Iriomoteolides-9a and 11a: two new odd-numbered macrolides from the marine dinoflagellate Amphidinium species

Keiko Kumagai; Masayuki Tsuda; Eri Fukushi; Jun Kawabata; Atsunori Masuda; Masashi Tsuda

doi:10.1007/s11418-017-1080-y

Iriomoteolides-9a and 11a: two new odd-numbered macrolides from the marine dinoflagellate Amphidinium species

J Nat Med. 2017 Jul;71(3):506-512. doi: 10.1007/s11418-017-1080-y. Epub 2017 Mar 2.

Authors

Keiko Kumagai¹, Masayuki Tsuda¹, Eri Fukushi², Jun Kawabata², Atsunori Masuda³, Masashi Tsuda⁴

Affiliations

¹ Science Research Center, Kochi University, Nankoku, Kochi, 783-8505, Japan.
² Research Faculty of Agriculture, Hokkaido University, Sapporo, Hokkaido, 060-8589, Japan.
³ College of Agriculture, Tamagawa University, Machida, Tokyo, 194-8610, Japan.
⁴ Center for Advanced Marine Core Research and Department of Agriculture and Marine Science, Kochi University, Nankoku, Kochi, 783-8502, Japan. mtsuda@kochi-u.ac.jp.

PMID: 28255848
DOI: 10.1007/s11418-017-1080-y

Abstract

Iriomoteolides-9a (1) and 11a (2), new 15- and 19-membered macrolides, respectively, have been isolated from the marine dinoflagellate Amphidinium species (strain KCA09052). Compounds 1 and 2 were obtained from the extracts of the algal cells inoculated in the PES and TKF seawater medium, respectively. The structures of 1 and 2 were assigned on the basis of detailed NMR analyses. Compounds 1 and 2 exhibited cytotoxic activity against human cervix adenocarcinoma HeLa cells.

Keywords: Amphidinium; Cytotoxic activity; Dinoflagellate; Macrolide.

MeSH terms

Adenocarcinoma / drug therapy
Animals
Antineoplastic Agents / chemistry
Antineoplastic Agents / isolation & purification
Antineoplastic Agents / pharmacology
Biological Products / chemistry
Biological Products / isolation & purification*
Biological Products / pharmacology
Dinoflagellida / chemistry*
Female
HeLa Cells
Humans
Macrolides / chemistry
Macrolides / isolation & purification*
Macrolides / pharmacology
Magnetic Resonance Spectroscopy
Molecular Structure
Uterine Cervical Neoplasms / drug therapy

Substances

Antineoplastic Agents
Biological Products
Iriomoteolide 11a
Iriomoteolide 9a
Macrolides