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Flavonoids in Citrus and Related Genera Part III

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Flavonoids in Citrus and Related Genera Part III [Agr. Biol. Chem., Vol. 35, No. 11, p. 1691-1706, 1971] Flavonoids in Citrus and Related Genera Part III. Flavonoid Pattern and Citrus Taxonomy By Masao NISHIURA, Shintaro KAMIYA" and Sachiko ESAKI* Okitsu Branch, The Horticultural Research Station, Shimizu City, Japan *Shizuoka Women's College , Shizuoka City, Japan Received April 7, 1971 The occurrence and distribution of flavanone glycosides in flowers, young and mature leaves, young and ripe fruits, dividing them into peels, segment membranes and juices, of many kinds of citrus were investigated. The occurrence of narirutin, eriocitrin and neoeriocitrin is fairly common to a number of species in genus citrus. Results also indicate that flavonoid patterns in citrus can be classified into eleven groups or more and further they can be summarized in two large groups: (a) those composed of flavanone rutinosides and (b) those composed of flavanone neohesperidosides. Thus the chemotaxonomic table of citrus was given as the results of our study in connection with the Tanaka's classification. Flavonoids in some artificial citrus hydrids were also studied. In the previous paper," the authors consider- and juices, of many species and varieties of ed that flavanone glycosides are so rich and citrus in more detail by using the same tech characteristic in citrus tissues that among many nique and attempts to show how the differences secondary constituents these flavonoids seem in the flavonoid compositions of citrus may to make a significant contribution as taxonomic be used as a supplemental means for the citrus marker to the citrus systematics. From the classification. above standpoint, the isolation, identification Additionally, data showing the occurrence and distribution of several flavonoid glycosides of flavonoids in some artificial citrus hybrids in citrus have been reported but the data are were given. still far from being complete. Recently, citrus flavanones could be successfully separated on EXPERIMENTAL thin-layers of polyamide by using none aqueous solvent systems. Albach and Redman2) have Materials and methods. Unless otherwise mention surveyed the composition and inheritance of ed, samples (flowers, leaves and fruits) were collected from the trees planted in this station. Mature leaf flavanones in citrus by thin-layer chromato samples were harvested from trees in December, 1968. graphy and discussed the species problem of Each sample consist of 5 to 10 leaves and is 8 to 9 citrus in connection with flavanone glycosides. month old ones from the spring cycle. Likewise, in The current study is also concerned with their 1969, several young but well expanded leaves and distribution in the leaves, flowers and fruits, flowers were collected, respectively, from each tree dividing them into peels, segment membranes, at the middle of May, while several young and ripe fruits were sampled at the beginning of July and at the middle of December, resectively. 1) M. Nishiura, S . Esaki and S. Kamiya, Agr. Biol. Chem., 33, 1109 (1969). In the case of flowers and leaves, finely chopped 2) R. F. Albach and G. H. Redman, Phytochemistry, fresh material was extracted with 80 ml of boiling 8, 127 (1969) . methanol for 2 hr. After cooling the filtrate was con- 1692 M. NISHIURA, S. KAMIYA and S. ESAKI centrated in vacuo to a sirup and then was dissolved branes and juices) of ripe fruit and also be in a small amount of hot water and filtered. The tween young and ripe ones within the same filtrate was washed with ether two times and extract- sample. ed with 20 ml of ethyl acetate several times. The Results also indicate that different taxonomic combined extract was evaporated under vacuum to units occassionally have different flavonoid dryness and the residue was dissolved in a minimum amount of pyridine and subjected to thin-layer chro patterns, which fall into the following groups. In dividing flavonoid patterns into groups, matography. Segment membranes and juices of mature fruits were minor constituents were not taken into con treated as described in the previous report., Young sideration. (* sign shows a variety which has fruits and ripe peels were also treated according to not yet scientific name.) the procedure previously reported) and all the cry Flowers (arranged in alphabetical order.) stals separated on the way of the procedure were col a) Naringin group. Ampullacea, grandis lected and weighed. The mother liquids were extracted (Hirado, Anseikan, Mato, Honda, Kao pan, with ethyl acetate repeatedly and the combined ex- Kao phuang, Banhakuyu, Hogen, Cuban tract was concentrated to a sirup. Both the crystals shaddock), intermedia, mitsuharu, otachibana, and sirups were combined and dissolved in a small amount of pyridine and subjected to thin-layer chro paradisi (Triumph, Duncan, McCarty, Marsh, matography. Little Seedless, Imperial), wilsonii. Thin-layer chromatography was carried out as de b) Neohesperidin group. funadoko. scribed before.) Spot colors (Rf value) of flavanones c) Naringin, neohesperidin and neoericitrin are; 3•L-methylhesperidin, purple (0.80), 3•L-methylneo group. asahikan, aurantium (Crispa, Kabusu, hesperidin, purple (0.73), didymin, red (0.67), pon- Cyathifera, Choshuto), glaberrima, grandis cirin, red, (0.60), hesperidin, purple (0.50), neohes (Banokan, Tanikawana), hassaku, hiroshimana, peridin, purple, (0.43), narirutin, red, (0.38), naringin, Kinkoji-unshu,* medioglobosa, natsudaidai, red, (0.32), eriocitrin, blue, (0.22), neoeriocitrin, blue, obovoidea, rugulosa, taiwanica. (0.18). 3•L-Methylneohesperidin was prepared accord d) Narirutin group. pseudogulgul, tengu. ing to the method of Tsutsumi and Miyao.3) Color- e) Hesperidin group. genshokan, keraji, kino less needles, mp 186°C. UVEtOHmaxmƒÊ: 285. Anal. kuni, (kinokuni, Mukaku, Hira), madurensis, Found: C, 53.62; H 6.24. Calcd. for C29H36O15. H2O: C, 54.24; H, 5.9240. Intensely bitter. meyerii (meyerii, Grant) reticulata, rokugatsu, succosa, tangerina (Dancy, Obeni). f) Hesperidin and narirutin group. cleoptra, RESULTS ponki, pseudoaurantium, reticulata, sudachi, sunki, tankan, unshiu, yatsushiro. The occurrence and distribution of flavanone g) Hesperidin and eriocitrin group. deliciosa, glycosides in young and mature leaves, young leiocarpa, limon (Eureka, Lisbon, Luteopulpa, and mature fruits and flowers of many kind Semperflorens, Sicily, Villafranca), lumia. of citrus are descibed below. The contents of h) Hesperidin, narirutin and eriocitrin group. crude flavonoids in young and mature fruits canaliculata, hanaju, iyo, junos, kotokan, limet are also given in Table I. ta, nobilis, shunkokan, sphaerocarpa, sulcata, As the result of experiment, no difference tachibana, Takagi-mikan,* tumida, ujukitsu, in the composition of flavanone glycosides be tween young and mature leaves within any yamabuki. i) Didymin, hesperidin, narirutin and eriocitrin given species or variety was observed. How ever, flavonoid compositions are occassionally group. tamurana. Leaves (young and matured) different in the parts (peels, segment mem a) Naringin group. ampullacea, assamensis, 3) J. Tsutsumi and K. Miyao, Japan patent, 6927031 aurantiaca, balotina, grandis (Anseikan, Egami, (CI 16E41), 11, Nov. (1969). Cuban shaddock, Honda, Hirado, Kao pan, Flavonoids in Citrus and Related Genera . Part III 1693 TABLE I. YIELD AND TASTE OF FLAVONOID FROM YOUNG TOTAL FRUIT AND RIPE PEEL OF CITRUS 1694 M. NISHIURA, S. KAMIYA and S. ESARI Flavonoids in Citrus and Related Genera. Part 111 1695 (Y) young fruit, (R) ripe peel. 1696 M. NISHIURA, S. KAMIYA and S. ESAKI Kao phuang, Mato), ichangensis, intermedia, lata, jambhiri, kinokuni (Hira), leiocarpa Itoshima-bankan,* Kawachi-bankan,* mitsu (Monoemblyota), limonia (limonia, Otaitensis), haru, otachibana, paradisi (Duncan, Imperial, limon (Eureka, Lisbon, Luteopulpa, Semper Marsh, McCarty, Little Seedless, Triumph), florens, Sicily, Villafranca), lumia, platymam wilsonii. ma, tachibana. b) Neohesperidin group. funadoko, macro k) Hesperidin, narirutin and eriocitrin group. ptera. iwaikan, junos, kotokan, luteo-turgida, sudachi, c) Neohesperidin and naringin group. auran sulcata, tamurana, yamabuki, yuko. tium (Crispa), pyriformis, sinograndis, yan Fruit ( young) baruensis. a) Naringin group. ampullacea, aurantiaca, d) Neohesperidin, naringin and neoeriocitrin grandis (anseikan, Cuban shaddock, Kao pan, group. asahikan, aurantium (aurantium, Cho Hirado, Hogen, Kao phuang, Mato), inter- shuto, Cyathifera, Kabusu, Daidaihana, Fuiri), media, mitsuharu, otachibana, paradisi (Dun- bergamia, glaberrima (glaberrima, oblata), can, Imperial, Little Seedless, Marsh, McCarty, grandis (Banokan, Tanikawana), hassaku, hiro Triumph), Wilsonii. shimana, kinkoji-unshu,* kobayashi-mikan,* b) Neohesperidin group. funadoko, truncata. medioglobosa, myrtifolia, natsudaidai, neo c) Neohesperidin and naringin group. asahikan, aurantium, obovoidea, ogonkitsu,* pseudo aurantium (aurantium, Choshuto, Cyathifera, paradisi, rugulosa, taiwanica, Taiwanyuzu,* Kabusu), grandis (Banokan, Tanikawana), Takuma grape,* truncata. glaberrima, hassaku, hiroshimana, Kinkoji- e) Poncirin and naringin group. macroptera, unshu,* Kobayashi-mikan,* medioglobosa, P. trifoliata (trifoliata, monstrosa) myrtifolia, natsudaidai, neoaurantium, obo f) Poncirin, neohesperidin, naringin and neo voidea, Ogonkitsu,* rugulosa, taiwanica, eriocitrin group. excelsa. Takuma-kinukawa,* Takuma-grape.* g) Hesperidin group. aurantifolia, aurea, d) Neohesperidin, naringin and neoreiocitrin amblycarpa, clementina, deliciosa, depressa, group. bergamia, pseudoparadisi,
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