2014
DOI: 10.1007/s12272-014-0525-z
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Germacrane sesquiterpenes isolated from the rhizome of Curcuma xanthorrhiza Roxb. inhibit UVB-induced upregulation of MMP-1, -2, and -3 expression in human keratinocytes

Abstract: Four sesquiterpenes were isolated from the rhizome of Curcuma xanthorrhiza Roxb.: furanodiene (1), germacrone (2), furanodienone (3), and 13-hydroxygermacrone (4). Importantly, this was the first time compounds 1 and 4 were isolated from this plant. The chemical structures of these compounds were determined using 1D- and 2D-nuclear magnetic resonance, infrared spectroscopy, and electron ionization mass spectrometry analyses. Among the isolated compounds, compounds 2 and 4 inhibited UVB-induced upregulation of … Show more

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Cited by 10 publications
(4 citation statements)
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“…Therefore, the prevention of UVB-induced skin damage caused by collagen breakdown could be, at least in the past, attributed to a reduction in the overexpression of MMP-1. In addition, our finding is consistent with other reports demonstrating that (-)-xanthorrhizol (2), isolated from Curcuma xanthorrhiza, significantly reduced MMP-1 expression in a dose-dependent manner [43], while germacrone (3), also isolated from the same plant species, inhibited protein expression levels of MMP-1, MMP-2, and MMP-3 in human keratinocytes and UVB-induced upregulation of the mRNA [44]. However, the molecular mechanism by which the CA and CC extracts Human skin keratinocytes were pre-treated with the tested samples for 24 h before repeated UVB irradiation (100 mJ/cm 2 × 10 times).…”
Section: Evaluation Of the Extracts And Isolated Constituents On Cell...supporting
confidence: 92%
“…Therefore, the prevention of UVB-induced skin damage caused by collagen breakdown could be, at least in the past, attributed to a reduction in the overexpression of MMP-1. In addition, our finding is consistent with other reports demonstrating that (-)-xanthorrhizol (2), isolated from Curcuma xanthorrhiza, significantly reduced MMP-1 expression in a dose-dependent manner [43], while germacrone (3), also isolated from the same plant species, inhibited protein expression levels of MMP-1, MMP-2, and MMP-3 in human keratinocytes and UVB-induced upregulation of the mRNA [44]. However, the molecular mechanism by which the CA and CC extracts Human skin keratinocytes were pre-treated with the tested samples for 24 h before repeated UVB irradiation (100 mJ/cm 2 × 10 times).…”
Section: Evaluation Of the Extracts And Isolated Constituents On Cell...supporting
confidence: 92%
“…Dehydrocurdione 13 13 7α-hydroxyneocurdione (16) No data 7β-hydroxycurdione (17) No data 13 13-hydroxygermacrone (20) [29] Colorless oil (CHCl 3 ); IR (KBr) cm À1 : 3452, 1679. 1 13…”
Section: Resultsmentioning
confidence: 99%
“…Currently, 54 germacrane sesquiterpenoids have been isolated from Curcumae Rhizoma (Figure 2, Table 2). These natural products frequently engage in the formation of a five-membered ring at C-8 and C-12, yielding diverse structural moieties, such as furan rings (139)(140)(141)(142)(143)(144)(145), lactone rings (146)(147)(148)(149)(150)(151)(152)(153)(154)(155)(156)(157)(158), and lactam rings (161-168). This type of compound is prone to oxidation, which can produce aldehydes, ketones, esters, or oxygen bridges.…”
Section: Germacrane-type Sesquiterpenoids Of Curcumae Rhizomamentioning
confidence: 99%