Abstract
Halosmysin A, a new 14-membered macrodiolide with an unprecedented skeleton, was isolated from the fungus Halosphaeriaceae sp. OUPS-135D-4, which, in turn, was obtained from the marine algae Sargassum thunbergii. The chemical structure of the macrodiolide was elucidated using 1D and 2D NMR, as well as high resolution fast atom bombardment mass (HRFABMS) spectral analysis. The absolute stereochemistry was determined via chemical derivatization and comparison with a known compound, (6R,11R,12R,14R)-colletodiol. Additionally, halosmysin A was shown to be very potent against murine P388 leukemia, human HL-60 leukemia, and murine L1210 leukemia cell lines, with IC50 values ranging from 2.2 ± 3.1 to 11.7 ± 2.8 μM.
Highlights
Marine-derived microorganisms are renowned for producing secondary metabolites, which have diverse structures and exhibit unexpected biological properties, making them excellent antitumor chemotherapy agents [1,2,3,4]
Our group has published numerous papers featuring exploratory research on marine-derived fungal metabolites [5]. As part of this ongoing study, the metabolites of Halosphaeriaceae sp.—a fungus which was separated from the marine algae Sargassum thunbergii—were isolated and characterized
A new 14-membered macrodiolide was designated as halosmysin A (1), together with the known colletodiol (2) [6] from this fungal strain, (Figure 1)
Summary
Marine-derived microorganisms are renowned for producing secondary metabolites, which have diverse structures and exhibit unexpected biological properties, making them excellent antitumor chemotherapy agents [1,2,3,4]. Other members of this family, namely acaulones, were isolated from the fungus Acaulium sp.; these acaulones possessed a new skeleton or functional group with the olefin moiety in the macrodiolide [17]. The stereostructures of these compounds were established by applying the several rules of chirality [6,10], X-ray crystallographic analysis [18], and asymmetric total synthesis [19,20,21,22,23]. After revisions were conducted [10,12,13,15], it was confirmed that these macrodiolides consisted of two unsymmetrical subunits, which were grouped into two
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