Fu Yong-Ge, Huang Yi-Qi, Xu Zhi-Hong, Liu Xia, Yang Xing-Wei
School of Pharmaceutical Sciences (Shenzhen), Sun Yat-Sen University, Shenzhen, 518107, People's Republic of China.
Department of Pharmacy, Chongqing Traditional Chinese Medicine Hospital, Chongqing, 400021, China.
Nat Prod Bioprospect. 2025 May 26;15(1):34. doi: 10.1007/s13659-025-00519-6.
Our continuous study of the fruits of Garcinia xanthochymus and Garcinia subelliptica led to the isolation and structural characterization of six new polyprenylated acylphloroglucinols, xanthochymusones N and O (1 and 2), (-)-garciyunnanin L (3), and garsubelones C-E (4-6), together with two known analogues. Their structures were elucidated by interpretation of NMR and MS spectroscopic data. It was found that the Grossman-Jacobs rule is no longer applicable to determination of the C-7 configuration of compounds 1-3, as they possess a complex 6/6/6/6/6 fused ring system. The inhibitory activities of all the compounds against two human hepatocellular carcinoma cell lines Huh-7 and HepG2 were evaluated, and compound 1 exhibited moderate cytotoxic activities against HepG2 cells with IC value 7.3 μM. Furthermore, the previous assignments of some polyprenylated acylphloroglucinols have been proved to be incorrect in this study, and analysis of NMR data enabled the structural revision of seven analogues: hyperselancins A and B, garcinielliptones F and G, garxanthochins A and B, and 13,14-didehydroxygarcicowin C. The revised structures of garcinielliptone F and garxanthochin A were shown to have the same structures of garsubelone B and xanthochymusone K, respectively, and the revised structures of other five compounds have not been reported.
我们对山竹子和椭圆叶藤黄果实的持续研究，导致了六种新的多异戊烯基化酰基间苯三酚的分离和结构表征，即山竹素N和O（1和2）、（-）-藤黄云南素L（3）以及藤黄椭圆酮C-E（4-6），同时还有两种已知类似物。通过对核磁共振（NMR）和质谱（MS）光谱数据的解释阐明了它们的结构。发现格罗斯曼-雅各布斯规则不再适用于确定化合物1-3的C-7构型，因为它们具有复杂的6/6/6/6/6稠环系统。评估了所有化合物对两种人肝癌细胞系Huh-7和HepG2的抑制活性，化合物1对HepG2细胞表现出中等细胞毒性活性，IC值为7.3 μM。此外，本研究证明了一些多异戊烯基化酰基间苯三酚之前认定的结构是错误 的，对NMR数据的分析使得七种类似物的结构得以修正：超椭圆菌素A和B, 藤黄椭圆酮F和G, 藤黄山竹素A和B, 以及13,14-二脱氢藤黄考因C。藤黄椭圆酮F和藤黄山竹素A修正后的结构分别与藤黄椭圆酮B和山竹素K的结构相同，其他五种化合物修正后的结构尚未见报道。
