9747. Triptolide

Nomenclature

CAS number: 38748-32-2
(3bS,4aS,5aS,6R,6aR,7aS,7bS,8aS,8bS)-3b,4,4a,6,6a,7a,7b,8b,9,10-Decahydro-6-hydroxy-8b-methyl-6a-(1-methylethyl)trisoxireno[4b,5:6,7:8a,9]phenanthro[1,2-c]furan-1(3H)-one; PG490.
C20H24O6; mol wt 360.40.
C 66.65%, H 6.71%, O 26.64%.

Description and references

Diterpenoid triepoxide with immunosuppressant and antitumor properties; isolated from the Chinese medicinal herb, Tripterygium wilfordii Hook. f., Celastraceae, commonly known as thunder god vine, q.v. Isoln and structure determn: S. M. Kupchan et al., J. Am. Chem. Soc. 94, 7194 (1972) DOI PubMed. Synthesis of racemate: R. S. Buckanin et al., ibid. 102, 1200 (1980); of naturally occurring ()-form: D. Yang et al., ibid. 121, 5579 (1999). HPLC and SPE determn in Tripterygium root extracts: A. M. Brinker, I. Raskin, J. Chromatogr. A 1070, 65 (2005) DOI PubMed. Animal studies of male antifertility effects: A. P. S. Hikim et al., J. Androl. 21, 431 (2000) PubMed; P. N. Huynh et al., ibid. 689. Mechanistic studies of apoptotic and antitumor activities: W.-T. Chang et al., J. Biol. Chem. 276, 2221 (2001) DOI PubMed; T. M. Kiviharju et al., Clin. Cancer Res. 8, 2666 (2002) PubMed; S. J. Leuenroth, C. M. Crews, Chem. Biol. 12, 1259 (2005) DOI PubMed. Review of anti-inflammatory and immunosuppressive properties: B. J. Chen, Leuk. Lymphoma 42, 253-265 (2001) DOI PubMed.

Chemical structure

Properties

mp 226-227°. [α]D25 154° (c = 0.369 in CH2Cl2). uv max (ethanol): 218 nm (ε 14000). Sol in DMSO, ethanol. LD50 i.p. in mice: 1.93 mg/kg (Chen).

Derivative

14-Succinyl triptolide sodium salt.

Nomenclature

CAS number: 195883-09-1
PG490-88.
C24H27NaO9; mol wt 482.46.
C 59.75%, H 5.64%, Na 4.77%, O 29.85%.

Description and references

Semi-synthetic water soluble prodrug. Prepn: Y. M. Qi, J. H. Musser, US 5663335 (1997 to Pharmagenesis). Animal model studies of prevention of graft-vs-host disease: B. J. Chen et al., Transplantation 70, 1442 (2000) DOI PubMed; of antitumor effects: J. M. Fidler et al., Mol. Cancer Ther. 2, 855 (2003) PubMed; of allograft survival in organ transplantation: F. Pan et al., Transplant. Proc. 37, 134 (2005) DOI PubMed.