Iakyricidins A-D, Antiproliferative Piericidin Analogues Bearing a Carbonyl Group or Cyclic Skeleton from Streptomyces iakyrus SCSIO NS104

Kunlong Li; Zhi Liang; Weihao Chen; Xiaowei Luo; Wei Fang; Shengrong Liao; Xiuping Lin; Bin Yang; Junfeng Wang; Lan Tang; Yonghong Liu; Xuefeng Zhou

doi:10.1021/acs.joc.9b01270

Iakyricidins A-D, Antiproliferative Piericidin Analogues Bearing a Carbonyl Group or Cyclic Skeleton from Streptomyces iakyrus SCSIO NS104

J Org Chem. 2019 Oct 4;84(19):12626-12631. doi: 10.1021/acs.joc.9b01270. Epub 2019 Aug 7.

Authors

Kunlong Li^{1

2}, Zhi Liang³, Weihao Chen^{1

2}, Xiaowei Luo^{1

2}, Wei Fang⁴, Shengrong Liao¹, Xiuping Lin¹, Bin Yang¹, Junfeng Wang¹, Lan Tang³, Yonghong Liu^{1

2}, Xuefeng Zhou^{1

2}

Affiliations

¹ CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Materia Medica , South China Sea Institute of Oceanology, Chinese Academy of Sciences Guangzhou 510301 , China.
² University of Chinese Academy of Sciences , Beijing 100049 , China.
³ Biopharmaceutics, Guangdong Provincial Key Laboratory of New Drug Screening, School of Pharmaceutical Sciences , Southern Medical University , Guangzhou 510515 , China.
⁴ Hubei Biopesticide Engineering Research Center , Hubei Academy of Agricultural Sciences , Wuhan 430064 , China.

PMID: 31347367
DOI: 10.1021/acs.joc.9b01270

Abstract

Iakyricidins A-D (1-4), a carbonyl-containing piericidin derivative and three novel piericidin analogues bearing cyclic skeletons, were isolated from the mangrove sediment derived strain Streptomyces iakyrus SCSIO NS104. These structures were established by spectroscopic techniques, Mosher's method, and ECD calculations. Compounds 2-4 represent a novel skeleton of piericidins with branched chain C-C cyclization, and their biosynthetic pathways are proposed. Compound 1, the first natural carbonyl-containing piericidin derivate, exhibited potent antiproliferative activity against ACHN with an IC₅₀ value of 20 nM.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents / chemistry
Antineoplastic Agents / isolation & purification
Antineoplastic Agents / pharmacology*
Apoptosis / drug effects
Cell Cycle / drug effects
Cell Proliferation / drug effects
Drug Screening Assays, Antitumor
Humans
Mitochondria / drug effects
Molecular Structure
Pyridines / chemistry
Pyridines / isolation & purification
Pyridines / pharmacology*
Streptomyces / chemistry*
Tumor Cells, Cultured

Substances

Antineoplastic Agents
Pyridines
piericidin A

Supplementary concepts

Streptomyces iakyrus