WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 558065
CAS#: 73981-34-7
Description: Kamebakaurin is isolated from leaves and stems of Radbosia serra (Maxim) Hara.
MedKoo Cat#: 558065
Name: Kamebakaurin
CAS#: 73981-34-7
Chemical Formula: C20H30O5
Exact Mass: 350.21
Molecular Weight: 350.45
Elemental Analysis: C, 68.55; H, 8.63; O, 22.83
This product is not in stock, which may be available by custom synthesis.
For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge).
Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.
Synonym: 1,7,14,20-Tetrahydroxykaur-16-en-15-one (1alpha,7alpha,14R);
IUPAC/Chemical Name: Kaur-16-en-15-one, 1,7,14,20-tetrahydroxy-, (1alpha,7alpha,14R)-
InChi Key: WHSUEVLJUHPROF-BIGDWJEQSA-N
InChi Code: InChI=1S/C20H30O5/c1-10-11-4-5-12-19(9-21)13(18(2,3)7-6-14(19)22)8-15(23)20(12,16(10)24)17(11)25/h11-15,17,21-23,25H,1,4-9H2,2-3H3/t11-,12-,13+,14-,15+,17+,19-,20-/m0/s1
SMILES Code: C=C([C@H](CC1)[C@H]2O)C([C@@]32[C@H](O)C[C@]4([H])C(C)(C)CC[C@H](O)[C@@]4(CO)[C@@]31[H])=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 350.45 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Kim JY, Kim HS, Kim YJ, Lee HK, Kim JS, Kang JS, Hong JT, Kim Y, Hwang BY, Han SB. Inhibition of TAK1 by kamebakaurin in dendritic cells. Int Immunopharmacol. 2013 Jan;15(1):138-43. doi: 10.1016/j.intimp.2012.11.004. Epub 2012 Nov 15. PubMed PMID: 23159603.
2: Wang KS, Ma J, Mi C, Li J, Lee JJ, Jin X. Kamebakaurin inhibits the expression of hypoxia-inducible factor-1α and its target genes to confer antitumor activity. Oncol Rep. 2016 Apr;35(4):2045-52. doi: 10.3892/or.2016.4576. Epub 2016 Jan 19. PubMed PMID: 26781327.
3: Kim BW, Koppula S, Kim IS, Lim HW, Hong SM, Han SD, Hwang BY, Choi DK. Anti-neuroinflammatory activity of Kamebakaurin from Isodon japonicus via inhibition of c-Jun NH₂-terminal kinase and p38 mitogen-activated protein kinase pathway in activated microglial cells. J Pharmacol Sci. 2011;116(3):296-308. Epub 2011 Jun 25. PubMed PMID: 21705843.
4: Lee JH, Choi JK, Noh MS, Hwang BY, Hong YS, Lee JJ. Anti-inflammatory effect of kamebakaurin in in vivo animal models. Planta Med. 2004 Jun;70(6):526-30. PubMed PMID: 15241890.
5: Zhou WS, Cheng YX. The stereo-, regio-, and chemo-selective conversion of diterpenoids, kamebakaurin to oriaonin. Sci China B. 1992 Feb;35(2):194-9. PubMed PMID: 1581004.
6: Lee JH, Koo TH, Hwang BY, Lee JJ. Kaurane diterpene, kamebakaurin, inhibits NF-kappa B by directly targeting the DNA-binding activity of p50 and blocks the expression of antiapoptotic NF-kappa B target genes. J Biol Chem. 2002 May 24;277(21):18411-20. Epub 2002 Mar 4. PubMed PMID: 11877450.
7: Zhang J, Wu XY, Yu FS. Inflammatory responses of corneal epithelial cells to Pseudomonas aeruginosa infection. Curr Eye Res. 2005 Jul;30(7):527-34. PubMed PMID: 16020286; PubMed Central PMCID: PMC2666384.
8: Nam NH. Naturally occurring NF-kappaB inhibitors. Mini Rev Med Chem. 2006 Aug;6(8):945-51. Review. PubMed PMID: 16918500.
9: Pickering BM, de Mel S, Lee M, Howell M, Habens F, Dallman CL, Neville LA, Potter KN, Mann J, Mann DA, Johnson PW, Stevenson FK, Packham G. Pharmacological inhibitors of NF-kappaB accelerate apoptosis in chronic lymphocytic leukaemia cells. Oncogene. 2007 Feb 22;26(8):1166-77. Epub 2006 Aug 21. PubMed PMID: 16924235.
10: Wu YX, Zhang W, Li JC, Liu N. Chemical constituents of flowers and fruits of Rabdosia excisa. Chin J Nat Med. 2012 Jan;10(1):43-7. doi: 10.1016/S1875-5364(12)60010-7. PubMed PMID: 23302530.
11: Okuda J, Arikawa Y, Takeuchi Y, Mahmoud MM, Suzaki E, Kataoka K, Suzuki T, Okinaka Y, Nakai T. Intracellular replication of Edwardsiella tarda in murine macrophage is dependent on the type III secretion system and induces an up-regulation of anti-apoptotic NF-kappaB target genes protecting the macrophage from staurosporine-induced apoptosis. Microb Pathog. 2006 Dec;41(6):226-40. Epub 2006 Oct 16. PubMed PMID: 17049431.
12: Zhang N, Li C, Yi X. [Study on the chemical components of Rabdosia excisa]. Zhong Yao Cai. 1998 Jul;21(7):347-9. Chinese. PubMed PMID: 12569856.
13: Yoshioka H, Aoyagi Y, Fukuishi N, Gui MY, Jin YR, Li XW, Adachi Y, Ohno N, Takeya K, Hitotsuyanagi Y, Miura N, Nonogaki T. Suppressive effect of kamebakaurin on acetaminophen-induced hepatotoxicity by inhibiting lipid peroxidation and inflammatory response in mice. Pharmacol Rep. 2017 Oct;69(5):903-907. doi: 10.1016/j.pharep.2017.04.004. Epub 2017 Apr 12. PubMed PMID: 28624597.
14: Zheng Q, Cui J, Fu H. [Studies on chemical constituents of Rabdosia serra]. Zhongguo Zhong Yao Za Zhi. 2011 Aug;36(16):2203-6. Chinese. PubMed PMID: 22097330.
15: Yao S, Xu NY, Chu CJ, Zhang J, Chen DF. [Chemical constituents of Rabdosia japonica var. glaucocalyx and their anti-complementary activity]. Zhongguo Zhong Yao Za Zhi. 2013 Jan;38(2):199-203. Chinese. PubMed PMID: 23672041.
16: Lee C, Hong SS, Han XH, Jin Q, Li D, Kim TO, Kim HK, Lee J, Kwon SH, Kim YB, Lee MK, Hwang BY. A new abietane diterpenoid from Isodon inflexus. Arch Pharm Res. 2008 Nov;31(11):1381-4. doi: 10.1007/s12272-001-2120-3. Epub 2008 Nov 21. PubMed PMID: 19023532.
17: Gui MY, Aoyagi Y, Jin YR, Li XW, Hasuda T, Takeya K. Excisanin H, a novel cytotoxic 14,20-epoxy-ent-kaurene diterpenoid, and three new ent-kaurene diterpenoids from Rabdosia excisa. J Nat Prod. 2004 Mar;67(3):373-6. PubMed PMID: 15043413.
18: Xiao Y, Zhong Y, Su H, Zhou Z, Chiao P, Zhong G. NF-kappa B activation is not required for Chlamydia trachomatis inhibition of host epithelial cell apoptosis. J Immunol. 2005 Feb 1;174(3):1701-8. PubMed PMID: 15661934.
19: Jin RL, Cheng PY, Xu GY. [The structure of rabdoserrin A, isolated from Rabdosia serra (Maxim) Hara]. Yao Xue Xue Bao. 1985 May;20(5):366-71. Chinese. PubMed PMID: 3841254.
20: Hwang BY, Lee JH, Koo TH, Kim HS, Hong YS, Ro JS, Lee KS, Lee JJ. Kaurane diterpenes from Isodon japonicus inhibit nitric oxide and prostaglandin E2 production and NF-kappaB activation in LPS-stimulated macrophage RAW264.7 cells. Planta Med. 2001 Jul;67(5):406-10. PubMed PMID: 11488452.
