PT  - JOURNAL ARTICLE
AU  - Yan Lou
AU  - Hui Zhang
AU  - Hao He
AU  - Kaifeng Peng
AU  - Ning Kang
AU  - Xingchuan Wei
AU  - Xuegai Li
AU  - Lixia Chen
AU  - Xinsheng Yao
AU  - Feng Qiu
TI  - Isolation and Identification of Phase 1 Metabolites of Curcumol in Rats
AID  - 10.1124/dmd.110.034215
DP  - 2010 Nov 01
TA  - Drug Metabolism and Disposition
PG  - 2014--2022
VI  - 38
IP  - 11
4099  - http://dmd.aspetjournals.org/content/38/11/2014.short
4100  - http://dmd.aspetjournals.org/content/38/11/2014.full
SO  - Drug Metab Dispos2010 Nov 01; 38
AB  - Curcumol is one of the major components of the essential oil of Curcuma wenyujin with the structure of a guaiane-type sesquiterpenoid hemiketal. It exhibits clear antitumor, antihepatic fibrosis, antioxidant, and antimicrobial activities. In this article, the metabolism of curcumol in rats was investigated by characterizing metabolites excreted into urine. Sixteen phase 1 metabolites of curcumol were isolated from the urine of rats after an oral dose of 40 mg/kg, and their structures were elucidated on the basis of spectroscopic data. The metabolites were characterized as 2α-hydroxycurcumol (M-1), (11αH)-3α-hydroxy-9-en-8,13-epoxycurcumol (M-2), (11αH)-14-hydroxy-9-en-8,13-epoxycurcumol (M-3), (11βH)-14-hydroxy-9-en-8,12-epoxycurcumol (M-4), 10α,14-dihydroxy-(1αH,7βH)-guai-4-en-3,8-dione (M-5), 10β,14-dihydroxy-(1αH,7βH)-guai-4-en-3,8-dione (M-6), 10β-hydroxy-(1αH,7βH,11αH)-guai-8(13),8(14)-diepoxy-4-en-3-one (M-7), 10β-hydroxy-(1αH,7βH,11βH)-guai-8(12),8(14)-diepoxy-4-en-3-one (M-8), 10α-hydroxy-(1αH,7βH,11αH)-guai-8(13), 8(14)-diepoxy-4-en-3-one (M-9), 10α-hydroxy-(1αH,7βH,11βH)-guai-8(12),8(14)-diepoxy-4-en-3-one (M-10), 10α,14,15-trihydroxy-(1αH,7βH)-guai-4-en-3,8-dione (M-11), 10β-hydroxy-(1αH,7βH)-guai-4-en-3,8-dioxo-13-oic acid (M-12), (1αH,7βH)-guai-4,10(14)-dien-3, 8-dioxo-13-oic acid (M-13), 5β,10β-dihydroxy-(1αH,7βH,11αH)-guai-8(13),8(14)-diepoxide (M-14), 10β,14-dihydroxycurcumol (M-15), and 5β,10β,14-trihydroxy-(1αH,7βH)-guai-8-one (M-16). All were newly identified compounds, among which M-3 and M-4, M-5 and M-6, and M-7, M-8, M-9, and M-10 are three groups of epimers. On the basis of the metabolite profile, the possible metabolic pathways of curcumol in rats are proposed. This is the first study of the metabolites of guaiane-type sesquiterpene in animals.