633. Andrographolide

Nomenclature

CAS number: 5508-58-7
(3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-2(3H)-furanone; 3α,14,15,18-tetrahydroxy-5β,9βH,10α-labda-8(20),12-dien-16-oic acid γ-lactone.
C20H30O5; mol wt 350.45.
C 68.54%, H 8.63%, O 22.83%.

Description and references

Main bitter constituent and medicinally active principle isolated from the leaves of andrographis, q.v. Isoln: M. K. Gorter, Rec. Trav. Chim. 30, 151 (1911). Rapid isoln method: M. Rajani et al., Pharm. Biol. 38, 204 (2000). Characterization: D. Chakravarti, R. N. Chakravarti, J. Chem. Soc. 1952, 1697; R. Schwyzer et al., Helv. Chim. Acta 34, 652 (1951). Structure: M. P. Cava, B. Weinstein, Chem. Ind. (London) 1959, 851. Revised structure: M. P. Cava et al., ibid. 1963, 167; M. P. Cava et al., Tetrahedron 21, 2617 (1965). X-ray crystallographic analysis: T. Fujita et al., Chem. Pharm. Bull. 32, 2117 (1984). HPLC determn in plant material: A. Sharma et al., Phytochem. Anal. 3, 129 (1992). Determn in Chinese medicinal prepns: Z. Yanfang et al., J. Pharm. Biomed. Anal. 40, 157 (2006). Mechanism of anti-inflammatory action: Y.-F. Xia et al., J. Immunol. 173, 4207 (2004). Clinical pharmacokinetics and bioavailability from herbal preparations: A. Panossian et al., Phytomedicine 7, 351 (2000).

Chemical structure

Properties

Colorless plates from ethanol or methanol, mp 218° (dec) (Gorter). Also reported as mp 218-221° (Fujita). [α]D25 96.2° (c = 1.00 in C5H5N). d421 1.2317. uv max (alcohol): 223 nm (log ε 4.09). Sparingly sol in water; sol in acetone, methanol, chloroform, ether.

Derivative

Triacetyl derivative.
C26H36O8; mol wt 476.56.
C 65.53%, H 7.61%, O 26.86%.

Properties

Fine needles from alcohol + ether, mp 126-126.5°.