Crotonpenoids A and B, Two Highly Modified Clerodane Diterpenoids with a Tricyclo[7.2.1.0<sup>2,7</sup>]dodecane Core from <i>Croton yanhuii</i>: Isolation, Structural Elucidation, and Biomimetic Semisynthesis
Wei Li, Ruimin Wang, Yue-Hua Pan, Ying-Yuan Zhao, Fang-Yu Yuan, Dong Huang, Gui‐Hua Tang, Huichang Bi, Sheng Yin
Abstract
Crotonpenoids A (1) and B (2), two highly modified clerodane diterpenoids featuring a new 10-(butan-2-yl)-1,6,12-trimethyltricyclo[7.2.1.02,7]dodecane skeleton, were isolated from the leaves and twigs of Croton yanhuii. Their structures including the absolute configurations were determined by spectroscopic analysis, single-crystal X-ray diffraction, and biomimetic semisynthesis. Compounds 1 and 2 exhibited an agonistic effect on pregnane X receptor at 10 μM.
Topics & Concepts
ChemistrySemisynthesisDodecaneStereochemistryCrotonDiterpeneTerpeneBiomimetic synthesisOrganic chemistryBioactive Natural Diterpenoids ResearchTraditional and Medicinal Uses of AnnonaceaePlant biochemistry and biosynthesis