Resin glycosides from Convolvulaceae plants

Abstract

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.

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>

“…The remaining glycosidic acid fraction was treated with trimethylsilyldiazomethane-hexane and then subjected to ODS column chromatography and HPLC using πNAP and ODS columns to yield four methyl esters (7-10) of glycosidic acids, among which 9 was identified as muricatic acid C methyl ester, based on its reported physical and 1 H-and 13 C-NMR spectral data. 3) Upon alkaline hydrolysis, 7-10 gave the corresponding free glycosidic acids (7a-10a). Compounds 7a and 8a were identified as muricatic acids A and B, respectively, based on their NMR spectral data 1) (Fig.…”

“…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.…”

Downregulation of Aquaporin 3 Mediated the Laxative Effect in the Rat Colon by a Purified Resin Glycoside Fraction from Pharbitis Semen

“…Recently, herbal plants have received increasing attention as new therapeutic drugs for the treatment of constipation and related diseases [21, 22]. In order to develop drugs for the treatment of constipation, we studied the therapeutic effect of Pharbitis Semen (Convolvulaceae), which is used as a traditional stimulant laxative herb in Korea, China, and Japan [23]. It is reported that resin glycosides are the material basis that account for the purgative action of convolvulaceous species as traditional purgative medicine throughout the world [8].…”

Phenolic Composition and Antioxidant Activity of Purple Sweet Potato (Ipomoea batatas (L.) Lam.): Varietal Comparisons and Physical Distribution

“…Most studies have used a whole purple sweet potato to determine anthocyanins and other phenolic compounds [ 23 , 24 ]. When a purple sweet potato is cut horizontally, a white round band divides the outer and inner layers; the outer layer is often discarded during processing [ 25 ]. However, the outer layer is a possible commercial source of phenolics, especially anthocyanin pigments.…”