Bioactive steroids and triterpenes from Melilotus messanensis and their allelopathic potential

Journal of Chemical Ecology

Volumn 23, Issue 7, 1997, Pages 1781-1803

  Macías, Francisco A ^a   Simonet, Ana M ^a   Galindo, Juan C G ^a  

^a UNIVERSITY OF CÁDIZ   (Spain)

Author keywords

Allelopathy; Allium cepa; Ergosterol peroxide; Gammacer 16 en 3 one; Hordeum vulgare; Lactuca sativa; Lupane triterpenes; Lycopersicon esculentum; Melilotus messanensis; Messagenic acids; Messagenolide; Oleanane triterpenes; Soyasapogenol G; Steroids; Stigmasterols

Indexed keywords

ALLIUM CEPA; DICOTYLEDONEAE; HORDEUM; HORDEUM VULGARE; HORDEUM VULGARE SUBSP. VULGARE; LACTUCA; LACTUCA SATIVA; LILIOPSIDA; LYCOPERSICON ESCULENTUM; MELILOTUS; MELILOTUS MESSANENSIS; MELILOTUS OFFICINALIS; TRIFOLIUM;

EID: 0030803467     PISSN: 00980331     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:JOEC.0000006451.19649.a0     Document Type: Article

References (36)

1. APLIN, R. T., HALSALL, T. G., and NORIN, T. 1963. The chemistry of triterpenes and related compounds (XLIII). The constituents of the bark of Platanus hybrida and the structure of platanic acid. J. Chem. Soc. 85:3269-3273.
2. 1H NMR spectra of soyasapogenol. J. Nat. Prod. 53:298-302.
3. BRADOW, J. M. 1985. Germination regulation by Amaranthus palmeri and Ambrosia artemisiifolia, pp. 285-300, in A. C. Thompson (ed.). The Chemistry of Allelopathy, Vol 268, ACS Symposium Series. American Chemical Society, Washington, DC.
4. BUDZIKIEWICZ, H., WILSON, J. M., and DJERASSI, C. 1963. Mass spectrometry in structural and stereochemical problems. XXXII. Pentacyclic triterpenes. J. Am. Chem. Soc. 85:3688-3699.
5. CASTELLANO, D. 1997. In search of a standard laboratory allelopathic bioassay. MS dissertation. University of Cádiz, Puerto Real, Cádiz, Spain.
6. DELLA GRECA, M., MONACO, P., and PREVITERA, L. 1990a. Stigmasterols from Typha latifolia. J. Nat. Prod. 53:1430-1435.
7. DELLA GRECA, M., MANGONI, L., MOLINARO, A., MONACO, P., and PREVITERA, L. 1990b. (20S)-4α-methylenecholest-7-en-3β-ol, an allelopathic sterol from Typha latifolia. Phytochemistry 29:1797-1798.
8. DURRANI, A. A., and IKRAM, M. 1966. Melilotus indica. Pak. J. Sci. Ind. Res. 9:173-174.
9. EINHELLIG, F. A. 1986. Mechanisms and modes of action of allelochemicals, pp. 171-188, in A. R. Putnam and C.-S. Tang (eds.). The Science of Allelopathy. John Wiley & Sons, New York.
10. EINHELLIG, F. A. 1987. Interactions among allelochemicals and other stress factors of the plant environment, pp. 343-357, in G. R. Waller (ed.). Allelochemicals: Role in Agriculture and Forestry, Vol 330, ACS Symposium Series. American Chemical Society, Washington D.C.
11. FIJIOKA, T., KASHIWADA, Y., KILKUSKIE, R. E., COSENTINO, L. M., BALLAS, L. M., JIANG, J. B., JAUZEN, W. P., CHEN, I., and LEE, K. 1994. Anti-AIDS agents, 11. Betulinic acid and platanic acid as anti-HIV principles from Syzigium claviflorum, and the anti-HIV activity of structurally related triterpenoids. J. Nat. Prod. 57:243-247.
12. GONZÁLEZ, A. G., JIMÉNEZ, I. A., and RAVELO, A. G. 1992. Triterpenes from Maytenus canariensis and synthesis of a derivative from betulin. Phytochemistry 31:2069-2072.
13. GUERRIERO, A., D'AMBROSIO, M., and PIETRA, F. 1993. Pteridines, sterols, and indole derivatives from the lithistid sponge Corallistes undulatos of the coral sea. J. Nat. Prod. 56:1962-1970.
14. GUNATILAKA, A. A. L., GOPICHAND, Y., SCHMITZ, F. J., and DJERASSI, C. 1981. Minor and trace sterols in marine invertebrates. 26. Isolation and structure elucidation of nine new 5α,8α-epidioxy sterols from four marine organisms. J. Org. Chem. 46:3860-3866.
15. HUI, W., and LI, M. 1977. Further triterpenoids from the stems of Lithocarpus polystachya. Phytochemistry 16:111-112.
16. KANG, S. S., LIM, C. H., LEE, S. Y., and SOOK, Y. 1987. Soyasapogenols B and E from Melilotus officinalis. Arch. Pharmacol. Res. 10:9-13.
17. KASHIWADA, Y., ZHANG, D., CHEN, Y., CHENG, C., CHEN, H., CHANG, H., CHANG, J., and LEE, K. 1993. Antitumor agents, 145. Cytotoxic asprellic acids A and C and asprellic acid B, new p-cumaroyl triterpenes, from Ilex asprella. J. Nat. Prod. 56:2077-2082.
18. KHAFAGY, S. M., SABRI, N. N., and ABOU DONIA, A. H. 1980. Pharmacognostical study of Melilotus indicus (L.) All var. Tommasinii Jord. Egypt J. Pharm. Sci. 19:293-300.
19. MACÍAS, F. A., GALINDO, J. C. G., MASSANET, G. M., RODRÍGUEZ-LUÍS, F., and ZUBÍA, E. 1993. Allelochemicals from Pilocarpus goudotianus leaves. J. Chem. Ecol. 19:1371-1379.
20. MACÍAS, F. A., SIMONET, A. M., and ESTEBAN, M. D. 1994. Potential allelopathic lupane triterpenes from bioactive fractions of Melilotus messanensis. Phytochemistry 36:1369-1379.
21. MACÍAS, F. A., SIMONET, A. M., ESTEBAN, M. D., and GALINDO, J. C. G. 1996. Triterpenoids from Melilotus messanensis L; Soyasapogenol G, the first natural carbonate derivative. Phytochemistry 41:1573-1577.
22. MANDAVA, N. B., SASSE, J. M., and YOPP, J. H. 1981. Brassinolide, a growth-promoting steroidal lactone. II. Activity in selected gibberellin and cytokinin bioassays. Physiol. Plant. 53:453-61.
23. MAUGH, T. H., II. 1981. New chemicals promise larger crops. Science 212:33-34.
24. OLESZEK, W. 1993. Allelopathic potentials of alfalfa (Medicago sativa) saponins: Their relation to antifungal and hemolytic activities. J. Chem. Ecol. 19:1063-1074.
25. PATHAK, N. K. R., NEOGI, P., BISWAS, M., TRIPATHI, Y. C., and PAUDEY, V. B. 1988. Betulin-aldehyde, an anti-tumor agent from the bark of Tectona grandis. Indian J. Pharm. Sci. 50:124-125.
26. RASULOV, F. A., and BELYI, M. B. 1985. Chemical study of Melilotus caspius and Achillea vermicularis. Izv. Akad. Nauk Az. SSR, Ser. Biol. Nauk 2:22-24.
27. SIDDIQUI, S., SIDDIQUI, B. S., NAEED, A., and BEGUM, S. 1992. Pentacyclic triterpenoids from the leaves of Plumeria obtusa. Phytochemistry 31:4279-4283.
28. TCHIVOUNDA, H., KOUDOGBO, P., BESACE, Y., and CASADEVALL, E. 1990. Cylicosidic acid, a dihydroxy pentacyclic triterpene carboxylic acid from Cylicodiscus gabunensis. Phytochemistry 29:3255-3258.
29. TSICHRITZIS, F., and JAKUPOVIC, J. 1990. Diterpenes and other constituents from Relhania species, Phytochemistry 29:3173-3187.
30. VYSTRCIL, A., POUZAR, V., and KŘEČEK, V. 1973. Triterpenes. XXXII. Absolute configuration at C(20) in 29-substituted lupane derivatives. Coll. Czech. Chem. Commun. 38:3902-3911.
31. WALLER, G. R., JURZYSTA, M., and THORNE, R. L. Z. 1993. Allelopathic activity of root saponins from alfalfa (Medicago sativa L.) on weeds and wheat. Bot. Bull Acad. Sin. 34:1-11.
32. WANG, H. and FUJIMOTO, Y. 1993. Triterpene esters from Eucalyptus fereticornis. Phytochemistry 33:151-153.
33. WEIDENHAMER, J. D., MACÍAS, F. A., FISCHER, N. H., and WILLIAMSON, G. B. 1990. Just how insoluble are monoterpenes? J. Chem. Ecol. 19:1799-1807.
34. WENKERT, E., BADDELEY, G. V., BURFITT, I. R., and MORENO, L. N. 1978. Carbon-13 nuclear magnetic resonance spectroscopy of naturally-occurring substances. LVII. Triterpenes related to lupane and hopane. Org. Mag. Res. 11:337-343.
35. WYMAN-SIMPSON, C. L., WALLER, G. R., JURZYSTA, M., MCPHERSON, J. D., and YOUNG, C. C. 1991. Biological activity and chemical isolation of root saponins of six cultivars of alfalfa (Medicago sativa L.). Plant Soil 135:83-94.
36. YOPP, J. H., MANDAVA, N. B., and SASSE, J. M. 1981. Brasinolide, a growth-promoting steroidal lactone. I. Activity in selected auxin bioassays. Physiol. Plant. 53:445-452.