Identification of cyprinol and cyprinol sulfate from grass carp bile and their toxic effects in rats

Hwang, Deng‐Fwu; Yeh, Yen-Hung; Lai, Yi-Show; Deng, Jou‐Fang

doi:10.1016/s0041-0101(00)00134-3

Cited by 24 publications

(14 citation statements)

References 9 publications

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“…In this connection, 5α-cyprinol sulfate, which was present in gallbladder bile at high concentration (0.3 M), has been shown to be the toxic component of carp bile [34]. It was reported that the toxic effect of 5α-cyprinol sulfate on the kidney functions was more harmful than that of 5α-cyprinol [35]. The concentration of 5α-cyprinol sulfate in the carp gallbladder was reported to be 284 ± 48 mM (M ± SD, n = 4) [33].…”

Section: Discussionmentioning

confidence: 99%

Food Poisonings by Ingestion of Cyprinid Fish

Asakawa

Noguchi

2014

Toxins

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Raw or dried gallbladders of cyprinid fish have long been ingested as a traditional medicine in the Asian countries, particularly in China, for ameliorating visual acuity, rheumatism, and general health; however, sporadic poisoning incidences have occurred after their ingestion. The poisoning causes complex symptoms in patients, including acute renal failure, liver dysfunction, paralysis, and convulsions of limbs. The causative substance for the poisoning was isolated, and its basic properties were examined. The purified toxin revealed a minimum lethal dose of 2.6 mg/20 g in mouse, when injected intraperitoneally. The main symptoms were paralysis and convulsions of the hind legs, along with other neurological signs. Liver biopsy of the euthanized mice clearly exhibited hepatocytes necrosis and infiltration of neutrophils and lymphocytes, suggesting the acute dysfunction of the liver. Blood tests disclosed the characteristics of acute renal failure and liver injury. Infrared (IR) spectrometry, fast atom bombardment (FAB) mass spectrometry, and 1H- and 13C-nuclear magnetic resonance (NMR) analysis indicated, a molecular formula of C27H48O8S, containing a sulfate ester group for the toxin. Thus, we concluded that the structure of carp toxin to be 5α-cyprinol sulfate (5α-cholestane-3α, 7α, 12α, 26, 27-pentol 26-sulfate). This indicated that carp toxin is a nephro- and hepato- toxin, which could be the responsible toxin for carp bile poisoning in humans.

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Section: Discussionmentioning

confidence: 99%

Food Poisonings by Ingestion of Cyprinid Fish

Asakawa

Noguchi

2014

Toxins

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“…(31) The identification of cyprinol sulfate from grass carp bile and its toxic effects in rats has been reported. (32) The West Indian manatee (Trichechus manatus latirostris) produces a novel major bile alcohol trichechol, (5a-cholestane-3a,6b,7a-25,26-pentol) and its sulfo-conjugate, which has been purported to serve as a detergent during lipid digestion similar to other mammals. (33) Thus cholestanes are 27-carbon compounds that either have a 5a or 5b orientation, with typical trihydroxy substituents (a or b orientation) at 3, 7 and 12 and varied hydroxyls at 24, 25, 26 and 27.…”

Section: Chemistry Of Bile Acids and Alcoholsmentioning

confidence: 99%

Petromyzonol sulfate and its derivatives: the chemoattractants of the sea lamprey

Venkatachalam

2005

Bioessays

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Petromyzonol sulfate (PZS) and 3 keto-PZS are bile alocohol derivatives that serve as chemoattractants during the life cycle of sea lamprey (Petromyzon marinus). The sulfonate moiety is crucial perhaps conferring the required solubility for the pheromone that is released into the streams and for the specificity to bind to its receptor. During the life cycle of lamprey, larvae produce copious amounts of 5 alpha-cholan-PZS, and trace amounts of allocholic acid (ACA), which attracts adults to the same breeding ground. Later the spermeating males produce 3keto-PZS, and trace amounts of 3-keto-ACA, which attracts the ovulating females, signaling both its reproductive status and its nesting location for successful reproduction. In both stages, a mixture of components serves as pheromone plume, similar to insects. The receptors for the migratory and the reproductive pheromones need to be molecularly cloned and characterized in order to understand the molecular biology of olfaction in the sea lamprey.

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“…Mild poisoning causes only gastroenteritis, liver and kidneys are affected in moderate poisoning, and multiorgan failure occurs in severe poisoning. The toxin involved in fish gall bladder poisoning is believed to be 5-alpha cyprinol sulphate, a C-27 bile acid [8,9]. Poisoning (ichthyotoxism) occurs in 3 forms [10], e.g., (a) ichthyosarcotoxic involving visceral organ, (b) ichthyootoxic involving reproductive organs and (c) ichthyohemotoxic causing hemolysis like feature.…”

Section: Discussionmentioning

confidence: 99%

Indian Carp (Labeo Rohita) Gall Bladder Poisoning-Report of Four Cases in a Single Family

et al. 2011

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The ingestion of Indian carp gallbladder may result in transient hepatitis with subsequent acute renal failure. This case series also illustrates the importance of understanding the use and potential serious complications of alternative medicines. So fish gallbladder poisoning should be considered in unexplained acute renal failure in Chinese and Asian patients. We report four family members who developed acute renal failure and toxic hepatitis at the same time following ingestion of raw Indian carp (Labeo rohita) gall bladder.

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Identification of cyprinol and cyprinol sulfate from grass carp bile and their toxic effects in rats

Cited by 24 publications

References 9 publications

Food Poisonings by Ingestion of Cyprinid Fish

Food Poisonings by Ingestion of Cyprinid Fish

Petromyzonol sulfate and its derivatives: the chemoattractants of the sea lamprey

Indian Carp (Labeo Rohita) Gall Bladder Poisoning-Report of Four Cases in a Single Family

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