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)

Two types of single-site heterogeneous catalysts have been designed so as to facilitate either the side-chain oxidation or ring-hydroxylation of toluene in O2 (solvent-free) or by employing aqueous (H2O2) or organic (cumene hydroperoxide) hydroperoxides in high yield. The use of H2O2 and cumene hydroperoxide in particular, facilitates the ring-hydroxylation of toluene when zeolite-encapsulated metal complexes, such as perhalogenated or tetra-nitro-substituted phthalocyanines, are used as catalysts. Nanoporous, redox molecular sieves, display a higher tendency for the side-chain oxidation of toluene with air as an oxidant, with benzoic acid as the predominant product.. Full text not available from this repository.. ...
11-o,o-isopropylidenebis-aboia-7(14)-ene 1beta,8-diangeloyloxy-2beta-acetoxy-4alpha-chloro-3beta-hydroxy-10: antineoplastic from Cremanthodium discoideum; structure in first source
Bufadienolide is a chemical compound with steroid structure. Its derivatives are collectively known as bufadienolides, including many in the form of bufadienolide glycosides (bufadienolides that contain structural groups derived from sugars). These are a type of cardiac glycoside, the other being the cardenolide glycosides. Both bufadienolides and their glycosides are toxic; specifically, they can cause an atrioventricular block, bradycardia (slow heartbeat), ventricular tachycardia (a type of rapid heartbeat), and possibly lethal cardiac arrest. The term derives from the toad genus Bufo that contains bufadienolide glycosides, the suffix -adien- that refers to the two double bonds in the lactone ring, and the ending -olide that denotes the lactone structure. Consequently, related structures with only one double bond are called bufenolides,[citation needed] and the saturated equivalent is bufanolide. According to MeSH, bufadienolides and bufanolides are classified as follows: Polycyclic compounds ...
Reproduction of kalanchoe is done by means of seeds, although propagation through cuttings or leaves is the most common. These plants are shrubs. They can be grown in the garden during any time of year. The indications given in this article are related to a medium size plant. The most suitable temperature is about 20 or 25 degrees. The less advantageous in gardening can acquire already developed plants, even flowered, that only have to be transplanted to a larger pot or garden floor. For growth to be unbeatable, the substrate must consist of peat, sand and mulch. It is important that the soil is well drained to avoid the accumulation of liquid, which could cause decay of the vegetable base. Therefore, it is necessary to avoid excessive watering and let the soil dry between one water supply and the next. During the winter a slight water supply will be necessary every two weeks. It is a plant very resistant to diseases, although occasionally affect aphids, which produce in the plant disorders in ...
Details of medicinal properties of Kalanchoe or patharchatta. It is effective in treatment of Stone problems, recurrent stones, Jaundice, High blood pressure.
The aim of the present study was to determine the effects of kalanchoe pinnata aqueous extract on some biochemical makers in salt loaded rats. 30 rats were randomly divided into 6 groups of 5 animals each. All the animals were administered NaCl (18%) except the neutral animals that received just tap water. groups 3, 4 and 5 received the aqueous extract of k. pinnata at increasing doses (50, 100, 150 mg/kg respectively) Groups 2, 3, 4 and 5 received Isoproterenol (150 mg/kg) subcutaneously for two days before sacrifice. During sacrifice, blood was collected through cardiac puncture and serum was separated.
I am currently investigating the mechanism of the iron-dependent enzyme, phenylalanine hydroxylase (PAH), a liver enzyme that is responsible for maintaining phenylalanine homeostasis in humans. Defects in the PAH gene lead to the genetic defect, phenylketonuria (PKU), which is the most common inborn metabolic genetic disorder of clinical significance. Approximately 1:10,000 individuals suffer from PKU in the United States due to abnormal function of the phenylalanine hydroxylase (PAH) enzyme. PAH and missense mutations that give rise to PKU in the human population can now be readily expressed and investigated in a laboratory setting. Work in the Caradonna laboratory characterizing two missense mutations that cause PKU showed that the mutant forms of the enzyme were more susceptible to an inactivation process than the wildtype enzyme. This inactivation process is thought to be the direct consequence of irreversible specific side-chain oxidation chemistry induced by the nonproductive decay of the ...
PubMed journal article: Gastroprotective and Antioxidant Activity of Kalanchoe brasiliensis and Kalanchoe pinnata Leaf Juices against Indomethacin and Ethanol-Induced Gastric Lesions in Rats. Download Prime PubMed App to iPhone, iPad, or Android
Abstract:. Kalanchoe pinnata (Lmk) Pers (KP) has an immunosuppressive effect on delayed-type hypersensitivity test. Based on it, this research aimed to determine the repairing effects of aqueous extract of KP on lupus nephritis mice and identified its active compound. The KP extract profile was determined using UPLC-QTOF-MS/MS instrument. We examined six mice groups consisting of three curative treatment groups, one standard group receiving prednisone, one preventive group receiving KP extract, and one healthy (healthy and untreated) group. At the end of the experiment, we measured the proteinuria and renal histology parameters. To recognize the active compound in the KP profile, we performed in silico assays for the flavonoid compounds to bind to the glucocorticoid receptor. We played in silico tests for the flavonoid compounds to identify the active compound in the KP profile. We found the repairing effect of KP was detected in the kidney, demonstrated by its low proteinuria level and its ...
Kalanchoe thyrsiflora, commonly called flapjack plant, is often used interchangeably with the similar Kalanchoe luciae. The plant resembles nothing more than a rosette of silver-dollar pancakes ...
For plant lovers who lack a green thumb, growing kalanchoe (Kalanchoe spp.) can be a good way to boost self-confidence. This hearty tropical succulent tolerates obsessive attention, or neglect and poor growing conditions, seeming to thrive in spite of the usual good intentions gone bad scenario that tragically takes ...
28-norlup-20(29)-en-3beta-hydroxy-17beta-hydroperoxide: antiproliferative triterpene from leaves of Melaleuca ericifolia; structure in first source
The beauty of Kalanchoe (Kalanchoe blossfeldania) is known to flower lovers and horticulturists. Moreover, this plant is very often used to give stamp to a
Hi, I have a Kalanchoe blossfeldiana and is has been blooming all winter. Now the flower stalks have grow very high and awkward. They are still blooming at the top, but bending over more. Does anyone know if I can trim them off and wait for them to reflower from the leaves again?
Not so many professionals in the cultivation of succulents and care. They create special conditions for their pets, achieve greater decorativeness, and bring out new varieties. But what attracts Kalanchoe lovers of greenery on the windowsill? First of all, its undemanding. Enough a few minutes a day to brush away the dust from the leaves, rearrange to the best place, check the soil moisture and the pet will be pleased. Flowering in the winter next to the ripening room mandarin, when all other plants are frozen in anticipation of the summer, makes these plants pets. ...
Marc Marí-DellOlmo, Mercè Gotsens, Laia Palència, Bo Burström, Diana Corman, Giuseppe Costa, Patrick Deboosere, Èlia Díez, Felicitas Domínguez-Berjón, Dagmar Dzúrová, Ana Gandarillas, Rasmus Hoffmann, Katalin Kovács, Pekka Martikainen, Moreno Demaria, Hynek Pikhart, Maica Rodríguez-Sanz, Marc Saez, Paula Santana, Cornelia Schwierz, Lasse Tarkiainen, Carme Borrell ...
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... 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. ...
Amphibian Venoms , Chemistry , Animals , Bufanolides , Bufo bufo , Cholenes , Cyclodextrins , Drug Carriers , Drug Stability , ...
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