从蔓性千斤拔的根部分离得到的新型甜 C21 孕烷糖苷。

New Sweet-Tasting C21 Pregnane Glycosides from the Roots of Myriopteron extensum.

机构信息

Key Laboratory of Economic Plants and Biotechnology, Yunnan Key Laboratory for Wild Plant Resources , Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201 , Yunnan China.

University of Chinese Academy of Sciences , Beijing 100049 , China.

出版信息

J Agric Food Chem. 2018 Jul 25;66(29):7735-7739. doi: 10.1021/acs.jafc.8b02348. Epub 2018 Jul 16.

DOI:10.1021/acs.jafc.8b02348

PMID:29965760

Abstract

To investigate the sweet-tasting components in the roots of Myriopteron extensum, the phytochemical study of its roots was conducted, which led to the discovery of 12 new C21 pregnane glycosides (extensumside M-X, 1-12) and two known ones (extensumside C and extensumside E, 13-14). Their chemical structure elucidation was accomplished by means of spectroscopic methods: IR, UV, ESI-MS, and NMR (H NMR, C NMR, HSQC, H-H COSY, HMBC, HSQC-TOCSY, and ROESY), as well as the chemical evidence. Sensory analysis of these compounds revealed that nine of them (1, 3, 4, 5, 6, 7, 8, 13, and 14) are highly sweet-tasting compounds. Their sweetness intensities are 25 to 400 times greater than that of sucrose. Analysis of the structure-activity relationship (SAR) indicated that the sweet intensities of the isolated compounds are closely related to the aglycone 3β,16α-dihydroxy-pregn-5-en-20-one, the number and type of the monosaccharide in the sugar chain linked to C-3 and C-16 and the position of the mBe group.

摘要

为了研究延龄草根中的甜味成分，对其根的植物化学进行了研究，发现了 12 个新的 C21 孕烷糖苷（extensumside M-X，1-12）和 2 个已知的（extensumside C 和 extensumside E，13-14）。通过光谱方法：IR、UV、ESI-MS 和 NMR（H NMR、C NMR、HSQC、H-H COSY、HMBC、HSQC-TOCSY 和 ROESY）以及化学证据确定了它们的化学结构。对这些化合物的感官分析表明，其中 9 种（1、3、4、5、6、7、8、13 和 14）是高甜度化合物。它们的甜度比蔗糖强 25 到 400 倍。对构效关系（SAR）的分析表明，分离化合物的甜度与糖苷配基 3β,16α-二羟基孕甾-5-烯-20-酮、与 C-3 和 C-16 相连的糖链中单糖的数量和类型以及 mBe 基团的位置密切相关。