Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, Ohio 43210, United States.
J Nat Prod. 2012 Mar 23;75(3):444-52. doi: 10.1021/np200879p. Epub 2012 Jan 12.
Eight new 16,23-epoxycucurbitacin derivatives, designated as elaeocarpucins A-H (1-8), and five known cucurbitacins (9-13) were isolated from the chloroform-soluble partitions of separate methanol extracts of the fruits and stem bark of Elaeocarpus chinensis collected in Vietnam. Isolation work was facilitated using a LC/MS dereplication procedure, and bioassay-guided fractionation was monitored using HT-29 human cancer cells. The structures of compounds 1-8 were determined on the basis of spectroscopic data interpretation, with the absolute configurations of isomers 1 and 2 established by the Mosher ester method. Compounds 1-13 were evaluated in vitro against the HT-29 cell line and using a mitochondrial transmembrane potential assay. Elaeocarpucin C (3), produced by partial synthesis from 16α,23α-epoxy-3β,20β-dihydroxy-10αH,23βH-cucurbit-5,24-dien-11-one (13), was found to be inactive when evaluated in an in vivo hollow fiber assay using three different cancer cell types (dose range 0.5-10 mg/kg/day, i.p.).
从越南采集的山柑属植物果实和茎皮的甲醇提取物的氯仿可溶部分中分离得到了 8 种新的 16,23-环氧葫芦素衍生物，命名为山柑素 A-H（1-8），和 5 种已知的葫芦素（9-13）。采用 LC/MS 去重复程序进行分离工作，并通过 HT-29 人癌细胞的生物测定指导进行了分馏监测。根据光谱数据分析确定了化合物 1-8 的结构，通过莫斯勒酯法确定了异构体 1 和 2 的绝对构型。对化合物 1-13 进行了体外抗 HT-29 细胞系和线粒体跨膜电位测定的评价。通过从 16α,23α-环氧-3β,20β-二羟基-10αH,23βH-葫芦-5,24-二烯-11-酮（13）部分合成得到的山柑素 C（3），在使用三种不同的癌细胞类型的体内中空纤维测定（剂量范围 0.5-10 mg/kg/天，i.p.）中被发现没有活性。
