Abstract
Alchornea floribunda (Euphorbiaceae) leaves are widely used in African ethnomedicine for the management
of acute and chronic inflammatory disorders. In the present study, bioactivity-guided
fractionation led to the isolation of two known (1 and 3) and one new (2) stigmastane steroids from the hexane extract of Alchornea floribunda leaves. The anti-inflammatory activities of these compounds were evaluated using
in vitro and in vivo animal models. The compounds 1, 2, and 3 at 50 and 100 µg/ear significantly (p < 0.05) inhibited xylene-induced ear edema
in mice in a dose-dependent manner. The topical anti-inflammatory effect of 1 and 2 are significantly (p < 0.05) higher than that of indomethacin and prednisolone. At
20 mg/kg (i. p.), all the compounds significantly (p < 0.05) inhibited acute inflammation
induced by subplantar injection of egg albumen in rats. Compound 1 exhibited an anti-inflammatory effect (50.9 % edema inhibition) comparable (p < 0.05)
to that of prednisolone (48.0 % edema inhibition) at 3 h. Compounds 1, 2, and 3 (50 µg/mL) significantly (p < 0.05) inhibited heat-induced haemolysis of human erythrocytes
in vitro, but had no effect on hypotonicity-induced hemolysis. The compounds were elucidated
as (24R)-5α-stigmast-3,6-dione (1), 5α-stigmast − 23-ene-3,6-dione (2), and 3β-hydroxy-5α-stigmast-24-ene (3) by spectral analysis. The results of this study show that these compounds may, in
part, account for the anti-inflammatory effect of Alchornea floribunda leaves. This is the first report on the isolation and structure elucidation of these
anti-inflammatory steroids from Alchornea floribunda leaves.
Key words
anti‐inflammatory - stigmastane steroids -
Alchornea floribunda
- Euphorbiaceae - egg albumen‐induced edema - membrane stabilization
References
- 1 Duke J A, Mary J B, Judi D. Handbook of medicinal herbs. Boca Raton; CRC Press 2002:
527
- 2
Okoye F B C, Osadebe P O.
Studies on the mechanisms of anti-inflammatory activity of the extracts and fractions
of Alchornea floribunda leaves.
Asian Pac J Trop Med.
2009;
2
7-14
- 3
Okoye F B C, Ebi G C.
Preliminary antimicrobial and phytochemical investigation of the extracts and column
fractions of Alchornea floribunda leaves.
J Pharm Allied Sci.
2007;
4
395-402
- 4
Tubaro A, Dri P, Delbello G, Zilli C, Della L R.
The croton oil ear test revisited.
Agents Actions.
1985;
17
347-349
- 5
Okoli C O, Akah P A.
Mechanisms of anti-inflammatory activity of the leave extracts of Culcasia scandens P. Beauv (Araceae).
Pharmacol Biochem Behav.
2004;
79
473-481
- 6
Osadebe P O, Okoye F B C.
Anti-inflammatory effects of crude methanolic extrats and fractions of Alchornea cordifolia leaves.
J Ethnopharmacol.
2003;
89
19-24
- 7
Perez G R M.
Anti-inflammatory activity of Ambrosia artemisaefolia and Rheo spathacea.
Phytomedicine.
1996;
3
163-167
- 8
Shinde U A, Phadke A S, Nari A M, Mungantiwar A A, Dikshit V J, Saraf M N.
Membrane stabilization activity – a possible mechanism of action for the anti-inflammatory
activity of Cedrus deodora wood oil.
Fitoterapia.
1999;
70
251-257
- 9
Gaspar E M M, Das Neves H J C.
Steroidal constituents from mature wheat straw.
Phytochemistry.
1993;
34
523-527
- 10
Fernandez M I, Pedro J R, Seoane E.
Constituents of a hexane extract of Phoenix dactylifera.
Phytochemistry.
1983;
22
2087-2088
- 11
Della Greca M, Monaco P, Previtera L.
Stigmasterols from Typha latifolia.
J Nat Prod.
1990;
53
1430-1435
- 12
Guerriero A, Debitus C, Pietra F.
On the 1st marine stigmastane sterols and sterols having a 24,25-double bond – isolation
from the sponge Stelletta sp of deep coral sea.
Helv Chim Acta.
1991;
74
487-494
- 13
Miles D U, Tunsuwan K, Vallapa C, Heldin P A, Kokpolu U.
Boll weevil antifeedants from Elleocharis dulcis Trin.
J Agric Food Chem.
1994;
42
1561-1562
- 14 Harbourne J B. Phytochemical methods: a guide to modern techniques of plant analysis,
3rd edition. London; Chapman and Hall 1998: 107-150
- 15
Wahidulla S, D'Souza L, Patel J.
5α-Cholstane-3,6-dione from the red alga Acantophora spicifera.
Phytochemistry.
1987;
26
2864-2865
- 16 Goad L J, Akihisa T. Analysis of sterols, 1st edition. London; Blackie Academic
and Professional 1997: 146
- 17
Di Rosa M, Sorrentino L.
The mechanism of the inflammatory effect of carrageenin.
Eur J Pharmacol.
1969;
4
340-342
- 18
Damas J, Baurdon V, Remade-Volon G, Adam A.
Kinins and peritoneal exudates induced by carrageenan and zymosan.
Br J Pharmacol.
1990;
101
418-422
- 19
Raychaudhuri A, Colombo C, Pastor G, Wong M, Jeng A Y.
Effects of capsaicun on carrageenan-induced inflammation in rat pleurisy and exudates
substance p level.
Agents Actions.
1991;
34
251-253
- 20
Utsunomiya I, Nagai S, Oh-ishi S.
Sequential appearance of 1L-1 and 1L-6 activities in rat carrageenan-induced pleuriisy.
J Immunol.
1991;
147
1803-1809
- 21
Ialenti A, Ianaro A, Moncada S, Di Rosa M.
Modulation of acute inflammation by endogenous nitric oxide.
Eur J Pharmacol.
1992;
211
177-182
- 22
Weissmann G.
The role of lysosomes in inflammation and disease.
Annu Rev Med.
1967;
18
97-112
- 23
Chandran P G R, Balaji S.
Phytochemical investigation and pharmocological studies of the flowers of Pithecellobium dulce.
Ethnobot Leafl.
2008;
12
245-253
- 24
Mavar-Manga H, Haddad M, Pieters L, Baccelli C, Penge A, Quetin-Leclercq J.
Anti-inflammatory compounds from leaves and root bark of Alchornea cordifolia (Schumach. & Thonn.) Müll. Arg.
J Ethnopharmacol.
2008;
115
25-29
- 25
Cioffi G, Sanogo R, Diallo D, Romussi G, De Tommasi N.
New compounds from an extract of Vernonia colorata leaves with anti-inflammatory activity.
J Nat Prod.
2004;
67
389-394
Festus Basden Chiedu Okoye
Department of Pharmaceutical and Medicinal Chemistry
Faculty of Pharmaceutical Sciences
University of Nigeria
Nsukka
410001 Enugu State
Nigeria
Phone: + 23 4 80 33 60 76 39
Email: basdenc@yahoo.com
