JBNB  Vol.4 No.3 A , June 2013
The Phenols of the Genus Agave (Agavaceae)
ABSTRACT

A review is presented about the studies that have been carried out on the phenolic composition of the species of the genus Agave in order to show which species of the genus has been analyzed, what is the potential of the species of Agave as source of phenolics with important biological activities, and what is the significance of the phenolic profiles as chemotaxonomic markers in the genus. The results of the analysis of a dozen of Agave species reveal an important richness of phenolic compounds, including flavonoids, homoisoflavonoids, and phenolic acids, and a broad diversity of biological activities associated to those compounds, as antioxidant, antibacterial, antifungal, antinematod, and immunomodulatory capabilities. The phenols of Agave also have a major potential as specific chemotaxonomic markers.


Cite this paper
N. Almaraz-Abarca, E. Delgado-Alvarado, J. Ávila-Reyes, J. Uribe-Soto and L. González-Valdez, "The Phenols of the Genus Agave (Agavaceae)," Journal of Biomaterials and Nanobiotechnology, Vol. 4 No. 3, 2013, pp. 9-16. doi: 10.4236/jbnb.2013.43A002.
References
[1]   A. P. Da Cunha and O. R. Roque, “A Farmacognosia nos Estudios Farmacéuticos,” In: A. P. Da Cunha, Ed., Farmacognosia e Fitoquímica, Fundação Calouste Gulbenkain, Lisboa, 2005, pp. 3-15.

[2]   J. C. M. Barreira, I. C. F. R. Ferreira, M. B. P. P. Oliveira and J. A. Pereira, “Antioxidant Activities of the Extracts from Chesnut Flower, Leaf Skins and Fruit,” Food Chemistry, Vol. 107, No. 3, 2008, pp. 1106-1113. doi:10.1016/j.foodchem.2007.09.030

[3]   A. Champagne, G. Hilbert, L. Legendre and V. Lebot, “Diversity of Anthocyanins and Other Phenolic Compounds Among Tropical Root Crops from Vanuatu, South Pacific,” Journal of Food Composition and Analysis, Vol. 24, No. 3, 2011, pp. 315-325. doi:10.1016/j.jfca.2010.12.004

[4]   Z. Tai, L. Cai, L. Dai, L. Dong, M. Wang, Y. Yang, Q. Cao and Z. Ding, “Antioxidant Activity and Chemical Constituents of Edible Flower of Sophora viccifolia,” Food Chemistry, Vol. 126, No. 4, 2011, pp. 1648-1654. doi:10.1016/j.foodchem.2010.12.048

[5]   M. Jai, “C-Glycosylflavonoids,” In: J. B. Harborne, Ed., The Flavonoids Advances in Research Since 1986, Chapman & Hall, London, 1994, pp. 57-93.

[6]   M. B. Botura, J. D. G. dos Santos, G. D. da Silva, H. G. de Lima, J. V. A. de Oliveira, M. A. O. de Almeida, M. J. M. Atatinha and A. Blanco, “In Vitro Ovicidal and Larvacidal Activity of Agave sisalana Perr (sisal) on Gastrointestinal Nematodes of Goats,” Veterinary Parasitology, Vol. 192, No. 1-3, 2013, pp. 211-217. doi:10.1016/j.vetpar.2012.10.012

[7]   P. Y. Chen, Y. C. Kuo, C. H. Chen, Y. H. Kuo and C. K. Lee, “Isolation and Immunomodulatory Effect of Homoisoflavones and Flavones from Agave sisalana Perrine ex Engelm,” Molecules, Vol. 14, No. 5, 2009, pp. 17891795. doi:10.3390/molecules14051789

[8]   M. M. Win, A. Abdul-Hamid, B. S. Baharin, F. Anwar, M. C. Sabu and M. S. Pak-Dek, “Phenolic Compounds and Antioxidant Activity of Peanut’s Skin, Hull, Raw Kernel and Roated Kernel Flour,” Pakistan Journal of Botany, Vol. 43, No. 3, 2011, pp. 1635-1642.

[9]   E. Jr. Middleton and C. Kandaswami, “The Impact of Plant Flavonoids on Mammalian Biology: Implications for Immunity, Inflammation, and Cancer,” In: J. B. Harborne, Ed., The Flavonoids. Advances in Research Since 1986, Chapman & Hall, London, 1994, pp. 619-652.

[10]   V. S. Good-Ávila, V. Souza, S. B. Gaut and E. L. Eguiarte, “Timing and Rate of Speciation in Agave (Agavaceae),” Proceedings of the National Academy of Science USA, Vol. 103, No. 24, 2006, pp. 9124-9129. doi:10.1073/pnas.0603312103

[11]   M. Rocha, S. V. Good-Ávila, F. Molina-Freaner, H. T. Arita, A. Castillo, A. García-Mendoza, A. Silva-Montellano, B. S. Gaut, V. Souza and L. E. Eguiarte, “Pollination Biology and Adaptive Radiation of Agavaceae, with Special Emphasis on the Genus Agave,” Aliso, Vol. 22, 2006, pp. 329-344.

[12]   H. S. Gentry, “Agaves of Continental North America,” The University of Arizona Press, Tucson, 1982.

[13]   P. E. Zwane, M. T. Masarirambi, N. T. Nagagula, A. M. Dlamini and E. Bhebhe, “Exploitation of Agave americana L. Plant for Food Security in Swaziland,” American Journal of Food and Nutrition, Vol. 1, No. 2, 2011, pp. 82-88. doi:10.5251/abjna.2011.1.2.82.88

[14]   A. García-Mendoza, “Riqueza y Endemismos de la Familia Agavacea en México,” In: E. Linares, P. Dávila, F. Chiang, R. Bye and T. Elias, Eds., Conservación de Plantas en Peligro de Extinción: Diferentes Enfoques, UNAM, México, D. F., 1995, pp. 51-75.

[15]   M. González-Elizondo, R. Galván-Villanueva, I. L. LópezEnríquez, L. Reséndiz-Rojas and M. S. González-Elizondo, “Agaves. Magueyes, Lechuguillas y Noas del Estado de Durango y sus Alrededores,” IPN-CONABIO-COCYTED, México, 2009.

[16]   A. Sotelo, S. López-García and F. Basurto-Peña, “Content of Nutrient and Antinutrient in Edible Flowers of Wild Plants in Mexico,” Plant Foods for Human Nutrition, Vol. 62, No. 3, 2007, pp. 133-138. doi:10.1007/s11130-007-0053-9

[17]   N. A. Mancilla-Margalli and M. G. López, “Water-Soluble Carbohydates and Fructan Structure Patterns from Agave and Dasylirion Species,” Journal of Agricultural and Food Chemistry, Vol. 54, No. 20, 2006, pp. 78327839. doi:10.1021/jf060354v

[18]   C. Michel-Cuello, B. I. Juárez-Flores, J. R. AguirreRivera and J. M. Pinos-Rodríguez, “Quantitative Characterization of Nonstructural Carbohydrates of Mezcal Agave (Agave salmiana Otto ex Salm-Dick),” Journal of Agricultural and Food Chemistry, Vol. 56, No. 14, 2008, pp. 5753-5757. doi:10.1021/jf800158p

[19]   L. Madrigal and E. Sangronis, “La Inulina y Derivados como Ingredientes Claves en Alimentos Funcionales,” Archivos Latinoamericanos de Nutrición, Vol. 57, No. 4, 2007, pp. 387-396.

[20]   J. A. ávila-Reyes, N. Almaraz-Abarca, E. A. DelgadoAlvarado, L. S. González-Valdez, G. Valencia-del Toro and E. Durán-Páramo, “Phenol Profile and Antioxidant Capacity of Mescal Aged in Oak Wood Barrels,” Food Research International, Vol. 43, No. 1, 2010, pp. 296300. doi:10.1016/j.foodres.2009.10.002

[21]   L. Santos-Zea, A. M. Leal-Diaz, E. Cortes-Ceballos and A. J. Gutiérrez-Uribe, “Agave (Agave spp.) and Its Traditional Products as a Source of Bioactive Compounds,” Current Bioactive Compounds, Vol. 8, No. 3, 2012, pp. 218-231. doi:10.2174/157340712802762410

[22]   M. A. Morales, “Steroidal Sapogenins from Agave cocui,” Phytochemistry, Vol. 11, No. 3, 1972, pp. 11911192. doi:10.1016/S0031-9422(00)88496-4

[23]   V. A. Bodeiko and P. K. Kintya, “Steroid Saponins. VIII. The Structure of Agave Saponins C’ and D from the Leaves of Agave Americana,” Chemistry of Natural Compounds, Vol. 11, No. 6, 1975, pp. 775-777. doi:10.1007/BF00568468

[24]   B. Wilkomirski, V. A. Bobeyko and P. K. Kintia, “New Steroidal Saponins of Agave Americana,” Phytochemistry, Vol. 14, No. 12, 1975, pp. 2657-2659. doi:10.1016/0031-9422(75)85245-9

[25]   G. Blunden, Y. Yi and K. Jewer, “Steroidal Sapogenins from Leaves of Agaveae Species,” Phytochemistry, Vol. 17, No. 11, 1978, pp. 1923-1925. doi:10.1016/S0031-9422(00)88734-8

[26]   G. Pant, O. P. Sati, K. Miyahara and T. Kawasaki, “Search for Molluscicidal Agents Saponins from Agave cantala Leaves,” Pharmaceutical Biology, Vol. 25, No. 1, 1987, pp. 35-38. doi:10.3109/13880208709060908

[27]   G. C. Uniyal, P. K. Agrawal, O. P. Sati and R. S. Thaker, “Agaveside C, a Steroidal Glycoside from Agave cantala,” Phytochemistry Vol. 30, No. 4, 1991, pp. 13361339. doi:10.1016/S0031-9422(00)95232-4

[28]   W. F. Tinto, J. L. Simmons-Boyce, S. McLean and W. F. Reynolds, “Constituents of Agave americana and Agave barbadensis,” Fitoterapia, Vol. 76, No. 6, 2005, pp. 594597. doi:10.1016/j.fitote.2005.04.013

[29]   G. J. Orestes, A. Meneses, A. M. Simonet, F. A. Macías, C. Nogueiras, A. Gomez and J. A. Escario, “Saponinas Esteroidales de la Planta Agave brittoniana (Agavaceae) con Actividad Contra el Parásito Trichomona vaginalis”. Revista de Biología Tropical, Vol. 56, No. 4, 2008, pp. 1645-1652.

[30]   A. Yokosuka, M. Jitsuno, S. Yui, M. Yamazadi and Y. Mimaki, “Steroidal Glycosides from Agave utahensis and their Cytotoxic Activity,” Journal of Natural Products, Vol. 72, No. 8, 2009, pp. 1399-1404. doi:10.1021/np900168d

[31]   J. Eskander, C. Lavaud and D. Harakat, “Steroidal Saponins from the Leaves of Agave macroacantha,” Fitoterapia, Vol. 81, No. 5, 2010, pp. 371-374. doi:10.1016/j.fitote.2009.11.002

[32]   M. Debnath, M. Pandey, R. Sharma, G. S. Thakur and P. Lal, “Biotechnological Intervention of Agave sisalana: A Unique Fiber Yielding Plant with Medicinal Property,” Journal of Medicinal Plants Research, Vol. 4, No. 3, 2010, pp. 177-187.

[33]   X. Mouren, P. Caillard and F. Schwartz, “Study of the Antiischemic Action of EGb 761 in the Treatment of Peripheral Artherial Occlusive Disease by TcPo2 Determination,” Angiology, Vol. 45, No. 6, 1994, pp. 413-417. doi:10.1177/000331979404500601

[34]   Q. Zhang and H. Cui, “Simultaneus Determination of Quercetin, Kaempferol, and Isorrhamnetin in Phytopharmaceuticals of Hippophae rhamnoides L. by High-Performance Liquid Chromatography with Chemiluminescence Detection,” Journal of Separation Science, Vol. 28, No. 11, 2005, pp. 1171-1178. doi:10.1002/jssc.200500055

[35]   S. S. Subramanian and A. G. R. Nair, “Chlorogenein and Kaempferol Glycosides from the Flowers of Agave amaricana,” Phytochemistry, Vol. 9, No. 12, 1970, p. 2582. doi:10.1016/S0031-9422(00)85782-9

[36]   N. Almaraz-Abarca, E. A. Delgado-Alvarado, V. Hernández-Vargas, M. Ortega-Chávez, G. Orea-Lara, A. Cifuentes-Díaz de León, J. A. ávila-Reyes and R. MuñizMartínez, “Profiling of Phenolic Compounds of Somatic and Reproductive Tissues of Agave durangensis Gentry (Agavaceae),” American Journal of Applied Sciences, Vol. 6, No. 6, 2009, pp. 1076-1085. doi:10.3844/ajassp.2009.1076.1085

[37]   J. A. Morales-Serna, A. Jiménez, R. Estrada-Reyes, C. Márquez, J. Cárdenas and M. Salmón, “Homoisoflavanones from Agave tequilana Weber,” Molecules, Vol. 15, No. 5, 2010, pp. 3295-3301. doi:10.3390/molecules15053295

[38]   N. Almaraz-Abarca, M. S. González-Elizondo, M. G. Campos, Z. E. ávila-Sevilla, E. A. Delgado-Alvarado and J. A. ávila-Reyes, “Variability of the Foliar Phenol Profiles of the Agave victoriae-reginae Complex (Agavaceae),” Botanical Science, 2013, in press.

[39]   V. S. Parmar, H. N. Jha, A. K. Gupta and A. K. Prasad, “Agamanona, a Flavanona from Agave Americana,” Phytochemistry, Vol. 31, No. 7, 1992, pp. 2567-2568. doi:10.1016/0031-9422(92)83333-T

[40]   S. Nasri and H. B. Salem, “Effect of Oral Administration of Agave americana or Quillaja saponaria Extracts on Digestion and Growth of Barbarine Female Lamb,” Livestock Sciences, Vol. 147, No. 1-3, 2012, pp. 59-65. doi:10.1016/j.livsci.2012.04.001

[41]   A. M. B. Hamissa, M. Seffen, B. Aliakbarian, A. A. Casazza, P. Perego and A. Converti, “Phenolics Extraction from Agave americana (L.) Leaves Using High-Temperature, High-Pressure Reactor,” Food and Bioproducts Processing, Vol. 90, No. 1, 2012, pp. 17-21. doi:10.1016/j.fbp.2010.11.008

[42]   M. T. J. Khan, K. Ahmad, M. N. Alvi, N. U. Amin, B. Mansoor, M. A. Saeed, F. Z. Khan and M. Jamshaid, “Antibacterial and Irritant Activities of Organic Solvent Extracts of Agave americana Linn., Albizzia lebbek Benth., Achryranthes aspera Linn., and Abutilon indicum Linn.—A Preliminary Investigation,” Pakistan Journal of Zoology, Vol. 42, No. 1, 2010, pp. 93-97.

[43]   P. V. Kadam, K. N. Yadav, R. S. Deoda, N. S. Narappanawar, R. S. Shivatare and M. J. Patel, “Pharmacognostic and Phytochemical Studies on Roots of Agave americana (Agavaceae),” International Journal of Pharmacognosy and Phytochemical Research, Vol. 4, No. 3, 2012, pp. 92-96.

[44]   A. F. Ade-Ajayi, C. Hammuel, C. Ezeayanaso, E. E. Ogabiela, U. U. Udiba, B. Anyim and O. Olabanji, “Preliminary Phytochemical and Antimicrobial Screning of Agave sisalana Perrine Juice (Waste),” Journal of Environmental Chemistry and Ecotoxicology, Vol. 3, No. 7, 2011, pp. 180-183.

[45]   K. Rizwan, M. Zubair, N. Rasool, M. Riaz, M. Zia-UlHaq and V. de Feo, “Phytochemical and Biological Studies of Agave attenuata,” International Journal of Molecular Sciences, Vol. 13, No. 5, 2012, pp. 6440-6451. doi:10.3390/ijms13056440

[46]   M. S. González-Elizondo, M. González-Elizondo, I. L. López-Enriquez, L. Reséndiz-Rojas, J. A. Tena-Flores and F. I. Retana-Rentería, “El Complejo Agave victoriaereginae (Agavaceae),” Acta Botanica Mexicana, Vol. 95, 2011, pp. 65-94.

[47]   A. Martínez-Palacios, L. E. Eguiarte and G. R. Furnier, “Genetic Diversity of the Endangered Endemic Agave victoriae-reginae (Agavaceae) in the Chihuahuan Desert,” American Journal of Botany, Vol. 86, No. 8, 1999, pp. 1093-1098. doi:10.2307/2656971

[48]   G. Hrazdina, “Biosynthesis of Flavonoids,” In: R. W. Hemingway and P. E. Laks, Eds., Plant Polyphenols, Plenum Press, New York. 1992, pp. 61-72. doi:10.1007/978-1-4615-3476-1_4

[49]   W. Heller and G. Forkmann, “Biosynthesis of Flavonoids,” In: J. B. Harborne, Ed., The Flavonoids. Advances in Research since 1986, Chapman & Hall, London, 1994, pp. 499-535.

[50]   D. S. Seigler, “Plant Secondary Metabolism,” Kluwer Academic Publishers, Massachusetts, 2002.

[51]   G. Wallace and S. C. Fry, “Phenolic Compounds of the Plant Cell,” International Review of Cytology, Vol. 151, 1994, pp. 229-267. doi:10.1016/S0074-7696(08)62634-0

[52]   A. N. Binns, R. H. Chen, H. N. Wood and D. G. Lynn, “Cell Division Promoting Activity of Naturally Occurring Dehydrodiconiferyl Glucosides: Do Cell Wall Components Control Cell Division?” Proceedings of the National Academy of Sciences of the United States of America, Vol. 84, No. 4, 1987, pp. 980-984. doi:10.1073/pnas.84.4.980

[53]   A. D. M. Glass and J. Dunlop, “Influence of Phenolic Acids on Ion Uptake,” Plant Physiology, Vol. 54, No. 6, 1974, pp. 855-858. doi:10.1104/pp.54.6.855

[54]   C. A. Rice-Evans, N. J. Miller and G. Papanga, “Antioxidant Properties of Phenolic Compounds,” Trends in Plant Science, Vol. 2, No. 4, 1997, pp. 152-159. doi:10.1016/S1360-1385(97)01018-2

[55]   N. Almaraz-Abarca, M. G. Campos, J. A. ávila-Reyes, N. Naranjo-Jiménez, J. Herrera-Corral and L. S. GonzálezValdez, “Antioxidant Activity of Polyphenolic Extract of Monofloral Honeybee-Collected Pollen from Mesquite (Prosopis juliflora, Leguminosae),” Journal of Food Composition and Analysis, Vol. 20, No. 2, 2007, pp. 119124. doi:10.1016/j.jfca.2006.08.001

[56]   M. Veit, C. Beckert, C. Höhne, K. Bauer and H. Geiger, “Iterspecific and Intraspecific Variation of Phenolics in the Genus Equisetum Subgenus Equisetum,” Phytochemistry, Vol. 38, No. 4, 1995, pp. 881-891. doi:10.1016/0031-9422(94)00658-G

[57]   M. Fu, Z. He, Y. Zhao, J. Yang and L. Mao, “Antioxidant Properties and Involved Compounds of Daylily Flowers in Relation to Maturity,” Food Chemistry, Vol. 114, No. 4, 2009, pp. 1192-1197. doi:10.1016/j.foodchem.2008.10.072

[58]   R. Wierman and K. Vietth, “Outer Pollen Wall, an Important Accumulation Site for Flavonoids,” Protoplasma, Vol. 118, No. 3, 1983, pp. 230-233. doi:10.1007/BF01281807

[59]   E. Sánchez, N. Heredia and S. García, “Inhibition of Growth and Mycotoxin Production of Aspergillus flavus and Aspergillus parasiticus by Extracts of Agave species,” International Journal of Food Microbiology, Vol. 98, No. 3, 2005, pp. 271-279. doi:10.1016/j.ijfoodmicro.2004.07.009

[60]   M. G. Campos, “Caracterização do Pólen Apícola pelo seu Perfil em Compostos Fenólicos e Pesquisa de Algumas Actividades Biológicas,” Ph.D. Thesis, Coimbra University, Coimbra, 1997.

[61]   J. Fiasson, L. K. Gluchoff-Fiasson and G. Dahlgren, “Flavonoid Patterns in European Ranunculus L. Subgenus Batrachium (Ranunculaceae),” Biochemical Systematics and Ecology, Vol. 25, No. 4, 1997, pp. 327-333. doi:10.1016/S0305-1978(97)00021-5

[62]   N. Almaraz-Abarca, M. G. Campos, J. A. Ávila-Reyes, N. Naranjo-Jiménez, J. Herrera-Corral and L. S. GonzálezValdez, “Variability of Antioxi-dant Activity Among Honeybee-Collected Pollen of Different Botanical Origin,” Interciencia, Vol. 29, No. 10, 2004, pp. 574-578.

[63]   N. Almaraz-Abarca, M. S. González-Elizondo, J. A. Tena-Flores, J. A. ávila-Reyes, J. Herrera-Corral and N. Naranjo-Jiménez, “Foliar Flavonoids Distinguish Pinus leiophylla and Pinus chihuahuana (Coniferales: Pinaceae),” Proceedings of the Biological Society of Washington, Vol. 119, No. 3, 2006, pp. 426-436. doi:10.2988/0006-324X(2006)119[426:FFDPLA]2.0.CO;2

 
 
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