Resin Glycosides. XIII. Operculins VI, XI, XII, XIII, XIV and XV, the Ether-Soluble Resin Glycosides (Jalapin) from Rhizoma Jalapae Braziliensis (Roots of Ipomoea operculata).

Ono, M.; Fujimoto, Kyoko; Kawata, Miki; Fukunaga, Tomoji; Kawasaki, Terukazu; Miyahara, Kazumoto

doi:10.1248/cpb.40.1400

Cited by 18 publications

(7 citation statements)

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“…The crude jalapin fraction was subjected to silica gel and ODS column chromatography and HPLC on silica, ODS, and octyl silica columns to yield operculins I–XVIII ( 43 – 60 ) [19, 28–30]. Preparative recycling HPLC was a useful method for the isolation of two constitutional isomers, in which the n -decanoyl group and n -dodecanoyl group were mutually interchanged between the same positions ( 49 and 50 ; 51 and 52 ) [28, 29].…”

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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“…Finding the most favorable analytical factors (stationary and mobile phases, isocratic or gradient modes of elution, and maximum sample loading) and scaling them into preparative conditions so as to retain the chromatographic resolution are the major challenges. In addition to normal phase [47], the use of C8 [48,49], C18 [35,50], ciano [51] and phenyl [52,53] Si-gel bonded phases has been reported although the most successful as well as the now most commonly employed, is the amino column (aminopropylmethyl silicabonded phase), also called column for carbohydrate analysis [33,[42][43][44]. The purification of the tricolorin A and its analogues was successfully achieved by recycling HPLC using an amino bonded-phase and the following instrumental conditions [33]: column: 150 × 19 mm µBondapak-amino; mobile phase: CH 3 CN-H 2 O, 92:8; flow rate = 6 ml/min; detector: refractive index; sample injection: 10 mg/500 µL (Fig.…”

Section: Isolation Techniquesmentioning

confidence: 99%

Biodynamic Constituents in the Mexican Morning Glories: Purgative Remedies Transcending Boundaries

Pereda‐Miranda¹,

Bah

2003

CTMC

125

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Jalap, a pre-Hispanic herbal remedy still considered a useful laxative, is an ingredient in some over-the-counter products sold by herbalists in contemporary Mexico. The purgative crude drugs are prepared from the roots of several morning glories species which all have been identified as members of the Ipomoea genus (Convolvulaceae). Their incorporation as therapeutical agents into Europe is an outstanding example of the assimilation of botanical drugs from the Americas as substitutes for traditional Old World remedies. Phytochemical investigations on the resin glycosides, main constituents of these drugs, were initiated during the second half of the XIX century; however, the structures of their active ingredients had remained poorly known, and still are for some members of these purgative root species. Modern analytical techniques with higher resolution capabilities (HPLC) for the isolation of the active principles of these crude drugs used in conjunction with powerful spectroscopic methods (high field NMR) have facilitated the investigation of these relevant, to the herbal product market, convolvulaceous species during the last decade. The advantages and limitations of theses techniques will be discussed. This review will also describe the ethnobotanical information associated with the Mexican morning glory species and how the traditional usages of these plants have played an important role in the selection of these materials for chemical studies. Little is as yet known about either the mechanism of purge action caused by the resin glycosides or the ecological significance of these same compounds for the producing plants. Over the five centuries of Mexican herbal medicine, one hundred years of phytochemistry has only partially elucidated the active ingredients of the jalap roots but has exemplified how to further contemporary drug discoveries through the investigation of those plants traditionally held to be economically and medicinally important in developing countries.

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“…Resin glycosides represent a mixture of some different glycolipids formed by monohydroxy and dihydroxy long-chain fatty acids (C 14 –C 17 ) bonded to linear or branched heteropolysaccharides. − The ether-soluble resin glycosides (the jalapin fraction) of O. macrocarpa were first analyzed through saponification, where operculinic acids A–G were identified as the glycosidic acid cores with all of them constituted by the same aglycone, jalapinolic acid (11 S -hydroxyhexadecanoic acid), and different tetra- and pentasaccharides . Operculins I–XVIII were isolated as macrolactone-type resin glycosides from this lipophilic fraction . From the convolvulin fraction (ether-insoluble resin glycosides), recently analyzed by saponification, operculinic acid H ( 1 ) was isolated.…”

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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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Resin Glycosides. XIII. Operculins VI, XI, XII, XIII, XIV and XV, the Ether-Soluble Resin Glycosides (Jalapin) from Rhizoma Jalapae Braziliensis (Roots of Ipomoea operculata).

Cited by 18 publications

References 0 publications

Resin glycosides from Convolvulaceae plants

Resin glycosides from Convolvulaceae plants

Biodynamic Constituents in the Mexican Morning Glories: Purgative Remedies Transcending Boundaries

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

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