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Chemical Compound Review

AC1MI1ZZ     (5S,8R,9R,10S,13R,14S,17R)- 4,4,8,10,14...

Synonyms: 545-22-2
 
 
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Disease relevance of Dammarane

 

High impact information on Dammarane

  • Phanoside is a dammarane-type saponin, and four stereoisomers differing in configurations at positions 21 and 23 were identified, each of which were found to stimulate insulin release from isolated rat pancreatic islets [4].
  • The present study reports a novel LXR-alpha activator, (20S)-2alpha, 3beta, 12beta, 24(S)-pentahydroxydammar-25-ene 20-O-beta-d-glucopyranoside (TR1), a dammarane-type gynosaponin, isolated from the herbal medicine, Gynostemma pentaphyllum [5].
  • Varieties of ginsenosides in adjuvant activity might be attributed to the varieties of molecular conformations determined by the side sugar chains attaching to their dammarane skeleton [6].
  • It has been reported that ginsenoside Rh(2), a purified ginseng saponin with a dammarane skeleton, has anticarcinogenic effects on mammalian cells [7].
  • Taraxastane, oleanane, ursane, lupane, taraxane, cycloartane, dammarane and tirucallane triterpenoids isolated from flowers of Compositae plants have been previously reported to exhibit anti-inflammatory effects and are variously competitive and non-competitive inhibitors of the serine proteases trypsin and chymotrypsin [8].
 

Biological context of Dammarane

 

Anatomical context of Dammarane

  • Dammarane-type Saponins from Panax japonicus and their neurite outgrowth activity in SK-N-SH cells [12].
  • New dammarane-type triterpene oligoglycosides, jujubosides A1 and C and acetyljujuboside B1 were isolated from Zizyphi Spinosi Semen, the seeds of Zizyphus jujuba MILL. var. spinosa Hu, together-with three known saponins [13].
  • Members of the cycloartane, lupane, ursane, oleanane, friedelane (especially quinone methides), dammarane, cucurbitacin, and limonoid triterpenoids, have demonstrated anti-proliferative activity on various cancer cell lines [14].
 

Associations of Dammarane with other chemical compounds

 

Gene context of Dammarane

 

Analytical, diagnostic and therapeutic context of Dammarane

References

  1. Plant-glycoside modulation of cell surface related to control of differentiation in cultured B16 melanoma cells. Ota, T., Fujikawa-yamamoto, K., Zong, Z.P., Yamazaki, M., Odashima, S., Kitagawa, I., Abe, H., Arichi, S. Cancer Res. (1987) [Pubmed]
  2. Cdk2 activity is associated with depolarization of mitochondrial membrane potential during apoptosis. Jin, Y.H., Yim, H., Park, J.H., Lee, S.K. Biochem. Biophys. Res. Commun. (2003) [Pubmed]
  3. Ginsenoside Rh2 induces apoptosis via activation of caspase-1 and -3 and up-regulation of Bax in human neuroblastoma. Kim, Y.S., Jin, S.H. Arch. Pharm. Res. (2004) [Pubmed]
  4. A novel insulin-releasing substance, phanoside, from the plant Gynostemma pentaphyllum. Norberg, A., Hoa, N.K., Liepinsh, E., Van Phan, D., Thuan, N.D., Jörnvall, H., Sillard, R., Ostenson, C.G. J. Biol. Chem. (2004) [Pubmed]
  5. A novel LXR-alpha activator identified from the natural product Gynostemma pentaphyllum. Huang, T.H., Razmovski-Naumovski, V., Salam, N.K., Duke, R.K., Tran, V.H., Duke, C.C., Roufogalis, B.D. Biochem. Pharmacol. (2005) [Pubmed]
  6. Adjuvant effects of protopanaxadiol and protopanaxatriol saponins from ginseng roots on the immune responses to ovalbumin in mice. Sun, J., Hu, S., Song, X. Vaccine (2007) [Pubmed]
  7. Anticarcinogenic effect and enhancement of metastatic potential of BALB/c 3T3 cells by ginsenoside Rh(2). Tatsuka, M., Maeda, M., Ota, T. Jpn. J. Cancer Res. (2001) [Pubmed]
  8. Inhibition of trypsin and chymotrypsin by anti-inflammatory triterpenoids from Compositae flowers. Rajic, A., Akihisa, T., Ukiya, M., Yasukawa, K., Sandeman, R.M., Chandler, D.S., Polya, G.M. Planta Med. (2001) [Pubmed]
  9. Caspase 3 specifically cleaves p21WAF1/CIP1 in the earlier stage of apoptosis in SK-HEP-1 human hepatoma cells. Park, J.A., Kim, K.W., Kim, S.I., Lee, S.K. Eur. J. Biochem. (1998) [Pubmed]
  10. Isolation, Structural Determination, and Evaluation of the Biological Activity of 20(S)-25-methoxyl-dammarane-3beta, 12beta, 20-triol [20(S)-25-OCH(3)-PPD], a Novel Natural Product from Panax notoginseng. Zhao, Y., Wang, W., Han, L., Rayburn, E.R., Hill, D.L., Wang, H., Zhang, R. Medicinal chemistry (Sh⁻ariqah, United Arab Emirates) (2007) [Pubmed]
  11. New saponins from Vietnamese ginseng: highlights on biogenesis of dammarane triterpenoids. Duc, N.M., Kasai, R., Ohtani, K., Ito, A., Yamasaki, K., Nguyen, T.N., Tanaka, O. Adv. Exp. Med. Biol. (1996) [Pubmed]
  12. Dammarane-type Saponins from Panax japonicus and their neurite outgrowth activity in SK-N-SH cells. Zou, K., Zhu, S., Meselhy, M.R., Tohda, C., Cai, S., Komatsu, K. J. Nat. Prod. (2002) [Pubmed]
  13. Bioactive saponins and glycosides. X. On the constituents of zizyphi spinosi semen, the seeds of Zizyphus jujuba Mill. var. spinosa Hu (1): structures and histamine release-inhibitory effect of jujubosides A1 and C and acetyljujuboside B. Yoshikawa, M., Murakami, T., Ikebata, A., Wakao, S., Murakami, N., Matsuda, H., Yamahara, J. Chem. Pharm. Bull. (1997) [Pubmed]
  14. Plant-derived triterpenoids as potential antineoplastic agents. Setzer, W.N., Setzer, M.C. Mini reviews in medicinal chemistry. (2003) [Pubmed]
  15. Gycomoside I: a new dammarane saponin from Gynostemma compressum. Ding, S.L., Zhu, Z.Y. Planta Med. (1993) [Pubmed]
  16. Cleogynol, a novel dammarane triterpenoid from Cleome gynandra. Das, P.C., Patra, A., Mandal, S., Mallick, B., Das, A., Chatterjee, A. J. Nat. Prod. (1999) [Pubmed]
  17. Further bisabolenes and dammarane triterpenes of Commiphora kua resin. Manguro, L.O., Ugi, I., Lemmen, P. Chem. Pharm. Bull. (2003) [Pubmed]
  18. Dammarane derivatives protect cultured rat cortical cells from glutamate-induced neurotoxicity. Kim, S.R., Sung, S.H., Kwon, S.W., Park, J.H., Huh, H., Kim, Y.C. J. Pharm. Pharmacol. (2000) [Pubmed]
  19. Beta-amyrin synthase--cloning of oxidosqualene cyclase that catalyzes the formation of the most popular triterpene among higher plants. Kushiro, T., Shibuya, M., Ebizuka, Y. Eur. J. Biochem. (1998) [Pubmed]
  20. Enzymatic modification of natural compounds with pharmacological properties. Riva, S., Monti, D., Luisetti, M., Danieli, B. Ann. N. Y. Acad. Sci. (1998) [Pubmed]
  21. Activation of caspase-3 protease via a Bcl-2-insensitive pathway during the process of ginsenoside Rh2-induced apoptosis. Park, J.A., Lee, K.Y., Oh, Y.J., Kim, K.W., Lee, S.K. Cancer Lett. (1997) [Pubmed]
  22. Immunological-adjuvant saponins from the roots of Panax notoginseng. Sun, H., Ye, Y., Pan, Y. Chem. Biodivers. (2005) [Pubmed]
 
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