A novel sperm-activating and attracting factor from the ascidian Ascidia sydneiensis

Nobuaki Matsumori; Yuki Hiradate; Hajime Shibata; Tohru Oishi; Shuichi Shimma; Michisato Toyoda; Fumiaki Hayashi; Manabu Yoshida; Michio Murata; Masaaki Morisawa

doi:10.1021/ol303172n

A novel sperm-activating and attracting factor from the ascidian Ascidia sydneiensis

Org Lett. 2013 Jan 18;15(2):294-7. doi: 10.1021/ol303172n. Epub 2013 Jan 4.

Authors

Nobuaki Matsumori¹, Yuki Hiradate, Hajime Shibata, Tohru Oishi, Shuichi Shimma, Michisato Toyoda, Fumiaki Hayashi, Manabu Yoshida, Michio Murata, Masaaki Morisawa

Affiliation

¹ Department of Chemistry, Graduate School of Science, Osaka Universit , Toyonaka, Osaka 560-0043, Japan. matsmori@chem.sci.osaka-u.ac.jp

PMID: 23289404
DOI: 10.1021/ol303172n

Abstract

A novel SAAF was isolated from the title ascidian. The structure was elucidated using the entire sample of 4 nmol, suggesting that the position of the OH group confers genus-specificity to sperm chemotaxis in ascidians. This study not only provides insight into the chemical tactics in sperm chemotaxis but demonstrates that the innovative techniques allow structure determination of natural products in trace amounts.

Publication types

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

MeSH terms

Animals
Cholestanols / chemistry
Cholestanols / isolation & purification*
Cholestanols / metabolism
Male
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Spermatozoa / physiology*
Structure-Activity Relationship
Sulfuric Acid Esters / chemistry
Sulfuric Acid Esters / isolation & purification*
Sulfuric Acid Esters / metabolism
Urochordata / chemistry*
Urochordata / genetics

Substances

3,4,7,26-tetrahydroxycholestane-3,26-disulfate
Cholestanols
Sulfuric Acid Esters
sperm-activating and attracting factor, Ascidia sydneiensis