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04-T. Iwashina-4.02 Bull. Natl. Mus. Nat. Sci., Ser. B, 36(1), pp. 27–32, February 22, 2010 Flavone O- and C-Glycosides from Pothos chinensis (Araceae) Tsukasa Iwashina1,*, Ching-I Peng2 and Goro Kokubugata1 1 Department of Botany, National Museum of Nature and Science, Amakubo 4–1–1, Tsukuba, 305–0005 Japan 2 Research Center of Biodiversity Academia Sinica, Taipei, Nangang, Taipei 115, Taiwan *E-mail: [email protected] (Received 23 October 2009; accepted 18 December 2009) Abastract Nine flavonoid glycosides were isolated from the aerial parts of Pothos chinensis. Of their flavonoids, eight ones were identified as vitexin, vitexin 7-O-glucoside, isovitexin 7-O-gluco- side, scoparin 7-O-glucoside, isoscoparin 7-O-glucoside, schaftoside, isoschaftoside and chrysoe- riol 7-O-rhamnosylglucoside. Another flavonoid was characterized as vitexin 7-O-diglucoside or vitexin 7,XЉ-di-O-glucoside. The flavonoids of P. chinensis were reported in this paper for the first time. Key words : Araceae, flavone glycosides, flavonoids, Pothos chinensis. (L.) Schott) and identified as orientin, isoori- Introduction entin, isovitexin, vicenin-2, orientin 7-O-gluco- The genus Pothos belongs to the family side, isovitexin 4Ј-O-glucoside, vitexin XЉ-O- Araceae and consists of ca. 50 species (Mabber- glucoside, and luteolin 7-O-glucoside (Iwashina ley, 1997). In Taiwan and Japan, P. chinensis et al., 1999). The anthocyanins, cyanidin and (Raf.) Merr. is only growing. Though the species pelargonidin glycosides were found in two An- is abundant at medium elevations through Tai- thurium species, and cyanidin and delphinidin wan (Huang, 2000), it is endemic to Daito Is- glycosides in three Philodendron species lands in Japan (Hatusima and Amano, 1994) and (Forsyth and Simmonds, 1954), cyanidin 3,5-di- nominated as endangered plant by the Ministry O-glucoside in the spathe of Arisaema serratum of Environment, Japan (Environment Agency of Schott. f. thunbergii Makino (Ueno et al., 1969), Japan, 2000). pelargonidin 3-O-glucoside, cyanidin 3-O-rham- Flavonoids of the family Araceae have roughly noside and cyanidin 3-O-glucoside in the peeled been investigated by Williams et al. (1981). They corms of taro (Chan Jr. et al., 1977), and cyani- were surveyed the leaf flavonoids of 144 species din and peonidin glycosides in the spathe of Sym- from 58 genera and showed that flavone C-glyco- plocarpus foetidus Nutt. var. latissimus (Makino) sides are the most characteristic flavonoid con- Hara (Yoshitama et al., 1980). Common flavones stituents of the family. In inflorescence, fruits, and C-glycosylflavones, apigenin, luteolin, vitex- leaf or petiole of 59 representative species, they in, isovitexin, orientin, isoorientin and isovitexin were detected cyanidin 3-O-rutinoside as a com- 7-O-glucoside were isolated from the leaves of mon anthocyanin, together with pelargonidin Synandrospadix vermitoxicus (Grisebach) Engler 3-O-rutinoside and cyanidin 3-O-glucoside which is a monotypic species and grows in Ar- (Williams et al., 1981). Eight C-glycosylflavones gentina and Bolivia (Sosa et al., 1978). Vitexin and a flavone O-glycoside were isolated from the 2Љ-O-glucoside and its sinapoyl derivative were leaves of cultivated taro (Colocasia esculenta reported from Cryptocoryne spp. as their chemo- 28 Tsukasa Iwashina et al. Fig. 1. Pothos chinensis (Raf.) Merr. taxonomic marker (Franke et al., 2006). The for- Extraction and isolation of flavonoids mer compound was also found in Lasia spinosa Fresh aerial parts (35.4 g) of P. chinensis were (L.) Thw. native to Vietnam, together with vitex- extracted with MeOH. The concentrated extracts in and a flavonol glycoside, isorhamnetin 3-O- were applied to preparative paper chromatogra- rutinoside (Hong Van et al., 2006). Another phy using solvent systems: BAW (n-BuOH/ ϭ flavonol glycoside, kaempferol 3-O-sophoroside- HOAc/H2O 4 : 1 : 5, upper phase), 15% HOAc ϭ 7-O-rhamnoside was isolated from the leaves of and then BEW (n-BuOH/EtOH/H2O 4 : 1 : 2.2). Gymnostachys anceps R. Br. (Williams et al., The isolated flavonoids were purified by 1971). However, flavonoid compounds in Pothos Sephadex LH-20 column chromatography using species have not been reported until now. In this solvent system: 70% MeOH. paper, flavonoid glycosides in the aerial parts of Pothos chinensis are described. High performance liquid chromatography (HPLC) HPLC was performed with Shimadzu HPLC systems using a PEGASIL ODS column (I.D. Materials and Methods 6.0ϫ150 mm: Senshu Scientific Co. Ltd.), at a Plant materials flow-rate of 1.0 ml minϪ1. Detection was 190– Pothos chinensis (Raf.) Merr. (Fig. 1) was col- 700 nm and eluent was MeCN/H2O/H3PO4 lected in hiking way to Shihfen Waterfall, (18 : 82 : 0.2). Pingchi Hsiang, Taipei, Taiwan, during 5 Novem- ber, 2006. Liquid chromatograph-mass spectra (LC-MS) LC-MS was measured using a PEGASIL ODS column (I.D. 2.0ϫ150 mm, Senshu Scientific Co. Flavone Glycosides from Pothos chinensis 29 Ltd.), at a flow-rate of 0.2 ml minϪ1, eluent was 274, 285sh, 351. LC-MS: m/z 625 [MϩH]ϩ, 623 ϩ Ϫ Ϫ ϩ MeCN/H2O/HCOOH (15 : 80 : 5), by ESI [M H] (chrysoeriol 2 mol hexose). 4.5 kV and ESIϪ 3.5 kV, 250°C. Isoscoparin 7-O-glucoside (5). TLC: Rf 0.08 (BAW), 0.06 (BEW), 0.12 (15% HOAc); UV— Identification of flavonoids dark purple, UV/NH3—yellow. HPLC: Rt 8.03 The isolated flavonoids were identified by UV min. UV: l max (nm) MeOH 252, 270sh, 348; ϩ ϩ spectra according to Mabry et al. (1970), LC- NaOMe 250, 264sh, 392 (inc.); AlCl3 264, ϩ MS, acid hydrolysis and characterization of their 273sh, 304sh, 361; AlCl3/HCl 274sh, 305sh, products, and direct TLC and HPLC compar- 360; ϩNaOAc 258, 286sh, 410; ϩNaOAc/ isons with authentic standards. TLC, HPLC, UV H3BO3 267sh, 286sh, 349. LC-MS: m/z 625 and LC-MS data of the isolated flavonoids were [MϩH]ϩ, 623 [MϪH]Ϫ (chrysoeriolϩ2 mol hex- as follows. ose). Vitexin (1). TLC: Rf 0.45 (BAW), 0.48 Schaftoside (6). TLC: Rf 0.22 (BAW), 0.18 (BEW), 0.16 (15% HOAc); UV—dark purple, (BEW), 0.51 (15% HOAc); UV—dark purple, UV/NH3—dark greenish yellow. HPLC: Rt 10.90 UV/NH3—dark greenish yellow. HPLC: Rt 6.63 ϩ ϩ min. UV: l max (nm) MeOH 270, 331; NaOMe min. UV: l max (nm) MeOH 273, 333; NaOMe ϩ ϩ 279, 328, 393 (inc.); AlCl3 276, 305, 354, 283, 331, 400 (inc.); AlCl3 278, 306, 354, ϩ ϩ 384sh; AlCl3/HCl 276, 303, 349, 383sh; 386sh; AlCl3/HCl 278, 304, 349, 386sh; ϩ ϩ ϩ ϩ NaOAc 279, 311, 389; NaOAc/H3BO3 272, NaOAc 282, 398; NaOAc/H3BO3 276sh, 344. LC-MS: m/z 433 [MϩH]ϩ, 431 [MϪH]Ϫ 285, 322, 348sh. LC-MS: m/z 565 [MϩH]ϩ, 563 (apigeninϩ1 mol hexose). [MϪH]Ϫ (apigeninϩeach 1 mol hexose and pen- Vitexin 7-O-glucoside (isosaponarin, 2). TLC: tose). Rf 0.09 (BAW), 0.10 (BEW), 0.20 (15% HOAc); Isoschaftoside (7). TLC: Rf 0.22 (BAW), 0.18 UV—dark purple, UV/NH3—dark yellow. (BEW), 0.33 (15% HOAc); UV—dark purple, HPLC: Rt 6.81 min. UV: l max (nm) MeOH 269, UV/NH3—dark greenish yellow. HPLC: Rt 6.47 ϩ ϩ ϩ 332; NaOMe 275, 384 (inc.); AlCl3 275, min. UV: l max (nm) MeOH 273, 333; NaOMe ϩ ϩ 303, 349, 377sh; AlCl3/HCl 276, 302, 343, 283, 331, 400 (inc.); AlCl3 278, 306, 354, ϩ ϩ ϩ 375sh; NaOAc 257sh, 269, 392; NaOAc/ 386sh; AlCl3/HCl 278, 304, 349, 386sh; ϩ ϩ ϩ ϩ H3BO3 270, 342. LC-MS: m/z 595 [M H] , 593 NaOAc 282, 398; NaOAc/H3BO3 276sh, [MϪH]Ϫ (apigeninϩ2 mol hexose). 285, 322, 348sh. LC-MS: m/z 565 [MϩH]ϩ, 563 Isovitexin 7-O-glucoside (saponarin, 3). TLC: [MϪH]Ϫ (apigeninϩeach 1 mol hexose and pen- Rf 0.25 (BAW), 0.26 (BEW), 0.60 (15% HOAc); tose). UV—dark purple, UV/NH3—dark yellow. Chrysoeriol 7-O-rhamnosylglucoside (8). TLC: HPLC: Rt 6.34 min. UV: l max (nm) MeOH 272, Rf 0.44 (BAW), 0.43 (BEW), 0.08 (15% HOAc); ϩ ϩ 333; NaOMe 274, 386 (inc.); AlCl3 278, UV—dark purple, UV/NH3—yellow. UV: l max ϩ ϩ 301, 352, 376sh; AlCl3/HCl 278, 300, 345, (nm) MeOH 251, 268, 345; NaOMe 264, ϩ ϩ ϩ 375sh; NaOAc 257sh, 270, 391; NaOAc/ 300sh, 391 (inc.); AlCl3 273sh, 300, 360, ϩ ϩ ϩ H3BO3 271, 338. LC-MS: m/z 595 [M H] , 593 387sh; AlCl3/HCl 273sh, 301, 358, 387sh; Ϫ Ϫ ϩ ϩ ϩ [M H] (apigenin 2 mol hexose). NaOAc 258, 264sh, 405; NaOAc/H3BO3 267, Scoparin 7-O-glucoside (4). TLC: Rf 0.21 348. LC-MS: m/z 609 [MϩH]ϩ (chrysoeriolϩ (BAW), 0.26 (BEW), 0.50 (15% HOAc); UV— each 1 mol hexose and rhamnose), 463 [MϪ ϩ ϩ ϩ dark purple, UV/NH3—dark yellow. HPLC: Rt 146 H] (chrysoeriol 1 mol hexose). Љ 7.18 min. UV: l max (nm) MeOH 255sh, 272, 342; Vitexin 7-O-diglucoside or 7,X -di-O-gluco- ϩ ϩ NaOMe 281, 398 (inc.); AlCl3 264sh, 277, side (9). TLC: Rf 0.11 (BAW), 0.13 (BEW), 0.75 ϩ 301, 358; AlCl3/HCl 260sh, 278, 301, 354; (15% HOAc); UV—dark purple, UV/NH3—dark ϩ ϩ NaOAc 271, 280sh, 406; NaOAc/H3BO3 yellow. HPLC: Rt 5.38 min. UV: l max (nm) 30 Tsukasa Iwashina et al. MeOH 269, 332; ϩNaOMe 275, 384 (inc.); ϩ ϩ AlCl3 275, 303, 349, 377sh; AlCl3/HCl 276, 302, 343, 375sh; ϩNaOAc 257sh, 269, 392; ϩ NaOAc/H3BO3 270, 342. LC-MS: m/z 757 [MϩH]ϩ (apigeninϩ3 mol hexose), 595 [MϪ 162ϩH]ϩ (apigeninϩ2 mol hexose).
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