Ipomeolides A and B, Resin Glycosides from <i>Ipomoea pes-caprae</i> and Combination Therapy of Ipomeolide A with Doxorubicin

Sura, Madhu Babu; Ponnapalli, Mangala Gowri; Annam, Suresh; Bobbili, V. V. Pardhasaradhi

doi:10.1021/acs.jnatprod.8b01100

Cited by 12 publications

(15 citation statements)

References 29 publications

(24 reference statements)

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“…Consequently, operculinic acid K ( 5 ) was characterized as 7 R -hydroxydecanoic acid 7- O -β- d -quinovopyranoside. Levorotatory ( R )-hydroxylated fatty acids have been rarely found as aglycones or acylating residues in Convolvulaceous resin glycosides; only two examples have been described: (−)-11( R )-hydroxyhexadecanoic acid ( ent -jalapinolic acid) in ipomeic acid from I. pes-caprae and (−)-8( R )-hydroxydodecanoic in murucoidin X, isolated from I. murucoides …”

Section: Resultsmentioning

confidence: 99%

“…Operculinic acid H (1): white solid, mp 158−160 °C; ORD (c 0.02, MeOH) [α] 22 589 −35.0, [α] 578 −50.0, [α] 546 −50.2 [α] 436 −60.0; 1 H NMR (800 MHz, C 5 D 5 N) and 13 C NMR (200 MHz, C 5 D 5 N) data, see Tables 1 and 2 −20.0, [α] 578 −21.4, [α] 546 −24.3, [α] 436 −37.1; 1 H NMR (700 MHz, C 5 D 5 N) δ 4.79 (1H, d, J = 7.4 Hz, Qui-1), 4. 19 (1H,dd,J = 8.7,8.7 Hz,3.96 (1H,dd,J = 8.7,7.4 Hz,3.87 (1H,1H,m,3.77 (1H,dq,J = 8.7,6.3 Hz,3.71 (1H,dd,J = 8.7,8.7 Hz,, 2.54 (2H, m, CH 2 Agl-2), 1.62 (3H, d, J = 6.3 Hz), 0.93 (3H, t, J = 7.1 Hz, Agl-10); 13 C NMR (175 MHz, C 5 D 5 N) 175.7 (Agl-1), 103.8 (Qui-1), 79.1 (Agl-7), 78.2 (Qui-3), 77.2 (Qui-4), 75.8 (Qui-2), 73.1 (Qui-5), 38.1 (Agl-8), 37.3 (Agl-2), 35.0 (Agl-6), 30.4 (Agl-4), 26.7 (Agl-3), 25.2 (Agl-5), ; HRESIMS m/z 357.18801 [M + Na] + (calcd for C 16 H 30 O 7 Na requires 357.188 37, δ = −1.0 ppm).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…Macrocarposidic acid A (6): white solid, mp 117−119 °C; ORD (c 0.29, MeOH) [α] 22 589 −18.6, [α] 578 −19.3, [α] 546 −22.1, [α] 436 −35.2, [α] 365 −49.3; ATR-FTIR (neat) ν max 3372,2957,2931,2873,2856,1737,1718,1650,1467,1370,1295,1262,1162,1125,1076,1025,1007,983,916,891,837,809,730,674,628, 579 cm −1 ; 1 H NMR (400 MHz, C 5 D 5 N) and 13 C NMR (100 MHz, C 5 D 5 N) data, see Tables 7 and 8 Macrocarposidic acid B (7): white solid, mp 158−160 °C; ORD(c 0.26, MeOH) [α] 22 589 −20.0, [α] 578 −20.4, [α] 546 −23.1, [α] 436 −37.7, [α] 365 −53.1; ATR-FTIR (neat) ν max 3396,2962,2928,2855,1738,1715,1648,1460,1376,1295,1257,1158,1125,1076,1012,981,917,886,...…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Resin Glycosides from the Roots of Operculina macrocarpa (Brazilian Jalap) with Purgative Activity

et al. 2019

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Analysis of the methanol-soluble resin glycosides from the roots of Operculina macrocarpa was assessed by generating NMR profiles of five glycosidic acids obtained through saponification, acetylation, and recycling HPLC purification. Operculinic acid H (1), two novel hexasaccharides, operculinic acids I (2) and J (3), the known purgic acid A (4), and a quinovopyranoside of (−)-(7R)-hydroxydecanoic acid, operculinic acid K (5), were isolated. Three intact resin glycosides related to 1, the novel macrocarposidic acids A (6) and B (7), in addition to the previously known macrocarposidic acid C (8), were also purified with isovaleroyl, tigloyl, and exogonoyl [(3S,9R)-3,6:6,9-diepoxydecanoyl] groups as esterifying residues. A selective intramolecular lactonization was produced to generate a macrocyclic artifact (17) during acetylation of 1, resembling the distinctive structure of the Convolvulaceous resin glycosides.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Resin Glycosides from the Roots of Operculina macrocarpa (Brazilian Jalap) with Purgative Activity

et al. 2019

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“…China, India, Mexico, and Thailand Whole plant Pescapreins X-XVII [190]; β-Damascenone, Phytol [191]; Pescaproside A and B, Pescapreins I-IX, Stoloniferin III [192]; Ipomeolides A and B, Presqualene alcohol, Icosyl (E)-3-(4-hydroxyphenyl)acrylate, β-Sitosterol-3-O-β-D-glucopyranoside, Stigmasterol, Lupeol [193].…”

Section: Hibiscus Tiliaceus L (Malvaceae)mentioning

confidence: 99%

Indigenous Uses, Phytochemical Analysis, and Anti-Inflammatory Properties of Australian Tropical Medicinal Plants

Yeshi

Turpin

Jamtsho³

et al. 2022

Molecules

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Australian tropical plants have been a rich source of food (bush food) and medicine to the first Australians (Aboriginal people), who are believed to have lived for more than 50,000 years. Plants such as spreading sneezeweed (Centipeda minima), goat’s foot (Ipomoea pes-caprae), and hop bush (Dodonaea viscosa and D. polyandra) are a few popular Aboriginal medicinal plants. Thus far, more than 900 medicinal plants have been recorded in the tropical region alone, and many of them are associated with diverse ethnomedicinal uses that belong to the traditional owners of Aboriginal people. In our effort to find anti-inflammatory lead compounds in collaboration with Aboriginal communities from their medicinal plants, we reviewed 78 medicinal plants used against various inflammation and inflammatory-related conditions by Aboriginal people. Out of those 78 species, we have included only 45 species whose crude extracts or isolated pure compounds showed anti-inflammatory properties. Upon investigating compounds isolated from 40 species (for five species, only crude extracts were studied), 83 compounds were associated with various anti-inflammatory properties. Alphitolic acid, Betulinic acid, Malabaric acid, and Hispidulin reduced proinflammatory cytokines and cyclooxygenase enzymes (COX-1 and 2) with IC50 values ranging from 11.5 to 46.9 uM. Other promising anti-inflammatory compounds are Brevilin A (from Centipeda minima), Eupalestin, and 5′-methoxy nobiletin (from Ageratum conyzoides), Calophyllolide (from Calophyllum inophyllum), and Brusatol (from Brucea javanica). D. polyandra is one example of an Aboriginal medicinal plant from which a novel anti-inflammatory benzoyl ester clerodane diterpenoid compound was obtained (compound name not disclosed), and it is in the development of topical medicines for inflammatory skin diseases. Medicinal plants in the tropics and those associated with indigenous knowledge of Aboriginal people could be a potential alternative source of novel anti-inflammatory therapeutics.

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“…Two new resin glycosides, ipomeolides A ( 77 ) and B ( 78 ), were isolated from aerial parts of Ipomoea pes‐caprae , and have ipomeic acid ( 79 ) as the glycosidic acid 31 . Ipomeolides A ( 77 ) and B ( 78 ) both possessed a rare 11 R ‐hydroxyhexadecanoic acid as the aglycone.…”

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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Ipomeolides A and B, Resin Glycosides from Ipomoea pes-caprae and Combination Therapy of Ipomeolide A with Doxorubicin

Cited by 12 publications

References 29 publications

Resin Glycosides from the Roots of Operculina macrocarpa (Brazilian Jalap) with Purgative Activity

Resin Glycosides from the Roots of Operculina macrocarpa (Brazilian Jalap) with Purgative Activity

Indigenous Uses, Phytochemical Analysis, and Anti-Inflammatory Properties of Australian Tropical Medicinal Plants

Chemistry and biological activity of resin glycosides from Convolvulaceae species

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