Four New Acylated Glycosidic Acid Methyl Esters Isolated from the Convolvulin Fraction of Seeds of &lt;i&gt;Quamoclit pennata&lt;/i&gt; after Treatment with Indium(III) Chloride in Methanol

Ono, M.; Akiyama, Kousuke; Yamamoto, Kazutaka; Mineno, Tomoko; Okawa, Masafumi; Kinjo, Junei; Miyashita, Hiroyuki; Yoshimitsu, Hitoshi; Nohara, Toshihiro

doi:10.1248/cpb.c14-00277

Cited by 5 publications

(2 citation statements)

References 17 publications

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“…Treatment of the crude convolvulin fraction with indium(III) chloride in MeOH afforded nine acylated glycosidic acid methyl esters, named QM-1 ( 99 ), QM-2 ( 100 ), QM-3 ( 101 ), QM-9 ( 102 ), QM-10 ( 103 ), QM-11 ( 104 ), QM-12 ( 105 ), QM-13 ( 106 ), and QM-14 ( 107 ), and five acylated methyl glycosides, named QM-4 ( 108 ), QM-5 ( 109 ), QM-6 ( 110 ), QM-7 ( 111 ), and QM-8 ( 112 ). Their structures were elucidated on the basis of spectroscopic data and chemical conversions [46–48] (Fig. 8).…”

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 quamoclinic acids methyl esters were also isolated from Q. pennata and Q. multifida , including QM‐10‐13 ( 240 – 243 ) derived from quamoclinic acid C ( 236 ), 100,101 QM‐14 ( 244 ) derived from quamoclinic acid G ( 238 ), 101 and multifdin VIII ( 245 ) and multifdin IX ( 246 ) derived from quamoclinic acid D ( 237 ) 48 . They all had a quamoclinic acid B ( 3 ) acylated at the C‐2 of Rha unit, except an Mba group for 245 .…”

Section: Structures and Classification Of Resin Glycosidesmentioning

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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Seven new resin glycosides from the seeds of Quamoclit × multifida

et al. 2018

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Seven new resin glycosides, multifidins III (1)-IX (7), were isolated from the seeds of Quamoclit × multifida (syn. Q. sloteri House) (Convolvulaceae), along with five known glycosides, quamoclinic acid B methyl ester (8), operculin XIII (9), quamoclin I (10), QM-10 (11), and QM-12 (12). Their structures were determined on the basis of spectroscopic data and chemical evidence. These compounds were of two different types, i.e., those with macrolactone structures and those with non-macrolactone structures. Additionally, cytotoxic activity towards HL-60 human leukemia cells of 1, 2, 5, 8, 9, 11, and 12 was evaluated. Among them, macrolactone-type resin glycosides (jalapins), 1, 2, and 9, specifically demonstrated clear cytotoxic activity with IC values of 3.46, 14.7, and 10.9 μM, respectively.

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Four New Acylated Glycosidic Acid Methyl Esters Isolated from the Convolvulin Fraction of Seeds of <i>Quamoclit pennata</i> after Treatment with Indium(III) Chloride in Methanol

Cited by 5 publications

References 17 publications

Resin glycosides from Convolvulaceae plants

Resin glycosides from Convolvulaceae plants

Chemistry and biological activity of resin glycosides from Convolvulaceae species

Seven new resin glycosides from the seeds of Quamoclit × multifida

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