Nuclear magnetic resonance spectroscopy of 3β,7β-dihydroxy-5-cholen-24-oic acid multi-conjugates: unusual bile acid metabolites in human urine

Kakiyama, Genta; Ogawa, Shoujiro; Iida, Takashi; Fujimoto, Yasuo; Mushiake, Kumiko; Goto, Takaaki; Mano, Nariyasu; Goto, Junichi; Nambara, Toshio

doi:10.1016/j.chemphyslip.2006.01.003

Cited by 3 publications

(2 citation statements)

References 17 publications

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“…These 1 H and 13 C data for compound A also agreed very well with those reported for 3a-sulfo-7b-(2-acetamido-2-deoxy-a-D-glucopyranosyl)-5-cholen-24-oyl taurine (14), again providing evidence for the presence of the N-acylamido linkage with taurine in the side chain.…”

Section: Resultssupporting

confidence: 78%

Identification of a novel bile acid in swans, tree ducks, and geese: 3α,7α,15α-trihydroxy-5β-cholan-24-oic acid

Kakiyama

Iida

Goto

et al. 2006

Journal of Lipid Research

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By HPLC, a taurine-conjugated bile acid with a retention time different from that of taurocholate was found to be present in the bile of the black-necked swan, Cygnus melanocoryphus. The bile acid was isolated and its structure, established by 1 H and 13 C NMR and mass spectrometry, was that of the taurine N-acyl amidate of 3a,7a,15a-trihydroxy5b-cholan-24-oic acid. The compound was shown to have chromatographic and spectroscopic properties that were identical to those of the taurine conjugate of authentic 3a,7a,15a-trihydroxy-5b-cholan-24-oic acid, previously synthesized by us from ursodeoxycholic acid. By HPLC, the taurine conjugate of 3a,7a,15a-trihydroxy-5b-cholan-

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Section: Resultssupporting

confidence: 78%

Identification of a novel bile acid in swans, tree ducks, and geese: 3α,7α,15α-trihydroxy-5β-cholan-24-oic acid

Kakiyama

Iida

Goto

et al. 2006

Journal of Lipid Research

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“…This assignment is in accordance with the previous reports, which describe compounds with similar structures as that of 1 . In the case of 3β,7β-dihydroxy-5-chole-24-oic acid, which was sulfated at C-3 and N -acetylglucosaminidated at C-7, the H-7 of the α-orientation appeared at δ 3.80 ppm, with a coupling constant of 7.8 to 8.4 Hz [ 12 ]. In other reports, comparative data are provided for the C-7 epimers of the synthesized 5-androstene-3,7,17-triol derivative.…”

Section: Resultsmentioning

confidence: 99%

Three New Cytotoxic Steroidal Glycosides Isolated from Conus pulicarius Collected in Kosrae, Micronesia

et al. 2017

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Three new sulfated steroidal glycosides (3–5), along with known cholesterol derivatives (1,2), were isolated from the visceral extract of the cone snail Conus pulicarius. The structure of each new compound was elucidated by nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry. The three new compounds exhibited significant in vitro cytotoxicity (GI50 values down to 0.49 μM) against the K562 human leukemia cell line.

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LC/ESI-MS/MS analysis of urinary 3β-sulfooxy-7β-N-acetylglucosaminyl-5-cholen-24-oic acid and its amides: New biomarkers for the detection of Niemann–Pick type C disease

et al. 2013

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Nuclear magnetic resonance spectroscopy of 3β,7β-dihydroxy-5-cholen-24-oic acid multi-conjugates: unusual bile acid metabolites in human urine

Cited by 3 publications

References 17 publications

Identification of a novel bile acid in swans, tree ducks, and geese: 3α,7α,15α-trihydroxy-5β-cholan-24-oic acid

Identification of a novel bile acid in swans, tree ducks, and geese: 3α,7α,15α-trihydroxy-5β-cholan-24-oic acid

Three New Cytotoxic Steroidal Glycosides Isolated from Conus pulicarius Collected in Kosrae, Micronesia

LC/ESI-MS/MS analysis of urinary 3β-sulfooxy-7β-N-acetylglucosaminyl-5-cholen-24-oic acid and its amides: New biomarkers for the detection of Niemann–Pick type C disease

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