Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 25, Pages 14163-14170Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202102453
Keywords
absolute configuration; antibiotics; diterpenoid; terpene synthase
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Funding
- OSU
- UF start-up funds
- NIH [S10 OD021758-01A1, R00 GM124461, R01 EB009772]
- NSF [1808717]
- Oregon State University's NMR Facility by the National Institutes of Health, HEI [1S10OD018518]
- M. J. Murdock Charitable Trust [2014162]
- US NSF [DMR-1644779]
- State of Florida
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1808717] Funding Source: National Science Foundation
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A new bicyclic diterpenoid, benditerpenoic acid, was isolated from soil-dwelling Streptomyces sp. (CL12-4). The bacterial genome was sequenced, the biosynthetic gene cluster and terpene synthase responsible for its production were identified, and the compound showed moderate antibacterial activity against Gram-positive bacteria.
A new bicyclic diterpenoid, benditerpenoic acid, was isolated from soil-dwelling Streptomyces sp. (CL12-4). We sequenced the bacterial genome, identified the responsible biosynthetic gene cluster, verified the function of the terpene synthase, and heterologously produced the core diterpene. Comparative bioinformatics indicated this Streptomyces strain is phylogenetically unique and possesses nine terpene synthases. The absolute configurations of the new trans-fused bicyclo[8.4.0]tetradecanes were achieved by extensive spectroscopic analyses, including Mosher's analysis, J-based coupling analysis, and computations based on sparse NMR-derived experimental restraints. Interestingly, benditerpenoic acid exists in two distinct ring-flipped bicyclic conformations with a rotational barrier of approximate to 16 kcal mol(-1) in solution. The diterpenes exhibit moderate antibacterial activity against Gram-positive bacteria including methicillin and multi-drug resistant Staphylococcus aureus. This is a rare example of an eunicellane-type diterpenoid from bacteria and the first identification of a diterpene synthase and biosynthetic gene cluster responsible for the construction of the eunicellane scaffold.
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