Akazamicin, a cytotoxic aromatic polyketide from marine-derived Nonomuraea sp

Taehui Yang; Katsuhisa Yamada; Tao Zhou; Enjuro Harunari; Yasuhiro Igarashi; Takeshi Terahara; Takeshi Kobayashi; Chiaki Imada

doi:10.1038/s41429-018-0139-7

Akazamicin, a cytotoxic aromatic polyketide from marine-derived Nonomuraea sp

J Antibiot (Tokyo). 2019 Apr;72(4):202-209. doi: 10.1038/s41429-018-0139-7. Epub 2019 Jan 10.

Authors

Taehui Yang¹, Katsuhisa Yamada², Tao Zhou³, Enjuro Harunari³, Yasuhiro Igarashi³, Takeshi Terahara¹, Takeshi Kobayashi¹, Chiaki Imada⁴

Affiliations

¹ Graduate School of Marine Science and Technology, Tokyo University of Marine Science and Technology, 4-5-7, Konan, Minato-ku, Tokyo, 108-8477, Japan.
² DHC corporation, 2-7-1 Minami-Azabu, Minato-ku, Tokyo, 106-8571, Japan.
³ Biotechnology Research Center, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama, 939-0398, Japan.
⁴ Graduate School of Marine Science and Technology, Tokyo University of Marine Science and Technology, 4-5-7, Konan, Minato-ku, Tokyo, 108-8477, Japan. imada@kaiyodai.ac.jp.

PMID: 30631113
DOI: 10.1038/s41429-018-0139-7

Abstract

In our screening program on marine-derived actinomycetes, Nonomuraea sp. AKA32 isolated from deep-sea water collected from a depth of 800 m in Sagami Bay, Japan was found to produce compounds cytotoxic to cancer cells. Activity-guided purification led to the isolation of a new aromatic polyketide, akazamicin (1), along with two known compounds, actinofuranone C (2) and N-formylanthranilic acid (3). Structures of these compounds were elucidated through the interpretation of NMR and MS spectroscopic data. Compounds 1, 2, and 3 displayed cytotoxicity against murine B16 melanoma cell line with the IC₅₀ value of 1.7, 1.2, and 25 μM, respectively.

MeSH terms

Actinobacteria / metabolism*
Animals
Antineoplastic Agents / chemistry
Antineoplastic Agents / isolation & purification*
Antineoplastic Agents / pharmacology
Aquatic Organisms / metabolism*
Biological Products / chemistry
Biological Products / isolation & purification*
Biological Products / pharmacology
Cell Line, Tumor
Cell Proliferation / drug effects
Hydrocarbons, Aromatic / chemistry
Hydrocarbons, Aromatic / isolation & purification
Hydrocarbons, Aromatic / pharmacology
Inhibitory Concentration 50
Japan
Magnetic Resonance Spectroscopy
Mass Spectrometry
Melanocytes / drug effects
Mice
Molecular Structure
Polyketides / chemistry
Polyketides / isolation & purification
Polyketides / pharmacology
Seawater / microbiology

Substances

Antineoplastic Agents
Biological Products
Hydrocarbons, Aromatic
Polyketides