{\beta}$ ‐ D ‐[2‐ O ‐sulfate]‐glucopyranosyl‐(1 → 2)‐ $\bf{\alpha}$ ‐ L ‐arabinopyranosyl 21‐ O ‐{4‐(secbutylamido)‐butanoyl ester} ( 2 ) and 3‐ O ‐ $\bf{\beta}$ ‐ D ‐glucopyranosyl‐(1 → 2)‐ $\bf{\beta}$ ‐ D ‐galactopyranosyl saikogenin G ( 3 ). The cytotoxic activities of these compounds were evaluated against the HT‐29 and HCT 116 human colon cancer cell lines. Copyright © 2011 John Wiley & Sons, Ltd.