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United States Department of Agriculture

Agricultural Research Service

Phenolics:References

Survey of Phenolic Compounds Produced in Citrus

References

Afek, U., A. Sztejnberg, and S. Carmely, 1986. 6,7–Dimethoxycoumarin, a citrus phytoalexin conferring resistance against Phytophthora gummosis. Phytochemistry 25:1855–1856.

Agrawal, P.K., and M.C. Bansal. 1989. Carbon–13 of flavonoids. In P.K. Agrawal, ed., Studies in Organic Chemistry, p. 282. Elsevier, Amsterdam.

Albach, R F., A.T. Juarez, and B.J. Lime. 1969. Time of naringin production in grapefruit. Journal of the American Horticultural Society 94:605–609.

Albach, R.F., and G.H. Redman. 1969. Composition and inheritance of flavanones in citrus fruit. Phytochemistry 8:127–143.

Albach, R.F., G.H. Redman, and R.R. Cruse. 1981. Annual and seasonal changes in naringin concentrations of ruby red grapefruit juice. Journal of Agricultural and Food Chemistry 29:808–811.

Albach, R.F., and H.K. Wutscher. 1988. Flavanone content of whole grapefruit and juice as influenced by fruit development. Journal of the Rio Grande Valley Horticultural Society 41:89–95.

Anis, M., and Aminuddin. 1981. Flavonoid patterns of leaves of some Citrus species and their hybrids. Plant Biochemical Journal 8:56–60.

Anonymous. 1990. Medfly on commercial lemons. Citrography 75:59–60.

Back, E.A., and C.E. Pemberton. 1918. The Mediterranean fruit fly. USDA Bulletin No. 640:1–43.

Barrett, H.C., and A.M. Rhodes. 1976. Numerical taxonomic study of affinity relationships in cultivated Citrus and its close relatives. Systematic Botany 1:105–136.

Beier, R.C., and E.H. Oertli. 1983. Psoralen and other linear furocoumarins as phytoalexins in celery. Phytochemistry 22:2595–2597.

Berhow, M.A., R.D. Bennett, K. Kanes, et al. 1991. A malonic acid ester derivative of naringin in grapefruit. Phytochemistry 30:4198–4200.

Berhow, M.A., C.H. Fong, and S. Hasegawa. 1996. Limonoid and flavonoid composition in varieties of papeda and papedocitrus. Biochemical and Systematic Ecology 24:237–242.

Berhow, M.A., and C.A. Vandercook. 1989. Biosynthesis of naringin and prunin in detached grapefruit. Phytochemistry 28:1627–1630.

Brunet, G., and R. Ibrahim. 1973. Tissue culture of citrus peel and its potential for flavonoid synthesis. Zeitschrift für Pflanzenphysiology 69:52–162.

Cameron, J.W., and R.K. Soost. 1968. Genetics, breeding, and nucellar embryony. In W. Reuther, L.D. Batchelor, and H.J. Webber, eds., The Citrus Industry, vol. 1, pp. 325–370. University of California, Division of Agricultural Sciences, Berkeley.

Cameron, J.W., and R.K. Soost. 1969. Characters of new populations of Citrus polyploids, and the relation between tetraploidy in the pollen parent and hybrid tetraploid progeny. In H.D. Chapman, ed., Proceedings of the First International Citrus Symposium, University of California at Riverside, March 16–26, 1968, vol. 1, pp. 199–205. Publications Department, University of California, Riverside.

Cameron, J.W., R.K. Soost, and E.O. Olson. 1964. Chimeral basis for color in pink and red grapefruit. Journal of Heredity 55:23–28.

Coffin, D.E. 1971. A method for the isolation and identification of the flavanone glycosides of citrus fruit juices. Journal of Agricultural and Food Chemistry 19:513–516.

Dixon, R.A. 1986. The phytoalexin response: elicitation, signaling and control of host gene expression. Biological Review 61:239–291.

Dreyer, D.L., and P. Huey. 1974. Coumarins in Eremocitrus glauca. Phytochemistry 13:237–1239.

Elliger, C.A., B.C. Chan, and A.C. Waiss, Jr. 1980. Flavonoids as larval growth inhibitors. Naturwissenschaften 67:358.

Feldman, A.W. and R.W. Hanks. 1968. Phenolic content in the roots and leaves of tolerant and susceptible citrus cultivars attacked by Radopholus similis. Phytochemistry 7:5–12.

Fisher, J.F. 1968. A procedure for obtaining radioactive naringin from grapefruit leaves fed l–phenylalanine–14C. Phytochemistry 7:769–771.

Gaydou, E.M., J.–P. Bianchini, and R.P. Randriamiharisoa. 1987. Orange and mandarin peel oils differentiation using polymethoxylated flavone composition. Journal of Agricultural Food and Chemistry 35:525–529.

Grieve, C.M., and R.W. Scora. 1980. Flavonod distribution in the Aurantioidaea (Rutaceae). Systematic Botany 5:39–53.

Guadagni, D.G., V.P. Maier, and J.G. Turnbaugh. 1973. Effect of some citrus juice constituents on taste thresholds for limonin and naringin bitterness. Journal of Scientific Food Agriculture 24:1277–1288.

Hagen, R.E., W.J. Dunlap, J.W. Mizelle, et al. 1965. A chromatographic–fluorometric method for determination of naringin, naringenin rutinoside, and related flavanone glycosides in grapefruit juice and juice sacs. Analytical Biochemistry 12:472–482.

Hagen, R.E., W.J. Dunlap, and S.H. Wender. 1966. Seasonal variation of naringin and certain other flavanone glycosides in juice sacs of Texas ruby red grapefruit. Journal of Food Science 31:542–547.

Hahlbrock, K., and H. Grisebach. 1979. Enzymatic controls in biosynthesis of lignin and flavonoids. Annual Review of Plant Physiology 30:105–130.

Hahlbrock, K., and D. Scheel. 1989. Physiology and molecular biology of phenypropanoid metabolism. Annual Review of Plant Physiology of Plant Molecular Biology 40:347.

Hattori, S., M. Shimokoriyama, and M. Kanao. 1952. Studies on flavanone glycosides. IV. The glycosides of ripe fruit peel and flower petals of Citrus aurantium L. Journal of the American Chemical Society 74:3614–3615.

Heller, W., and G. Forkmann. 1988. Biosynthesis. In J.B. Harborne, ed., The Flavonoids, pp. 399–425. Chapman and Hall, London.

Hodgson, R.W. 1967. Horticultural varieties of Citrus. In W. Reuther, H.J. Webber, and L.D. Batchelor, eds., The Citrus Industry, vol. 1, pp. 431–591. University of California, Berkeley.

Horowitz, R.M. 1986. Taste effects of flavonoids. In V. Cody, E. Middleton, Jr., and J. Harborne, eds., Plant Flavonoids in Biology and Medicine, Biochemical, Pharmacological, and Structure-Activity , pp. 163–175. Alan R. Liss, New York.

Horowitz, R.M., and B. Gentili. 1960. Flavonoids of the Ponderosa lemon. Nature 185:319–320.

Horowitz, R.M., and B. Gentili. 1961. Phenolic glycosides of grapefruit: a relation between bitterness and structure. Archives of Biochemistry Biophysics 92:191–192.

Horowitz, R.M., and B. Gentili. 1977. Flavonoid constituents of Citrus. In S. Nagy, P.E. Shaw, and M.K. Veldhuis, eds., Citrus Science and Technology, vol. 1, pp. 397–426. Avi Publishers, Westport, CT.

Jacobs, M., and P.H. Rubery. 1988. Naturally occurring auxin transport regulators. Science 241:346–349.

Jourdan, P.S., C.A. MacIntosh, and R.L. Mansell. 1985. Naringin levels in citrus tissues. II. Quantitative distribution of naringin in Citrus paradisi Macfad. Plant Physiology 77:903–908.

Kamiya, S., S. Esaki, and F. Konishi. 1979. Flavonoids in citrus hybrids. Agricultural and Biological Chemistry 43:1529–1536.

Kanes, K., B. Tisserat, M.A. Berhow, and C.E. Vandercook. 1993. Phenolic composition of various tissues of Rutaceae species. Phytochemistry 32:967–974.

Kumamoto, H., Y. Matsubara, Y. Iizuka, et al. 1986. Structure and hypotensive effect of flavonoid glycosides in orange (Citrus sinensis Osbeck) peelings. Agriculturical and Biological Chemistry 50:781–783.

Laks, P.E., and M.S. Pruner. 1989. Flavonoid biocides: structure/activity relations of flavonoid phytoalexin analogues. Phytochemistry 28:87–91.

Lawrence, B.M. 1982. Coumarins and psoralens in citrus oils. Perfumer and Flavorist 7:57–58, 60–65.

Maier, V.P., and D.M. Metzler. 1967. Grapefruit phenolics. II. Principal aglycones of endocarp and peel and their possible biosynthetic relationship. Phytochemistry 6:1127–1135.

Malik, M.N., R.W. Scora, and R.K. Soost. 1974. Studies on the origin of the lemon. Hilgardia 42:361–382.

Markham, K.R., and B. Ternai. 1976. 13C NMR of flavonoids. II. Flavonoids other than flavone and aglycones. Tetrahedron 32:2607–2612.

Matsubara, Y., H. Kumamoto, Y. Iizuka, et al. 1985. Structure and hypotensive effect of flavonoid glycosides in Citrus unshiu peelings. Agricultural and Biological Chemistry 49:909–914.

McHale, D., P.J. Khopkar, and J.B. Sheridan. 1987. Coumarin glycosides from citrus flavedo. Phytochemistry 26:2547–2549.

Metzler, D.E. 1977. Biochemistry. Academic Press, New York.

Mizelle, J.W., W.J. Dunlap, R.E. Hagen, et al. 1965. Isolation and identification of some flavanone rutinosides of the grapefruit. Analytical Biochemistry 12:316–324.

Mizelle, J.W., W.J. Dunlap, and S.H. Wender. 1967. Isolation and identification of two isomeric naringenin rhamnodiglucosides from grapefruit. Phytochemistry 6:1305–1307.

Mizrahi, S., and Z. Berk. 1970. Physio-chemical characteristics of orange juice cloud. Journal of Science and Food Agriculture 21: 250–253.

Mizuno, M., Y. Matoba, T. Tanaka, et al. 1987. Two new flavones in Citrus reticulata. Journal of Natural Products 50:751–753.

Nahrstedt, A. 1990. The significance of secondary metabolites for interactions between plants and insects. Planta Medica 55:333–338.

Nakatani, N., Y. Yamada, and H. Fuwa. 1987. 7–Geranyloxycoumarin from juice oil of hassaku (Citrus hassaku) and antimicrobial effects of related coumarins. Agricultural and Biological Chemistry 51:419–423.

Nguyen, R., and S. Fraser. 1989. Lack of suitability of commercial limes and lemons as hosts of Anastrepha suspensa (Diptera: Tephritidae). Florida Entomologist 72:718–720.

Nishiura, M., S. Esaki, and S. Kamiya. 1969. Flavonoids in Citrus and related genera. Part I. Distribution of flavonoid glycosides in Citrus and Poncirus. Agricultural and Biological Chemistry 33:1109–1118.

Nishiura, M., S. Kamiya, and S. Esaki. 1971a. Flavonoids in citrus and related genera. Part III. Flavonoid pattern and citrus taxonomy. Agricultural and Biological Chemistry 35:1691–1706.

Nishiura, M., S. Kamiya, S. Esaki, and F. Ito. 1971b. Flavonoids in citrus and related genera. Part II. Isolation and identification of isonaringin and neoeriocitrin from citrus. Agricultural and Biological Chemistry 35:1683–1690.

Park, G.L., S.M. Avery, J.L. Byers, and D.B. Nelson. 1983. Identification of bioflavonoids from citrus. Food Technology 37:98–105.

Ray, R., and L. Walheim. 1980. Citrus: how to select, grow and enjoy. Horticultural Publishing Co., Inc., HP Books, Inc. Tucson, AZ.

Robak, J., and R.J. Gryglewski. 1988. Flavonoids are scavengers of superoxide anions. Biochemistry and Pharmacology 37:837–841.

Robbins, R. 1980. Medical and nutritional aspects of citrus bioflavonoids. In S. Nagy and J. Attaway, eds., Citrus Nutrition and Quality, pp. 43–59. American Chemistry Society, Washington, DC.

Rousseff, R.L., S.F. Martin, and C.O. Youtsey. 1987. Quantitative survey of narirutin, naringin, hesperidin and neohesperidin in citrus. Journal of Agricultural and Food and Chemistry 35:1027–1030.

Rowell, K.M., and C.G. Beisel. 1963. Isolation of gram quantities of a phamnoglucoside of apigenin from grapefruit. Journal of Food Science 28:195–197.

Sarin, P.S., and T.R. Seshadri. 1960. New components of Citrus aurantium. Tetrahedron 8:64–66.

Scora, R.W. 1975a. On the history and origin of citrus. Bulletin of the Torrey Botanical Club 102:369–375.

Scora, R.W. 1975b. Volatile oil components in Citrus taxonomy. International Flavorings and Food Additives 6:342–346.

Scora, R.W. 1988. Biochemistry, taxonomy and evolution of modern cultivated citrus. In R. Goren and K. Mendel, eds., Proceedings of the Sixth International Citrus Congress, pp. 277–289. Baleben Publishers, Philadelphia.

Scora, R.W., and J. Kumamoto. 1983. Chemotaxonomy of the genus Citrus. In P.G. Waterman and M.F. Grundon, eds., Chemistry and Chemical Taxonomy of the Rutales, pp. 343–351. Academic Press, New York.

Scora, R.W., J. Kumamoto, A. Esen, and B. Stone. 1976. A phytochemical investigation of Citrus halimii. Biochemical Systematics and Ecology 4:255–258.

Scora, R.W., and D.H. Nicolson. 1986. The correct name for the shaddock, Citrus maxima not C. grandis (Rutaceae). Taxon 35:592–595.

Singh, R., and N. Nath. 1969. Practical approach to the classification of Citrus. In H.D. Chapman, ed., Proceedings of the First International Citrus Symposium, University of California at Riverside, March 16–26, 1968, vol. 1, pp. 435–449. Publications Department, University of California, Riverside.

Snyder, B.A., and R.L. Nicholson. 1990. Synthesis of phytoalexins in sorghum as a site-specific response to fungal ingress. Science 248:1637–1639.

Soost, R.K., and J.W. Cameron. 1981. 'Oroblanco', a triploid pummelo-grapefruit hybrid. Proceedings of the International Society of Citriculture 1:59–60.

Stolk, L.M.L., and A.H. Siddiqui. 1988. Minireview: biopharmaceutics, pharmacokinetics and pharmacology of psoralens. General Pharmacology 19:649–653.

Stone, B.C., J.B. Lowry, R.W. Scora, and K. Jong. 1973. Citrus halimii: a new species from Malaysia and peninsular Thailand. Biotropia 5:102–110.

Swingle, W.T., and P.C. Reece. 1967. The botany of Citrus and its wild relatives. In W. Reuther, H.J. Webber, and L.D. Batchelor, eds., The Citrus Industry, vol. 1, pp. 190–430. University of California, Berkeley.

Tatum, J.H., and R.E. Berry. 1979. Coumarins and psoralens in grapefruit peel oil. Phytochemistry 18:500–502.

Tatum, J.H., C.J. Hearn, and R.E. Berry. 1978. Characterization of citrus cultivars by chemical differentiation. Journal of the American Horticultural Society 103:492–496.

Ting, S.V., R.L. Rouseff, M.H. Dougherty, and J.A. Attaway. 1979. Determination of some methoxylated flavones in citrus juices by high performance liquid chromatography. Journal of Food Science 44:69–71.

Tisserat, B., C.E. Vandercook, and M. Berhow. 1989. Citrus juice vesicle culture: a potential research tool for improving juice yield and quality. Food Technology 43:95–100.

Tomas, F., O. Carpena Artes, R. Pastor, and J.J. Mataix Beneyeto. 1978. Flavonoids in flowers of Citrus limon cv. Eureka. Proceedings of the International Society of Citriculture 1:74–76.

Vandercook, C.E., R.L. Price, and C.A. Harrington. 1975. Multiple automated analyses for orange juice content: Determination of total sugars, reducing sugars, total acidity, total amino acids and phenolics. Journal of the Association of Official Analytical Chemists 58:482–487.

Vandercook, C.E., and B. Tisserat. 1989. Flavonoid changes in developing lemons grown in vivo and in vitro. Phytochemistry 28:799–803.

Vandercook, C.E., B. Tisserat, and M.A. Berhow. 1990. Influence of external factors on quality and composition of citrus. Food Technology 44:142–148.

Wiermann, R. 1981. Secondary plant products and cell and tissue differentiation. In E.E. Conn, ed., The Biochemistry of Plants, vol. 7, pp. 85–116. Academic Press, New York.

Zaat, S.A.J., A.A.N. van Brussel, T. Tak, et al. 1987. Flavonoids induce Rhizobium leguminosarum to produce nodDABC gene-related factors that cause thick, short roots and root hair responses on common vetch. Journal of Bacteriology 169:3388–3391


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United States Department of Agriculture
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Original posting: April 1, 1999.

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