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.

Two new halimane-type diterpenoids, viteagnusins A and B, and three new labdane-type diterpenoids, viteagnusins C, D, and E, were isolated from the fruit of Vitex agnus-castus L. (Chasteberry, Verbenaceae) along with two known diterpenoids. Their chemical structures were determined on the basis of spectroscopic data.

Five new resin glycosides having macrolactone structures (jalapins), named calysolins V–IX (1–5), were isolated from the leaves, stems, and roots of Calystegia soldanella ROEM. et SCHULT. (Convolvulaceae). Their structures were determined on the basis of spectroscopic data as well as chemical evidence. The isolated compounds could be classified into two macrolactone types—one having a 22-membered ring (1–4) and the other with a 27-membered ring (5). The sugar moieties of 1–5 were found to exist in partially acylated forms comprising 2S-methylbutyric acid and tiglic acid. Compounds 4 and 5 are the first representatives of the calysolic acid C as the component glycosidic acid. Additionally, the antiviral activity of 1–5, together with calysolins I–IV and soldanelline B, which are previously isolated jalapins from this plant, toward herpes simplex virus type 1 was evaluated. All the compounds showed antiviral activity.

A new labdane-type diterpenoid glucoside and two new labdane-type diterpenoids were isolated from the fruit (chasteberry) of Vitex agnus-castus L. (Verbenaceae) along with 14 known compounds comprising seven labdane-type diterpenoids, one halimane-type diterpenoid, two oleanane-type triterpenoids, two ursane-type triterpenoids, one aromadendrane-type sesquiterpenoid, and one flavonoid. Their structures were characterized on the basis of spectroscopic data as well as chemical evidence. Furthermore, the antioxidative activities of the flavonoid were evaluated using five different analyses.

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