Secondary Metabolites and Bioactivities of Aspergillus ochraceopetaliformis Isolated from Anthurium brownii

Hao-Chun Hu; Chi-Ying Li; Yi-Hong Tsai; Dai-Yun Yang; Yang-Chang Wu; Tsong-Long Hwang; Shu-Li Chen; Ferenc Fülöp; Attila Hunyadi; Chia-Hung Yen; Yuan-Bin Cheng; Fang-Rong Chang

doi:10.1021/acsomega.0c02489

Secondary Metabolites and Bioactivities of Aspergillus ochraceopetaliformis Isolated from Anthurium brownii

ACS Omega. 2020 Aug 14;5(33):20991-20999. doi: 10.1021/acsomega.0c02489. eCollection 2020 Aug 25.

Authors

Hao-Chun Hu¹, Chi-Ying Li², Yi-Hong Tsai¹, Dai-Yun Yang¹, Yang-Chang Wu³, Tsong-Long Hwang^{4

5

6}, Shu-Li Chen¹, Ferenc Fülöp^{7

8}, Attila Hunyadi⁹, Chia-Hung Yen¹, Yuan-Bin Cheng^{1

10}, Fang-Rong Chang^{1

11

10}

Affiliations

¹ Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
² Department of Pharmacology and Pharmaceutical Sciences, School of Pharmacy, University of Southern California, 1985 Zonal Avenue, Los Angeles, California 90089, United States.
³ Graduate Institute of Integrated Medicine and Chinese Medicine Research and Development Center, China Medical University, Taichung 404, Taiwan.
⁴ Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan 333, Taiwan.
⁵ Research Center for Chinese Herbal Medicine, Research Center for Food and Cosmetic Safety, and Graduate Institute of Health Industry Technology, College of Human Ecology, Chang Gung University of Science and Technology, Taoyuan 333, Taiwan.
⁶ Department of Anesthesiology, Chang Gung Memorial Hospital, Taoyuan 333, Taiwan.
⁷ Institute of Pharmaceutical Chemistry, University of Szeged, Szeged 6720, Hungary.
⁸ MTASZTE Stereochemistry Research Group, Hungarian Academy of Sciences, Szeged 6720, Hungary.
⁹ Institute of Pharmacognosy, Interdisciplinary Excellence Center, and Interdisciplinary Centre for Natural Products, University of Szeged, Szeged 6720, Hungary.
¹⁰ Department of Marine Biotechnology and Resources, National Sun Yat-Sen University, Kaohsiung 804, Taiwan.
¹¹ Drug Development and Value Creation Research Center and Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung Medical University, Kaohsiung 807, Taiwan.

Abstract

Five new polyketides, asperochrapyran (1) and asperochralactones A-D (2-5), along with 12 known polyketides (6-17), were obtained from the fungal strain Aspergillus ochraceopetaliformis. Structures of all isolates were elucidated by their spectroscopic parameters. The relative configurations of the new compounds were deduced by the data of coupling constants and NOESY spectra. The absolute configurations were determined by the comparison of experimental and calculated ECD spectra. Moreover, the plausible biosynthesis pathway of major isolates was proposed as well. Anti-inflammatory activity of compounds 5 and 7-17 were evaluated with human neutrophils in response to the stimulation of formyl-methionyl-leucyl phenylalanine (fMLP). Asperlactone (9), aspyrone (13), and (-)-(3R)-mellein (14) exerted superoxide anion inhibition at 30 ± 9%, 29 ± 9%, and 26 ± 12%, respectively, at 10 μM. The capacities of asperlactone (9), aspilactonol B (10), penicillic acid (12), and (-)-(3R)-mellein (14) in elastase release inhibition were revealed as 25 ± 4%, 38 ± 8%, 25 ± 5%, and 34 ± 9%, respectively, at 10 μM.