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Title: VERTINOID POLYKETIDES FROM THE SALT WATER CULTURE OF THE FUNGUS TRICHODERMALONGIBRACHIATUM SEPARATED FROM A HALICLONA MARINE SPONGE

Author
item SPERRY, SAM - UNIV. OF CALIFORNIA
item Samuels, Gary
item CREWS, PHILLIP - UNIV. OF CALIFORNIA

Submitted to: Journal of Organic Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 9/30/1998
Publication Date: N/A
Citation: N/A

Interpretive Summary: Wherever scientists have searched, they have found an amazing array of interesting and unusual microorganisms that may be useful to humankind, yet many ecological niches remain unexplored. This paper reports the presence of a filamentous fungus that was isolated from a deep sea sponge. This fungus was identified and found to be related to fungi that are used in biological control of other fungi. The deep-sea fungus when cultivated in salt water was found to produce two interesting chemicals, one of which is new to science. These new chemicals will be screened for their potentially useful properties. Results of this research will be used by pharmaceutical companies and natural products chemists searching for new anti-cancer and other useful chemicals.

Technical Abstract: Two vertinoid polyketides, a known bislongiquinolide (a.k.a. trichotetronine) (1) and a new epoxysorbicillinol (2), have been isolated from the salt water culture of a sponge-derived fungus Trichoderma longibrachiatum. The structural elucidation of 2 was based on its spectroscopic and chiroptical properties. Additonally, biosynthetic analysis is used to infer the absolute sterochemistry of 1. Metabolites discovered to date from the cultures of marine-derived fungi are either parallel or identical to those of terrestrial fungi. This may be analogous to the less pronounced phenomenon of parallel metabolism observed for the metabolites of some marine and terrestrial macroorganisms. Fungi are screened by using a combination of bioassay (antimicrobial, brine shrimp toxicity, and cellular cytotoxicity) and molecular ion (electrospray ionizatin mass spectrometry profiling. Such screening methods led us to discover compounds with interesting properties including a diketopiperazin dimer, asperazine, a series of chlorinated terpenoids, the chloriolins; and a family of chlorianted polyketides, the chlorcarolides. Other slightly unusual polyketides have also been uncovered via this approach including the pitholides, the nectriapyrones, and secocurvularin.