logo
CONTENT TYPES

A Novel Sperm-Activating and Attracting Factor from the Ascidian Ascidia sydneiensis

View Author Information
Department of Chemistry and Department of Physics, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan, Department of Biology, Faculty of Science, Yamagata University, Kojirakawa, Yamagata 990-8560, Japan, Misaki Marine Biological Station, Graduate School of Science, University of Tokyo, Miura, Kanagawa 238-0225, Japan, Department of Chemistry, Graduate School of Sciences, Kyushu University, Higashi-ku, Fukuoka 812-8581, Japan, and RIKEN Systems and Structural Biology Center, RIKEN Yokohama Institute, Yokohama, Kanagawa, 230-0045, Japan
†Department of Chemistry, Osaka University.
‡Department of Biology, Yamagata University.
§Misaki Marine Biological Station, University of Tokyo.
∥Department of Chemistry, Kyushu University.
⊥Department of Physics, Osaka University.
#RIKEN Systems and Structural Biology Center, RIKEN Yokohama Institute.
&Present address: Department of Animal Biology, Graduate School of Agricultural Science, Tohoku University, Aoba-ku, Sendai, Miyagi 981-8555, Japan.
@Present address: National Cancer Center Research Institute, Chuo-ku, Tokyo 104-0045, Japan.
̂Present address: Project Research Center for Fundamental Sciences, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan,
$Present address: Tokyo Kasei Gakuin University, Machida, Tokyo 194-0292, Japan.
△These authors contributed equally to this work.
Cite this: Org. Lett. 2013, 15, 2, 294–297
Publication Date (Web):January 4, 2013
https://doi.org/10.1021/ol303172n
Copyright © 2013 American Chemical Society
Article Views
1424
Altmetric
-
Citations
LEARN ABOUT THESE METRICS

Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.

Read OnlinePDF (977 KB)
Supporting Info (1)»

Abstract

Abstract Image

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.

Supporting Information

ARTICLE SECTIONS
Jump To

Experimental details of purification and structure analysis of Ascidia-SAAF 2, NMR spectra of Ascidia-SAAF 2, and spectral simulation of 1H NMR of the olefin (H-22 and H-23) signals. This material is available free of charge via the Internet at http://pubs.acs.org.

Terms & Conditions

Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

Cited By


This article is cited by 20 publications.

  1. Laurence K. Jennings, Dale W. Prebble, Mingming Xu, Merrick G. Ekins, Alan L. Munn, George D. Mellick, Anthony R. Carroll. Anti-prion and α-Synuclein Aggregation Inhibitory Sterols from the Sponge Lamellodysidea cf. chlorea. Journal of Natural Products 2020, 83 (12) , 3751-3757. https://doi.org/10.1021/acs.jnatprod.0c01168
  2. Tomohiro Watanabe, Hajime Shibata, Makoto Ebine, Hiroshi Tsuchikawa, Nobuaki Matsumori, Michio Murata, Manabu Yoshida, Masaaki Morisawa, Shu Lin, Kosei Yamauchi, Ken Sakai, Tohru Oishi. Synthesis and Complete Structure Determination of a Sperm-Activating and -Attracting Factor Isolated from the Ascidian Ascidia sydneiensis. Journal of Natural Products 2018, 81 (4) , 985-997. https://doi.org/10.1021/acs.jnatprod.7b01052
  3. Hiroshi Tsuchikawa, Tohru Oishi. Chemical Synthesis, Structure Determination, and Evaluation of Biological Activity of Sperm Activating and Attracting Factors Isolated from Ascidias. Journal of Synthetic Organic Chemistry, Japan 2020, 78 (3) , 213-220. https://doi.org/10.5059/yukigoseikyokaishi.78.213
  4. Jumpei Ikenaga, Manabu Yoshida. Chapter 3 Sperm Activation and Chemotaxis in Invertebrates. 2020,,, 31-46. https://doi.org/10.1007/978-981-15-2290-1_4
  5. , . Reproduction in Aquatic Animals. 2020,,https://doi.org/10.1007/978-981-15-2290-1
  6. Krista R. Gert, Andrea Pauli. Species-specific mechanisms during fertilization. 2020,,, 121-144. https://doi.org/10.1016/bs.ctdb.2019.10.005
  7. . Maternal Effect Genes in Development. 2020,,https://doi.org/
  8. Nengzhong Wang, Puli Saidhareddy, Xuefeng Jiang. . Natural Product Reports 2020,,, 246. https://doi.org/10.1039/C8NP00093J
  9. Melany P. Puglisi, Jennifer M. Sneed, Raphael Ritson-Williams, Ryan Young. Marine chemical ecology in benthic environments. Natural Product Reports 2019, 36 (3) , 410-429. https://doi.org/10.1039/C8NP00061A
  10. Kaoru Yoshida, Kogiku Shiba, Ayako Sakamoto, Jumpei Ikenaga, Shigeru Matsunaga, Kazuo Inaba, Manabu Yoshida. Ca2+ efflux via plasma membrane Ca2+-ATPase mediates chemotaxis in ascidian sperm. Scientific Reports 2018, 8 (1) https://doi.org/10.1038/s41598-018-35013-2
  11. Kimberly Stephens, Richard A. Cardullo, Catherine D. Thaler. Culex pipiens sperm motility is initiated by a trypsin-like protease from male accessory glands. Molecular Reproduction and Development 2018, 85 (5) , 440-448. https://doi.org/10.1002/mrd.22980
  12. Manabu Yoshida, Kaoru Yoshida. Modulation of Sperm Motility and Function Prior to Fertilization. 2018,,, 437-462. https://doi.org/10.1007/978-4-431-56609-0_21
  13. , , , . Reproductive and Developmental Strategies. 2018,,https://doi.org/10.1007/978-4-431-56609-0
  14. Mikhail E. Elyashberg, Antony J. Williams. Structure Elucidation Using Strict Structure Generation. 2015,,, 183-306. https://doi.org/10.1007/978-3-662-46402-1_4
  15. Mikhail E. Elyashberg, Antony J. Williams. Computer–Based Structure Elucidation from Spectral Data. 2015,,https://doi.org/10.1007/978-3-662-46402-1
  16. John W. Blunt, Brent R. Copp, Robert A. Keyzers, Murray H. G. Munro, Michèle R. Prinsep. Marine natural products. Natural Product Reports 2015, 32 (2) , 116-211. https://doi.org/10.1039/C4NP00144C
  17. Manabu Yoshida. Sperm Chemotaxis: The First Authentication Events Between Conspecific Gametes Before Fertilization. 2014,,, 3-11. https://doi.org/10.1007/978-4-431-54589-7_1
  18. , , . Sexual Reproduction in Animals and Plants. 2014,,https://doi.org/10.1007/978-4-431-54589-7
  19. Catherine D. Thaler, Haruhiko Miyata, Leah T. Haimo, Richard A. Cardullo. Waveform Generation Is Controlled by Phosphorylation and Swimming Direction Is Controlled by Ca2+ in Sperm from the Mosquito Culex quinquefasciatus1. Biology of Reproduction 2013, 89 (6) https://doi.org/10.1095/biolreprod.113.109488
  20. Manabu Yoshida, Yuki Hiradate, Noburu Sensui, Jacky Cosson, Masaaki Morisawa. Species-Specificity of Sperm Motility Activation and Chemotaxis: a Study on Ascidian Species. The Biological Bulletin 2013, 224 (3) , 156-165. https://doi.org/10.1086/BBLv224n3p156

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

You’ve supercharged your research process with ACS and Mendeley!

STEP 1:
Click to create an ACS ID

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

OOPS

You have to login with your ACS ID befor you can login with your Mendeley account.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect

This website uses cookies to improve your user experience. By continuing to use the site, you are accepting our use of cookies. Read the ACS privacy policy.

CONTINUE