2,3-Seco- and 3,4-seco-tirucallane triterpenoid derivatives from the stems of Aphanamixis grandifolia Blume

• Published in: Phytochemistry (Oxford) Vol. 80; pp. 148 - 155
• Main Authors: Zeng, Qi, Guan, Bin, Qin, Jiang-Jiang, Wang, Chun-Hui, Cheng, Xiang-Rong, Ren, Jie, Yan, Shi-Kai, Jin, Hui-Zi, Zhang, Wei-Dong
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.08.2012; Elsevier
• Subjects: 2,3-Seco-tirucallane triterpenoid; 3,4-Seco-tirucallane triterpenoid; Aphanamixis; Aphanamixis grandifolia Blume; Biochemistry & Molecular Biology; crystals; Life Sciences & Biomedicine; Meliaceae; Meliaceae - chemistry; Models, Molecular; Molecular Conformation; Plant Sciences; Plant Stems - chemistry; Science & Technology; stems; Triterpenes - chemistry; Triterpenes - isolation & purification; triterpenoids; X-radiation; Aphanamixis grandifolia Blume; 3,4-Seco-tirucallane triterpenoid; 2,3-Seco-tirucallane triterpenoid; Meliaceae; TIRUCALLANE TRITERPENES; Aphanambcis granchfolia Blume; CONSTITUENTS
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2012.05.017

Twelve unreported and three known tirucallane triterpenoids were isolated from the stems of Aphanamixis grandifolia Blume. [Display omitted] ► Fifteen triterpenoids were indentified from Aphanamixis grandifolia Blume, among them 12 were hitherto unknown compounds. ► Aphanamgrandins A–F were 2,3-seco tirucallane type triterpenoid derivatives. ► Aphanamgrandins G–I were 3,4-seco-29-nor tirucallane type triterpenoid derivatives. ► The absolute configurations of aphanamgrandins A and B were determined by X-ray analysis. Six 2,3-seco-tirucallane triterpenoid derivatives (aphanamgrandins A–F), three 3,4-seco-29-nor-tirucallane triterpenoid derivatives (aphanamgrandins G–I), one 3,4-seco-tirucallane triterpenoid (aphanamgrandin J), two tirucallane triterpenoids [aphanamgrandin K and (23Z)-25-hydroxy-tirucalla-7,23-diene-3-one], and three known triterpenoids were isolated from stems of Aphanamixis grandifolia Blume, and their structures were established by extensive spectroscopic and X-ray crystal diffraction studies.