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Limonoid Glucosides in Citrus Seeds Yoshihiko Ozaki,* Chi H

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Limonoid Glucosides in Citrus Seeds Yoshihiko Ozaki,* Chi H Agric. Biol. Chem., 55 (1), 137-141, 1991 137 Limonoid Glucosides in Citrus Seeds Yoshihiko Ozaki,* Chi H. Fong, Zareb Herman, Hisao Maeda,* Masaki Miyake,* Yasushi Ifuku* and Shin Hasegawa Fruit & Vegetable Chemistry Laboratory, U.S. Department of Agriculture, ARS, 263 South Chester Avenue, Pasadena, California 91106, U.S.A. * WakayamaAgri-Bio Research Institute Center, Momoyama, Wakayama 649-61, Japan Received July 6, 1990 The amounts of limonoid glucosides were measured in the seeds of grapefruit (Citrus paradisi), lemon (C limon), Valencia orange (C. sinensis), tangerine (C reticulata), Fukuhara (C sinensis Osbeck Hort.), Hyuganatsu (C tamurana Hort. ex Tanaka), Shimamikan (C. kinokuni Hort. ex Tanaka) and Sanbokan (C. sideata Hort. ex Takahashi). All the seeds contained 17-/J-D- glucopyranosides of limonin, nomilin, obacunone, deacetylnomilin, nomilinic acid and deacetylnomilinic acid. The total limonoid glucoside content ranged from 0.31 to 0.87% of the dry weight. The concentration of nomilin glucoside was highest among the glucosides found in the seeds. All the seeds also contained the major neutral limonoid aglycones commonly found in citrus, namely limonin, nomilin, deacetylnomilin, obacunone and ichangin. As previously reported, limonin was the predominant aglycone. Limonoids are a group of chemically related 17-/?-D-glucopyranoside (4) in mature fruit triterpenoids found in the Rutaceae and tissues and seeds.1"3) Ten such glucoside Meliaceae families. Among 37 limonoids derivatives have been isolated from citrus and reported to occur in citrus and its hybrids, identified.1>2) Surprisingly, these glucosides limonin (1, Fig. 1) is intensely bitter and is were present in high concentrations relative to largely responsible for delayed bitterness in the aglycones in citrus juices.3'4) For example, citrus juices and processed products. Recently, commercial orange juices contain an average wehave found that limonoids were also present of 320 ppm of total limonoid glucosides. These as glucoside derivatives such as limonin glucosides maybe of significance for limonoid metabolism, catabolism, the taste of citrus products and human nutrition. Citrus seeds contain large amounts of limonoids.5) They can biosynthesize both limonoids and limonoid glucosides.5'6) The aglycones begin to accumulate early in seed development, whereas the glucosides accumu- late only in mature seeds.5'6) In this study, the amounts oflimonoids and their glucosides were mesuredin various citrus seeds. Materials and Methods Materials. Seeds of Fukuhara, a sweet orange {Citrus sinensis osbeck Hort), hyuganatsu, a pummelo-like fruit Fig. 1. Structures of Limonoids (C. tamurana Hort. ex Tanaka), Shimamikan,a sour orange 138 Y. Ozaki et al. (C. kinokuni Hort. ex Tanaka) and Sanbokan, also a sour orange (C. sulcata Hort. ex Takahashi) were obtained from mature fruits harvested at Wakayamain 1989. Grapefruit (C. paradisi), lemon (C limon), Valencia orange (C. sinensis) and tangerine (C. reticulata) seeds were obtained from fruit trees grown at University of California, Riverside. The seeds were ground with a Retsch mill (Brinkmann, Westbury, NY, U.S.A.) after drying at 55°C for 2 days. TLC plates (silica gel HLF) were purchased from Analtech (Newark, DE, U.S.A.). HPLC column, C18 reverse-phase (4.6x250mm, 5^m particle size) was purchased from Alltech Associates (Deer field, IL, U.S.A.). Hesperidinase and naringinase were obtained from Sigma Chemical (St. Louis, MO, U.S.A.) and C18 reverse-phase SEP-PAKs were purchased from Waters Associates (Milford, MA, U.S.A.). Extraction. Fifty grams of each seed meal were placed Fig. 2. HPLCTrace of Limonoid Glucosides Extracted in a Soxhlet extractor and washed overnight with hexane from Fukuhara Orange Seeds. to removethe oil. Limonoidaglycones were then extracted 1 7-/?-D-Glucopyranosides ofA, limonin; B, deacetylnomili- with CH2C12, which was followed by MeOHto extract the nic acid; C, deacetylnomilin; D, ichangin; E, nomilin; F, limonoid glucosides. nomilinic acid; G, obacunone. Limonoid glucoside analysis. The limonoid glucoside content in the seeds was determined by TLCand HPLC methods. For the TLCanalysis, each MeOHextract was evaporated, dissolved in a measured volume of MeOH and spotted on a plate, which was developed with EtOAc- MeCOEt-HCO2H-H2O (5:3:1:1). The plates were sprayed with Ehrlich's regent, and color was developed in an HC1gas chamber.7) The spots were compared with those of a standard, and the total limonoid glucoside content was estimated by two judges. This analysis was done in triplicate, and average values are reported. For the HPLCanalysis, a portion of the MeOHextract was evaporated. Theaqueous residue was treated with hesperidinase and naringinase in a 0.1 mNa formate buffer at pH3.8 for 20hr at room temperature. This treatment was necessary to obtain good peak resolution by cleaving the sugars from interfering flavonoids. The sample was Fig. 3. HPLCTrace of Neutral Limonoid Aglycones further treated with SEP-PAKand analyzed by HPLC. Extracted from Sanbokan Seeds. Duplicate 100/xl, injections were made into a C18 A, ichangin; B, limonin; C, deacetylnomilin; D, nomilin; reverse-phase column, the column being eluted at one ml E, obacunone. per min with a linear gradient system, starting with 15% acetonitrile in 3mMH3PO4and ending with 26% after paired-sample t test gave no significant variance at the 33min. The elution was monitored by UVabsorption at p=0.05 level. 210nm, and a standard curve was run for each limonoid glucoside. Each peak was characterized by the procedure Limonoid analysis. The CH2C12fraction was evaporated of Herman et al.,4) and each compound was quantified by and used to analyze the limonoid aglycones. The extract its peak area. Average values from the two injections were was spotted onto TLCplates, which were developed with used. A typical HPLCchromatogram is shown in Fig. 2, three solvent systems: a) cyclohexane-EtOAc (2: 3), b) retention times for the glucosides oflimonin, deacetylnomi- CH2Cl2-MeOH (49 : 1) and c) EtOAc-CH2Cl2 (2 : 3). Rfs linic acid, deacetylnomilin, ichangin, nomilin, nomilinic were compared with those of standards for identification acid and obacunone being 13.0, 16.6, 21.0, 22.3, 25.8, 27.8 purposes. The extract was also used for a quantitative and 30.3min, respectively. As shown in Table 1, data on analysis by the procedure of Hashinaga et al.8) The sample the total limonoid glucoside contents obtained from the was injected into a C18 reverse-phase HPLCcolumn, the two methods, TLCand HPLC, agreed very well. A column being eluted isocratically with acetonitrile- Limonoid Glucosides in Citrus Seeds 139 MeOH-H2O (10:41 :49). A typical chromatogram is seeds analyzed, Valencia orange contained the shown in Fig. 3, the retention times for ichangin, limonin, highest amount of total limonoid glucosides, deacetylnomilin, nomilin and obacunone being 10.7, 12.1, followed by Fukuhara, grapefruit, Shima- 15.8, 22.6 and 36.1 min, respectively. mikan and lemon in this order. Hyuganatsu was the lowest. Unlike fruit tissue in which 4 is the pre- Results and Discussion dominant glucoside,4) the concentration of 4 Limonoid glucosides were first isolated from in the seeds was relatively low. In Hyuganatsu grapefruit seeds and identified. 1'2* As expected, seeds, the concentration of 4 was not wefound in this study that all the citrus seeds measurable under the conditions used, and analyzed contained 1 7-jS-D-glucopyranosides grapefruit and lemon seeds contained a of the major limonoids found in commoncitrus moderate amount of 4. species (Table I). They included glucosides of Nomilin glucoside was the major glucoside limonin, nomilin, obacunnone, deacetylnomi- in the majority of the seeds (Table I). Par- lin, nomilinic acid and deacetylnomilinic acid. ticularly, in fukuhara and Valencia orange, The total concentration of limonoid glucosides nomilin glucoside made up 42 and 51% of the in the seeds ranged from 0.31 to 0.87% and total limonoid glucosides, respectively. How- averaged 0.61% of the dry weight (Tables I ever, the glucosides of obacunone and de- and III). This concentration is approximately acetylnomilinic acid were the major gluco- 20-fold higher than in juice.3'4) Among the sides in Shimamikan and tangerine, respec- Table I. Limonoid Glucosides in Various Citrus Seeds" Seeds DAG NG NAG OG LG DG Total TLCfc Fukuhara 0.28 3.22 0.98 1.09 0.5 1 1.32 7.40 7.92 Hyuganatsu 0.42 1. 10 0.76 0.65 Trace 0.37 3.3 1 2.92 Sanbokan 0.37 1.13 0.55 0.90 0.51 0.89 4.36 3.96 Shimamikan 0.48 1.89 1.29 2.35 0.37 0.69 7.08 6.45 Grapefruit 0.75 2.01 0.89 0.86 1.48 0.68 6.67 7.28 Lemon 0.14 1.53 1.39 1.49 1.44 0.55 6.54 6.20 Valencia 0. 1.3 4.48 0.98 1.06 0.59 1.69 8.94 8.48 Tangerine 1.69 0.42 0.96 0.45 0.90 0.93 5.36 5. 1 5 a Determinedb ByTLC. by HPLC, mg/g of dry seeds. G, glucoside; DA, deacetylnomilinic acid; N, nomilin; NA, nomilinic acid; O, obacunone; L, limonin; D, deacetylnomilin. Table II. Limonoid Aglycones in Various Citrus Seeds Seeds Limonin Nomilin Obacunone Ichangin ... Total nomilin Fukuhara 9.77 3.88 0.37 Trace 2. 14 1 5.92 Hyuganatsu 4.68 3.73 0.28 Trace 0.35 9.04 Sanbokan 3.95 1.02 0.30 0.16 1.36 6.79 Shimamikan 7.85 2.01 0.28 0.16 2.01 12.31 Grapefruit 19.06 1.84 1.8.6 Trace 1. 1-0 23.86 Lemon 8.95 3.03 0.58 Trace Trace 12.56 Valencia 10.00 2.30 0.08 1. 16 1.24 14.78 Tangerine 4.10 1.37 0.35 0.38 3.1 1 9.31 Units are mg/g of dry seed.
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