Acylated iridoid glycosides with hyaluronidase inhibitory activity from the rhizomes of Picrorhiza kurroa Royle ex Benth. (January 2020)

• Record Type: Journal Article
• Authors: Morikawa, Toshio; Nakanishi, Yusuke; Inoue, Naoki; Manse, Yoshiaki; Matsuura, Hideyuki; Hamasaki, Shinya; Yoshikawa, Masayuki; Muraoka, Osamu; Ninomiya, Kiyofumi
• Is Part Of: Phytochemistry. Volume 169(2020)
• Publication Date: 2020-01
• Subjects: Picrorhiza kurroa Royle ex Benth. -- Plantaginaceae -- Iridoids -- Picrorhizaosides -- Hyaluronidase inhibitors; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2019.112185
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Seven new acylated iridoid glycosides, picrorhizaosides A–G (1 –7 ), were isolated from the methanol extract of the rhizomes of Picrorhiza kurroa Royle ex Benth. (Plantaginaceae), in addition to six known iridoid glycosides (8 –13 ). The structures of these new iridoids, including their stereochemistry, were determined based on chemical and physicochemical evidence derived from NMR and MS analysis. Of the isolates, picrorhizaosides D (4, IC50 = 43.4 μ M) and E (5, 35.8 μ M); picrosides I (8, 60.7 μ M), II (9, 22.3 μ M), and IV (11, 59.2 μ M); and minecoside (13, 57.2 μ M), exhibited a similar or stronger hyaluronidase inhibitory activity than those of the antiallergic medicines disodium cromoglycate (64.8 μ M), ketotifen fumarate (76.5 μ M), and tranilast (227 μ M). Graphical abstract: Image 1 Highlights: Seven new acylated iridoid glycosides, picrorhizaosides A–G, were isolated. Picrorhizaosides D and E showed hyaluronidase inhibitory activity. Several iridoids exhibited stronger hyaluronidase inhibitory activity than DSCG.