Biotransformation of Curcumenol by Mucor polymorphosporus

被引：14

作者：

Chen, Li-Xia ^{[1
]}

Zhao, Qian ^{[1
]}

Zhang, Meng ^{[1
]}

Liang, Yan-Yan ^{[1
]}

Ma, Jiang-Hao ^{[1
]}

Zhang, Xue ^{[1
]}

Ding, Li-Qin ^{[2
]}

Zhao, Feng ^{[3
]}

Qiu, Feng ^{[1
,2
]}

机构：

[1] Shenyang Pharmaceut Univ, Dept Nat Prod Chem, Sch Tradit Chinese Mat Med, Key Lab Struct Based Drug Design & Discovery,Mini, Shenyang 110016, Peoples R China

[2] Tianjin Univ Tradit Chinese Med, Sch Chinese Mat Med, Tianjin State Key Lab Modern Chinese Med, Tianjin 300193, Peoples R China

[3] Yantai Univ, Sch Pharm, Laishan Dist 264005, Yantai, Peoples R China

来源：

JOURNAL OF NATURAL PRODUCTS | 2015年 / 78卷 / 04期

基金：

中国国家自然科学基金;

关键词：

GUAIANE-TYPE SESQUITERPENES; MICROBIAL TRANSFORMATION; NITRIC-OXIDE; STRUCTURAL DETERMINATION; GLYCYRRHETINIC ACID; DIARYLHEPTANOIDS; RHIZOMES; DEHYDROCOSTUSLACTONE; BIOCATALYSIS; PHAEOCAULIS;

D O I：

10.1021/np500845z

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

Biocatalysis of curcumenol (1) was performed by Mucor polymorphosporus AS 3.3443. Six metabolites including five new compounds were obtained, and their structures were elucidated as 10 beta-hydroxy-9,10-dihydrocurcumenol (2), 2 beta-hydroxycurcumenol (3), 15-hydroxycurcumenol (4), 12-hydroxycurcumenol (5), 1-hydroxy-4 alpha H-guai-1,6,9-triene-2,8-dione (6), and 5-hydroxycarbonyl-1-oxo-3,7-dimethylindane (7) by spectroscopic analysis. M. polymorphosporus catalyzed unusual degradation and rearrangement reactions to generate a ring-contracted metabolite (7) of curcumenol (1). Curcumenol (1) and metabolites 47 exhibited inhibitory activities against lipopolysaccharide-induced nitric oxide production in RAW 264.7 macrophages, with 7 exhibiting more potent activity than curcumenol.

引用

页码：674 / 680

页数：7

共 42 条

[1] [Anonymous], 2017, PHARM, V524, P257
[2] Transformation of Isosteviol Lactam by Fungi and the Suppressive Effects of Its Transformed Products on LPS-Induced iNOS Expression in Macrophages
Chou, Bo-Hon
Yang, Li-Ming
Chang, Shwu-Fen
Hsu, Feng-Lin
Wang, Li-Hsuan
Lin, Wen-Kuang
Liu, Pan-Chun
Lin, Shwu-Jiuan
[J]. JOURNAL OF NATURAL PRODUCTS, 2011, 74 (06): : 1379 - 1385
[3] Expanding the organic toolbox: a guide to integrating biocatalysis in synthesis
Clouthier, Christopher M.
Pelletier, Joelle N.
[J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (04) : 1585 - 1605
[4] The Griess assay: Suitable for a bio-guided fractionation of anti-inflammatory plant extracts?
Dirsch, VM
Stuppner, H
Vollmar, AM
[J]. PLANTA MEDICA, 1998, 64 (05) : 423 - 426
[5] Synergistic anticancer effects of curcumin and resveratrol in Hepa1-6 hepatocellular carcinoma cells
Du, Qin
Hu, Bing
An, Hong-Mei
Shen, Ke-Ping
Xu, Ling
Deng, Shan
Wei, Meng-Meng
[J]. ONCOLOGY REPORTS, 2013, 29 (05) : 1851 - 1858
[6] Grogan G, 2012, ANNU REP PROG CHEM B, V108, P202, DOI 10.1039/c2oc90012b
[7] Guzik TJ, 2003, J PHYSIOL PHARMACOL, V54, P469
[8] Jurenka JS, 2009, ALTERN MED REV, V14, P141
[9] Kröncke KD, 1998, CLIN EXP IMMUNOL, V113, P147
[10] MACROPHAGES AND INFLAMMATORY MEDIATORS IN TISSUE-INJURY
LASKIN, DL
PENDINO, KJ
[J]. ANNUAL REVIEW OF PHARMACOLOGY AND TOXICOLOGY, 1995, 35 : 655 - 677

← 1 2 3 4 5 →