2. Academic Validation
  3. Absolute Configuration and Antibiotic Activity of Piceamycin

Absolute Configuration and Antibiotic Activity of Piceamycin

  • J Nat Prod. 2020 Feb 28;83(2):277-285. doi: 10.1021/acs.jnatprod.9b00678.
Yern-Hyerk Shin 1,  Saeyeon Kang 2,  Woong Sub Byun 1,  Chang-Wook Jeon 3,  Beomkoo Chung 2,  Ji Yoon Beom 4,  Suckchang Hong 5,  Jeeyeon Lee 5,  Jongheon Shin 1,  Youn-Sig Kwak 3,  Sang Kook Lee 1,  Ki-Bong Oh 2,  Yeo Joon Yoon 4,  Dong-Chan Oh 1
Affiliations

Affiliations

  • 1 Natural Products Research Institute, College of Pharmacy , Seoul National University , 1 Gwanak-ro , Gwanak-gu , Seoul 08826 , Republic of Korea.
  • 2 Department of Agricultural Biotechnology, College of Agriculture & Life Sciences , Seoul National University , 1 Gwanak-ro , Gwanak-gu , Seoul 08826 , Republic of Korea.
  • 3 Department of Plant Medicine and IALS , Gyeongsang National University , 501 Jinju-daero , Jinju , Gyeongsang Nam-do 52828 , Republic of Korea.
  • 4 Department of Chemistry and Nanoscience , Ewha Womans University , Seoul 03760 , Republic of Korea.
  • 5 College of Pharmacy , Seoul National University , 1 Gwanak-ro , Gwanak-gu , Seoul 08826 , Republic of Korea.
PMID: 32073848 DOI: 10.1021/acs.jnatprod.9b00678
Abstract

The cultivation of a Streptomyces sp. SD53 strain isolated from the gut of the silkworm Bombyx mori produced two macrolactam Natural Products, piceamycin (1) and bombyxamycin C (2). The planar structures of 1 and 2 were identified by a combination of NMR, MS, and UV spectroscopic analyses. The absolute configurations were assigned based on chemical and chromatographic methods as well as ECD calculations. A new chromatography-based experimental method for determining the configurations of stereogenic centers β to nitrogen atoms in macrolactams was established and successfully applied in this report. These compounds exhibited significant bioactivities against the silkworm entomopathogen Bacillus thuringiensis and various human pathogens as well as human Cancer cell lines. In particular, piceamycin potently inhibited Salmonella enterica and Proteus hauseri with MIC values of 0.083 μg/mL and 0.025 μg/mL, respectively. The biosynthetic pathway involved in the formation of the cyclopentenone moiety in piceamycin is discussed.

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