Liaw Chia-Ching, Lo I-Wen, Lin Yu-Chi, Huang Hung-Tse, Zhang Li-Jie, Hsiao Pin-Chun, Li Tsung-Lin, Kuo Yao-Haur
Division of Chinese Material Medica Development, National Research Institute of Chinese Medicine, Taipei 112026, Taiwan.
Department of Biochemical Science and Technology, National Chiayi University, Chiayi 600355, Taiwan.
Food Chem X. 2022 Mar 16;14:100286. doi: 10.1016/j.fochx.2022.100286. eCollection 2022 Jun 30.
Four novel triterpene glycosides, taimordisins A-D (-), were discovered from fresh fruits of Taiwanese . The chemical framework and relative stereochemistry of these four natural products were isolated, purified, and determined by using various separation and spectroscopy techniques. Each of them features a unique bicyclic-fused or trifuso-centro-fused ring system. Notably, and are cucurbitane-based compounds possessing a new C-24 and C-2″ carbon-carbon linkage with 5-hydroxy-2-(hydroxymethyl)tetrahydro-4-pyran-4-one and 6-(hydroxymethyl)tetrahydro-4-pyran-3,4,4-triol units, respectively, and represented an unprecedented molecular skeleton. In terms of biosynthesis, they all originate from a common precursor 3-hydroxycucurbita-5,24-dien-19-al-7,23-di---glucopyranoside. Of two sugar moieties, the one at 23---glucopyranoside grants each individual congener uniqueness likely through microbial symbiont-mediated intramolecular transformation into two major types of furo[2,3-]pyranone and furo[3,2-]pyranone derivatives. These new products possess desirable anti-inflammatory biological activities in addition to being generally regarded as safe.
从台湾新鲜水果中发现了四种新型三萜糖苷，即台莫地辛A-D（-）。通过各种分离和光谱技术对这四种天然产物的化学结构和相对立体化学进行了分离、纯化和测定。它们各自具有独特的双环稠合或三环中心稠合环系统。值得注意的是，台莫地辛A和台莫地辛B是基于葫芦素的化合物，分别与5-羟基-2-（羟甲基）四氢-4-吡喃-4-酮和6-（羟甲基）四氢-4-吡喃-3,4,4-三醇单元具有新的C-24和C-2″碳-碳键，代表了一种前所未有的分子骨架。在生物合成方面，它们都起源于共同的前体3-羟基葫芦巴-5,24-二烯-19-醛-7,23-二-O-葡萄糖苷。在两个糖部分中，23-O-葡萄糖苷处的糖部分可能通过微生物共生体介导的分子内转化为两种主要类型的呋喃并[2,3-b]吡喃酮和呋喃并[3,2-b]吡喃酮衍生物，赋予每个同系物独特性。这些新产品除了通常被认为是安全的之外，还具有理想的抗炎生物活性。
