Acylated iridoid glycosides with hyaluronidase inhibitory activity from the rhizomes of Picrorhiza kurroa Royle ex Benth

  • Phytochemistry. 2020 Jan;169:112185. doi: 10.1016/j.phytochem.2019.112185.
Toshio Morikawa  1 ,  Yusuke Nakanishi  2 ,  Naoki Inoue  2 ,  Yoshiaki Manse  2 ,  Hideyuki Matsuura  2 ,  Shinya Hamasaki  2 ,  Masayuki Yoshikawa  2 ,  Osamu Muraoka  3 ,  Kiyofumi Ninomiya  3
Affiliations
  • 1. Pharmaceutical Research and Technology Institute, 3-4-1 Kowakae, Higashi-osaka, Osaka, 577-8502, Japan; Antiaging Center, Kindai University, 3-4-1 Kowakae, Higashi-osaka, Osaka, 577-8502, Japan. Electronic address: [email protected].
  • 2. Pharmaceutical Research and Technology Institute, 3-4-1 Kowakae, Higashi-osaka, Osaka, 577-8502, Japan.
  • 3. Pharmaceutical Research and Technology Institute, 3-4-1 Kowakae, Higashi-osaka, Osaka, 577-8502, Japan; Antiaging Center, Kindai University, 3-4-1 Kowakae, Higashi-osaka, Osaka, 577-8502, Japan.
PMID: 31678786 DOI: 10.1016/j.phytochem.2019.112185
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 μM) and E (5, 35.8 μM); picrosides I (8, 60.7 μM), II (9, 22.3 μM), and IV (11, 59.2 μM); and minecoside (13, 57.2 μM), exhibited a similar or stronger hyaluronidase inhibitory activity than those of the antiallergic medicines disodium cromoglycate (64.8 μM), ketotifen fumarate (76.5 μM), and tranilast (227 μM).

Keywords
Hyaluronidase inhibitors; Iridoids; Picrorhiza kurroa Royle ex Benth.; Picrorhizaosides; Plantaginaceae.
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