Juanlimycins A and B, Ansamycin Macrodilactams from Streptomyces sp.

Abstract

Ansamycins are a family of macrolactams characterized by an aromatic chromophore with an aliphatic chain (ansa chain) connected back to a nonadjacent position through an amide bond. This family has shown a high degree of druggability exemplified by rifamycins, maytansinoids, and geldanamycins. In this study, the isolation of two novel ansamycin macrodilactams with unprecedented features, juanlimycins A (1) and B (2), from Streptomyces sp. LC6 were reported. The structures of 1 and 2 were assigned on the basis of analysis of NMR spectroscopic data and X-ray single crystal diffraction.

Activating a Cryptic Ansamycin Biosynthetic Gene Cluster To Produce Three New Naphthalenic Octaketide Ansamycins with n-Pentyl and n-Butyl Side Chains

“…All of them were fully characterized by the analysis of HR ESI-MS and NMR data (Tables S7−S9 and Figures S11−29). The molecular formula (C 30 H 37 NO 7 ) of neo- 6 , and identified as a "degradation" product of 2 as previously proposed for hygrocins. 23 The single-crystal X-ray diffraction experiment fully confirmed the proposed structure and the relative configuration (Figure 4, deposition no.…”

Ansavaricins A–E: five new streptovaricin derivatives from Streptomyces sp. S012

“…Previously, we have approached to new ansamycins through PCR screening of the AHBA synthase genes of plantassociated, soil-dwelling and marine-derived actinomycetes, 8 which afforded the characterization of the biosynthesis of hygrocins, 8,9 divergolides, 10,11 ansamycins juanlimycins 12 and neoansamycins, 13 and the isolation of ansatrienols B-H with diverse post-PKS modications from the strain Streptomyces sp. XZQH13OEDastC.…”

Neoansamycins from Streptomyces sp. LZ35

“…3 Over the past ten years, we have focused on discovering ansamycin-producing strains, and obtained twenty-six 3-amino-5-hydroxyl benzoic acid (AHBA) synthase gene-positive strains from plant-associated and marine-derived actinomycetes through PCR screening of AHBA synthase genes. 4 From these AHBA synthase gene-positive strains, we isolated dozens of ansamycins, including hygrocins, [5][6][7] divergolides, 8,9 juanlimycins, 10 ansatrienes, 11,12 and streptovaricin derivatives ansavaricins A-I. 13,14 Recently, Streptomyces sp.…”