USP Electronic Research Repository

Structures and absolute configurations of sulfate-conjugated triterpenoids including an antifungal chemical defense of the green macroalga Tydemania expeditionis

Jiang, R.W. and Lane, A.L. and Mylacraine, L. and Hardcastle, K. and Fairchild, C.R. and Aalbersberg, William G.L. and Hay, M.E. and Kubanek, J. (2008) Structures and absolute configurations of sulfate-conjugated triterpenoids including an antifungal chemical defense of the green macroalga Tydemania expeditionis. Journal of Natural Products, 71 (9). pp. 1616-1619. ISSN 0163-3864

Full text not available from this repository.

Abstract

Cytotoxicity-guided fractionation of the green macroalga Tydemania expeditionis led to isolation of four sulfate-conjugated triterpenoids including one new lanostane-type triterpenoid disulfate, lanosta-8-en-3,29-diol-23-oxo-3,29-disodium sulfate (1), and three known cycloartane-type triterpenoid disulfates, cycloartan-3,29-diol-23-one 3,29-disodium sulfate (2), cycloart-24-en-3,29-diol-23-one 3,29-disodium sulfate (3), and cycloartan-3,23,29-triol 3,29-disodium sulfate (4). Extensive 1D and 2D NMR analyses in combination with X-ray crystallography established the structure and absolute configuration of 1 and allowed determination of the absolute configurations of 2-4 with a revision of previously assigned configuration at C-5. Each natural product was moderately cytotoxic in tumor cell and invertebrate toxicity assays. Of the natural products, only 4 exhibited significant antifungal activity at whole-tissue natural concentrations against the marine pathogen Lindra thalassiae. Comparison of the biological activities of natural products with their desulfated derivatives indicated that sulfation does not appear to confer cytotoxicity or antifungal activity.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science, Technology and Environment (FSTE) > Institute of Applied Science
Depositing User: Ms Neha Harakh
Date Deposited: 11 Jan 2008 12:34
Last Modified: 10 Jul 2012 21:13
URI: http://repository.usp.ac.fj/id/eprint/185
UNSPECIFIED

Actions (login required)

View Item