Transformation of Isosteviol Lactam by Fungi and the Suppressive Effects of Its Transformed Products on LPS-Induced iNOS Expression in Macrophages

被引：15

作者：

Chou, Bo-Hon ^{[1
]}

Yang, Li-Ming ^{[1
,5
]}

Chang, Shwu-Fen ^{[4
]}

Hsu, Feng-Lin ^{[3
]}

Wang, Li-Hsuan ^{[2
,6
]}

Lin, Wen-Kuang ^{[1
]}

Liu, Pan-Chun ^{[1
]}

Lin, Shwu-Jiuan ^{[1
]}

机构：

[1] Taipei Med Univ, Dept Med Chem, Taipei 110, Taiwan

[2] Taipei Med Univ, Dept Clin Pharm, Taipei 110, Taiwan

[3] Taipei Med Univ, Grad Inst Pharmacognosy, Coll Pharm, Taipei 110, Taiwan

[4] Taipei Med Univ, Coll Med, Grad Inst Med Sci, Taipei 110, Taiwan

[5] Natl Res Inst Chinese Med, Div Med Chem, Taipei 112, Taiwan

[6] Taipei Med Univ Hosp, Dept Pharm, Taipei 110, Taiwan

来源：

JOURNAL OF NATURAL PRODUCTS | 2011年 / 74卷 / 06期

关键词：

NITRIC-OXIDE SYNTHASE; MICROBIAL TRANSFORMATION; LIPOPOLYSACCHARIDE; BIOTRANSFORMATION; INHIBITION; LACTONE; CHEMISTRY; SERIES;

D O I：

10.1021/np100915q

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

From the screening of 21 microbial strains, Absidia pseudocylindrospora ATCC 24169 and Aspergillus niger BCRC 32720 were found to reproducibly transform isosteviollactam (4 alpha-carboxy-13 alpha-amino-13,16-seco-ent-19-norbeyeran-16-oic acid 13,16-lactam) (3) into various compounds. Preparative-scale transformation of 3 with Abs. pseudocylindrospora yielded two new hydroxylated compounds (4 and 5), with conservation of the lactam ring. Preparative-scale transformation of 3 with Asp. niger afforded seven new compounds, 6 and 9-14, together with the known compounds 7 and 8. A single-crystal X-ray diffraction experiment confirmed the structure of 14. The suppressive effects of compounds 1-14 on the lipopolysaccharide-induced expression of the inducible nitric oxide synthase gene in RAW 264.7 macrophages were examined by a reverse-transcription real-time PCR analysis. With the exception of 7, all other compounds significantly reduced levels of iNOS mRNA relative to control cells, which were induced by LPS alone. Compounds 2, 3, and 5 were similar in activity to dexamethasone, while 9 was more potent.

引用

页码：1379 / 1385

页数：7

共 34 条

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