ChemInform Abstract: Details of the Structure Determination of the Sulfated Steroids PSDS and PADS: New Components of the Sea Lamprey (Petromyzon marinus) Migratory Pheromone.

Hoye, Thomas R.; Dvornikovs, Vadims; Fine, Jared M.; Anderson, Kari R.; Jeffrey, Christopher S.; Muddiman, David C.; Shao, Feng; Sorensen, Peter W.; Wang, Jizhou

doi:10.1002/chin.200806170

Cited by 6 publications

(13 citation statements)

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“…3). Sea lamprey is known to synthesize unique 5α-bile acids and 5α-bile alcohols: allocholic acid (ACA) (26) and its derivative 3-dehydro-ACA (3k-ACA) (27), petromyzonol sulfate (PZS) (28) and its derivative 3-dehydro-PZS (3k-PZS) (29), petromyzonsterol disulfate (PSDS), and petromyzonamine disulfate (PADS) (30). We analyzed their concentrations throughout life stages.…”

Section: Resultsmentioning

confidence: 99%

“…Sulfation of taurine-conjugated bile acids is considered an adaptive detoxification mechanism (44). In larval and adult lamprey, bile alcohol sulfates are released into water in large quantities as putative pheromones (29,30) and sulfation facilitates this process (29). In contrast to the dominance of bile alcohol sulfates in larvae and mature adults, taurine-conjugated bile salts were prominent in parasites ( Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Sea lamprey biliary atresia is a developmental process that resembles human pathogenic biliary atresia in many cellular features. Aductular parasites secrete bile salts during their rapid growth but slow-growing larvae and atrophic mature adults use bile alcohol sulfates as pheromones (29,30,48). The complex lifestyle and bile salt utilization are facilitated by two organs, the liver and the intestine, synthesizing different conjugated bile salts throughout the sea lamprey life cycle.…”

Section: Resultsmentioning

confidence: 99%

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Intestinal synthesis and secretion of bile salts as an adaptation to developmental biliary atresia in the sea lamprey

Yeh

Chung-Davidson

Wang

et al. 2012

Proc. Natl. Acad. Sci. U.S.A.

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Bile salt synthesis is a specialized liver function in vertebrates. Bile salts play diverse roles in digestion and signaling, and their homeostasis is maintained by controlling input (biosynthesis) and intestinal conservation. Patients with biliary atresia (i.e., obliteration of the biliary tree) suffer liver fibrosis and cirrhosis. In contrast, sea lamprey thrives despite developmental biliary atresia. We discovered that the sea lamprey adapts to biliary atresia through a unique mechanism of de novo synthesis and secretion of bile salts in intestine after developmental biliary atresia, in addition to known mechanisms, such as the reduction of bile salt synthesis in liver. During and after developmental biliary atresia, expression of cyp7a1 in intestine increased by more than 100-fold ( P < 0.001), whereas in liver it decreased by the same magnitude ( P < 0.001). Concurrently, bile salt pools changed in similar patterns and magnitudes in these two organs and the composition shifted from C24 bile alcohol sulfates to taurine-conjugated C24 bile acids. In addition, both in vivo and ex vivo experiments showed that aductular sea lamprey secreted taurocholic acid into its intestinal lumen. Our results indicate that the sea lamprey, a jawless vertebrate, may be in an evolutionarily transitional state where bile salt synthesis occurs in both liver and intestine. Understanding the molecular basis of these mechanisms may shed light on the evolution of bile salt synthesis and possible therapy for infant biliary atresia.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Intestinal synthesis and secretion of bile salts as an adaptation to developmental biliary atresia in the sea lamprey

Yeh

Chung-Davidson

Wang

et al. 2012

Proc. Natl. Acad. Sci. U.S.A.

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“…Our extensive survey of vertebrate bile acids ( 82 ) has established that most bile alcohols have an iso-octanoic acid ( ␣ , -dimethylhexanoic acid) side chain. The exceptions identifi ed to date are C 26 and C 25 alcohols that are present in the bile of some frog species ( 25,26 ), as well as a C 24 bile alcohol, petromyzonol that occurs in the lamprey as a disulfate ( 103,104 ). Trace proportions of C 24 bile alcohols with the nuclear structure of cholic acid and CDCA are found in the bile of many species ( 105 ).…”

Section: Bile Acid Structure: History and Current Conceptsmentioning

confidence: 99%

Key discoveries in bile acid chemistry and biology and their clinical applications: history of the last eight decades

Hofmann

Hagey

2014

Journal of Lipid Research

296

284

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conceptions are rare, and provocative judgments stand the test of time. Let us also hope that this effort will be both useful and entertaining. Each of the topics discussed merits at least a full length article, so there will be, of necessity in many instances, consideration of only what we perceive to be the highlights. THE EBB AND FLOW OF MEDICAL INTEREST IN BILE ACIDSAfter the elucidation of the true chemical structure of bile acids in 1932 (see below), there was little interest in bile acids in the Western world. One exception to this statement was the laboratory of Siegfried Thannhauser, who wrote the fi rst textbook of metabolic biochemistry in Germany. He studied cholesterol and bile acid balance in the biliary fi stula dog ( 1 ). During this time, bile acids were sold as liver tonics and laxatives, but there were no placebo-controlled studies showing effi cacy. Indeed, bile acids were considered by the medical profession to have no useful therapeutic properties. The tri-oxo derivative of cholic acid (called "dehydrocholic acid") was known to induce bile fl ow in animals ( 2 ), and was occasionally used to stimulate bile fl ow in patients; but again there were no controlled studies showing effi cacy in hepatobiliary disease.

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“…The migratory pheromone utilized by adult sea lamprey has been established as a mixture of petromyzonol sulfate (PS), petromyzonamine disulfate (PADS), and petromyzosterol disulfate (PSDS) (Li et al, 1995;Polkinghorne et al, 2001;Fine and Sorensen, 2005;Sorensen et al, 2005;Hoye et al, 2007). Other northern hemisphere lamprey species in the family Petromyzontidae also release PS, PADS, and PSDS (Fine et al, 2004;Baker et al, 2009), and thus this migratory pheromone may not be species-specific.…”

Section: Introductionmentioning

confidence: 96%

A Sensitive Analytical Method for Quantifying Petromyzonol Sulfate in Water as a Potential Tool for Population Monitoring of the Southern Pouched Lamprey, Geotria Australis, in New Zealand Streams

Stewart

Baker

2012

J Chem Ecol

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The migratory southern pouched lamprey, Geotria australis, is a culturally important fish native to New Zealand. Anecdotal evidence suggests that populations of G. australis have declined from historic levels, and presently, this species is rare in many New Zealand rivers and streams. Migratory sea lamprey (Petromyzon marinus) use a pheromone mixture to locate suitable spawning sites. This mixture is comprised of three steroids: petromyzonol sulfate (PS), petromyzonamine disulfate (PADS), and petromyzosterol disulfate (PSDS). We examined the migratory pheromone mixture released by G. australis ammocetes and found that they excrete predominantly PS. PADS has been detected on some occasions in low concentrations, and PSDS either is not released, or is released in extremely low concentrations. By using a recently developed sensitive mass spectrometry method, we compared passive sampling techniques against more traditional active water sampling as methods for estimating lamprey populations in local streams. Passive sampling provided quantitative data for PS from all sites surveyed, with uptake rates of 0.3 to 45.7 pg/day observed. Conversely, active sampling returned only one positive result out of 19 samples, and with a method detection limit of 2.5 × 10(-14) M, this suggests that concentrations of PS in these streams are either extremely low or variable. The combination of passive sampling and triple quadrupole mass spectrometry is a promising tool for monitoring of G. australis in New Zealand streams.

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ChemInform Abstract: Details of the Structure Determination of the Sulfated Steroids PSDS and PADS: New Components of the Sea Lamprey (Petromyzon marinus) Migratory Pheromone.

Cited by 6 publications

References 1 publication

Intestinal synthesis and secretion of bile salts as an adaptation to developmental biliary atresia in the sea lamprey

Intestinal synthesis and secretion of bile salts as an adaptation to developmental biliary atresia in the sea lamprey

Key discoveries in bile acid chemistry and biology and their clinical applications: history of the last eight decades

A Sensitive Analytical Method for Quantifying Petromyzonol Sulfate in Water as a Potential Tool for Population Monitoring of the Southern Pouched Lamprey, Geotria Australis, in New Zealand Streams

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