Journal
JOURNAL OF ANTIBIOTICS
Volume 75, Issue 10, Pages 542-551Publisher
SPRINGERNATURE
DOI: 10.1038/s41429-022-00559-x
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Funding
- JSPS KAKENHI [JP19K05848]
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A bisprenyl naphthoquinone (1) and a calcimycin congener with unusual modifications (2) were isolated from Phytohabitans sp. RD003013. Compound 1 exhibited an unprecedented prenylation pattern, while compound 2 represented a new modification pattern in the known calcimycin family natural products. Interestingly, compound 2 showed moderate antimicrobial activity against Ralstonia solanacearum and inhibited the migration of EC17 cancer cells at noncytotoxic concentrations.
A bisprenyl naphthoquinone, phytohabinone (1), and a calcimycin congener with unusual modifications, phytohabimicin (2), were isolated from the culture extract of Phytohabitans sp. RD003013. The structures of 1 and 2 were determined by NMR and MS analyses, and the absolute configuration of 2 was established by using electronic circular dichroism (ECD) calculation. The prenylation pattern of 1 was unprecedented among the known prenylated naphthoquinones. Compound 2 represents a spiroacetal core of polyketide origin substituted with a thiazole carboxylic acid and a dichrolopyrrole moiety, which is an unprecedented modification pattern in the known calcimycin family natural products. Remarkably, 2 showed moderate antimicrobial activity against a Gram-negative bacterium Ralstonia solanacearum while calcimycin was inactive. Additionally, 2 inhibits the migration of EC17 cancer cells at noncytotoxic concentrations.
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