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Mar. Drugs 2018, 16(7), 231; https://doi.org/10.3390/md16070231

Four New C9 Metabolites from the Sponge-Associated Fungus Gliomastix sp. ZSDS1-F7-2

1
National Engineering Research Center of Navel Orange, Gannan Normal University, Ganzhou 341000, China
2
School of Life Science and Engineering, Southwest University of Science and Technology, Mianyang 621010, China
3
Department of Chemistry, Jinan University, Guangzhou 510000, China
4
Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510000, China
*
Authors to whom correspondence should be addressed.
Received: 26 May 2018 / Revised: 6 July 2018 / Accepted: 6 July 2018 / Published: 9 July 2018
(This article belongs to the Special Issue Marine Natural Products from Symbiotic Ecosystems)
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Abstract

Four new structurally related metabolites, one γ-lactone named gliomasolide F (1), one δ-lactone named gliomasolide G (2), and two medium-chain fatty acids named gliomacids A–B (34), each containing nine carbons in total, were identified from the sponge-associated fungus Gliomastix sp. ZSDS1-F7-2. The planar chemical structures of these novel C9 metabolites were elucidated by nuclear magnetic resonance (NMR) spectroscopic methods, in connection with the analysis of high-resolution mass spectrometry (HRMS) and infrared (IR) data. The absolute configuration of 1, was determined by comparisons of experimental circular dichroism (CD) and optical rotation (OR) value with corresponding ones computed by quantum chemistry. The relative configuration of 2 was determined by the Nuclear Overhauser effect spectroscopy (NOESY) spectrum, while its absolute configuration was tentatively determined in view of the biogenetic and biosynthetic relationships between 1 and 2. Compounds 34, originally as an inseparable mixture, were successfully isolated after chemical modifications. The stereo-chemistries of compounds 34 were assumed by comparison of 13C NMR with those of the similar moiety reported in literature, in addition to the biogenetic and biosynthetic relationships with 1. The plausible biosynthetic relationships among these four C9 metabolites were supposed. Biologically, compounds 14 showed no cytotoxic effect against HeLa cell line at concentrations up to 25 μg/mL, while 1 exhibited moderate antifouling activity against the settlement of Balanus amphitrite larvae with IC50 being 12.8 μg/mL and LC50 > 25 μg/mL. The co-occurrence of macrolides gliomasolides A—E and four C9 metabolites in the same fermentation culture made us assume that these C9 metabolites might be biosynthetic building blocks toward the construction of more complex macrolides such as gliomasolides A—E or other unidentified polyketides. View Full-Text
Keywords: Gliomastix sp.; sponge-associated fungus; γ-lactone; δ-lactone; C9 metabolites Gliomastix sp.; sponge-associated fungus; γ-lactone; δ-lactone; C9 metabolites
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Zhang, J.; Yang, Z.; Liang, Y.; Zhong, L.; Lin, H.; Zhong, B.; Li, L.; Xu, S.; Liu, Y. Four New C9 Metabolites from the Sponge-Associated Fungus Gliomastix sp. ZSDS1-F7-2. Mar. Drugs 2018, 16, 231.

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