Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-Machi, Nagasaki 852-8521, Japan.
Phytochemistry. 2011 Nov;72(16):2006-14. doi: 10.1016/j.phytochem.2011.07.007. Epub 2011 Aug 8.
Triterpene hexahydroxydiphenoyl (HHDP) esters have only been isolated from Castanopsis species, and the distribution of these esters in nature is of chemotaxonomical interest. In this study, the chemical constituents of the leaves of Castanopsis fissa were examined in detail to identify and isolate potential HHDP esters. Together with 53 known compounds, 3,4-di-O-galloyl-1-O-purpurogallin carbonyl quinic acid (1) and 3,24-(S)-HHDP-2α,3β,23,24-tetrahydroxytaraxastan-28,20β-olide (2) were isolated and their structures were elucidated by spectroscopic and chemical methods. The polyphenols of the leaves were mainly composed of galloyl quinic acids, triterpenes HHDP esters, ellagitannins and flavonol glycosides. In particular, the isolation yields of 1,3,4-trigalloyl quinic acid and compound 2 were 1.53% and 0.27%, respectively, from the fresh leaves. The presence of lipid soluble HHDP esters of oleanane-type triterpenes as one of the major metabolites is an important chemotaxonomical discovery. Lipase inhibition activities and ORAC values of the major constituents were compared. The triterpene HHDP ester showed moderate lipase inhibition activity and myricitrin gave the largest ORAC value.
三萜六羟基二苯酰基（HHDP）酯仅从柯属植物中分离得到，这些酯在自然界中的分布具有化学生态学意义。本研究详细研究了甜槠叶的化学成分，以鉴定和分离潜在的 HHDP 酯。除了 53 种已知化合物外，还分离得到了 3,4-二-O-没食子酰基-1-O-鞣花酰基奎宁酸（1）和 3,24-(S)-HHDP-2α,3β,23,24-四羟基达玛烷-28,20β-内酯（2），并通过光谱和化学方法阐明了它们的结构。叶中的多酚主要由没食子酰奎宁酸、三萜 HHDP 酯、鞣花单宁和黄酮醇糖苷组成。特别是，1,3,4-三没食子酰奎宁酸和化合物 2 的分离产率分别为新鲜叶片的 1.53%和 0.27%。作为主要代谢物之一的齐墩果烷型三萜 HHDP 酯的脂溶性存在是一个重要的化学生态学发现。比较了主要成分的脂肪酶抑制活性和 ORAC 值。三萜 HHDP 酯表现出中等的脂肪酶抑制活性，杨梅素具有最大的 ORAC 值。
