2. Academic Validation
  3. Asperanstinoids A-E: Undescribed 3,5-dimethylorsellinic acid-based meroterpenoids from Aspergillus calidoustus

Asperanstinoids A-E: Undescribed 3,5-dimethylorsellinic acid-based meroterpenoids from Aspergillus calidoustus

  • Phytochemistry. 2021 Oct;190:112892. doi: 10.1016/j.phytochem.2021.112892.
Shuyuan Mo 1,  Jie Yin 1,  Zi Ye 1,  Fengli Li 1,  Shuang Lin 1,  Sitian Zhang 1,  Beiye Yang 1,  Jun Yao 1,  Jianping Wang 2,  Zhengxi Hu 3,  Yonghui Zhang 4
Affiliations

Affiliations

  • 1 Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, 430030, People's Republic of China.
  • 2 Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, 430030, People's Republic of China. Electronic address: jpwang1001@163.com.
  • 3 Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, 430030, People's Republic of China. Electronic address: hzx616@126.com.
  • 4 Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, 430030, People's Republic of China. Electronic address: zhangyh@mails.tjmu.edu.cn.
PMID: 34343886 DOI: 10.1016/j.phytochem.2021.112892
Abstract

Large-scale culture is a complementary and practical method for genome mining and OSMAC approaches to discover novel Natural Products through accumulation and reprocessing effects. By employing a large-scale culture approach, twelve 3,5-dimethylorsellinic acid (DMOA)-based meroterpenoids, including five undescribed compounds, namely asperanstinoids A-E, were obtained from fungus Aspergillus calidoustus, which was isolated from the wetland soil collected at Dianchi Lake, Yunnan Province. The structures and absolute configurations of asperanstinoids A-E were determined by various spectroscopic analyses, including NMR spectroscopy, high-resolution electrospray ionization mass spectrometry (HRESIMS), single-crystal X-ray diffraction, and electronic circular dichroism (ECD) calculations, and the absolute configurations of three known compounds, dehydroaustinol, austinol, and austin, were confirmed via single-crystal X-ray diffraction for the first time. Notably, asperanstinoid A represents the second example of a DMOA-based meroterpenoid featuring a unique 6/5/6/6/6/5-fused hexacyclic skeleton with a rare "1,13-epoxy" moiety. The cytotoxicity assay of all these isolates revealed that asperanstinoid D, dehydroaustinol, and austin displayed considerable cytotoxicity against the HL-60 and SU-DHL-4 tumor cell lines with IC50 values ranging from 15.7 to 27.8 μM.

Keywords

Aspergillus calidoustus; Cytotoxicity; Meroterpenoids; Trichocomaceae.

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