New Meroterpenoids from Aspergillus terreus with Inhibition of Cyclooxygenase-2 Expression

被引：38
作者：
Liaw, Chih-Chuang [1 ,2 ,4 ]
Yang, Yu-Liang [1 ,3 ,4 ]
Lin, Chun-Kuang [1 ]
Lee, Jin-Ching [4 ,5 ]
Liao, Wen-Ying [6 ]
Shen, Chia-Ning [6 ]
Sheu, Jyh-Horng [1 ,2 ,4 ]
Wu, Shih-Hsiung [1 ,7 ,8 ,9 ]
机构：
[1] Natl Sun Yat Sen Univ, Doctoral Degree Program Marine Biotechnol, Kaohsiung 80424, Taiwan
[2] Natl Sun Yat Sen Univ, Dept Marine Biotechnol & Resources, Kaohsiung 80424, Taiwan
[3] Acad Sinica, Agr Biotechnol Res Ctr, Taipei 115, Taiwan
[4] Kaohsiung Med Univ, Grad Inst Nat Prod, Kaohsiung, Taiwan
[5] Kaohsiung Med Univ, Dept Biotechnol, Kaohsiung, Taiwan
[6] Acad Sinica, Genom Res Ctr, Taipei 115, Taiwan
[7] Natl Taiwan Univ, Dept Chem, Taipei 106, Taiwan
[8] Natl Taiwan Univ, Inst Biochem Sci, Taipei 106, Taiwan
[9] Acad Sinica, Inst Biol Chem, Taipei 115, Taiwan
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 10期
关键词：
PHYSICOCHEMICAL PROPERTIES; ALZHEIMERS-DISEASE; ACETYLCHOLINESTERASE; CELLS; COX-2;
D O I：
10.1021/acs.orglett.5b00739
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two novel meroterpenoids, yaminterritrems A (1) and B (2), were isolated from Aspergillus terreus collected from hot spring zones in Yang-Ming Mountain, Taiwan, and cultured at 40 degrees C. The structures of 1 and 2 were elucidated by NMR, MS spectral and X-ray crystallographic analyses. The biosynthetic route for 1 and 2 involving the conversion of the sesquiterpene with phenyl-alpha-pyrone is proposed. Besides, 2 exhibited a dose-dependent inhibitory effect on COX-2 expression in LPS-stimulated RAW264.7 macrophages.
引用
收藏
页码：2330 / 2333
页数：4
相关论文
共 11 条
[1]   DELAYED-ONSET OF ALZHEIMERS-DISEASE WITH NONSTEROIDAL ANTIINFLAMMATORY AND HISTAMINE-H2 BLOCKING-DRUGS [J].
BREITNER, JCS ;
WELSH, KA ;
HELMS, MJ ;
GASKELL, PC ;
GAU, BA ;
ROSES, AD ;
PERICAKVANCE, MA ;
SAUNDERS, AM .
NEUROBIOLOGY OF AGING, 1995, 16 (04) :523-530
[2]   Forced COX-2 expression induces PGE2 and invasion in immortalized urothelial cells [J].
Gee, Jason ;
Lee, I-Ling ;
Grossman, H. Barton ;
Sabichi, Anita L. .
UROLOGIC ONCOLOGY-SEMINARS AND ORIGINAL INVESTIGATIONS, 2008, 26 (06) :641-645
[3]   COX-2 as a target for cancer chemotherapy [J].
Ghosh, Nilanjan ;
Chaki, Rituparna ;
Mandal, Vivekananda ;
Mandal, Subhash C. .
PHARMACOLOGICAL REPORTS, 2010, 62 (02) :233-244
[4]   Terreulactones A, B, C, and D:: Novel acetylcholinesterase inhibitors produced by Aspergillus terreus -: II.: Physico-chemical properties and structure determination [J].
Kim, WG ;
Cho, KM ;
Lee, CK ;
Yoo, ID .
JOURNAL OF ANTIBIOTICS, 2003, 56 (04) :351-357
[5]   Deletion of the prostaglandin E2 EP2 receptor reduces oxidative damage and amyloid burden in a model of Alzheimer's disease [J].
Liang, XB ;
Wang, Q ;
Hand, T ;
Wu, LJ ;
Breyer, RM ;
Montine, TJ ;
Andreasson, K .
JOURNAL OF NEUROSCIENCE, 2005, 25 (44) :10180-10187
[6]   Asperjinone, a Nor-Neolignan, and Terrein, a Suppressor of ABCG2-Expressing Breast Cancer Cells, from Thermophilic Aspergillus terreus [J].
Liao, Wen-Ying ;
Shen, Chia-Ning ;
Lin, Li-Hua ;
Yang, Yu-Liang ;
Han, Hsin-Ying ;
Chen, Jing-Wei ;
Kuo, Sheng-Chu ;
Wu, Shih-Hsiung ;
Liaw, Chih-Chuang .
JOURNAL OF NATURAL PRODUCTS, 2012, 75 (04) :630-635
[7]   ISOLATION, CHEMICAL-STRUCTURE, ACUTE TOXICITY, AND SOME PHYSICOCHEMICAL PROPERTIES OF TERRITREM-C FROM ASPERGILLUS-TERREUS [J].
LING, KH ;
LIOU, HH ;
YANG, CM ;
YANG, CK .
APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 1984, 47 (01) :98-100
[8]   PYRIPYROPENES, HIGHLY POTENT INHIBITORS OF ACYL-COA - CHOLESTEROL ACYLTRANSFERASE PRODUCED BY ASPERGILLUS-FUMIGATUS [J].
OMURA, S ;
TOMODA, H ;
KIM, YK ;
NISHIDA, H .
JOURNAL OF ANTIBIOTICS, 1993, 46 (07) :1168-1169
[9]   ARISUGACIN, A NOVEL AND SELECTIVE INHIBITOR OF ACETYLCHOLINESTERASE FROM PENICILLIUM SP FO-4259 [J].
OMURA, S ;
KUNO, F ;
OTOGURO, K ;
SUNAZUKA, T ;
SHIOMI, K ;
MASUMA, R ;
IWAI, Y .
JOURNAL OF ANTIBIOTICS, 1995, 48 (07) :745-746
[10]   ACETYLCHOLINESTERASE INHIBITION BY TERRITREM-B DERIVATIVES [J].
PENG, FC .
JOURNAL OF NATURAL PRODUCTS-LLOYDIA, 1995, 58 (06) :857-862
12