Characterization of a Novel Bile Alcohol Sulfate Released by Sexually Mature Male Sea Lamprey (Petromyzon marinus)

PLoS ONE

Volumn 8, Issue 7, 2013, Pages

  Li, Ke ^a   Brant, Cory O ^a   Siefkes, Michael J ^b   Kruckman, Hanna G ^a   Li, Weiming ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

^b GREAT LAKES FISHERY COMMISSION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 KETO PETROMYZONOL SULFATE; 3,12 DIKETO 4,6 PETROMYZONENE 24 SULFATE; BILE ALCOHOL SULFATE; BILE SALT; PHEROMONE; UNCLASSIFIED DRUG; WATER;

ANIMAL TRAPPING; ARTICLE; BIOASSAY; CHEMICAL STRUCTURE; CONTROLLED STUDY; FRACTIONATION; LAKE; MALE; NONHUMAN; OLFACTOMETRY; PETROMYZON; PETROMYZON MARINUS; SEXUAL BEHAVIOR; SEXUAL MATURATION; SPECTROSCOPY; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

ANIMALS; BEHAVIOR, ANIMAL; BILE; CHOLIC ACIDS; FEMALE; MALE; MICHIGAN; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PETROMYZON; SEXUAL MATURATION;

PETROMYZON MARINUS; VERTEBRATA;

EID: 84879962595     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0068157     Document Type: Article

References (33)

1. Hofmann AF, Hagey LR, Krasowski MD, (2010) Bile salts of vertebrates structural variation and possible evolutionary significance. J Lipid Res 51: 226-246.
2. Hofmann AF, Hagey LR, (2008) Bile acids: chemistry, pathochemistry, biology, pathobiology, and therapeutics. Cell Mol Life Sci 65: 2461-2483.
3. Hagey LR, Vidal N, Hofmann AF, Krasowski MD, (2010) Evolutionary diversity of bile salts in reptiles and mammals, including analysis of ancient human and extinct giant ground sloth coprolites. BMC Evol Biol 10: 133-155.
4. Døving KB, Hansson KA, Backström T, Hamdani EH, (2011) Visualizing a set of olfactory sensory neurons responding to a bile salt. J Exp Bio 214: 80-87.
5. Huertas M, Hagey L, Hofmann AF, Cerdà J, Canáriol AVM, et al. (2010) Olfactory sensitivity to bile fluid and bile salts in the European eel (Anguilla anguilla), goldfish (Carassius auratus) and Mozambique tilapia (Oreochromis mossambicus) suggests a 'broad range' sensitivity not confined to those produced by conspecifics alone. J Exp Biol 213: 308-317.
6. Li W, Sorensen PW, (1997) Highly independent olfactory receptor sites for naturally occurring bile acids in the sea lamprey. Petromyzon marinus. J Comp Physiol A 180: 429-438.
7. Carey MC, Small DM, (1972) Micelle formation by bile salts, physical-chemical and thermodynamic considerations. Arch Intern Med 130: 506-527.
8. Li W, Scott AP, Siefkes MJ, Yan H, Liu Q, et al. (2002) Bile acid secreted by male sea lamprey that acts as a sex pheromone. Science 296: 138-141.
9. Sorensen PW, Fine JM, Dvornikovs V, Jeffrey CS, Shao F, et al. (2005) Mixture of new sulfated steroids functions as a migratory pheromone in the sea lamprey. Nat Chem Biol 1: 324-328.
10. Li W, Sorensen PW, Gallaher DG, (1995) The olfactory system of the migratory sea lamprey (Petromyzon marinus) is specifically and acutely sensitive to unique bile acids released by conspecific larvae. J Gen Physiol 105: 569-587.
11. Yun SS, Scott AP, Li W, (2003) Pheromones of the male sea lamprey, Petromyzon marinus L: structural studies on a new compound, 3-keto allocholic acid, and 3-keto petromyzonol sulfate. Steroids 68: 297-304.
12. Siefkes MJ, Winterstein SR, Li W, (2005) Evidence that 3-keto petromyzonol sulphate specifically attracts ovulating female sea lamprey, Petromyzon marinus. Anim Behav 70: 1037-1045.
13. Johnson NS, Siefkes MJ, Li W, (2005) Capture of ovulating female sea lampreys in traps baited with spermiating male sea lampreys. N Am J Fish Manage 25: 67-72.
14. Johnson NS, Luehring MA, Siefkes MJ, Li W, (2006) Mating pheromone reception and induced behavior in ovulating female sea lampreys. N Am J Fish Manage 26: 88-96.
15. Johnson NS, Yun SS, Thompson HT, Brant CO, Li W, (2009) A synthesized pheromone induces upstream movement in female sea lamprey and summons them into traps. Proc Natl Acad Sci 106: 1021-1026.
16. Johnson NS, Yun SS, Buchinger TJ, Li W, (2011) Multiple functions of a multi-component mating pheromone in sea lamprey Petromyzon marinus. J Fish Biol 80: 538-554.
17. Hoye TR, Dvornikovs V, Fine JM, Anderson KR, Jeffrey CS, et al. (2007) Details of the structure determination of the sulfated steroids PSDS and PADS: New components of the sea lamprey (Petromyzon marinus) migratory pheromone. J Org Chem 72: 7544-7550.
18. Owen RW, Bilton RF, (1983) The degradation of cholic acid by Pseudomonas sp. N.C.I.B. 10590 under anaerobic conditions. Biochem J 216: 641-654.
19. Bai L, Wang L, Zhao M, Toki A, Hasegawa T, et al. (2007) Bioactive pregnanes from Nerium oleander. J Nat Prod 70: 14-18.
20. Qin JC, Gao JM, Zhang YM, Yang SX, Bai MS, et al. (2009) Polyhydroxylated steroids from an endophytic fungus, Chaetomium globosum ZY-22 isolated from Ginkgo biloba. Steroids 74: 786-790.
21. Yaoita Y, Amemiya K, Ohnuma H, Furumura K, Masaki A, et al. (1998) Sterol constituents from five edible mushrooms. Chem Pharm Bull 46: 944-950.
22. Hagey LR, Moller PR, Hofmann AF, Krasowski MD, (2010) Diversity of bile salts in fish and amphibians: evolution of a complex biochemical pathway. Physiol Biochem Zool 83: 308-321.
23. Huertas M, Canário AVM, Hubbard PC, (2009) Follow your nose: Chemical communication throughout the European eel (Anguilla anguilla, L.) life-cycle. Comp Biochem Physiol A 153A: S90.
24. Huertas M, Canário AVM, Hubbard PC, (2008) Changes in olfactory sensitivity during the European eel (Anguilla Anguilla) life cycle. Chem Senses 33: S150.
25. Linn Jr CE, Campbell MG, Roelofs WL, (1987) Pheromone components and active spaces: What do moths smell and where do they smell it? Science 237: 650-652.
26. Linn Jr CE, Roelofs WL, (1989) Response specificity of male moths to multicomponent pheromones. Chem Senses 14: 421-437.
27. Laberge F, Hara TJ, (2003) Behavioural and electrophysiological responses to F-prostaglandins, putative spawning pheromones in three salmonid fishes. J Fish Biol 62: 206-221.
28. Siefkes MJ, Bergstedt RA, Twohey MB, Li WM, (2003) Chemosterilization of male sea lampreys (Petromyzon marinus) does not affect sex pheromone release. Can J Fish Aqua Sci 60: 23-31.
29. Li W, Sorensen PW, (1992) The olfactory sensitivity of sea lamprey to amino acids is specifically restricted to arginine. Chem Senses 17: 658.
30. Siefkes MJ, Li W, (2004) Electrophysiological evidence for detection and discrimination of pheromonal bile acids by the olfactory epithelium of female sea lampreys (Petromyzon marinus). J Comp physiol A 190: 193-199.
31. Losey GS, Hugie DM, (1994) Prior anaesthesia impairs a chemically mediated fright response in a gobiid fish. J Chem Ecol 20: 1877-1883.
32. Li K, Wang H, Brant CO, Ahn S, Li W, (2011) Multiplex quantification of lamprey specific bile acid derivatives in environmental water using UHPLC-MS/MS. J Chromatogr B 879: 3879-3886.
33. Applegate VC, (1950) Natural history of the sea lamprey, Petromyzon marinus, in Michigan. Special scientific Report of U.S. Fish and Wildlife Service 55: 1-237.