Geospallins A⁻C: New Thiodiketopiperazines with Inhibitory Activity against Angiotensin-Converting Enzyme from a Deep-Sea-Derived Fungus Geosmithia pallida FS140

• Published in: Marine drugs Vol. 16; no. 12; p. 464
• Main Authors: Sun, Zhang-Hua, Gu, Jiangyong, Ye, Wei, Wen, Liang-Xi, Lin, Qi-Bin, Li, Sai-Ni, Chen, Yu-Chan, Li, Hao-Hua, Zhang, Wei-Min
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 23.11.2018; MDPI
• Subjects: Angiotensin; Circular dichroism; Communication; Conversion; Cotton; Deep sea; Deep sea environments; Deep water; deep-sea-derived fungus; Dichroism; Enzymes; Fungi; Geosmithia pallida; Hydroxyl groups; Hypertension; Mass spectrometry; Mass spectroscopy; Metabolites; Peptidyl-dipeptidase A; thiodiketopiperazines; thiodiketopiperazines; Geosmithia pallida; deep-sea-derived fungus
• ISSN: 1660-3397; 1660-3397
• DOI: 10.3390/md16120464

Three new thiodiketopiperazines, geospallins A⁻C ( ⁻ ), together with nine known analogues ( ⁻ ), were isolated from the culture of the deep-sea sediment-derived fungus FS140. Among them, geospallins A and B ( and ) represent rare examples of thiodiketopiperazines featuring an S-methyl group at C-10 and a tertiary hydroxyl group at C-11. Their structures were determined by high-resolution electrospray mass spectrometry (HRESIMS), spectroscopic analyses, and electronic circular dichroism (ECD) calculations. Their angiotensin-converting enzyme (ACE) inhibitory activity was reported, and geospallins A⁻C ( ⁻ ) showed inhibitory activity with IC values of 29⁻35 µM.