Igidamycins A–C, Rare Sugar-Bearing Anthracycline Glycosides from a Marine Actinomycete, <i>Streptomyces</i> sp.

Genome-guided mining of marine <i>Streptomyces</i> sp. GCU-142 led to the identification of three unprecedented sugar-bearing anthracycline glycosides, igidamycins A-C (<b>1</b>-<b>3</b>). The structures of <b>1</b>-<b>3</b> were assigned by spectroscopic analysis including NMR, HR-MS, and UV spectroscopy. Their configurations were determined by ROESY NMR data, the modified Mosher's method, l-cysteine methyl ester derivatization, and TD-DFT ECD calculations. Bioinformatic analysis suggested a plausible biosynthetic pathway of igidamycins, integrating type II polyketide assembly, extensive sugar tailoring, and late-stage nitration. Notably, igidamycin A (<b>1</b>), bearing a nitro group at C-6, exhibited potent antibacterial activity against various Gram-positive pathogens. In contrast, the non-nitrated congeners (<b>2</b> and <b>3</b>) were inactive, highlighting a key role of the nitro functionality in its antibacterial potency.

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Publication Details

Journal
Organic Letters
Published
2026-03-09
DOI
https://doi.org/10.1021/acs.orglett.6c00379
Primary Topic
Microbial Natural Products and Biosynthesis
Type
article
Field-Weighted Citation Impact
0.00
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article

Igidamycins A–C, Rare Sugar-Bearing Anthracycline Glycosides from a Marine Actinomycete, Streptomyces sp.

Yong‐Joon Cho, Munhyung Bae, Jungro Lee, Kyuho Moon
Organic Letters
Microbial Natural Products and Biosynthesis
article

Igidamycins A–C, Rare Sugar-Bearing Anthracycline Glycosides from a Marine Actinomycete, Streptomyces sp.

Yong‐Joon Cho, Munhyung Bae, Jungro Lee, Kyuho Moon
article en

Abstract

Genome-guided mining of marine <i>Streptomyces</i> sp. GCU-142 led to the identification of three unprecedented sugar-bearing anthracycline glycosides, igidamycins A-C (<b>1</b>-<b>3</b>). The structures of <b>1</b>-<b>3</b> were assigned by spectroscopic analysis including NMR, HR-MS, and UV spectroscopy. Their configurations were determined by ROESY NMR data, the modified Mosher's method, l-cysteine methyl ester derivatization, and TD-DFT ECD calculations. Bioinformatic analysis suggested a plausible biosynthetic pathway of igidamycins, integrating type II polyketide assembly, extensive sugar tailoring, and late-stage nitration. Notably, igidamycin A (<b>1</b>), bearing a nitro group at C-6, exhibited potent antibacterial activity against various Gram-positive pathogens. In contrast, the non-nitrated congeners (<b>2</b> and <b>3</b>) were inactive, highlighting a key role of the nitro functionality in its antibacterial potency.

Organic LettersVol. 28(11)
Gachon University (KR), Kangwon National University (KR), Kyung Hee University (KR)
Life below water
Openalex Percentile: Top 28%
Microbial Natural Products and Biosynthesis
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