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

Chih-Chuang Liaw; Yu-Liang Yang; Chun-Kuang Lin; Jin-Ching Lee; Wen-Ying Liao; Chia-Ning Shen; Jyh-Horng Sheu; Shih-Hsiung Wu

doi:10.1021/acs.orglett.5b00739

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

Org Lett. 2015 May 15;17(10):2330-3. doi: 10.1021/acs.orglett.5b00739. Epub 2015 Apr 27.

Authors

Chih-Chuang Liaw^{1

2

3}, Yu-Liang Yang^{1

4

3}, Chun-Kuang Lin¹, Jin-Ching Lee^{3

5}, Wen-Ying Liao⁶, Chia-Ning Shen⁶, Jyh-Horng Sheu^{1

2

3}, Shih-Hsiung Wu^{1

7

8}

Affiliations

¹ †Doctoral Degree Program in Marine Biotechnology, National Sun Yat-sen University, Kaohsiung 80424, Taiwan.
² ‡Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 80424, Taiwan.
³ §Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung, Taiwan.
⁴ ∥Agricultural Biotechnology Research Center, Academia Sinica, Taipei 115, Taiwan.
⁵ ▽Department of Biotechnology, Kaohsiung Medical University, Kaohsiung, Taiwan.
⁶ ΔGenomics Research Center, Academia Sinica, Taipei 115, Taiwan.
⁷ □Department of Chemistry and Institute of Biochemical Sciences, National Taiwan University, Taipei 106, Taiwan.
⁸ ○Institute of Biological Chemistry, Academia Sinica, Taipei 115, Taiwan.

PMID: 25915447
DOI: 10.1021/acs.orglett.5b00739

Abstract

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 °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-α-pyrone is proposed. Besides, 2 exhibited a dose-dependent inhibitory effect on COX-2 expression in LPS-stimulated RAW264.7 macrophages.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aspergillus / chemistry*
Crystallography, X-Ray
Cyclooxygenase 2 Inhibitors / chemistry*
Cyclooxygenase 2 Inhibitors / metabolism*
Lipopolysaccharides / pharmacology
Macrophages / drug effects
Magnetic Resonance Spectroscopy
Molecular Structure
Pyrones / chemistry*
Sesquiterpenes / chemistry*
Sesterterpenes / biosynthesis*
Sesterterpenes / chemistry*
Taiwan

Substances

Cyclooxygenase 2 Inhibitors
Lipopolysaccharides
Pyrones
Sesquiterpenes
Sesterterpenes
yaminterritrem A
yaminterritrem B