Nine New Norlabdane Diterpenoids from the Leaves of Austroeupatorium inulifolium

Abstract

Nine new norlabdane diterpenoids were isolated from the leaves of Austroeupatorium inulifolium collected in Indonesia. All of them have an acyl-furan unit connected to C(11), and oxygenated functions at C(2) and C(3). The structure elucidations and the assignment of the absolute configurations of the isolated natural products were carried out by extensive spectroscopic analysis and the extended Mosher method, as well as chemical correlations. Antimicrobial activities and cytotoxicity against HL-60 cells were determined using bioassays.

Preparation of a ε-caprolactonic diterpenoid derivate by unexpected oxidative cleavage/lactonization of 2-oxoaustroeupatol

“…Furano diterpenoids of labdane-type are representative products of Eupatorium inulifolium [ 1 – 3 ], now named Austroeupatorium inulifolium [ 4 ]. The substantial biological activity of these metabolites is responsible for the interest in developing methods for total synthesis of these compounds from terpenoids and chemical modifications of several available metabolites [ 5 ].…”

Phytotoxicity, cytotoxicity and antioxidant activity of the invasive shrub Austroeupatorium inulifolium (Kunth) R.M. King & H. Rob

“…In the present study, we attempted to investigate the potential role of bioactive compounds in A. inulifolium by using bioassays with extracts of different parts of the shrub including stems, roots, flowers and leaves and to relate them to its invasive success. Apart from the isolation of nine new norlabdane derivatives with antimicrobial activity in A. inulifolium (Saito et al, 2011), no studies have been carried out to assess the bioactive profile of A. inulifolium with an aim to explain its invasive nature of the plant. We report herein, the bioactivities of A. inulifolium including cytotoxic, phytotoxic, antioxidant and antifungal properties.…”

Diterpenoids of terrestrial origin

“…A number of labdanes, including a (4-3a)-methyl rearrangement product Department of Chemistry, University of Sussex, Brighton, BN1 9QJ, UK metasequoic acid C 7, and 12a-hydroxy-8,15-isopimaradien-18-oic acid, have been found 20 in Metasequoia glyptostroboides. Examination of Austroeupatorium inulifolium has afforded a series of norlabdanes exemplified by inulifolinone A 8 21.…”