New Bisabolane Sesquiterpenes from the Rhizomes of Curcuma xanthorrhiza Roxb. and Their Inhibitory Effects on UVB‐Induced MMP‐1 Expression in Human Keratinocytes |
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| Authors: | Ji‐Hae Park Ye‐Jin Jung Mohamed Antar?Aziz?Mohamed Tae Hoon?Lee Chang‐Ho Lee Daeseok Han Myung‐Chong Song Jiyoung Kim Nam‐In Baek |
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| Affiliation: | 1. Graduate School of Biotechnology and Research Institute of Life Sciences & Resources, Kyung Hee University, Yongin 446‐701, Korea, (phone: +82‐31‐201‐2610;2. fax: +82‐31‐204‐8116);3. Division of Matabolism and Functionality Research, Korea Food Research Institute, Sungnam 463‐746, Korea;4. Intelligent Synthetic Biology Center, KAIST, Daejeon 305‐701, Korea |
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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 ), β‐curcumene ( 6 ), and β‐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‐β‐D ‐glucopyranoside ( 1 ) and (?)‐curcuhydroquinone 2,5‐di‐O‐β‐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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| Keywords: | Anti‐aging (− )‐Curcuhydroquinone 2 5‐di‐O‐β ‐D‐glucopyranoside Xanthorrhizol 3‐O‐β ‐D‐glucopyranoside (7R 10R)‐10 11‐dihydro‐10 11‐dihydroxy‐ UV Irradiation MMP‐1 Expression |
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