Abstract
The effect on germination, shoot, and root growth by bergapten, xanthotoxin, imperatorin, xanthyletin, xanthoxyletin, luvangetin, donatin and alloxanthoxyletol fromPilocarpus goudotianus leaves, onLactuca sativa var. nigra seedlings has been evaluated. A structure-activity correlation is discussed based on the bioassay results. Furanocoumarins appear to be the most active compounds in comparison with pyrano- and simple coumarins. The presence of an oxygenated function at C-8 decreases the germination effect in furano- and pyranocoumarins, while C-5 substituents do not cause significant changes on the activity.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Agulló-Martínez, E., Estévez-Reyes, R., González, A.G., andRodríguez-Luis, F. 1967. Química de las Rutáceas VII. Cumarinas de las hojas de laRuta spec, no. 46782.An. Real Soc. Fis. Quim. 63(B):197–204.
Amaro-Luis, J.M., Massanet, G.M., Pando, E., Rodríguez-Luis, F., andZubía, E. 1990. New coumarins fromPilocarpus goudotianus.Planta Med. 56:304–306.
Arora, R.B., andMathur, C.N. 1963. Relation between structure and anticoagulant activity of coumarin derivatives.Br. J. Pharmacol. 20:29–35.
Baskin, J.M., Ludlow, C.J., Harris, T.M., andWolf, F.T. 1967. Psoralen, an inhibitor in the seeds ofPsoralea subacaulis (Leguminoseae).Phytochemistry 6:1209–1213.
Bennet, E.L., andBonner, J. 1953. Isolation of plant growth inhibitor fromThamnosa montana.Am. J. Bot. 40:29–33.
Bose, P.K. 1958. On some biochemical properties of natural coumarinsJ. Ind. Chem. Soc. 35:367–375.
Brown, S.A. 1981. Coumarins, pp. 269–300,in E.E. Conn. (eds.). The Biochemistry of Plants, A Comprehensive Treatise. Academic Press. New York.
Fischer, N.H. 1986. The function of mono and sesquiterpenes as plant germination and growth regulators, pp. 203–218,in A.R. Putnam and C.S. Tang (eds.). The Science of Allelopathy. John Wiley & Sons, New York.
Gawron, A., andGlowniak, K. 1987. Cytostatic activity of coumarins in vitro.Planta Med. 53:526–529.
González, A.G., Darias, V., Alonso, G., Boada, J.N., andRodríguez-Luis, F. 1977a. Cytostatic activity of some Canary Islands species of Rutaceae.Planta Med. 31:351–356.
González, A.G., Díaz, Chico, E., López Dorta, H., Luis, J.R., andRodríguez-Luis, F. 1977b. Nuevas fuentes de cumarinas naturales XXX. Componentes químicos de laRuta chalepensis L. y delDictamnus hispánicus Webb.An. Quím. 73:430–438.
González, A.G., López Dorta, H., Martín-Hierro, I., Medina, M.C., andRodriguez-Luis, F. 1982. Componentes de Umbelífera XXIII. Componentes deSeseli webbiicossom.An. Quim. 78(C):274–275.
Gosálvez, M., García-Canero, R., andBlanco, M. 1976. A screening for selective anticancer agents among plants respiratory inhibitors.Eur. J. Cancer 12:1003–1009.
Inderjit, andDakshini, K.M.M. 1991. Hespejridin 7-rutinoside (hesperidin) and taxifolin 3-arabinoside as germination and growth inhibitors in soils associated with the weedPluchea lanceolata (DC) C.B. Clarke (Asteraceae).J. Chem. Ecol. 17:1585–1591.
Jurd, L., King, A.D., JR., andMihara, K. 1971a. Antimicrobial properties of natural phenols III. Antimicrobial properties of umbelliferone derivatives.Phytochemistry 10:2965–2970.
Jurd, L., Corse, J., King, A.D., JR., Bayne, H., andMihara, K. 1971b. Antimicrobial properties of natural phenols IV. Antimicrobial properties of 6,7-dihydroxy-, 7,8-dihydroxy-, 6-hydroxy- and 8-hydroxycoumarins.Phytochemistry 10:2971–2974.
Kanne, D., Straub, K.M., Herast, J.E., andRapoport, H. 1982. Isolation and characterization of pyrimidine-psoralen-pyrimidine photodiadducts from DNA.J. Am. Chem. Soc. 104:6754–6764.
Kaufman, K.D., andKelly, R.C. 1965. New synthesis of coumarins.J. Heterocycl. Chem. 2:91–92.
Lassak, E.V., andPinhey, J.T. 1969. Constituents ofEriostemon trachyphyllus. Structure of trachyphyllin, a new coumarin.Aust. J. Chem. 22:2175–2185.
Leather, P.R., andEinhellig, F.A. 1986. Bioassays in the study of allelopathy, pp. 133–145,in A.R. Putnam and C.S. Tang (eds.). The Science of Allelopathy. John Wiley & Sons, New York.
Macías, F.A., Galindo, J.C.G., andMassanet, G.M. 1992. Potential allelopathic activity of several sesquiterpene lactone models.Phytochemistry 31:1969–1977.
Rodighiero, G. 1954. Influenza di furanocumarine naturali sulla germinazzione dei semi sullo sviluppo dei germogli e delle radici di lattuga.G. Biochim. 3:138–146.
Sethna, S., andPhadke, R. 1953. The Pechmann reactionOrg. React. 7:1–58.
Shimomura, H., Sashida, Y., andOhshima, Y. 1980. The chemical components ofArtemisia apiacea Hance. II. More coumarins from the flower heads.Chem. Pharm. Bull. 28:347–348.
Shimomura, H., Sashida, Y., Nakata, H., Kawasaki, J., andIto, Y. 1982. Plant growth regulators fromHeracleum lanatum.Phytochemistry 21:2213–2215.
Williams, P.D., andHoagland, R.E. 1982. The effect of natural occurring phenolic compounds on seed germination.Weed. Sci. 30:206–212.
Author information
Authors and Affiliations
Additional information
Part 2 in the series:Natural Product Models as Allelochemicals. For Part 1 see: Macíaset al. (1992).
Rights and permissions
About this article
Cite this article
Macías, F.A., Galindo, J.C.G., Massanet, G.M. et al. Allelochemicals fromPilocarpus goudotianus leaves. J Chem Ecol 19, 1371–1379 (1993). https://doi.org/10.1007/BF00984882
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00984882