Major Carotenoids of Meiothermus ruber Are Deinoxanthin Glucoside Esters, Not Meiothermoxanthin Glucoside Esters
Major Carotenoids of Meiothermus ruber Are Deinoxanthin Glucoside Esters, Not Meiothermoxanthin Glucoside Esters
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DOI：
10.1021/acs.jnatprod.2c00271
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发表时间：
2022-09-21
影响因子：
5.1
通讯作者：
Takaichi, Shinichi
中科院分区：
文献类型：
--
作者：
Asaka, Ryo;Ohshima, Kazuki;Takaichi, Shinichi
Meithermus ruber DSMZ 1279(T)是从堪察加的一处温泉中分离出来的，呈红色。据报道，皂化后存在的主要类胡萝卜素是1‘-(β-D-吡喃葡萄糖氧基)-3，4，3’，4‘-四氢-1’，2‘-二氢-β，psi-胡萝卜素-2-酮(Burgess et al.J·纳特。戳。1999、62、859-863)。在本研究中，我们在没有皂化的情况下提纯了该物种中的主要类胡萝卜素。然后，我们利用光谱学数据，包括电子圆二色谱(ECD)、核磁共振氢谱(H-1)、旋转框架核欧豪泽效应谱(ROESY)、碳-13核磁共振谱(C-13)、异核单量子相关谱(HSQC)、异核多键相关谱(HMBC)和MS，以及脂肪酸部分的酶解，重新鉴定了主要的类胡萝卜素，并发现了脱氧黄质糖苷异脂肪酸酯。存在的结合脂肪酸包括四种iso类型，它们的组成与细胞脂不同。此外，以前鉴定的类胡萝卜素葡萄糖苷是脱氧葡萄糖苷酯的皂化产物。还含有酮粘黄质葡萄糖苷酯和1‘-羟基托鲁烯葡萄糖苷酯。在对类胡萝卜素及其全基因组序列进行鉴定的基础上，我们提出了一种类胡萝卜素的生物合成途径，并记录了相应的基因。
Meiothermus ruber DSMZ 1279(T) was isolated from a hot spring in Kamchatka and was red in color. The major carotenoid present was reported to be 1 '-(beta-D-glucopyranosyloxy)-3,4,3 ',4 '- tetradehydro-1 ',2 '-dihydro-beta,psi-caroten-2-one after saponification (Burgess et al. J. Nat. Prod. 1999, 62, 859-863). In this study, we purified the major carotenoids in this species without saponification. We then reidentified the major carotenoids present using spectroscopic data, including electronic circular dichroism (ECD),H-1 NMR, rotating-frame nuclear Overhauser effect spectroscopy (ROESY),C- 13 NMR, heteronuclear single-quantum correlation spectroscopy (HSQC), heteronuclear multiple-bond correlation spectroscopy (HMBC), and MS, and enzymatic hydrolysis of fatty acid moieties and found deinoxanthin glucoside iso fatty acid esters. The bound fatty acids present included four iso types, and their composition differed from cellular lipids. Moreover, the previously identified carotenoid glucoside was a saponification artifact of deinoxanthin glucoside esters. Ketomyxocoxanthin glucoside esters and 1 '-hydroxytorulene glucoside esters were also present. On the basis of the identification of carotenoids and the whole genome sequence of M. ruber, we propose a carotenoid biosynthetic pathway and note the corresponding genes.