Abstract
Salvia hierosolymitana (Lamiaceae) leaves were investigated for their topical anti-inflammatory properties following a bioassay-guided fractionation. The chloroform extract showed a strong inhibition of the Croton oil-induced ear oedema in mice, comparable to that of indomethacin. Phytochemical and pharmacological investigations of this extract led to the isolation of eight anti-inflammatory polyhydroxylated triterpenes of the ursane and oleanane series. Four of them are new compounds, whose structures were elucidated by NMR and mass spectroscopy as 3β,6α,23-trihydroxyurs-12,19(29)-dien-28-oic acid, 23-(trans-p-coumaroyloxy)-3β, 6α,30-trihydroxyurs-12-en-28-oic acid, 2α,3β-dihydroxyolean-28-oic acid and 24-nor-2α,3β-dihydroxyolean-4(23),12-ene.
Key words
Salvia hierosolymitana
- Lamiaceae - triterpenes - anti-inflammatory activity - Croton oil ear test
References
-
1
Ulubelen A.
Cardioactive and antibacterial terpenoids from some Salvia species.
Phytochemistry.
2003;
64
395-9
-
2
Todorov S, Philianos S, Petkov V, Harvala C, Zamfirova R, Olimpiou H.
Experimental pharmacological study of three species from genus Salvia
.
Acta Physiol Pharmacol Bulg.
1984;
10
13-20
-
3
Baricevic D, Sosa S, Della Loggia R, Tubaro A, Simonovska B, Krasna A et al Topical anti-inflammatory activity of Salvia officinalis
L.
leaves: the relevance of ursolic acid.
J Ethnopharmacol.
2001;
75
125-32
-
4
Tukan S K, Takruri H R, Al-Eisawi D M.
The use wild edible plants in the Jordanian diet.
Int J Food Sci Nutr.
1998;
49
225-35
-
5 Feinbrun-Dothan N. Flora Palaestina, Part III. Jerusalem; The Israel Academy of Sciences and Humanities 1978: p 84
-
6
Pedreros S, Rodriguez B, de la Torre M C, Bruno M, Savona G, Perales A. et al .
Dammarane triterpenes of Salvia hierosolymitana: structure and absolute stereochemistry of salvilymitone and salvilymitol.
Phytochemistry.
1990;
29
919-22
-
7
Tubaro A, Dri P, Delbello G, Zilli C, Della Loggia R.
The Croton oil ear test revisited.
Agents Actions.
1985;
17
347-9
-
8
Cioffi G, Braca A, Autore G, Morelli I, Pinto A, Venturella F. et al .
Cytotoxic saponins from Schefflera fagueti
.
Planta Med.
2003;
69
1-7
-
9
Kashiwada Y, Hui-Kang N, Tsuneatsu K S, Yasuda I, Fujioka T, Yamagishi T. et al .
Anti-AIDS agents. 30. Anti-HIV activity of oleanolic acid, pomolic acid, and structurally related triterpenoids.
J Nat Prod.
1998;
61
090-5
-
10
Sung T V, Lavaud C, Porzel A, Steglich W, Adam G.
Triterpenoids and their glycosides from the bark of Schefflera octophylla
.
Phytochemistry.
1991;
31
227-31
-
11
Liang Z, Aquino R, De Feo V, De Simone F, Pizza C.
Polyhydroxylated triterpenes from Eriobotrya japonica
.
Planta Med.
1990;
56
330-2
-
12
Mahato S B, Kundu A P.
Review article: 13C NMR spectra of pentacyclic triterpenoids - a compilation and some salient features.
Phytochemistry.
1994;
37
1517-75
-
13
Tezuka Y, Kasimu R, Li J X, Basnet P, Tanaka K, Namba T. et al .
Constituents of roots of Salvia deserta Schang. (Xinjiang-Danshen).
Chem Pharm Bull.
1998;
46
107-12
-
14
Aquino R, De Simone F, Vincieri F F, Pizza C, Gacs-Baitz E.
New polyhydroxylated triterpenes from Uncaria tomentosa
.
J Nat Prod.
1990;
53
559-64
-
15
Villar A, Payà M, Hortiguela M D, Cortes D.
Tormentic acid, a new hypoglycemic agent from Poterium ancistroides
.
Planta Med.
1986;
1
43-5
-
16
Liang G Y, Gray A I, Waterman P G.
Pentacyclic triterpenes from fruits of Rosa sterilis
.
J Nat Prod.
1989;
52
162-6
-
17
Kojima H, Ogura H.
Triterpenoids from Prunella vulgaris
.
Phytochemistry.
1985;
25
729-33
-
18
Begum S, Farhat F, Siddiqui B S.
Triterpenes from the leaves of Eucalyptus camaldulensis var. obtusa
.
J Nat Prod.
1997;
60
20-3
-
19
De Tommasi N, Pizza C, Aquino R, Cumandà J, Mahmood N.
Flavonol and chalcone ester glycosides from Bidens leucantha
.
J Nat Prod.
1997;
60
270-3
-
20
Ismaili H, Tortora S, Sosa S, Fkih-Tetouani S, Ilidrissi A, Della Loggia R. et al .
Topical anti-inflammatory activity of Thymus willdenowii
.
J Pharm Pharmacol.
2001;
53
1645-52
-
21
Ismaili H, Sosa S, Brkic D, Fkih-Tetouani S, Ilidrissi A, Touati D. et al .
Topical anti-inflammatory activity of extracts and compounds from Thymus broussonettii
.
J Pharm Pharmacol.
2002;
54
1137-40
-
22
Ismaili H, Milella L, Fkih-Tetouani S, Ilidrissi A, Camporese A, Sosa S. et al .
In vivo topical anti-inflammatory and in vitro antioxidant activities of two extracts of Thymus satureioides leaves.
J Ethnopharmacol.
2004;
91
31-6
-
23
Fan Y M, Xu L Z, Gao J, Wang Y, Tang X H, Zhao X N. et al .
Phytochemical and anti-inflammatory studies on Terminalia catappa
.
Fitoterapia.
2004;
75
253-60
-
24
Iwu M M, Anyanwu B N.
Anti-inflammatory and antiarthritic properties of Terminalia ivorensis
.
Fitoterapia.
1982;
53
25-34
-
25
Sosa S, Braca A, Altinier G, Della Loggia R, Morelli I, Tubaro A.
Topical anti-inflammatory activity of Bauhinia tarapotensis leaves.
Phytomedicine.
2002;
9
646-53
-
26
Hian-hua J, Liang Z, Geng L, Dong L, Liwei W, Junshan Y.
Studies on constituents of triterpene acids from Eriobotrya japonica and their anti-inflammatory and antitussive effects.
Zhongguo Yaoxue Zazhi.
2003;
38
752-7
-
27
Osakabe N, Hirohisa T, Chiaki S, Akiko Y, Rie Y, Ken-ichiro I. et al .
Anti-inflammatory and anti-allergic effect of rosmarinic acid (RA); inhibition of seasonal allergic rhinoconjunctivitis (SAR) and its mechanism.
Biofactors.
2004;
21
127-31
-
28
Liu J.
Pharmacology of oleanolic and ursolic acid.
J Ethnopharmacol.
1995;
49
57-68
-
29
Ringbom T, Segura L, Noreen Y, Perera P, Bohlin L.
Ursolic acid from Plantago major, a selective inhibitor of cyclooxygenase-2 catalysed prostaglandin biosynthesis.
J Nat Prod.
1998;
61
1212-5
-
30
Safayhi H, Sailer E R.
Anti-inflammatory actions of pentacyclic triterpenes.
Planta Med.
1997;
63
487-93
-
31
Suh N, Honda T, Finlay H J, Barchowsky A, Williams C, Benoit N E. et al .
Novel triterpenoids suppress inducible nitric oxide synthase (iNOS) and inducible cyclooxygenase (COX-2) in mouse macrophages.
Cancer Res.
1998;
58
717-23
-
32
Najid A, Simon A, Cook J, Chable-Rabinovitch H, Delage C, Chulia A J. et al .
Characterization of ursolic acid as a lipoxygenase and cyclooxygenase inhibitor using macrophages, platelets and differentiated HL60 leukemic cells.
FEBS Lett.
1992;
299
213-7
-
33
Ying Q L, Rienehart A R, Simon S R, Cheronis C.
Inhibition of human leukocyte elastase by ursolic acid.
Biochem J.
1991;
277
521-6
-
34
Mitaine-Offer A C, Hornebeck W, Sauvain M, Zeches-Hanrot M.
Triterpenes and phytosterols as human elastase inhibitors.
Planta Med.
2002;
68
930-2
-
35
Kapil A, Sharma S.
Effect of oleanolic acid on complement in adjuvant- and carrageenan-induced inflammation in rats.
J Pharm Pharmacol.
1995;
47
585-7
Prof. Nunziatina De Tommasi
Dipartimento di Scienze Farmaceutiche
Università di Salerno
Via Ponte Don Melillo, 1
84084 Fisciano, (SA)
Italy
Phone: +39-089-96-2647
Fax: +39-089-96-2828
Email: detommasi@unisa.it