title: Anti-HSV-1, antioxidant and antifouling phenolic compounds from the deep-sea-derived fungus Aspergillus versicolor SCSIO 41502.
abstract: Chemical investigation of the deep-sea-derived fungus Aspergillus versicolor SCSIO 41502 resulted in the isolation of three new anthraquinones, aspergilols G-I (1-3), one new diphenyl ether, 4-carbglyceryl-3,3'-dihydroxy-5,5'-dimethyldiphenyl ether (4), and one new benzaldehyde derivative, 2,4-dihydroxy-6-(4-methoxy-2-oxopentyl)-3-methylbenzaldehyde (5), along with 23 known phenolic compounds (6-28). The structures of new compounds were elucidated by extensive spectroscopic analysis. The absolute configuration of 3 was established by CD spectrum and the modified Mosher method. Compounds 2, 3 and 9 had evident antiviral activity towards HSV-1 with EC50values of 4.68, 6.25, and 3.12μM, respectively. Compounds 15, 18, 20 and 22-24 showed more potent antioxidant activity than l-ascorbic acid with IC50values of 18.92-52.27μM towards DPPH radicals. Comparison of the structures and antioxidant activities of 1-28 suggests that the number of phenolic hydroxyl group that can freely rotate can significantly affect the antioxidant activity of phenolic compounds. In addition, 4, 22-24 and 27 had significant antifouling activity against Bugula neritina larval settlement with EC50values of 1.28, 2.61, 5.48, 1.59, and 3.40μg/ml, respectively.
authors.affiliation: Key Laboratory of Tropical Marine Bio-resources and Ecology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China; University of Chinese Academy of Sciences, Beijing 100049, China.
authors.forename: Zhonghui
authors.initials: Z
authors.lastname: Huang
authors.affiliation: Key Laboratory of Tropical Marine Bio-resources and Ecology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China.
authors.forename: Xuhua
authors.initials: X
authors.lastname: Nong
authors.affiliation: Guangzhou Jinan Biomedicine Research and Development Center, Guangzhou 510632, China.
authors.forename: Zhe
authors.initials: Z
authors.lastname: Ren
authors.affiliation: Key Laboratory of Tropical Marine Bio-resources and Ecology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China.
authors.forename: Jie
authors.initials: J
authors.lastname: Wang
authors.affiliation: Key Laboratory of Tropical Marine Bio-resources and Ecology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China.
authors.forename: Xiaoyong
authors.initials: X
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Tropical Marine Bio-resources and Ecology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China. Electronic address: shuhuaqi@scsio.ac.cn.
authors.forename: Shuhua
authors.initials: S
authors.lastname: Qi
mesh_terms: D000818:Animals; D000880:Anthraquinones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000975:Antioxidants / Q000737:chemistry* / Q000302:isolation & purification; D000998:Antiviral Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D001230:Aspergillus / Q000737:chemistry* / Q000378:metabolism; D057219:Biofouling / Q000517:prevention & control; D002013:Bryozoa / Q000187:drug effects / Q000254:growth & development; D002942:Circular Dichroism; D007814:Larva / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010636:Phenols / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D012623:Seawater / Q000382:microbiology; D013237:Stereoisomerism
chemical_list: D000880:Anthraquinones; D000975:Antioxidants; D000998:Antiviral Agents; D010636:Phenols
keywords: Antifouling; Antioxidant; Antiviral; Aspergillus versicolor; Phenolic compounds