Unsaturated derivatives of cholane with methyl groups at C-10 and C-13 and a branched five-carbon chain at C-17. They must have at least one double bond in the ring system.

New insecticidal bufadienolide, bryophyllin C, from Kalanchoe pinnata. (1/11)

Two insecticidal bufadienolides (1 and 2) were isolated from a methanol extract of the leaves of Kalanchoe pinnata by bioassay-guided fractionation. Compound 1 was identified as known bryophyllin A (bryotoxin C). The structure of new bufadienolide 2, named bryophyllin C, was determined by spectroscopic methods and the chemical transformation of 1. Compounds 1 and 2 showed strong insecticidal activity against third instar larvae of the silkworm (Bombyx mori), their LD50 values being evaluated as 3 and 5 microg/g of diet, respectively.  (+info)

Inhibitors of sterol synthesis. A highly efficient and specific side-chain oxidation of 3 beta-acetoxy-5 alpha-cholest-8(14)-en-15-one for construction of metabolites and analogs of the 15-ketosterol. (2/11)

As part of a program directed towards the chemical syntheses of potential metabolites and analogs of 3 beta-hydroxy-5 alpha-cholest-8(14)-en-15-one (I), a potent regulator of cholesterol metabolism, several routes have been explored for the preparation of 3 beta-hydroxy-15-keto-5 alpha-chol-8(14)-en-24-oic acid (IV). These investigations led to a remarkably specific and efficient side-chain oxidation of I. For example, treatment of the acetate of I with a mixture of trifluoroacetic anhydride, hydrogen peroxide, and sulfuric acid for 3.5 h at -2 degrees C gave a crude product consisting of 3 beta-acetoxy-24-trifluoroacetoxy-5 alpha-chol-8(14)-en-15-one (XI), 3 beta-acetoxy-24-hydroxy-5 alpha-chol-8(14)-en-15-one (XII), and 3 beta, 24-diacetoxy-5 alpha-chol-8(14)-en-15-one (XIII) in yields of 58%, 8%, and 3%, respectively, by HPLC analysis. XI was readily hydrolyzed to XII upon treatment with triethylamine in methanol at room temperature. Oxidation of XII with Jones reagent gave 3 beta-acetoxy-15-keto-5 alpha-chol-8(14)-en-24-oic acid (XVIII) from which its methyl ester (IX) was prepared by treatment with diazomethane. Mild alkaline hydrolysis of XVIII gave the 3 beta-hydroxy-delta 8(14)-15-keto C24 acid (IV). Hydrolysis of the crude product of the side-chain oxidation with K2CO3 in methanol gave 3 beta,24-dihydroxy-5 alpha-chol-8(14)-en-15-one (XIV) which was oxidized with Jones reagent to yield 3,15-diketo-5 alpha-chol-8(14)-en-24-oic acid (XV). Treatment of XV with diazomethane gave its methyl ester (XVI) which, upon controlled reduction with NaBH4, yielded methyl 3 beta-hydroxy-15-keto-5 alpha-chol-8(14)-en-24-oate (XVII). Compound IX was also prepared by an independent route. Full 1H and 13C NMR assignments are presented for 12 new compounds. IV caused a approximately 56% reduction of the level of 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in CHO-K1 cells at a concentration of 2.5 microM. In contrast, the corresponding 3,15-diketo acid XV had no detectable effect on reductase activity under the same conditions.  (+info)

Two ring-A-aromatized bile acids from the marine sponge Sollasella moretonensis. (3/11)

Two ring-A-aromatized bile acids, 1 and 2, were isolated from the sponge Sollasella moretonensis, collected from the seabed of northern Queensland. Structures were assigned on the basis of extensive 1D and 2D NMR studies, as well as analysis by HRESIMS. Compound 2 has previously been produced synthetically, though this marks its first isolation from a natural source.  (+info)

Synthesis and mutagenicity of a ring-A-aromatized bile acid, 3-hydroxy-19-nor-1,3,5(10)-cholatrien-24-oic acid. (4/11)

It has been presumed that ring-A-aromatized bile acids are produced from biliary bile acids by intestinal flora and the acids thus formed participate in the large bowel carcinogenesis. One of these acids is probably 3-hydroxy-19-nor-1,3,5(10)-cholatrien-24-oic acid, judged from the literatures. Consequently, this acid was synthesized from previously prepared 3-methoxy-19-nor-1,3,5(10)-cholatrien-24-ol. The phenolic ether was successively oxidized with pyridinium chlorochromate and wet silver oxide to give 3-methoxy-19-nor-1,3,5(10)-cholatrien-24-oic acid in high yield, which, after successive treatments with methanol containing a catalytic amount of p-toluenesulfonic acid, a combination of aluminum chloride and ethanethiol, and alkali, gave the desired compound in satisfactory yield. The compound was not mutagenic in Salmonella tester strains TA 98 and TA 100, but it increased the mutagenicity of 2-aminoanthracene when both were applied to plates together. When compared with cholic, deoxycholic, and lithocholic acids, the investigated compound exhibited about two to threefold increase of mutagenicity in the latter assay.  (+info)

Familial giant cell hepatitis associated with synthesis of 3 beta, 7 alpha-dihydroxy-and 3 beta,7 alpha, 12 alpha-trihydroxy-5-cholenoic acids. (5/11)

Urinary bile acids from a 3-mo-old boy with cholestatic jaundice were analyzed by ion exchange chromatography and gas chromatography-mass spectrometry (GC-MS). This suggested the presence of labile sulfated cholenoic acids with an allylic hydroxyl group, a conclusion supported by analysis using fast atom bombardment mass spectrometry (FAB-MS). The compounds detected by FAB-MS were separated by thin layer chromatography and high performance liquid chromatography. The sulfated bile acids could be solvolyzed in acidified tetrahydrofuran, and glycine conjugates were partially hydrolyzed by cholylglycine hydrolase. Following solvolysis, deconjugation, and methylation with diazomethane, the bile acids were identified by GC-MS of trimethylsilyl derivatives. The major bile acids in the urine were 3 beta,7 alpha-dihydroxy-5-cholenoic acid 3-sulfate, 3 beta,7 alpha,12 alpha-trihydroxy-5-cholenoic acid monosulfate, and their glycine conjugates. Chenodeoxycholic acid and cholic acid were undetectable in urine and plasma. The family pedigree suggested that abnormal bile acid synthesis was an autosomal recessive condition leading to cirrhosis in early childhood.  (+info)

Biosynthesis of a novel bile acid nucleotide and mechanism of 7 alpha-dehydroxylation by an intestinal Eubacterium species. (6/11)

Eubacterium species V.P.I. 12708 has inducible bile acid 7-dehydroxylase activity that can use either 7 alpha or 7 beta bile acids as substrates. Cell extracts prepared from bacteria grown in the presence of cholic acid catalyzed the rapid conversion of free bile acids into a highly polar bile acid metabolite (HPBA). This conjugation activity co-eluted with bile acid 7-dehydroxylase activity on high performance gel filtration chromatography (GFC). The HPBA was purified by a combination of high performance GFC and reverse-phase high performance liquid chromatography (HPLC). The intact HPBA eluted earlier from reverse-phase HPLC than deoxycholyl-CoA and had a Mr of 1102 by Bio-Gel P-2 (GFC). The HPBA had an absorption peak at 255 nm and was sensitive to treatment with phosphodiesterase I or nucleotide pyrophosphatase. The HPBA has a free phosphate as shown by an increase in elution volume on reverse-phase HPLC following treatment with alkaline phosphatase. Treatment of the purified HPBA with nucleotide pyrophosphate plus alkaline phosphatase yielded adenosine, whereas, treatment with nucleotide pyrophosphatase alone generated 5',3'-ADP. A bile acid metabolite was also generated by nucleotide pyrophosphatase treatment. The bile acid metabolite had different chromatographic properties (HPLC and TLC) than the corresponding free bile acid. Gas liquid chromatography-mass spectrometry showed the bile acid metabolite to be 12 alpha-hydroxy-3-oxo-4-cholenoic acid. We hypothesize that the HPBA is an intermediate in 7-dehydroxylation and consists of this compound linked at the C-24 with an anhydride bond to the beta phosphate (5') of ADP-3'-phosphate. These results suggest a novel mechanism of bile acid 7 alpha/7 beta-dehydroxylation in Eubacterium sp. V.P.I. 12708.  (+info)

Bile acid synthesis. Metabolism of 3 beta-hydroxy-5-cholenoic acid in the hamster. (7/11)

Synthesis of 3 beta-hydroxy-5-[1,2-3H]cholenoic acid has permitted a study of its metabolism in bile-fistula hamsters that received the compound by intravenous infusion. Metabolites in bile were identified by reverse isotope dilution after their complete resolution by high pressure liquid chromatography using muPorasil. Recovery of administered radioactivity ranged from 21-60% in three animals. In each study, lithocholic acid (0.8-4.4%) and chenodeoxycholic acid (7.8-11.3%) were identified as metabolites of 3 beta-hydroxy-5-cholenoate and can be considered primary bile acids in the side-chain pathway of bile acid synthesis beginning with the oxidation of cholesterol to 26-hydroxycholesterol.  (+info)

Radiation dosimetry of two new tellurium- 123m-labeled adrenal-imaging agents: concise communication. (8/11)

The absorbed radiation doses to humans from 23-(isopropyl[123mTe]telluro)-24-nor-5 alpha-cholan-3 beta-ol (Te-123m-23-ITC) and 24-(isopropyl[123mTe]telluro)-chol-5-en-3 beta-ol(Te-123m-24-ITC) have been calculated, based on rat biological data, to assess the relative radiation risks to humans from these two new adrenal-imaging agents. The estimated radiation doses to several critical organs have been compared with dose estimates for a variety of other radiolabeled steroids that have been designed as adrenal-imaging agents. Dose estimates to selected organs from Te-123m-23-ITC are as follows (rad/mCi): adrenals 98; ovaries 8.0; liver 1.6. Similar estimated values for Te-123m-24-ITC are: adrenals 210; ovaries 13; liver 2.0. The radiation dose estimates for these two agents are comparable to the calculated radiation doses from 6 beta-[(methyl[75Se]seleno)methyl]-19-nor-cholest-5(10)-en-3 beta-ol (Scintidren) and 19-[131I]iodocholest-5-en-3 beta-ol (NP-59), two agents currently in clinical use for the diagnosis of adrenal disease.  (+info)

I'm sorry for any confusion, but "Cholenes" is not a recognized medical term or abbreviation in English. It's possible that there may be a spelling mistake or it could be a term specific to a certain language or field of study. If you have more context or information, I'd be happy to help further!

... cholenes MeSH D04.808.221.430 - cholic acids MeSH D04.808.221.430.130 - cholic acid MeSH D04.808.221.430.130.330 - cholates ...
... cholenes MeSH D04.808.221.430 - cholic acids MeSH D04.808.221.430.130 - cholic acid MeSH D04.808.221.430.130.330 - cholates ...
Cholenes D4.808.221.263 D4.210.500.221.263 Cholestadienes D4.808.247.222.222 D4.210.500.247.222.222 Cholestadienols D4.808. ...
Cholenes D4.808.221.263 D4.210.500.221.263 Cholestadienes D4.808.247.222.222 D4.210.500.247.222.222 Cholestadienols D4.808. ...
Cholenes D4.808.221.263 D4.210.500.221.263 Cholestadienes D4.808.247.222.222 D4.210.500.247.222.222 Cholestadienols D4.808. ...
Cholenes D4.808.221.263 D4.210.500.221.263 Cholestadienes D4.808.247.222.222 D4.210.500.247.222.222 Cholestadienols D4.808. ...
Cholenes D4.808.221.263 D4.210.500.221.263 Cholestadienes D4.808.247.222.222 D4.210.500.247.222.222 Cholestadienols D4.808. ...
Cholenes D4.808.221.263 D4.210.500.221.263 Cholestadienes D4.808.247.222.222 D4.210.500.247.222.222 Cholestadienols D4.808. ...
Cholenes Preferred Term Term UI T008046. Date01/01/1999. LexicalTag NON. ThesaurusID NLM (1975). ... Cholenes Preferred Concept UI. M0004243. Registry Number. 0. Scope Note. Unsaturated derivatives of cholane with methyl groups ... Cholenes. Tree Number(s). D04.210.500.221.263. Unique ID. D002770. RDF Unique Identifier. http://id.nlm.nih.gov/mesh/D002770 ...
Cholenes Preferred Term Term UI T008046. Date01/01/1999. LexicalTag NON. ThesaurusID NLM (1975). ... Cholenes Preferred Concept UI. M0004243. Registry Number. 0. Scope Note. Unsaturated derivatives of cholane with methyl groups ... Cholenes. Tree Number(s). D04.210.500.221.263. Unique ID. D002770. RDF Unique Identifier. http://id.nlm.nih.gov/mesh/D002770 ...
do not confuse with CHOLENES. Allowable Qualifiers:. AD administration & dosage. AE adverse effects. AG agonists. AI ...
N0000008184 Cholanes N0000167453 Cholates N0000006996 Cholecalciferol N0000007750 Cholecystokinin N0000167414 Cholenes ...
Cholenes D4.808.221.263 D4.210.500.221.263 Cholestadienes D4.808.247.222.222 D4.210.500.247.222.222 Cholestadienols D4.808. ...
Cholenes D4.808.221.263 D4.210.500.221.263 Cholestadienes D4.808.247.222.222 D4.210.500.247.222.222 Cholestadienols D4.808. ...
Cholenes Cholera Cholera Morbus Cholera Toxin Cholera Vaccines Cholestadienes Cholestadienols Cholestanes Cholestanetriol 26- ...

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