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Ergopyrone, a Styrylpyrone-Fused Steroid with a Hexacyclic 6/5/6/6/6/5 Skeleton from a Mushroom Gymnopilus orientispectabilis.
Lee, Seulah; Kim, Chung Sub; Yu, Jae Sik; Kang, Heesun; Yoo, Min Jeong; Youn, Ui Joung; Ryoo, Rhim; Bae, Han Yong; Kim, Ki Hyun.
Afiliación
  • Lee S; School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
  • Kim CS; Division of Life Sciences, Korea Polar Research Institute, KIOST, Incheon 21990, South Korea.
  • Yu JS; School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
  • Kang H; Department of Biopharmaceutical Convergence, Sungkyunkwan University, Suwon 16419, Republic of Korea.
  • Yoo MJ; School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
  • Youn UJ; School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
  • Ryoo R; School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
  • Bae HY; Division of Life Sciences, Korea Polar Research Institute, KIOST, Incheon 21990, South Korea.
  • Kim KH; Department of Polar Sciences, University of Science and Technology, Incheon 21990, South Korea.
Org Lett ; 23(9): 3315-3319, 2021 05 07.
Article en En | MEDLINE | ID: mdl-33826851
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.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Esteroides / Ergosterol / Proteína 1 de Unión a los Elementos Reguladores de Esteroles Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2021 Tipo del documento: Article Pais de publicación: Estados Unidos
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Esteroides / Ergosterol / Proteína 1 de Unión a los Elementos Reguladores de Esteroles Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2021 Tipo del documento: Article Pais de publicación: Estados Unidos