(±)-Pabmaragramin, a scalemic meroterpenoid produced by Marasmius graminum via precursor-assisted biosynthesis. (19th January 2021)

• Record Type: Journal Article
• Authors: Ren, Panlong; Wang, Jing; Miao, Xinyu; Zhu, Weide; Wu, Yueting; Li, Yun; Gao, Kun; Yang, Yan-Long
• Is Part Of: Tetrahedron letters. Volume 63(2021)
• Publication Date: 2021-01-19
• Subjects: Pabmaragramin -- Marasmius graminum -- Precursor-assisted biosynthesis -- α-Glucosidase inhibitory activity; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.152715
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A pair of novel meroterpenoid dimers were obtained from Marasmius graminum . (±)-Pabmaragramin (1 ) possessed an unprecedented 6/6/5/6/6/6/5 polycyclic system. Their absolute configurations were determined by ECD calculations. (+)-1 and (−)-1 exhibited inhibitory activity against α-glucosidase. Abstract: A pair of novel scalemic meroterpenoid dimers, (+)- and (−)-pabmaragramin (1 ), featuring an unprecedented 6/6/5/6/6/6/5 seven-membered ring system, were obtained from Marasmius graminum via precursor-assisted biosynthesis (PAB). Their structures and absolute configurations were determined on the basis of extensive spectroscopic analysis, single-crystal X-ray diffraction, and electronic circular dichroism (ECD) calculations. A plausible biosynthetic pathway for 1 was proposed. Additionally, (+)-1 and (−)-1 exhibited inhibitory activity against α -glucosidase with IC50 values of 3.4 μM and 12.0 μM, respectively.