Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Indole Glycosides from Calanthe discolor with Proliferative Activity on Human Hair Follicle Dermal Papilla Cells
Toshio MorikawaYoshiaki ManseFenglin LuoHaruko FukuiYamato InoueTsuyoshi KaiedaKiyofumi NinomiyaOsamu MuraokaMasayuki Yoshikawa
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2021 Volume 69 Issue 5 Pages 464-471


A methanol extract from the underground part of Calanthe discolor Lindl. (Orchidaceae) demonstrated significant proliferative activity on human hair follicle dermal papilla cells (HFDPC, % of control: 120.8 ± 0.2%) at 100 µg/mL against HFDPC. Through bioassay-guided separation of the extract, a new indole glycoside named 6′-O-β-D-apiofuranosylindican (1) was isolated along with six known compounds (27) including three indole glycosides. The stereostructure of 1 was elucidated based on its spectroscopic properties and chemical characteristics. Among the isolates, 1 (110.0 ± 1.0%), glucoindican (3, 123.9 ± 6.8%), and calanthoside (4, 158.6 ± 7.1%) showed significant proliferative activity at 100 µM. Furthermore, the active indole glycosides (1, 3, and 4) upregulated the expression of vascular endothelial growth factor (VEGF) and fibroblast growth factor-7 (FGF-7) mRNA and protein in HFDPC, which could be the mechanism of their proliferative activity.

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