Synthesis and identification of an endogenous sperm activating and attracting factor isolated from eggs of the ascidian Ciona intestinalis; An example of nanomolar-level structure elucidation of novel natural compound

Tohru Oishi, Hiroshi Tsuchikawa, Michio Murata, Manabu Yoshida, Masaaki Morisawa

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

A sperm-activating and attracting factor (SAAF) was isolated from the eggs of the ascidian Ciona intestinalis, and its structure was deduced with only approximately 4 μg of the specimen. Based upon the proposed structure, two epimers were synthesized from chenodeoxycholic acid in 16 steps. Comparison between synthetic and natural compounds led to the unambiguous structure determination of SAAF to be (3R,4R,7R,25S)-3,4,7,26-tetrahydroxycholestane-3,26- disulfate. The synthetic pure specimen was also utilized to confirm that both sperm-activation and attraction were elicited by a single compound.

Original languageEnglish
Pages (from-to)6971-6980
Number of pages10
JournalTetrahedron
Volume60
Issue number33
DOIs
Publication statusPublished - Aug 9 2004
Externally publishedYes

Fingerprint

Ciona intestinalis
Lead compounds
Chenodeoxycholic Acid
Urochordata
Eggs
Spermatozoa
Chemical activation
3,4,7,26-tetrahydroxycholestane-3,26-disulfate

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Synthesis and identification of an endogenous sperm activating and attracting factor isolated from eggs of the ascidian Ciona intestinalis; An example of nanomolar-level structure elucidation of novel natural compound. / Oishi, Tohru; Tsuchikawa, Hiroshi; Murata, Michio; Yoshida, Manabu; Morisawa, Masaaki.

In: Tetrahedron, Vol. 60, No. 33, 09.08.2004, p. 6971-6980.

Research output: Contribution to journalArticle

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