Revision of NMR assignment for Morin-3-O-glucoside and microbial production of Morin-2’-O-glucoside

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines Pub Date : 2024-01-18 DOI:10.1007/s11418-023-01771-1

Muhammad Fitrah, Syatirah Djalaluddin, Zhichao Wang, Kana Nishida, Hideaki Otsuka, Katsuyoshi Matsunami

{"title":"Revision of NMR assignment for Morin-3-O-glucoside and microbial production of Morin-2’-O-glucoside","authors":"Muhammad Fitrah, Syatirah Djalaluddin, Zhichao Wang, Kana Nishida, Hideaki Otsuka, Katsuyoshi Matsunami","doi":"10.1007/s11418-023-01771-1","DOIUrl":null,"url":null,"abstract":"<div><p>Morin is a flavonol having 2’,4’-dihydroxy group on B-ring identified especially in <i>Moraceae</i> plants. While morin is widely known, its glycosides are relatively rare. To the best of our knowledge, morin-3-<i>O</i>-glucoside (<b>1</b>) was first reported in 2008. However, the reported chemical shift values of <b>1</b> were unsatisfactory with those of the aglycone, morin, which is rather similar to quercetin-3-<i>O</i>-glucoside (<b>2</b>). Therefore, we prepared morin-3-<i>O</i>-glucoside (<b>1</b>) by microbial transformation of morin with <i>Cunninghamella</i> sp., and the NMR assignment was reinvestigated. The microbial culture also produced another compound (<b>3</b>). The NMR and MS analyses of <b>3</b> revealed it as a novel compound, morin-2’-<i>O</i>-glucoside (<b>3</b>).</p><p>In this study, the revision of the NMR assignment of morin-3-<i>O</i>-glucoside (<b>1</b>), and the preparation and structural elucidation of a novel compound, morin-2’-<i>O</i>-glucoside (<b>3</b>), were described.</p><h3>Graphical abstract</h3><div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"78 2","pages":"403 - 410"},"PeriodicalIF":2.5000,"publicationDate":"2024-01-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Natural Medicines","FirstCategoryId":"3","ListUrlMain":"https://link.springer.com/article/10.1007/s11418-023-01771-1","RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}

引用次数: 0

Abstract

Morin is a flavonol having 2’,4’-dihydroxy group on B-ring identified especially in Moraceae plants. While morin is widely known, its glycosides are relatively rare. To the best of our knowledge, morin-3-O-glucoside (1) was first reported in 2008. However, the reported chemical shift values of 1 were unsatisfactory with those of the aglycone, morin, which is rather similar to quercetin-3-O-glucoside (2). Therefore, we prepared morin-3-O-glucoside (1) by microbial transformation of morin with Cunninghamella sp., and the NMR assignment was reinvestigated. The microbial culture also produced another compound (3). The NMR and MS analyses of 3 revealed it as a novel compound, morin-2’-O-glucoside (3).

In this study, the revision of the NMR assignment of morin-3-O-glucoside (1), and the preparation and structural elucidation of a novel compound, morin-2’-O-glucoside (3), were described.

Graphical abstract

Abstract Image

查看原文本刊更多论文

修订 Morin-3-O-glucoside 的 NMR 赋值和 Morin-2'-O-glucoside 的微生物生产。

吗啉是一种黄酮醇，其 B 环上有 2',4'-二羟基，特别是在桑科植物中被发现。虽然 Morin 广为人知，但其苷却相对罕见。据我们所知，吗啉-3-O-葡萄糖苷（1）于 2008 年首次被报道。然而，所报道的 1 的化学位移值与苷元 Morin 的化学位移值不尽相同，后者与槲皮素-3-O-葡萄糖苷（2）相当相似。因此，我们用 Cunninghamella sp.对吗啉进行微生物转化，制备了吗啉-3-O-葡萄糖苷（1），并对其核磁共振谱进行了重新研究。该微生物培养物还产生了另一种化合物（3）。本研究对吗啉-3-O-葡萄糖苷（1）的核磁共振赋值进行了修正，并制备和阐明了吗啉-2'-O-葡萄糖苷（3）这一新型化合物。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Journal of Natural Medicines 医学-药学

CiteScore

6.90

自引率

3.00%

发文量

审稿时长

1.7 months

期刊介绍： The Journal of Natural Medicines is an international journal publishing original research in naturally occurring medicines and their related foods and cosmetics. It covers: -chemistry of natural products -biochemistry of medicinal plants -pharmacology of natural products and herbs, including Kampo formulas and traditional herbs -botanical anatomy -cultivation of medicinal plants. The journal accepts Original Papers, Notes, Rapid Communications and Natural Resource Letters. Reviews and Mini-Reviews are generally invited.