Antartin, a Cytotoxic Zizaane-Type Sesquiterpenoid from a Streptomyces sp. Isolated from an Antarctic Marine Sediment

Dayoung Kim; Eun Ju Lee; Jihye Lee; Alain S Leutou; Yern-Hyerk Shin; Bomi Choi; Ji Sun Hwang; Dongyup Hahn; Hyukjae Choi; Jungwook Chin; Sung Jin Cho; Yong Deog Hong; Jaeyoung Ko; Chi Nam Seong; Katherine N Maloney; Dong-Chan Oh; Inho Yang; Hayoung Hwang; Sang-Jip Nam

doi:10.3390/md16040130

Antartin, a Cytotoxic Zizaane-Type Sesquiterpenoid from a Streptomyces sp. Isolated from an Antarctic Marine Sediment

Mar Drugs. 2018 Apr 16;16(4):130. doi: 10.3390/md16040130.

Authors

Dayoung Kim¹, Eun Ju Lee², Jihye Lee³, Alain S Leutou⁴, Yern-Hyerk Shin⁵, Bomi Choi⁶, Ji Sun Hwang⁷, Dongyup Hahn^{8

9}, Hyukjae Choi¹⁰, Jungwook Chin¹¹, Sung Jin Cho¹², Yong Deog Hong¹³, Jaeyoung Ko¹⁴, Chi Nam Seong¹⁵, Katherine N Maloney¹⁶, Dong-Chan Oh¹⁷, Inho Yang¹⁸, Hayoung Hwang¹⁹, Sang-Jip Nam²⁰

Affiliations

¹ Department of Chemistry and Nano Science, Ewha Womans University, Seoul 03760, Korea. [email protected].
² New Drug Development Center, Daegu-Gyeongbuk Medical Innovation Foundation (DGMIF), Daegu 41061, Korea. [email protected].
³ Department of Chemistry and Nano Science, Ewha Womans University, Seoul 03760, Korea. [email protected].
⁴ Department of Chemistry and Nano Science, Ewha Womans University, Seoul 03760, Korea. [email protected].
⁵ Natural Products Research Institute, College of Pharmacy, Seoul National University, San 56-1, Sillim, Gwanak, Seoul 08826, Korea. [email protected].
⁶ Department of Chemistry and Nano Science, Ewha Womans University, Seoul 03760, Korea. [email protected].
⁷ New Drug Development Center, Daegu-Gyeongbuk Medical Innovation Foundation (DGMIF), Daegu 41061, Korea. [email protected].
⁸ School of Food Science and Biotechnology, College of Agriculture and Life Sciences, Kyungpook National University, Daegu 41566, Korea. [email protected].
⁹ Institute of Agricultural Science & Technology, Kyungpook National University, Daegu 41566, Korea. [email protected].
¹⁰ College of Pharmacy, Yeungnam University, Gyeongsan-si, Gyeongsangbukdo 38541, Korea. [email protected].
¹¹ New Drug Development Center, Daegu-Gyeongbuk Medical Innovation Foundation (DGMIF), Daegu 41061, Korea. [email protected].
¹² New Drug Development Center, Daegu-Gyeongbuk Medical Innovation Foundation (DGMIF), Daegu 41061, Korea. [email protected].
¹³ Materials Lab Amorepacific R&D Unit, Yongin, Gyeonggi-do 17074, Korea. [email protected].
¹⁴ Materials Lab Amorepacific R&D Unit, Yongin, Gyeonggi-do 17074, Korea. [email protected].
¹⁵ Department of Biology, College of Life Science and Natural Resource, Sunchon National University, Suncheon 57922, Korea. [email protected].
¹⁶ Department of Chemistry, Point Loma Nazarene University, 3900 Lomaland Drive, San Diego, CA 92106, USA. [email protected].
¹⁷ Natural Products Research Institute, College of Pharmacy, Seoul National University, San 56-1, Sillim, Gwanak, Seoul 08826, Korea. [email protected].
¹⁸ Department of Convergence Study on the Ocean Science and Technology, Korea Maritime and Ocean University, Busan 49112, Korea. [email protected].
¹⁹ New Drug Development Center, Daegu-Gyeongbuk Medical Innovation Foundation (DGMIF), Daegu 41061, Korea. [email protected].
²⁰ Department of Chemistry and Nano Science, Ewha Womans University, Seoul 03760, Korea. [email protected].

Abstract

Antartin (1), a new zizaane-type sesquiterpene, was isolated from Streptomyces sp. SCO736. The chemical structure of 1 was assigned from the interpretation of 1D and 2D NMR in addition to mass spectrometric data. The relative stereochemistry of 1 was determined by analysis of NOE data, while the absolute stereochemistry was decided based on a comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Antartin (1) showed cytotoxicity against A549, H1299, and U87 cancer cell lines by causing cell cycle arrest at the G1 phase.

Keywords: Streptomyces sp.; cold water natural product; marine natural product; zizaane-type sesquiterpenoid.

MeSH terms

A549 Cells
Antarctic Regions
Cell Line, Tumor
Circular Dichroism
Cytotoxins / chemistry*
Cytotoxins / pharmacology
G1 Phase / drug effects
Geologic Sediments / microbiology
Humans
Magnetic Resonance Spectroscopy / methods
Sesquiterpenes / chemistry*
Sesquiterpenes / pharmacology
Streptomyces / chemistry*

Substances

Cytotoxins
Sesquiterpenes