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Anthocyanins and Other Flavonoids from Amorphophallus Titanum Having Largest Inflorescence in Plant Kingdom, and Other Two Species

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Anthocyanins and Other Flavonoids from Amorphophallus Titanum Having Largest Inflorescence in Plant Kingdom, and Other Two Species Bull. Natl. Mus. Nat. Sci., Ser. B, 41(1), pp. 33–44, February 20, 2015 Anthocyanins and Other Flavonoids from Amorphophallus titanum Having Largest Inflorescence in Plant Kingdom, and Other Two Species Tsukasa Iwashina1,*, Ayumi Uehara1,2, Junichi Kitajima3 and Tomohisa Yukawa1 1 Department of Botany, National Museum of Nature and Science, Amakubo 4–1–1, Tsukuba, Ibaraki 305–0005, Japan 2 Department of Chemistry, Hiyoshi Campus, Keio University, Hiyoshi 4–1–1, Kohoku-ku, Yokohama, Kanagawa 223–8521, Japan 3 Laboratory of Pharmacognosy, Showa Pharmaceutical University, Higashi-tamagawagakuen 3, Machida, Tokyo 194–8543, Japan * E-mail: [email protected] (Received 8 November 2014; accepted 24 December 2014) Abstracts Amorphophallus titanum has a largest inflorescence of the plant kingdom. In this sur- vey, five anthocyanins and 14 other flavonoids were isolated from the spathe and spadix appendix of A. titanum. Anthocyanins were identified as cyanidin 3-O-glucoside, cyanidin 3-O-rutinoside, peonidin 3-O-glucoside, peonidin 3-O-rutinoside and pelargonidin 3-O-rhamnosylglucoside. On the other hand, other flavonoids were characterized as vitexin, vitexin 2″-O-glucoside, isovitexin, isovitexin 2″-O-glucoside, orientin, isoorientin, vicenin-2, lucenin-2, schaftoside, isoschaftoside, isovitexin X″-O-rhamnoside, isoscoparin X″-O-glucoside (C-glycosylflavones), chrysoeriol 7-O-glucoside (flavone) and kaempferol 3-O-robinobioside (flavonol). Anthocyanins and other fla- vonoids in the inflorescences of other two Amorphophallus species, A. rivieri and A. paeoniifolius were also isolated and identified. Key words : Amorphophallus paeoniifolius, Amorphophallus rivieri, Amorphophallus titanum, Anthocyanins, Flavonols, C-Glycosylflavones. 2004). Introduction Amorphophallus paeoniifolius grows in Sri The genus Amorphophallus is mainly distrib- Lanka, the Philippines, Malaysia, Indonesia, and uted in the tropical zone of the Old World and other Southeast Asia countries. Flavonol, querce- consists of 80–90 species (Ohashi, 1982). Of tin, has been isolated from the corm of the spe- their species, A. titanum is endemic to Sumatra cies (Sharstry et al., 2010). Amorphophallus riv- Island and has the largest inflorescence, ca. 3 m ieri is native to Indochina and southern China high and 1 m wide, of the plant kingdom. Its and cultivated in Japan for edible. However, flowering in the botanical gardens is very rare. In polyphenols including flavonoids are not 2012 and 2014, the flowers of the species came reported until now. out at the Tsukuba Botanical Garden, National As the flavonoids of other Amorphophallus Museum of Nature and Science, Japan. The species, anthocyanin, cyanidin 3-O-rutinoside spathe and spadix appendix of the species are has been found in the spathe of A. abyssinicus dark purple and their anthocyanins have been (A.Rich.) N.E.Brown and A. stuhlmannii (Engl.) reported to be cyanidin 3-O-glucoside and Engl. & Gehrm. (Williams et al., 1981). A rare 3-O-rutinoside, and peonidin and pelargonidin flavonol, 3,5-diacetyltambulin (7,8,4′-trimethoxy- 3-O-(p-coumaloylglucosides) (Gallori et al., 3,5-diacetoxyflavone), has been isolated from the 34 Tsukasa Iwashina et al. tuberous roots of A. campanulatus Blume ex tems, BBPW (n-BuOH/benzene/pyridine/H2O＝ Decne (＝A. paeoniifolius) (Khan et al., 2008). 5 : 1 : 3 : 3) and BTPW (n-BuOH/toluene/pyridine/ Unknwon C-glycosylflavone was detected from H2O＝5 : 1 : 3 : 3). The solvent systems of qualita- the leaves of A. stuhlmannii (Williams et al., tive TLC (Merck, Germany) and preparative 1981). In this paper, we describe the isolation paper chromatography (PPC) are as follows; and identification of the anthocyanins, flavone, BAW (n-BuOH/HOAc/H2O＝4 : 1 : 5, upper phase), flavonols and C-glycosylflavones from the inflo- BEW (n-BuOH/EtOH/H2O＝4 : 1 : 2.2) and 15% rescences of three Amorphophallus species, A. HOAc. NMR spectra were measured in pyridine- 1 13 titanum, A. paeoniifolius and A. rivieri. d5 at 600 MHz ( H NMR) and 150 MHz ( C NMR). Materials and Methods Plant materials General Three Amorphophallus species, A. titanum UV spectra were recorded on a Shimadzu (Becc.) Becc. ex Arcangeli (TBG157495), A. MPS-2000 Multipurpose recording spectropho- paeoniifolius (Dennst.) Nicolson (TBG84663) tometer (Shimadzu, Japan) according to Mabry and A. rivieri Durieu (＝A. konjac K.Koch) et al. (1970). LC-MS were measured on Shi- (TBG157597) (Fig. 1) were used as plant materi- madzu LC-MS systems using Inertsil ODS-4 col- als. They are cultivated in the Tsukuba Botanical umn [I.D. 2.1×100 mm (GL Sciences, Japan)], Garden, National Museum of Nature and Sci- at a flow-rate of 0.1 ml min－1, eluting with ence, Tsukuba, Japan. MeCN/H2O/HCOOH (5 : 90 : 5) for anthocyanins and (12 : 83 : 5 or 15 : 80 : 5) for other flavonoids, Extraction and separation ESI＋ 4.5 kV and ESI－ 3.5 kV, 250˚C. HPLC sur- Fresh spathe (454 g) and spadix appendix vey of the isolated compounds and crude extracts (945 g) of A. titanum, and fresh inflorescences was performed with a Shimadzu HPLC systems (138 g and 300 g) of A. paeoniifolius and A. rivieri using Inertsil ODS-4 column (I.D. 6.0×150 mm) were extracted with MeOH : HCOOH (92 : 8). at a flow-rate of 1.0 ml min－1, eluting with After filtration, the concentrated extracts were MeCN/HOAc/H2O/H3PO4 (10 : 8 : 79 : 3) (Solv. I) applied to PPC using solvent systems, BAW and for anthocyanins, a Senshu Pak Pegasil ODS col- 15% HOAc. Other flavonoids were further sepa- umn (I.D. 6.0×150 mm, Senshu Scientific Co. rated with solvent system, BEW. The isolated Ltd., Japan) at a flow-rate of 1.0 ml min－1, elut- anthocyanins and other flavonoids were purified ing with MeCN/H2O/H3PO4 (15 : 85 : 0.2) (Solv. by Sephadex LH-20 column chromatography II) and (18 : 82 : 0.2) (Solv. III) for other flavo- using solvent systems, MeOH/H2O/HCOOH noids. Detection wave length was 530 nm for (70 : 25 : 5) and 70% MeOH, respectively. anthocyanins and 350 nm for other flavonoids. Acid hydrolyses of the anthocyanins and other Identification flavonoids were performed in 12% HCl, 100°C, The isolated compounds were identified by 30 min. After reaction, isoamyl alcohol (anthocy- UV spectroscopy, LC-MS, characterization of anins) or diethyl ether (other flavonoids) was acid hydrolysates, 1H and 13C NMR, and TLC added in the solution. Aglycones migrated to and HPLC comparisons with authentic samples. organic layer, and glycosidic sugars and C-glyco- TLC, HPLC, LC-MS and NMR data of the iso- sylflavones remained in aqueous layer. Agly- lated compounds are as follow. cones and C-glycosylflavones were identified by Cyanidin 3-O-glucoside (chrysanthemin, 1). HPLC comparisons with authentic samples, and HPLC: tR (min) 8.22 (solv. I). UV: λmax (nm) sugars were compared with authentic sugars by 0.01%MeOH-HCl 282, 529; ＋AlCl3 556; E440/ ＋ paper chromatography or TLC using solvent sys- Emax 28%. LC-MS: m/z 449 [M] (molecular ion Anthocyanins and Flavonoids from Amorphophallus titanum 35 Fig. 1. Three Amorphophallus species used as plant materials. peak, cyanidin＋1 mol glucose), m/z 287 pelargonidin). [M－162]＋ (fragment ion peak, cyanidin). Cyanidin 3-O-diglucoside (6). HPLC: tR (min) Cyanidin 3-O-rutinoside (keracyanin, 2). 6.18 (solv. I). UV: λmax (nm) 0.01%MeOH-HCl HPLC: tR (min) 9.22 (solv. I). UV: λmax (nm) 280, 527; ＋AlCl3 546; E440/Emax 25%. LC-MS: ＋ 0.01%MeOH-HCl 280, 527; ＋AlCl3 546; E440/ m/z 611 [M] (molecular ion peak, cyani- ＋ ＋ Emax 29%. LC-MS: m/z 595 [M] (molecular ion din＋2 mol glucose), m/z 287 [M－324] (frag- peak, cyanidin＋each 1 mol rhamnose and glu- ment ion peak, cyanidin). cose), m/z 287 [M－308]＋ (fragment ion peak, Pelargonidin 3-O-glucoside (callistephin, 7). cyanidin). HPLC: tR (min) 11.72 (solv. I). UV: λmax (nm) Peonidin 3-O-glucoside (oxycoccicyanin, 3). 0.01%MeOH-HCl 272, 512; ＋AlCl3 513; E440/ ＋ HPLC: tR (min) 16.81 (solv. I). LC-MS: m/z 463 Emax 42%. LC-MS: m/z 433 [M] (molecular ion [M]＋ (molecular ion peak, peonidin＋1 mol glu- peak, pelargonidin＋1 mol glucose). cose), m/z 301 [M－162]＋ (fragment ion peak, Vitexin (8). TLC: Rf 0.48 (BAW), 0.44 peonidin). (BEW), 0.16 (15%HOAc); color UV (365 nm) Peonidin 3-O-rutinoside (4). HPLC: tR (min) dark purple, UV/NH3 dark greenish yellow. 17.82 (solv. I). UV: λmax (nm) 0.01%MeOH- HPLC: tR (min) 6.11 (solv. II). UV: λmax (nm) HCl 280, 529; ＋AlCl3 528; E440/Emax 30%. MeOH 270, 329; ＋NaOMe 278, 326, 394 (inc.); ＋ LC-MS: m/z 609 [M] (molecular ion peak, ＋AlCl3 275, 304, 346, 377sh; ＋AlCl3/HCl 274, peonidin＋each 1 mol rhamnose and glucose), 303, 344, 376sh; ＋NaOAc 279, 310, 390; ＋ m/z 301 [M－308] (fragment ion peak, peoni- ＋NaOAc/H3BO3 271, 344. LC-MS: m/z 431 din). [M－H]– (molecular ion peak, apigenin＋1 mol Pelargonidin 3-O-rhamnosylglucoside (5). glucose). HPLC: tR (min) 13.86 (solv. I). UV: λmax (nm) Vitexin 2″-O-glucoside (9). TLC: Rf 0.36 0.01%MeOH-HCl 277, 512; ＋AlCl3 512. (BAW), 0.40 (BEW), 0.59 (15%HOAc); color ＋ LC-MS: m/z 579 [M] (molecular ion peak, UV (365 nm) dark purple, UV/NH3 dark greenish pelargonidin＋each 1 mol rhamnose and glu- yellow. HPLC: tR (min) 6.37 (solv. II). UV: cose), m/z 271 [M－308]＋ (fragment ion peak, λmax (nm) MeOH 270, 334; ＋NaOMe 280, 36 Tsukasa Iwashina et al. 330, 397 (inc.); ＋AlCl3 277, 303, 349, 383; (BEW), 0.40 (15%HOAc); color UV (365 nm) ＋AlCl3/HCl 278, 302, 343, 382sh; ＋NaOAc dark purple, UV/NH3 dark greenish yellow. 280, 312, 392; ＋NaOAc/H3BO3 271, 345.
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