|
Systematic studies on chemistry of A. paniculata
has been carried out by various researches during various times. Analysis
of the whole plant gave the following lactones (dry basis): andrographolide[1]
(C20H30O5; mp 230-239˚C), 0.6;
14-deoxy-11-oxoandrographolide[2] (C20H28O5, mp
98-100˚C), 0.12; 14-deoxy-11, 12-didehydroandrographolide[3] (C20H30O4,
mp 203-204˚C), 0.06; 14-deoxyandrographolide[4] (C20H30O4,
mp 175˚C), 0.02%; and a non-bitter constituent,
neoandrographolide[5] (C26H40O8, mp
167-168˚C), 0.005%. The leaves contain andrographolide (yield, 1%). From the
petroleum ether extract of the leaves from
Bangladesh, the following have been
isolated: α-,β-unsaturated lactone, homoandrographolide (C22H32O9,
mp 115˚C), andrographosterol (C23H38O,
mp 135˚C), andrographane (C40H82,
mp 67-68˚C), andrographone (C32H64O,
mp 85˚C), a wax and two esters containing hydroxy
groups.
The roots gave apigenin- 7, 4'-
di-O-methyl ether, andrographolide and a new natural
flavone, 5-hydroxy 7,8,2',3'- tetramethoxy
flavone
(C19H18O7, mp 150-151˚C; yield, 0.006%). They
also contain a monohydroxy
trimethyl
flavone, andrographin (C18H16O6,
mp 190-191˚C) and a dihydroxy-di-methoxyflavone,
panicolin (C17H4O6,
mp 263-264˚C). The presence of α-sitosterol
is also reported.
Andrographolide, chief constituent extracted from the leaves
of the plant, is exhibiting protective effects in carbon tetrachloride induced
hepatopathy
in rats. Its LD50 in male mice was 11.46gm/kg, ip
(Handa and Sharma, 1990). This bitter principle was
isolated in pure form by Gorter (1911).
Andrographolide is also attributed with such other activities like liver
protection under various experimental conditions of treatment with galactosamine (Saraswat et al,
1995), paracetamol (Visen
et al, 1993) etc. The hepatoprotective action of
andrographolide is related to activity of certain metabolic enzymes (Choudhury and Poddar, 1984, 1985;
Choudhury et al, 1987).
An excellent review of such compounds as
illustrated in 'Chemistry and pharmacology of Andrographis species' by Sudhanshu Saxena et al
published in Indian Drugs 35 (8) August 1998.
Extraction of
andrographolide - A new method
Rapid
Determination of Diterpenoids in Andrographis paniculata by
Microemulsion Electrokinetic Capillary Chromatography with Short-End
Injection.
Read the abstract or get
full paper
References
- Gorter, M.K. 1911. The
bitter constituent of Andrographis paniculata Nees. Rec Trav Chim 30: 151-
160.
- Saraswat, B., P.K.S.
Visan, G.K. Patnai and B.N. Dhawan. 1995. Effect of andrographolide against
galactosamine induced hepatotoxicity. Fitoterapia 66: 415-420.
- Visen, P.K.S., B.
Shukla, G.K. Patnaik and B.N. Dhawan. 1993. Andrographolide protects rat
hepatocytes against paracetamol-induced damage. J Ethnopharmacol 40:
131-136.
- Choudhury, B.R and M.K.
Poddar. 1985. Andrographolide and Kalmegh (Andrographis paniculata)
extract: effect on intestinal brush-border membrane bound hydrolases.
Methods Find Exp Clin
Pharmacol 7: 617-621
- Choudhury, R.B and M.K.
Poddar. 1984. Andrographolide and Kalmegh (Andrographis paniculata)
extract: in vivo and in vitro effect on hepatic lipid peroxidation. Methods
Find Exp Clin Pharmacol 6:
481.
- Choudhury, R.B, S.J.
Haque and M.K. Poddar. 1987. In vitro and in vivo effects of kalmegh
(Andrographis paniculata) extract and andrographolide on hepatic microsomal
drug metabolising
enzymes. Planta Medica 53: 135-140.
- Handa, S.S. and A. Sharma.
1990. Hepatoprotective activity of andrographolide from Andrographis
paniculata against carbontetrachloride. Ind J Med Res 92B: 276-283.
PhD Thesis on Andrographis paniculata
|
