Abstract
(−)-(4S, 8S)-Foedanolide (1a) and (+)-(4R, 8R)-foedanolide (1b), a pair of new spiro-γ-lactone enantiomers, were isolated from the fermentation broth of the plant endophytic fungus Pestalotiopsis foedan by HPLC using a chiral column, achieving over 7% ee. Their structures and absolute configurations were determined on the basis of extensive analysis of NMR spectra combined with computational methods via calculation of the electronic circular dichroism (ECD) and optical rotation (OR). Compounds 1a and 1b showed moderate activities against HeLa, A-549, U-251, HepG2 and MCF-7 tumor cell lines.
Highlights
Endophytic fungi, as one of the most promising resource for natural product discovery, live inside the normal tissues of host plants without causing apparent disease symptoms [1]
Taxomyces andreanae, the first report endophytic fungus colonizing the inner bark of Pacific yew Taxus brevifolia, is capable of producing taxol and its analogue baccatin III when grown in semi-synthetic medium [3]
Two olefinic quaternary carbons could be assigned to one olefin, together with the two carbonyls accounted for three of the five required degrees of unsaturation
Summary
Endophytic fungi, as one of the most promising resource for natural product discovery, live inside the normal tissues of host plants without causing apparent disease symptoms [1]. The study of natural products from plants and their endophytes has shown that endophytes have been found to produce a significant number of interesting novel and bioactive metabolites [2]. Taxomyces andreanae, the first report endophytic fungus colonizing the inner bark of Pacific yew Taxus brevifolia, is capable of producing taxol and its analogue baccatin III when grown in semi-synthetic medium [3]. During our continuing research for naturally occurring bioactive secondary metabolites from this genus, the present study was undertaken to investigate the chemical constituents of Pestalotiopsis foedan isolated from the branch of Bruguiera sexangula, and have led to the isolation of a pair of new spiro-γ-lactone enantiomers 1a and 1b (Figure 1). Structure elucidation and cytotoxic evaluation of 1a and 1b are reported
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