Son Jong Keun, Kim Dal Hwan, Woo Mi Hee
College of Pharmacy, Yeungnam University, Gyeongsan, 712-749, Korea.
J Nat Prod. 2003 Oct;66(10):1369-72. doi: 10.1021/np0301487.
Further studies on the seeds of Annona cherimolia have led to the isolation of two pairs of Annonaceous acetogenins, a mixture of epimers of annomolon A (1) and 34-epi-annomolon A (1'), and a mixture of epimers of annomolon B (2) and 34-epi-annomolon B (2'), containing a rare gamma-hydroxymethyl-gamma-lactone moiety and a carbonyl group. Their structures were elucidated on the basis of spectroscopic and chemical methods, and their absolute stereochemistry was solved by preparing their respective per-Mosher ester derivatives. These acetogenins showed substantial cytotoxicity, comparable to that of adriamycin, against a human pancreatic tumor cell line (MIA PaCa-2).
对番荔枝种子的进一步研究导致分离出两对番荔枝内酯，即番荔枝莫隆A（1）和34-表番荔枝莫隆A（1'）的差向异构体混合物，以及番荔枝莫隆B（2）和34-表番荔枝莫隆B（2'）的差向异构体混合物，它们含有一个罕见的γ-羟甲基-γ-内酯部分和一个羰基。基于光谱和化学方法阐明了它们的结构，并通过制备各自的全莫舍尔酯衍生物确定了它们的绝对立体化学。这些内酯对人胰腺肿瘤细胞系（MIA PaCa-2）显示出与阿霉素相当的显著细胞毒性。
