Janthinoid A, an unprecedented tri-nor-meroterpenoid with highly modified bridged 4a, 1-(epoxymethano)phenanthrene scaffold, produced by the endophyte of Penicillium janthinellum TE-43. Issue 22 (7th October 2021)

• Record Type: Journal Article
• Authors: Li, Xiao-Dong; Su, Jun-Cheng; Jiang, Bao-Zhen; Li, Ye-Ling; Guo, Yuan-Qiang; Zhang, Peng
• Is Part Of: Organic chemistry frontiers. Volume 8:Issue 22(2021)
• Page Start: 6196
• Page End: 6202
• Publication Date: 2021-10-07
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d1qo01066b
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : Janthinoid A (1 ), an unprecedented C22 meroterpenoid featuring a highly modified bridged 4a, 1-(epoxymethano)phenanthrene scaffold, was produced by Penicillium janthinellum . Abstract : Janthinoid A (1 ), an unprecedented C22 meroterpenoid featuring a highly modified bridged 4a, 1-(epoxymethano)phenanthrene scaffold incorporating eight continuous quaternary carbons, along with its biosynthetic-related C25 analogue andrastone I (2 ), were isolated from the endophytic fungus Penicillium janthinellum TE-43. Their structures were unambiguously established by comprehensive analyses of spectroscopic data, quantum chemical calculations, and X-ray diffraction. The tri- nor -meroterpenoid skeleton of 1 was produced by a unique biosynthetic pathway, involving the ring cleavage and continuous carbon degradations of the aromatic polyketide precursor, which is distinct from the commonly-observed meroterpenoids both structurally and biogenetically, representing a new type of meroterpenoid. Both compounds showed significant in vivo anti-tumor activities against NSCLC cells A549.