10370. Celastrol

Nomenclature

CAS number: 34157-83-0
(9β,13α,14β,20α)-3-Hydroxy-9,13-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid; tripterine.
C29H38O4; mol wt 450.61.
C 77.30%, H 8.50%, O 14.20%.

Description and references

Anti-inflammatory triterpenoid isolated from the Chinese medicinal herb, thunder god vine, Tripterygium wilfordii Hook. f., and other plants of the family, Celastraceae. Identification as red pigment in T. wilfordii: T. Q. Chou, P. F. Mei, Chin. J. Physiol. 10, 529 (1936); eidem, Chin. Med. J. 54, 37 (1938). Isoln from Celastrus scandens: O. Gisvold, J. Am. Pharm. Assoc. 28, 440 (1939). Identity of tripterine and celastrol: M. S. Schechter, H. L. Haller, J. Am. Chem. Soc. 64, 182 (1942) DOI. Structure: R. Harada et al., Tetrahedron Lett. 3, 603 (1962) DOI. Isoln from Reissantia buchananii: F.-R. Chang et al., J. Nat. Prod. 66, 1416 (2003) DOI PubMed. HPLC/MS/MS determn in human blood: Q. Xu et al., Chromatographia 66, 735 (2007) DOI. Antiangiogenic and antitumor activity: Y. Huang et al., Cancer Lett. 264, 101 (2008) DOI PubMed. Efficacy in rat models of arthritis: H. Li et al., J. Ethnopharmacol. 118, 479 (2008) DOI PubMed.

Chemical structure

Properties

Ruby red, cubic crystals, mp 205° (dec) (Gisvold). Also reported as orange powder, mp 196-199° (Chang). [α]D25 61.22° (c = 0.049 in methanol). abs max (methanol): 209, 424 nm. Sol in methanol, ethanol, DMSO, DMF. Sparingly sol in aq buffers.

Derivative

Methyl ester.

Nomenclature

CAS number: 1258-84-0
Pristimerin.
C30H40O4; mol wt 464.64.
C 77.55%, H 8.68%, O 13.77%.

Properties

Orange needles from ether + petr ether, mp 217.5-218°. [α]D24.5 157.43° (c = 0.101 in methanol). abs max (methanol): 211, 252, 428 nm.