1. Ergopyrone, a Styrylpyrone-Fused Steroid with a Hexacyclic 6/5/6/6/6/5 Skeleton from a Mushroom Gymnopilus orientispectabilis
- Author
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Min Jeong Yoo, Heesun Kang, Ki Hyun Kim, Rhim Ryoo, Han Yong Bae, Seulah Lee, Chung Sub Kim, Ui Joung Youn, and Jae Sik Yu
- Subjects
Ergosterol ,biology ,010405 organic chemistry ,Stereochemistry ,Chemistry ,medicine.medical_treatment ,Chemical structure ,Organic Chemistry ,Lipid metabolism ,010402 general chemistry ,biology.organism_classification ,01 natural sciences ,Biochemistry ,Cycloaddition ,0104 chemical sciences ,Steroid ,Sterol regulatory element-binding protein ,chemistry.chemical_compound ,Gymnopilus ,medicine ,Physical and Theoretical Chemistry ,Derivative (chemistry) - Abstract
A styrylpyrone-fused ergosterol derivative, ergopyrone (1), was isolated and structurally characterized from a mushroom, Gymnopilus orientispectabilis, along with five biosynthetically related metabolites (2-6). Compound 1 features an unprecedented hexacyclic 6/5/6/6/6/5 skeleton that would be formed from ergosterol and styrylpyrone precursors via [3 + 2] cycloaddition. The chemical structure of 1 was elucidated by conventional spectroscopic and spectrometric data analysis coupled with computational methods including DP4+ probability and ECD simulation and an NOE/ROE-based interproton distance measurement technique via peak amplitude normalization for the improved cross-relaxation (PANIC) method. Plausible biosynthetic pathways of 1-6 are proposed, and compound 6 significantly regulated lipid metabolism in adipocytes through the upregulation of the mRNA expression of Adipsin, Fabp4, SREBP1, and ATGL.
- Published
- 2021
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