Butenolide derivatives from the plant endophytic fungus Aspergillus terreus

Feng Guo; Zhanlin Li; Xiangwei Xu; Kaibo Wang; Meili Shao; Feng Zhao; Haifeng Wang; Huiming Hua; Yuehu Pei; Jiao Bai

doi:10.1016/j.fitote.2016.06.014

Butenolide derivatives from the plant endophytic fungus Aspergillus terreus

Fitoterapia. 2016 Sep:113:44-50. doi: 10.1016/j.fitote.2016.06.014. Epub 2016 Jun 28.

Authors

Feng Guo¹, Zhanlin Li¹, Xiangwei Xu¹, Kaibo Wang¹, Meili Shao¹, Feng Zhao², Haifeng Wang¹, Huiming Hua¹, Yuehu Pei¹, Jiao Bai³

Affiliations

¹ Key Laboratory of Structure-Based Drug Design and Discovery, Shenyang Pharmaceutical University, Ministry of Education, Shenyang 110016, PR China; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, PR China.
² School of Pharmacy, Key Laboratory of Molecular Pharmacology and Drug Evaluation (Yantai University), Ministry of Education, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, Yantai University, Yantai 264005, PR China. Electronic address: ytuzhaofeng@163.com.
³ Key Laboratory of Structure-Based Drug Design and Discovery, Shenyang Pharmaceutical University, Ministry of Education, Shenyang 110016, PR China; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, PR China. Electronic address: baijiao@hotmail.com.

PMID: 27370101
DOI: 10.1016/j.fitote.2016.06.014

Abstract

Three new butenolides containing 5-hydroxyfuran-2(5H)-one core, asperteretal A (1), asperteretal B (2), and asperteretal C (3), together with seven known butenolides (4-10), were obtained from an endophytic fungus Aspergillus terreus PR-P-2 isolated from the plant Camellia sinensis var. assamica. The structures of compounds 1-3 were elucidated on the basis of detailed spectroscopic analysis including UV, IR, HRESIMS, 1D and 2D NMR, and ECD spectra. Compounds 1, 3, 5 and 6-8 showed potent inhibitory effects on NO production in RAW 264.7 lipopolysaccharide-induced macrophages, and compounds 5 and 8 also exhibited moderate cytotoxicity against HL-60 cell line.

Keywords: Anti-inflammatory activity; Aspergillus terreus; Butenolides; Endophytic fungus; Structure elucidation.

MeSH terms

4-Butyrolactone / analogs & derivatives*
4-Butyrolactone / chemistry
4-Butyrolactone / isolation & purification
Animals
Anti-Inflammatory Agents / chemistry
Anti-Inflammatory Agents / isolation & purification
Antineoplastic Agents / chemistry
Antineoplastic Agents / isolation & purification
Aspergillus / chemistry*
Camellia sinensis / microbiology*
Endophytes / chemistry
HL-60 Cells
Humans
Mice
Molecular Structure
Nitric Oxide / metabolism
RAW 264.7 Cells

Substances

Anti-Inflammatory Agents
Antineoplastic Agents
Nitric Oxide
butenolide
4-Butyrolactone