Structures of the Largest Amphidinol Homologues from the Dinoflagellate Amphidinium carterae and Structure-Activity Relationships

Masayuki Satake; Kimberly Cornelio; Shinya Hanashima; Raymond Malabed; Michio Murata; Nobuaki Matsumori; Huiping Zhang; Fumiaki Hayashi; Shoko Mori; Jong Souk Kim; Chang Hoon Kim; Jong Soo Lee

doi:10.1021/acs.jnatprod.7b00345

Structures of the Largest Amphidinol Homologues from the Dinoflagellate Amphidinium carterae and Structure-Activity Relationships

Masayuki Satake, Kimberly Cornelio, Shinya Hanashima, Raymond Malabed, Michio Murata, Nobuaki Matsumori, Huiping Zhang, Fumiaki Hayashi, Shoko Mori, Jong Souk Kim, Chang Hoon Kim, Jong Soo Lee

Inorganic and Analytical Chemistry

Research output: Contribution to journal › Article › peer-review

25 Citations (Scopus)

Abstract

Amphidinols are polyketide metabolites produced by marine dinoflagellates and are chiefly composed of a long linear chain with polyol groups and polyolefins. Two new homologues, amphidinols 20 (AM20, 1) and 21 (AM21, 2), were isolated from Amphidinium carterae collected in Korea. Their structures were elucidated by detailed NMR analyses as amphidinol 6-type compounds with remarkably long polyol chains. Amphidinol 21 (2) has the longest linear structure among the amphidinol homologues reported so far. The congeners, particularly amphidinol 21 (2), showed weaker activity in hemolysis and antifungal assays compared to known amphidinols.

Original language	English
Pages (from-to)	2883-2888
Number of pages	6
Journal	Journal of Natural Products
Volume	80
Issue number	11
DOIs	https://doi.org/10.1021/acs.jnatprod.7b00345
Publication status	Published - Nov 22 2017

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1021/acs.jnatprod.7b00345

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Satake, M., Cornelio, K., Hanashima, S., Malabed, R., Murata, M., Matsumori, N., Zhang, H., Hayashi, F., Mori, S., Kim, J. S., Kim, C. H., & Lee, J. S. (2017). Structures of the Largest Amphidinol Homologues from the Dinoflagellate Amphidinium carterae and Structure-Activity Relationships. Journal of Natural Products, 80(11), 2883-2888. https://doi.org/10.1021/acs.jnatprod.7b00345

Satake, M, Cornelio, K, Hanashima, S, Malabed, R, Murata, M, Matsumori, N, Zhang, H, Hayashi, F, Mori, S, Kim, JS, Kim, CH & Lee, JS 2017, 'Structures of the Largest Amphidinol Homologues from the Dinoflagellate Amphidinium carterae and Structure-Activity Relationships', Journal of Natural Products, vol. 80, no. 11, pp. 2883-2888. https://doi.org/10.1021/acs.jnatprod.7b00345

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title = "Structures of the Largest Amphidinol Homologues from the Dinoflagellate Amphidinium carterae and Structure-Activity Relationships",

abstract = "Amphidinols are polyketide metabolites produced by marine dinoflagellates and are chiefly composed of a long linear chain with polyol groups and polyolefins. Two new homologues, amphidinols 20 (AM20, 1) and 21 (AM21, 2), were isolated from Amphidinium carterae collected in Korea. Their structures were elucidated by detailed NMR analyses as amphidinol 6-type compounds with remarkably long polyol chains. Amphidinol 21 (2) has the longest linear structure among the amphidinol homologues reported so far. The congeners, particularly amphidinol 21 (2), showed weaker activity in hemolysis and antifungal assays compared to known amphidinols.",

author = "Masayuki Satake and Kimberly Cornelio and Shinya Hanashima and Raymond Malabed and Michio Murata and Nobuaki Matsumori and Huiping Zhang and Fumiaki Hayashi and Shoko Mori and Kim, {Jong Souk} and Kim, {Chang Hoon} and Lee, {Jong Soo}",

note = "Funding Information: This work was partly supported by Scientific Research KAKENHIs (S), (A), and (C) with Grant Nos. 16H06315, 25242073, and15K01798, respectively, and also by Korea Institute of Marine Science & Technology Promotion (Project No. D11111112H390000140). Publisher Copyright: {\textcopyright} 2017 The American Chemical Society and American Society of Pharmacognosy.",

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doi = "10.1021/acs.jnatprod.7b00345",

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AU - Satake, Masayuki

AU - Cornelio, Kimberly

AU - Hanashima, Shinya

AU - Malabed, Raymond

AU - Murata, Michio

AU - Matsumori, Nobuaki

AU - Zhang, Huiping

AU - Hayashi, Fumiaki

AU - Mori, Shoko

AU - Kim, Jong Souk

AU - Kim, Chang Hoon

AU - Lee, Jong Soo

N1 - Funding Information: This work was partly supported by Scientific Research KAKENHIs (S), (A), and (C) with Grant Nos. 16H06315, 25242073, and15K01798, respectively, and also by Korea Institute of Marine Science & Technology Promotion (Project No. D11111112H390000140). Publisher Copyright: © 2017 The American Chemical Society and American Society of Pharmacognosy.

PY - 2017/11/22

Y1 - 2017/11/22

N2 - Amphidinols are polyketide metabolites produced by marine dinoflagellates and are chiefly composed of a long linear chain with polyol groups and polyolefins. Two new homologues, amphidinols 20 (AM20, 1) and 21 (AM21, 2), were isolated from Amphidinium carterae collected in Korea. Their structures were elucidated by detailed NMR analyses as amphidinol 6-type compounds with remarkably long polyol chains. Amphidinol 21 (2) has the longest linear structure among the amphidinol homologues reported so far. The congeners, particularly amphidinol 21 (2), showed weaker activity in hemolysis and antifungal assays compared to known amphidinols.

AB - Amphidinols are polyketide metabolites produced by marine dinoflagellates and are chiefly composed of a long linear chain with polyol groups and polyolefins. Two new homologues, amphidinols 20 (AM20, 1) and 21 (AM21, 2), were isolated from Amphidinium carterae collected in Korea. Their structures were elucidated by detailed NMR analyses as amphidinol 6-type compounds with remarkably long polyol chains. Amphidinol 21 (2) has the longest linear structure among the amphidinol homologues reported so far. The congeners, particularly amphidinol 21 (2), showed weaker activity in hemolysis and antifungal assays compared to known amphidinols.

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Structures of the Largest Amphidinol Homologues from the Dinoflagellate Amphidinium carterae and Structure-Activity Relationships

Abstract

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UN SDGs

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