(±)-Sinensilactam A, a pair of rare hybrid metabolites with Smad3 phosphorylation inhibition from Ganoderma sinensis.
(+)- and (-)-Sinensilactam A (1), novel hybrid metabolites possessing a unique 2H-pyrrolo[2,1-b][1,3]oxazin-6(7H)-one ring system, were isolated from the fruit bodies of Ganoderma sinensis. The structures of these substances and absolute configurations at their stereocenters were assigned using spectroscopic and computational methods along with X-ray crystallographic analysis. A plausible pathway for the biosynthesis of 1 is proposed. (-)-1 was found to be a Smad3 phosphorylation inhibitor in TGF-β1 induced human renal proximal tubular cells.
†State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, P. R. China.|§University of Chinese Academy of Sciences, Beijing 100049, P. R. China.
Qi
Q
Luo
†State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, P. R. China.|‡Henan College of Traditional Chinese Medicine, Zhengzhou 450008, P. R. China.
Lei
L
Tian
†State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, P. R. China.
Lei
L
Di
†State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, P. R. China.|§University of Chinese Academy of Sciences, Beijing 100049, P. R. China.
Yong-Ming
YM
Yan
∥Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Guangzhou 510650, P. R. China.
Xiao-Yi
XY
Wei
†State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, P. R. China.
Xin-Fang
XF
Wang
†State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, P. R. China.|‡Henan College of Traditional Chinese Medicine, Zhengzhou 450008, P. R. China.
Yong-Xian
YX
Cheng
D032902:Ganoderma / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D015394:Molecular Structure; D010766:Phosphorylation / Q000187:drug effects; D051900:Smad3 Protein / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism; D053773:Transforming Growth Factor beta1 / Q000187:drug effects*
D006576:Heterocyclic Compounds, 4 or More Rings; D051900:Smad3 Protein; D053773:Transforming Growth Factor beta1; C000600271:sinensilactam A