Economic Botany

, Volume 44, Issue 2, pp 174–182 | Cite as

Sweetening agents of plant origin: Phenylpropanoid constituents of seven sweet-tasting plants

  • R. A. Hussain
  • L. J. Poveda
  • J. M. Pezzuto
  • D. D. Soejarto
  • A. D. Kinghorn


Field inquiries and organoleptic tests for sweet taste led to the procurement of samples ofPiper marginatum (dried leaves),Tagetes filicifolia (fresh whole plants),Osmorhiza longistylis (fresh roots),Foeniculum vulgare (fresh aerial parts),Myrrhis odorata (fresh whole plants),Ocimum basilicum (fresh aerial parts), andIllicium verum (dried fruits). Follow-up laboratory studies of the leaves ofPiper marginatum demonstrated that trans-anethole (a phenylpropanoid) was the major sweet constituent of this species. In the remaining six species, GC/MS analysis also enabled us to demonstrate that sweetness is attributable, in each case, to the presence of high concentrations of the phenylpropanoids, trans-anethole and estragole, either alone or in combination.


Economic Botany Stevioside Steviol Ocimum Basilicum Estragole 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Compuestos Edulcorantes de Origen Vegetal: Constituyentes Fenilpropanoides de Siete Plantas con Sabor Dulce


Entrevistas y busqueda en el campo seguidas por pruebas organolépticas para detectar el sabor dulce nos dirigieron a la adquisición de muestras dePiper marginatum (hojas secas),Tagetes filicifolia (plantas enteras secas), Osmorhiza longistylis (raices frescas),Foeniculum vulgare (partes aéreas frescas),Myrrhis odorata (plantas enteras frescas),Ocimum basilicum (partes aéreas frescas), eIllicium verum (frutas secas). Estudios de laboratorio posterioresde las hojas dePiper marginatum demostraron quetrans-anetol (un fenilpropanoide) fué el principio edulcorante mayor de esta especie. En las seis especies restantes, el análisis por medio de la cromatografía gaseosa y espectrometría de masa nos permitieron a demostrar que el sabor dulce se debe tambien, en cada caso, a la presencia de altas concentraciones de fenilpropanoides, a sabertrans-anetol y estragol, tanto sólo como en conjunto.


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Literature Cited

  1. Arctander, S. 1969. Perfume and flavor chemicals. Vol. 1. Published by the author, Montclair, NJ.Google Scholar
  2. Caldwell, J., and J. D. Sutton. 1988. Influence of dose size on the disposition oftrans-[-methoxy-14C]anethole in human volunteers. Food Chem. Toxicol. 26:87–91.PubMedCrossRefGoogle Scholar
  3. Carro de la Torre, P. C, and J. A. Retamar. 1973. Essential oils of Tucuman province. Essence ofTagetes minuta. Arch. Bioquim. 18:39–42. (Original not seen; abstract in Chem. Abstr. 83: 183286d. 1975.)Google Scholar
  4. Colombo, E., and P. Manitto. 1971. Huile essentielle d’anis badiane. Parfums Cosmet. Savons France 1:347–350.Google Scholar
  5. Compadre, C. M., R. A. Hussain, R. L. Lopez de Compadre, J. M. Pezzuto, and A. D. Kinghorn. 1987. The intensely sweet sesquiterpene, hernandulcin: isolation, synthesis, characterization, and preliminary safety evaluation. J. Agric. Food Chem. 35:273–279.CrossRefGoogle Scholar
  6. Drinkwater, N. R., E. C. Miller, J. A. Miller, and H. C. Pitot. 1976. Hepatocarcinogenicity of estragole (l-allyl-4-methoxybenzene) and l’-hydroxyestragole in the mouse and mutagenicity of l’-ace- toxyestragole in bacteria. J. Natl. Cancer Inst. 57:1323–1331.PubMedGoogle Scholar
  7. Fullas, F., J. Kim, C. M. Compadre, and A. D. Kinghorn. 1989. Separation of natural product sweetening agents using overpressured layer chromatography. J. Chromatogr. 464:213–219.PubMedCrossRefGoogle Scholar
  8. Furia, T. E., and N. Bellanca, ed. 1975. Fenaroli’s handbook of flavor ingredients. 2nd ed. Vol. 1, 2. CRC Press, Cleveland, OH.Google Scholar
  9. Guenther, E. 1950. The essential oils. Vol. 4. Van Nostrand, New York.Google Scholar
  10. Gupta, Y. N., and K. S. Bhandari. 1975. Essential oil from the leaves ofTagetes minuta. Indian Perfum. 19:29–32. (Original not seen; abstract in Chem. Abstr. 87:90579u. 1977.)Google Scholar
  11. Heller, S. R., and G. W. A. Milne. 1978. EPA/NIH mass spectral database. Vol. 2. U.S. Department of Commerce, Washington, DC.Google Scholar
  12. —, and — 1980. EPA/NIH mass spectral database, Suppl. 1. U.S. Department of Commerce, Washington, DC.Google Scholar
  13. Hussain, R. A., J. Kim, T.-W. Hu, J. M. Pezzuto, D. D. Soejarto, and A. D. Kinghorn. 1986. Isolation of a highly sweet constituent fromCinnamomum osmophloeum leaves. Pl. Med. 52:403–404.CrossRefGoogle Scholar
  14. —, A. D. Kinghorn, and D. D. Soejarto. 1988. Sweetening agents of plant origin: literature search for candidate sweet plants. Econ. Bot. 42:267–283.Google Scholar
  15. Inglett, G. E. 1982. Unusual sweeteners of plant origin. Herbarist 48:67–78.Google Scholar
  16. Kinghorn, A. D. 1983. Carcinogenic and cocarcinogenic toxins from plants. Pages 239–298in R. F. Keeler and A. T. Tu, eds., Handbook of natural toxins. Vol. 1. Plant toxins. Marcel Dekker, New York.Google Scholar
  17. —, and D. D. Soejarto. 1986. Sweetening agents of plant origin. CRC Crit. Rev. PL Sci. 4:76–120.Google Scholar
  18. Lawrence, B. M., R. H. Powell, T. W. Smith, and S. Kramer. 1986. Chemical composition ofTagetes oil. Perfum. Flavor. 10(6):56–58. (Original not seen; abstract in Chem. Abstr. 104:95246n. 1986.)Google Scholar
  19. Nanayakkara, N. P. D., R. A. Hussain, J. M. Pezzuto, D. D. Soejarto, and A. D. Kinghorn. 1988. An intensely sweet dihydroflavonol derivative based on a natural product lead compound. J. Med. Chem. 31:1250–1253.PubMedCrossRefGoogle Scholar
  20. Naves, Y.-R., P. Ardizio, and C. Favre. 1958. Étude sur les matières végétales volatiles, CL (I). Isolement et caractérization ducis-anéthole. Bull. Soc. Chim. France 1958:566–569.Google Scholar
  21. Pezzuto, J. M., C. M. Compadre, S. M. Swanson, N. P. D. Nanayakkara, and A. D. Kinghorn. 1985. Metabolically activated steviol, the aglycone of stevioside, is mutagenic. Proc. Natl. Acad. U.S.A. 82:2478–2482.CrossRefGoogle Scholar
  22. Poveda, L. J. 1986. Hoja de estrella. Lo maravilloso de nuestra flora medicamentosa. Biocenosis 2: 36–38.Google Scholar
  23. Ramos, L. S., M. L. da Silva, A. I. R. Luz, M. G. B. Zoghbi, and J. G. S. Maia. 1986. Essential oil ofPiper marginatum. J. Nat. Prod. 49:712–713.CrossRefGoogle Scholar
  24. Sawicka, W. 1969.Myrrhis odorata as a source of anethole. I. Essential oil content in various organs ofMyrrhis odorata. Acta Pol. Pharm. 26:565–568. (Original not seen; abstract in Chem. Abstr. 72:107780t. 1970.)PubMedGoogle Scholar
  25. Skaltsa, H., and A. Loukis. 1986. Analysis of the essential oil of Greek sweet basil. PL Med. 52 (Suppl.):50–51.Google Scholar
  26. Soejarto, D. D., C. M. Compadre, P. J. Medon, S. K. Kamath, and A. D. Kinghorn. 1983. Potential sweetening agents of plant origin. II. Field search for sweet tastingStevia species. Econ. Bot. 37:71–79.Google Scholar
  27. —, A. D. Kinghorn, and N. R. Farnsworth. 1982. Potential sweetening agents of plant origin. III. Organoleptic evaluation of leaf herbarium samples for sweetness. J. Nat. Prod. 45:590–599.PubMedCrossRefGoogle Scholar

Copyright information

© The New York Botanical Garden 1990

Authors and Affiliations

  • R. A. Hussain
    • 1
  • L. J. Poveda
    • 2
  • J. M. Pezzuto
    • 1
  • D. D. Soejarto
    • 1
  • A. D. Kinghorn
    • 1
  1. 1.Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of PharmacyUniversity of Illinois at ChicagoChicagoIL
  2. 2.Herbario, Museo NacionalSan José

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