A New Resin Glycoside, Muricatin IX, from the Seeds of &lt;i&gt;Ipomoea muricata&lt;/i&gt;

Ono, M.; Taketomi, Saki; Kakiki, Yuichi; Yasuda, Shin; Okawa, Masafumi; Kinjo, Junei; Yoshimitsu, Hitoshi; Nohara, Toshihiro

doi:10.1248/cpb.c16-00359

Cited by 8 publications

(3 citation statements)

References 5 publications

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“…The structure of 136 was determined on the basis of spectroscopic data as well as chemical evidence. It should be noted that 136 is different from all the resin glycosides isolated so far, in that the carboxyl group of its aglycone moiety is linked with a hydroxyl group of the organic acid, which was attached to a sugar moiety by ester linkage, to form a macrocyclic ester ring [60] (Fig. 11).…”

Section: Introductionmentioning

confidence: 99%

Resin glycosides from Convolvulaceae plants

Ono

2017

J Nat Med

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Resin glycosides are well known as purgative ingredients, which are characteristic of certain crude drugs such as Mexican Scammony Radix, Orizabae Tuber, and Jalapae Tuber, all of which originate from Convolvulaceae plants. Depending on their solubility in ether, these are roughly classified into two groups-jalapin (soluble) and convolvulin (insoluble). Almost all jalapins hitherto isolated and characterized had common intramolecular macrocyclic ester structures. These are composed of 1 mol of oligoglycoside of hydroxyl fatty acid (glycosidic acid) partially acylated by some organic acids at the sugar moiety, some examples of which are ester-type dimers. On the other hand, convolvulin is regarded as an oligomer of a variety of acylated glycosidic acids. This review describes the isolation and structural elucidation of resin glycosides from some Convolvulaceae plants, including Ipomoea operculata, Pharbitis nil, Quamoclit pennata, Calystegia soldanella, and I. muricata.

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Section: Introductionmentioning

confidence: 99%

Resin glycosides from Convolvulaceae plants

Ono

2017

J Nat Med

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“…The methanol extract of I. muricata seeds afforded a new resin glycoside muricatin IX (34), which composes of muricatic acid C as glycosidic acid, along with one Nla unit aclyated at C-3 position of the Qui″ unit. 58 The carboxyl group of the aglycone moiety linked with the hydroxyl group of the Nla, making muricatin IX (34) the first representative of resin glycosides in which an organic acid connects the sugar moiety and the aglycone moiety to form macrocyclic ester ring. Moreover, four other resin glycosides derived from muricatic acid C, calonyctins F-H (35)(36)(37) and calonyctin J (38), were also identified from the seeds of I. muricata.…”

Section: Muricatic Acid Cmentioning

confidence: 99%

Chemistry and biological activity of resin glycosides from Convolvulaceae species

Fan

Jiang

et al. 2022

Medicinal Research Reviews

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Carbohydrate-based drug discovery has gained more and more attention during the last few decades. Resin glycoside is a kind of novel and complex glycolipids mainly distributed in plants of the family Convolvulaceae. Over the last decade, a number of natural resin glycosides and derivatives have been isolated and identified, and exhibited a broad spectrum of biological activities, such as cytotoxic, multidrug-resistant reversal on both microbial pathogens and mammalian cancer cells, antivirus, anticonvulsant, antidepressant, sedative, vasorelaxant, laxative, and α-glucosidase inhibitory effects, indicating their potential as lead compounds for drug discovery. A systematic review of the literature studies was carried out to summarize the chemistry and biological activity of resin glycosides from Convolvulaceae species, based on various data sources such as PubMed, Web of Science, Scopus, and Google scholar. The keyword "Convolvulaceae" was paired with "resin glycoside," "glycosidic acid," "glycolipid," or "oligosaccharide," and the references published between 2009 and June 2021 were covered. In this article, we comprehensively reviewed the structures of 288 natural resin glycoside and derivatives newly reported in the last decade. Moreover, we summarized the biological activities and mechanisms of action of the resin

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“…1) Noda et al reported that alkaline hydrolysis of the crude resin glycoside fraction of the seeds of I. muricata yielded three organic acids, namely, isobutyric, 2S-methylbutyric, and 2R-methyl-3R-hydroxybutyric (2R,3R-nilic) acid; and a glycosidic acid fraction composed of L-rhamnose, D-fucose, D-quinovose, and 11R-hydroxyhexadecanoic (jalapinolic) acid, 1) whose absolute configuration was later corrected as S. 2) They also discussed the isolation and structural elucidation of three glycosidic acids, namely, muricatic acids A-C. 1,3) Eight genuine resin glycosides having macrolactone structures (jalapins), 4) namely, muricatins I-VIII were also reported. 3,5) In a previous paper, we reported the isolation and structural elucidation of a new type of resin glycoside, namely, muricatin IX, from the seeds of I. muricata, in which an organic acid connects the sugar moiety and the aglycone moiety to form a macrocyclic ester ring. 6) Recently, Wang et al reported the isolation and structural elucidation of nine jalapins, namely, calonyctins B-J, from the seeds of I. muricata, four of which were structurally similar to muricatin IX.…”

Section: Introductionmentioning

confidence: 99%

A New Glycosidic Acid, Muricatic Acid D, and Resin Glycosides, Muricatins X and XI, from the Crude Resin Glycoside Fraction of the Seeds of <i>Ipomoea muricata</i>

et al. 2021

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Alkaline hydrolysis of crude resin glycoside fraction of the seeds of Ipomoea muricata (L.) Jacq. (Convolvulaceae) yielded a new glycosidic acid, muricatic acid D; three known glycosidic acids, namely, muricatic acids A, B, and C; and three known organic acids, namely, isobutyric, 2S-methylbutyric, and 2S-methyl-3Shydroxybutyric acid. Two new genuine resin glycosides with macrolactone structures (jalapins), muricatins X and XI, were also isolated from the fraction. Their structures were determined using spectroscopic data and chemical evidence.

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A New Resin Glycoside, Muricatin IX, from the Seeds of <i>Ipomoea muricata</i>

Cited by 8 publications

References 5 publications

Resin glycosides from Convolvulaceae plants

Resin glycosides from Convolvulaceae plants

Chemistry and biological activity of resin glycosides from Convolvulaceae species

A New Glycosidic Acid, Muricatic Acid D, and Resin Glycosides, Muricatins X and XI, from the Crude Resin Glycoside Fraction of the Seeds of <i>Ipomoea muricata</i>

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