☆ 4.3 Article

New Bisabolane Sesquiterpenes from the Rhizomes of Curcuma xanthorrhiza Roxb. and Their Inhibitory Effects on UVB-Induced MMP-1 Expression in Human Keratinocytes

HELVETICA CHIMICA ACTA (2014)

Journal

HELVETICA CHIMICA ACTA

Volume 97, Issue 3, Pages 438-446

Publisher

WILEY-V C H VERLAG GMBH

DOI: 10.1002/hlca.201300372

Keywords

MMP-1 Expression; (-)-Curcuhydroquinone 2,5-di-O-beta-D-glucopyranoside; Anti-aging; UV Irradiation; Xanthorrhizol 3-O-beta-D-glucopyranoside, (7R,10R)-10,11-dihydro-10,11-dihydroxy-

Categories

Chemistry, Multidisciplinary

Funding

Mental Health Food Development Program from the Korea Food Research Institute [20130352U0054101S000100]
National Coordinating Center for Global Cosmetics R&D of the Foundation of Korea Cosmetic Industry Institute [A103017]

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Abstract

Two new bisabolane sesquiterpenoids, 1 and 2, along with five known ones, 13-hydroxyxanthorrhizol (3), 12,13-epoxyxanthorrhizol (4), xanthorrhizol (5), beta-curcumene (6), and beta-bisabolol (7), were isolated from the rhizomes of Curcuma xanthorrhiza Roxb. The chemical structures of the new compounds were determined to be (7R,10R)-10,11-dihydro-10,11-dihydroxyxanthorrhizol 3-O-beta-D-glucopyranoside (1) and (-)-curcuhydroquinone 2,5-di-O-beta-D-glucopyranoside (2) on the basis of 1D- and 2D-NMR spectroscopic analyses and optical-rotation characteristics. Compounds 2 and 3 decreased MMP-1 expression in UVB-treated human keratinocytes by ca. 8.9- and 7.6-fold at the mRNA level, and by ca. 9.2- and 6.6-fold at the protein level, respectively. The results indicate that the isolated compounds may have anti-aging effects through inhibition of MMP-1 expression in skin cells.

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