In silico guided search for anti-viral properties of a natural methylenecyclopropane glucoside

K Kainz; D Schuster; L Krenn

doi:10.1055/s-0030-1264657

Planta Medica, Inhaltsverzeichnis

In silico guided search for anti-viral properties of a natural methylenecyclopropane glucoside

K Kainz ¹, D Schuster ², L Krenn ¹

¹University of Vienna, Department of Pharmacognosy, Althanstrasse 14, 1090 Wien, Austria
²University of Innsbruck, Department of Pharmaceutical Chemistry, Innrain 52c, 6020 Innsbruck, Austria

Abstract

(2E)-2-(6-hydroxyhexyliden)cyclopropyl-β-glucopyranoside (1) was isolated from the rhizomes of the tree fern Metaxya rostrata, Metaxyaceae, a Costa Rican traditional herbal remedy against intestinal diseases [1]. Literature research for similarity of the structural characteristics resulted in different related compounds with the very uncommon structural part of methylenecyclopropane [2,3,4], which showed anti-viral activitiy against Epstein-Barr-, Human Herpes-, Hepatitis B-, Human Immunodeficiency- and Human Cytomegalo-virus in vitro. Thus, an in silico guided search for possible anti-viral activities of (1) was realized. Pharmacophoric profiling against over 2200 models representing over 280 putative pharmacological targets [5] suggested α-glucosidase as potential target for (1). A structural similarity search in the MDL Drug Data Report (MDDR) database [6] confirmed this result making α-glucosidase a promising target for biological evaluation of compound (1).

Fig.1: (2E)-2-(6-hydroxyhexyliden)cyclopropyl-β-glucopyranoside (1)

References: 1. Kainz, K.P. et al. (2010)J. Nat. Prod.: submitted.

2. Rybak, R.J. et al. (2000) Antimicrob. Agents Chemother. 44/6: 1506–1511.

3. Qiu, Y.L. et al. (1998)J. Med. Chem. 41: 10–23.

4. Uchida, H. et al. (1999) Antimicrob. Agents Chemother. 43/6: 1487–1490.

5. Rollinger, J.M. et al. (2009) Planta Med. 75: 195–204.

6. Keiser, M.J. et al. (2007) Nat. Biotech. 25: 197–206.