cholenes

Summary

Summary: 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.

Top Publications

  1. Guo T, Song H, Zhao M, Zhang R, Li X. [Study on the preparation of venenum bufonis beta-cyclodextrin inclusion complexes]. Zhongguo Zhong Yao Za Zhi. 2002;27:835-7 pubmed
    ..The bufadienolide inclusion rate of Venenum Bufonis beta-cyclodextrin prepared with ball grinding method was 85.42%. Ball grinding method is the best method for the preparation of Venenum Bufonis beta-cyclodextrin inclusion complexes. ..
  2. Wang X, Liao G, Hou S. [Determination of the contents of bufadienolide and borneol in liushen pills]. Zhongguo Zhong Yao Za Zhi. 1994;19:25-7, 62 pubmed
    ..The average recover of bufadienolide by SDS was 100.12% (n = 6, RSD = 1.44%) and of borneol by GC 97.68% (n = 4, RSD = 1.32%). ..
  3. Supratman U, Fujita T, Akiyama K, Hayashi H. New insecticidal bufadienolide, bryophyllin C, from Kalanchoe pinnata. Biosci Biotechnol Biochem. 2000;64:1310-2 pubmed
    ..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. ..
  4. Botha C, Gehring R, van Rooyen J, Venter D. The effect of three bufadienolide cardiac glycosides on contraction of isolated rat jejunum. Onderstepoort J Vet Res. 2002;69:243-6 pubmed
    ..When combined with atropine (1 x 10(-6) M) the response of epoxyscillirosidin and tyledoside D decreased, indicating suppression of a cholinergic response caused by the cardiac glycosides. ..
  5. Kopp B, Krenn L, Draxler M, Hoyer A, Terkola R, Vallaster P, et al. Bufadienolides from Urginea maritima from Egypt. Phytochemistry. 1996;42:513-22 pubmed
  6. Ye M, Ning L, Zhan J, Guo H, Guo D. [Progress in biotransformation of triptolides and bufadienolides]. Beijing Da Xue Xue Bao Yi Xue Ban. 2004;36:82-9 pubmed
    ..The latest results from our research group in the biotransformation of triptolides and bufadienolides were reviewed. The trends in the development of biotransformation in the future were also briefly discussed. ..
  7. Natowicz M, Evans J. Abnormal bile acids in the Smith-Lemli-Opitz syndrome. Am J Med Genet. 1994;50:364-7 pubmed
  8. Li J, Li Y, Son C, Brodie A. Inhibition of androgen synthesis by 22-hydroximino-23,24-bisnor-4-cholen-3-one. Prostate. 1995;26:140-50 pubmed
    ..These results suggest that 22-oxime is effective in reducing androgen synthesis through the inhibition of 17 alpha-hydroxylase, C17,20-lyase, and 5 alpha-reductase both in vitro and in vivo. ..
  9. Namba T, Hirota T, Hayakawa S. Synthesis and mutagenicity of a ring-A-aromatized bile acid, 3-hydroxy-19-nor-1,3,5(10)-cholatrien-24-oic acid. J Lipid Res. 1988;29:809-14 pubmed
    ..When compared with cholic, deoxycholic, and lithocholic acids, the investigated compound exhibited about two to threefold increase of mutagenicity in the latter assay. ..

More Information

Publications28

  1. Herz J, Wilson W, Pinkerton F, Schroepfer G. Inhibitors of sterol synthesis. Synthesis and spectral properties of 3 beta-hydroxy-24-dimethylamino-5 alpha-chol-8(14)-en-15-one and its effects on HMG-CoA reductase activity in CHO-K1 cells. Chem Phys Lipids. 1991;60:61-9 pubmed
    ..The 25-aza analog (VII) of the 15-ketosterol (I), at a concentration of 1.0 microM, caused a 47% lowering of the level of 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in Chinese hamster ovary cells. ..
  2. Venter P, Naude R, Oelofsen W, Swan G. Ovine cardiac Na,K-ATPase: isolation by means of selective solubilization in Lubrol and the effect of 1 alpha,2 alpha-epoxyscillirosidin on this enzyme. Int J Biochem Cell Biol. 1997;29:1103-12 pubmed
  3. Ye M, Han J, Tu G, An D, Guo D. Microbial hydroxylation of bufalin by Cunninghamella blakesleana and Mucor spinosus. J Nat Prod. 2005;68:626-8 pubmed
    ..Metabolites 2, 3, 6, and 7 are new compounds, and their structures were fully characterized by NMR and MS spectroscopy. ..
  4. Ye M, Guo D. Substrate specificity for the 12beta-hydroxylation of bufadienolides by Alternaria alternata. J Biotechnol. 2005;117:253-62 pubmed
  5. Lu Z, Van Wagoner R, Harper M, Hooper J, Ireland C. Two ring-A-aromatized bile acids from the marine sponge Sollasella moretonensis. Nat Prod Commun. 2010;5:1571-4 pubmed
    ..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. ..
  6. Wang C, Liu L, Xu H, Zhang Z, Wang X, Liu H. Novel and efficient synthesis of 22-alkynyl-13,24(23)-cyclo-18,21-dinorchol-22-en-20(23)-one analogues. Steroids. 2011;76:491-6 pubmed publisher
  7. Watanabe K, Mimaki Y, Sakagami H, Sashida Y. Bufadienolide and spirostanol glycosides from the rhizomes of helleborusorientalis. J Nat Prod. 2003;66:236-41 pubmed
    ..The isolated compounds were evaluated for their cytotoxic activities against cultured tumor and normal cells...
  8. Xu L, Liu Y, Yao K, Liu H, Tao X, Wang F, et al. Unraveling and engineering the production of 23,24-bisnorcholenic steroids in sterol metabolism. Sci Rep. 2016;6:21928 pubmed publisher
    ..Through the combined modification of hsd4A and other genes, three HBCs producing strains were constructed that resulted in promising productivities of 0.127, 0.109 and 0.074 g/l/h, respectively. ..
  9. Cui B, Chai H, Constant H, Santisuk T, Reutrakul V, Beecher C, et al. Limonoids from Azadirachta excelsa. Phytochemistry. 1998;47:1283-7 pubmed
    ..The defection of nimbolide and 28-deoxonimbolide as cytotoxic constituents was facilitated by an electrospray LC/MS dereplication procedure. ..
  10. Hirano T, Oka K, Mimaki Y, Kuroda M, Sashida Y. Potent growth inhibitory activity of a novel Ornithogalum cholestane glycoside on human cells: induction of apoptosis in promyelocytic leukemia HL-60 cells. Life Sci. 1996;58:789-98 pubmed
    ..2 nM. These results provided the first evidence ever for the potent growth inhibitory activity of Ornithogalum glycoside on human leukemia cell lines and PBMC. ..
  11. Swan G, Schultz R, Kellerman T, Mulders M, Maartens B, Van der Walt J. In vivo effects of a novel calcium antagonist (R56865) against induced epoxyscillirosidin and tulp poisoning in sheep. Onderstepoort J Vet Res. 1995;62:163-6 pubmed
    ..The potential use of R56865 together with activated charcoal is discussed. ..
  12. Kigodi P, Blasko G, Thebtaranonth Y, Pezzuto J, Cordell G. Spectroscopic and biological investigation of nimbolide and 28-deoxonimbolide from Azadirachta indica. J Nat Prod. 1989;52:1246-51 pubmed
    ..For the first time, unambiguous 1H- and 13C-nmr assignments of compounds 1 and 2 are presented, as well as their in vitro cytotoxic activity against human tumor cell lines. ..
  13. Herz J, Swaminathan S, Pinkerton F, Wilson W, Schroepfer G. 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. J Lipid Res. 1992;33:579-98 pubmed
    ..5 microM. In contrast, the corresponding 3,15-diketo acid XV had no detectable effect on reductase activity under the same conditions...
  14. Asem E, Simpson D, Marrone B. Hormone stimulated steroid biosynthesis in granulosa cells studied with a fluorogenic probe for cytochrome P-450SCC. J Steroid Biochem Mol Biol. 1992;43:479-87 pubmed
    ..The results show that this fluorescent probe can be used in a rapid assay for the continuous measurement of the acute effects of hormone agonists on cholesterol conversion to pregnenolone in steroidogenic cells. ..
  15. Snyman L, Schultz R, Joubert J, Basson K, Labuschagne L. Conditioned feed aversion as a means to prevent tulp (Homeria pallida) poisoning in cattle. Onderstepoort J Vet Res. 2003;70:43-8 pubmed
    ..Occurrence of mild tulp poisoning, however, did not differ much between averted and non-averted control cattle. The results show that conditioned feed aversion effectively restricted severe poisoning in cattle on tulp-infested grazing. ..
  16. Daniel D, Süsal C, Kopp B, Opelz G, Terness P. Apoptosis-mediated selective killing of malignant cells by cardiac steroids: maintenance of cytotoxicity and loss of cardiac activity of chemically modified derivatives. Int Immunopharmacol. 2003;3:1791-801 pubmed
    ..The description of compounds without cardiac activity but with tumor-specific cytotoxicity suggests the potential of using them in cancer therapy. ..
  17. Sich B, Kirch U, Tepel M, Zidek W, Schoner W. Pulse pressure correlates in humans with a proscillaridin A immunoreactive compound. Hypertension. 1996;27:1073-8 pubmed
    ..The level of one of these substances (ED1) correlates with mean arterial and pulse pressures. ..
  18. Tait A, Abbs D, Teale P, Houghton E. Gas chromatographic and gas chromatographic/tandem mass spectrometric characterization of precursors on the sesterterpene pathway for steroid biosynthesis. Biomed Environ Mass Spectrom. 1989;18:572-5 pubmed
  19. Iqbal M, Elliott W. Bile acids, LXXIX. Synthesis and reduction of 1,4-dien-3-ones of various bile acids. Steroids. 1989;53:413-25 pubmed
    ..Lithium-ammonia reduction proved to be the better method for the reduction of these 1,4-dien-3-ones producing the 3-keto- and 3 beta-hydroxy-allo bile acids (Vb-d) and (VIb-d) in 66-72% yields. ..