Abstract
Two new xanthones, caledonixanthone M 1 and caloxanthone L 2 , and one new acid, caledonic acid 6 were isolated from the hexane-soluble extract of the stem bark of Calophyllum caledonicum . In the course of this phytochemical study, seven other known compounds - calothwaitesixanthone, calozeyloxanthone, allanxanthone, isoapetalic acid 3 , calolongic acid 4, apetalic acid 5 and isocalolongic acid 7 - were isolated. Their antifungal activity against the growth of the human pathogenic fungus Aspergillus fumigatus was then investigated. The results indicated that the crude extract, calolongic acid 4 and isocalolongic acid 7 exhibited strong inhibitory effects with MIC80 values of 8, 4, 2 μg/mL, respectively. Besides, calolongic acid 4 , its lactone derivative 4a and isocalolongic acid 7 markedly reduced the respiration of pea seed mitochondria.
Key words
Xanthones - chroman-4-one acids -
Calophyllum caledonicum
- Guttiferae - antifungal activity - mitochondrial respiration
References
1
Morel C, Séraphin D, Oger J M, Litaudon M, Sévenet T, Richomme P, Bruneton J.
New xanthones from Calophyllum caledonicum
.
J Nat Prod.
2000;
63
1471-4
2
Morel C, Séraphin D, Teyrouz A, Larcher G, Bouchara J P, Litaudon M. et al .
New and antifungal xanthones from Calophyllum caledonicum
.
Planta Med.
2001;
68
41-4
3
Morel C, Hay A E, Litaudon M, Sévenet T, Séraphin D, Bruneton J. et al .
Thirteen new xanthone derivatives from Calophyllum caledonicum (Clusiaceae).
Molecules.
2002;
7
38-50
4
Ernster L, Dallner G, Azzone G F.
Differential effects of rotenone and amytal on mitochondrial electron and energy transfer.
J Biol Chem.
1963;
238
1124-31
5
Ranjith H, Dharmaratne W, Sotheeswaran S, Balasubramaniam S, Reisch J.
Xanthones from roots of three Calophyllum species.
Phytochemistry.
1986;
25
1957-9
6
Gunasekara S P, Soteeswaran S, Sultanbawa M US.
Two new xanthones, calozeyloxanthone and zeyloxanthone from Calophyllum zeylanicum
.
J Chem Soc Perkin Trans.
1981;
1
1831-5
7
Nkengfack A E, Azebaze G A, Vardamides J C, Fomum Z T, Van Heerden F R.
A prenylated xanthone from Allanblackia floribunda
.
Phytochemistry.
2002;
60
381-4
8
Guerreiro E, Kunesch B and Polosky J.
Les constituants des graines de Calophyllum chapelieri (Guttiferae).
Phytochemistry.
1971;
10
2139-45
9
Breck G D.
The bark resins of some Calophyllum species.
Dissertation Abstract International.
1971;
31
3909-B
10
Govindachari T R, Prakash D, Viswanathan N.
Structure of apetalic acid.
Tetrahedron.
1968;
24
6411-5
11
Guerreiro E, Kunesch G, Polonsky J.
Chromanones de l’écorce de Calophyllum recedens
.
Phytochemistry.
1973;
12
185-9
12 National Committee for Clinical Laboratory S tandards. Reference method for broth dilution antifungal susceptibility testing of yeasts. Approved Standard M27-A. National Committee for Clinical Laboratory Standards Villanova, Pa; 1997
13
Benamar A, Tallon C, Macherel D.
Membrane integrity and oxidative properties of mitochondria isolated from imbibing pea seeds after priming or accelerated ageing.
Seed Sci Res.
2003;
13
35-45
14 Hostettmann K, Hostettmann M. Plant phenolics, 14. Xanthones, ultra-violet spectroscopy. In: Dey PM, Harborne JB, editors Methods in Plant Biochemistry . Vol. 1 London; Academic Press 1989: 502-3
15
Iinuma M, Tosa H, Toriyama N, Tanaka T, Ito T, Chelladurai V.
Six xanthones from Calophyllum austroindicum
.
Phytochemistry.
1996;
43
681-685
16
Ishikawa T.
Anti HIV-1 active Calophyllum coumarins: distribution, chemistry, and activity.
Heterocycles.
2000;
53
453-74
17
Ojala T, Remes S, Haansu P, Vuorela H, Hiltunen R, Haahtela K, Vuorela P.
Antimicrobial activity of some coumarin containing herbal plants growing in Finland.
J Ethnopharmacol.
2000;
73
299-305
18
Sadari S, Mori Y, Horita K, Micetich R G, Nishibe S, Daneshtalab M.
Synthesis and antifungal activity of coumarins and angular furanocoumarins.
Bioorg Med Chem.
1999;
7
1933-40
19
Latgé J P.
Aspergillus fumigatus and aspergillosis.
Clin Microbiol Rev.
1999;
12
310-50
20
Esposti M D.
Inhibitors of NADH-ubiquinone reductase: an overview.
Biochim Biophys Acta.
1998;
1364
222-35
21
Fontana A, Cimino G, Gavagnin M, Gonzales M C, Estornell E.
Novel inhibitors of mitochondrial respiratory chain: endoperoxides from the marine tunicate Stonolica socialis
.
J Med Chem.
2001;
44
2362-5
Prof. Dr. Pascal Richomme
Laboratoire de pharmacognosie
UFR Sciences pharmaceutiques
16 Bd Daviers
49100 Angers
France
Fax: +33-2-41-48-67-33
Email: pascal.richomme@univ-angers.fr