A pair of epimeric cassane-type diterpenoids and a new labdane-type derivative from Caesalpinia decapetala. Issue 28 (12th July 2018)

• Record Type: Journal Article
• Authors: Qiao, Yuben; Liu, Yanfei; Duan, Xueyan; Chen, Chunmei; Liu, Junjun; Zhu, Hucheng; Xue, Yongbo; Zhang, Yonghui
• Is Part Of: Tetrahedron. Volume 74:Issue 28(2018)
• Page Start: 3852
• Page End: 3857
• Publication Date: 2018-07-12
• Subjects: Caesalpinia decapetala (Roth) Alston -- Cassane-type furanoditerpenoid -- Mixture of epimers -- ECD calculations -- Antibacterial activities; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.05.028
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Caesaldecins A and B (1 a/1 b), a pair of epimeric cassane-type diterpenoids containing an ether linkage between C-6 and C-20 and an α, β -butenolide ring in the northern hemisphere, were isolated from the leaves of the medicinal plant Caesalpinia decapetala (Roth) Alston, along with a new labdane-type diterpenoid, termed as 8(17), 11( Z ), 13( E )-trien-15, 18-dioic acid (2 ). Structures of 1 and 2 were established by extensive spectroscopic analyses, including HRESIMS, 1D and 2D NMR, and electronic circular dichroism (ECD) calculations. The in vitro antibacterial and inhibitory activities against a panel of bacteria and cancer cell lines were evaluated, respectively. Compound 2 displayed moderate antibacterial activity against the methicillin-resistant Staphylococcus aureus subsp. aureus (MRSA) with an MIC50 value of 5.99 μg mL −1 . Graphical abstract: Image 1 Highlights: A pair of epimeric cassane and a new labdane diterpenoids were isolated from Caesalpinia decapetala (Roth) Alston. Compounds 1 a/1 b contained an ether linkage between C-6 and C-20 and an α, β -butenolide ring. Compound 2 displayed moderate antibacterial activity against MRSA with MIC50 value 5.99 μg mL −1 .