2013
DOI: 10.1021/ol303172n
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A Novel Sperm-Activating and Attracting Factor from the Ascidian Ascidia sydneiensis

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.

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Cited by 17 publications
(24 citation statements)
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“…912 A sperm activation and attractant 1135 was isolated from egg seawater of Ascidia sydneiensis; structure elucidation by NMR and MS was performed on 2.6 mg (4 nmol) of material. 913 The proposed planar and stereo structure of 1135 was supported by the synthesis of model compounds. The structure of this sperm attractant is very similar to that previously reported from Ciona intestinalis and C. savignyi.…”
Section: Molluscsmentioning
confidence: 91%
“…912 A sperm activation and attractant 1135 was isolated from egg seawater of Ascidia sydneiensis; structure elucidation by NMR and MS was performed on 2.6 mg (4 nmol) of material. 913 The proposed planar and stereo structure of 1135 was supported by the synthesis of model compounds. The structure of this sperm attractant is very similar to that previously reported from Ciona intestinalis and C. savignyi.…”
Section: Molluscsmentioning
confidence: 91%
“…This behavior is also mediated by [Ca 2+ ] i 18 . In the sperm of the ascidian, Ciona intestinalis , the sperm-activating and attracting factor (SAAF), which is a sulfate-conjugated hydroxysteroid 19 21 , mediates both activation of sperm motility and chemotaxis 3 , 19 , 22 . The phenomena requires extracellular Ca 2+ 3 , 23 , 24 .…”
Section: Introductionmentioning
confidence: 99%
“…In many animals, sperm motility activation is regulated by extracellular cues such as changes in viscosity or pH (Yoshida, Kawano, & Yoshida, ). Ascidians control motility activation using a sulfated steroid secreted by the egg (Izumi, Marian, Inaba, Oka, & Morisawa, ; Matsumori et al, ; Yoshida, Murata, Inaba, & Morisawa, ), whereas fish and amphibians control motility activation via changes in intracellular pH, calcium or cAMP (Cherr et al, ; Ingermann, Holcomb, Zuccarelli, Kanuga, & Cloud, ; Ohta, Kubo, Nakauchi, & Watanabe, ; Takayama‐Watanabe, Campanella, Kubo, & Watanabe, ; Takei, Mukai, & Okuno, ; Tholl et al, ; Watanabe et al, ; Watanabe, Takayama‐Watanabe, Vines, & Cherr, ; Zilli, Schiavone, Storelli, & Vilella, ; Zilli et al, ). In some organisms, chemical factors that activate sperm motility are released by the egg and, therefore, represent the first communication between sperm and egg.…”
Section: Discussionmentioning
confidence: 99%