Abstract
Twelve known diterpenes 1 - 11 and 13 , and three known sesquiterpenes 14 - 16 , along with a new C20 - C15 terpenoid 17 , with a structure based on an unprecedented skeleton in which a labdane diterpene
is linked to a monocyclic sesquiterpene by an ester bridge, were isolated from the
oleoresin of the Peruvian medicinal plant Copaifera paupera (Herzog) Dwyer (Leguminosae). Their structures were elucidated on the basis of spectral
analysis, including homo- and heteronuclear correlation NMR experiments (COSY, ROESY,
HMQC and HMBC), and by comparison with data in the literature. The leishmanicidal,
antimicrobial, cytotoxic, and aldose reductase inhibitory activities were studied.
Compounds 1 and 11 showed significant antimicrobial activity (MIC < 10 μg/ml) against Gram-positive
bacteria, comparable with cephotaxime used as control. Compound 2 exhibited moderate cytotoxic activity against four cancer cell lines.
Key words
Copaifera paupera
- Leguminosae - Copaiba oil - terpenoids - leishmanicidal - antimicrobial - cytotoxic
- aldose reductase inhibitory activities
References
1
Ohsaki A, Yan L T, Ito S, Edatsugi H, Iwata D, Komoda Y.
The isolation and in vivo potent antitumor activity of clerodane diterpenoid from the oleoresin of Brazilian
medicinal plant Copaifera langsdorfii Desfon.
Bioorg Med Chem Lett.
1994;
4
2889-92
2
Cascon V, Gilbert B.
Characterization of the chemical composition of oleoresins of Copaifera guianensis Desf., Copaifera duckei Dwyer and Copaifera multijuga Hayne.
Phytochemistry.
2000;
5
773-8
3
Monti H, Tiliacos N, Faure R.
Two diterpenoids from copaiba oil.
Phytochemistry.
1996;
42
1653-6
4 Lacase D, Alexiades M. Plantas medicinales y salud indígena en la cuenca del río
Madre de Dios, Perú. Lacaze D, Alexiades M, editors
CBC y FENAMAD . Cusco, Perú; 1995: 111-3
5
Richomme P, Godet M C, Foussard F, Toupet L, Sévenet T, Bruneton J.
A novel leishmanicidal labdane from Polyalthia macropoda
.
Planta Med.
1991;
57
552-4
6
Caputo R, Mangoni L.
Diterpenes from Araucaria bidwilli
.
Phytochemistry.
1974;
13
467-70
7
Gopinath K W, Govindachari T, Parthasarathy P C, Viswanathan N.
Structure and stereochemistry of polyalthic acid, a new diterpene acid.
Helv Chim Acta.
1961;
44
1040-9
8
Zdero C, Bohlmann F, King R M.
Guaianolides and labdanes from Brickellia Species.
Phytochemistry.
1991;
30
1591-5
9
Braun S, Breitenbach H.
Strukturaufklärung einer neuen Diterpensäure aus Metasequoia glyptostroboides mit Hilfe der 13 C-NMR-Spektroskopie.
Tetrahedron.
1977;
33
145-50
10
Sehenk H R, Gutmann H, Jeger O, Ruzicka L.
Zur Kenntnis der Diterpene.
Helv Chim Acta.
1952;
35
817-24
11
Bohlmann F, Ziesche J, King R M, Robinson H.
Eudesmanolides and diterpenes from Wedelia trilobata and a ent -kaurenic acid derivative from Aspilia parvifolia
.
Phytochemistry.
1981;
20
751-6
12
Ferrari M, Pagnoni U M, Pelizzoni F, Lukes V, Ferrari G.
Terpenoids from Copaifera langsdorfii
.
Phytochemistry.
1971;
10
905-7
13
Miyazawa M, Kameoka H.
Helianthol A, a sesquiterpene alcohol from Helianthus tuberosus
.
Phytochemistry.
1983;
22
1040-2
14
Hugel G, Oehlschlager A C, Ourisson G.
The structure and stereochemistry of diterpenes from Trachylobium verrucosum Oliv.-V.
Tetrahedron.
1967;
Suppl 8
203-16
15
Braga W F, Rezende C M, Antunes O AC, Pinto A C.
Terpenoids from Copaiba cearensis
.
Phytochemistry.
1998;
49
263-4
16
Kinoshita J H, Fukushi S, Kador P, Merola L.
Aldose reductase in diabetic complications of the eye.
Metabolism.
1979;
28
462-9
17 Evans D. Handbook on Isolation Characterization and Cryopreservation of Leishmania. In:
Special Programme for Research and Training in Tropical Diseases UNDP/WORLD BANK/WHO
1989: 1-45
18
Chraïbi D I, Giron S, Michel G.
Evaluation of the activity of four antimicrobial agents using an in vitro rapid micromethod against oral Streptococci and various bacterial strains implicated in periodontitis.
J Periodont Res.
1990;
25
201-6
19
Bergeron R J, Cavanaugh P F, Kline S J, Hughes R G, Elliot G T, Porter C W.
Antineoplastic and antiherpetic activity of spermidine catecholamide iron chelators.
Biochem Biophys Res Comm.
1984;
121
848-54
20
Nishimure C, Yamaoka T, Mizutani M, Yamashita K, Akera T, Tanimoto T.
Purification and characterization of the recombinant human aldose reductase expressed
in Baculovirus system.
Biochem Biophys Acta.
1991;
1078
171-8
21
Beyer-Mears A, Diecke F PJ, Mistry K, Cruz E.
Comparison of the effects of zopolrestat and sorbinil on lens myo -inositol influx.
Pharmacology.
1997;
54
76-83
1
† Deceased
Isabel López Bazzocchi
Instituto Universitario de Bio-Orgánica ”Antonio González”
Universidad de La Laguna
Avenida Astrofísico Fco Sánchez 2
La Laguna
38206 Tenerife
Spain
Email: ilopez@ull.es
Fax: +34-922-318571
Phone: +34-922-318576