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New Bisabolane Sesquiterpenes from the Rhizomes of Curcuma xanthorrhiza Roxb . and Their Inhibitory Effects on UVB‐Induced MMP‐1 Expression in Human Keratinocytes
Author(s) -
Park JiHae,
Jung YeJin,
Antar Aziz Mohamed Mohamed,
Hoon Lee Tae,
Lee ChangHo,
Han Daeseok,
Song MyungChong,
Kim Jiyoung,
Baek NamIn
Publication year - 2014
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201300372
Subject(s) - chemistry , rhizome , curcuma , inhibitory postsynaptic potential , stereochemistry , terpenoid , zingiberaceae , biochemistry , traditional medicine , biology , medicine , neuroscience
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 (7 R ,10 R )‐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.