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Ultraviolet-Absorbing Substances in the Translucent Bracts of Davidia Involucrata (Davidiaceae)

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Ultraviolet-Absorbing Substances in the Translucent Bracts of Davidia Involucrata (Davidiaceae) Bull. Natl. Mus. Nat. Sci., Ser. B, 35(1), pp. 1–9, March 22, 2009 Ultraviolet-absorbing Substances in the Translucent Bracts of Davidia involucrata (Davidiaceae) Seiko Takemura1, Junichi Kitajima2 and Tsukasa Iwashina1,3* 1 Graduate School of Agriculture, Ibaraki University, Ami, 300–0393 Japan 2 Laboratory of Pharmacognosy, Showa Pharmaceutical University, Higashi-tamagawagakuen 3, Machida, Tokyo, 194–8543 Japan 3 Department of Botany, National Museum of Nature and Science, Amakubo 4–1–1, Tsukuba, 305–0005 Japan * Corresponding author: E-mail: [email protected] Abstract Ultraviolet-absorbing substances in the bracts of Davidia involucrata, which is endem- ic to China, were surveyed. Two large translucent bracts of the species put on the inflorescence such as a parasol and selectively absorbed UV radiation, though visible light almost completely transmitted. It was shown by high performance liquid chromatography (HPLC) that much amounts of UV-absorbing substances are accumulated. Seven flavonol glycosides were isolated by various chromatographic techniques such as paper, column and HPLC, and identified as quercetin 3-O- sambubioside, quercetin 3-O-galactoside, quercetin 3-O-glucoside, quercetin 3-O-arabinoside, kaempferol 3-O-galactoside, quercetin 3-O-(2Љ-acetylgalactoside) and quercetin 3-O-(acetylgluco- side) by UV spectral survey, LC-MS, 1H and 13C NMR, acid hydrolysis, and direct TLC and HPLC comparisons with authentic samples. Thus, it was proved that the flavonol glycosides, especially quercetin 3-O-galactoside and 3-O-glucoside, act as the important UV shields in the translucent bracts of D. involucrata and protect the inflorescence from noxious UV radiation. Key words :Davidiaceae, Davidia involucrata, Flavonols, Quercetin 3-O-glycosides, UV shields. flavonoids and related UV-absorbing substances Introduction (Robberecht and Caldwell, 1978). Since many of Ultraviolet radiation is noxious for all organ- the UV-absorbing compounds of plant cells are isms including human. The plants, especially contained within the vacuole (McClure, 1975), green plants, are directly exposed to not only vis- this is the site for much of the UV absorption in ible light but also UV radiation. Photosyntheti- the epidermis. Thus, flavonoid compounds as UV cally active radiation penetrates effectively into shields have been reported from various plant the mesophyll and is attenuated by as little as 20 species, e.g., quercetin 3-O-(3Љ,6Љ-p-coumaroyl- to 30% as it passes through the epidermis (Cald- glucoside) and kaempferol 3-O-(3Љ,6Љ-p- well et al., 1983). Nuclei are organelles where coumaroylglucoside) from Pinus sylvestris L. primary lesions can result from UV radiation, es- (Pinaceae) (Jungblut et al., 1995), quercetin 3-O- pecially UV-B (Brandle et al., 1977; Howland, galactoside, myricetin 3-O-rutinoside and two p- 1975). Generally, radiation should be selectively coumaroyl kaempferol 3-O-glucosides from filtered to remove the short wavelength UV com- Quercus ilex L. (Fagaceae) (Skaltsa et al., 1994), ponent before it reaches the nuclei and chloro- and quercetin, apigenin and luteolin glycosides plasts. The wavelength selectivity of absorption from Olea europaea L. (Oleaceae) (Karabournio- in the epidermis of most plant species is much tis et al., 1992). more pronounced and can often be attributed to Recently, eight flavonol glycosides were isolat- 2 Seiko Takemura et al. Fig. 1. The bracts of Davidia involucrata, and UV-A and UV-B contents (w/m2) in sunshine before and after passing the translucent bract. ed as UV-absorbing substances from the translu- as Kyrgyz, Kazakhstan, Mongolia and China. cent bracts of Rheum nobile Hook. f. et Thomson From their bracts and also leaves, much amount (Polygonaceae), which grows in the alpine zone of quercetin 3-O-rutinoside, which may be acts of the eastern Himalayas (Iwashina et al., 2004). as UV shields, has been isolated together with Their flavonoids were identified as quercetin 3- four minor flavone glycosides, apigenin, luteolin, O-[6Љ-(3-hydroxy-3-methylglutaroyl)-glucoside], hispidulin and nepetin 7-O-glucosides (Kusano et quercetin 3-O-glucoside, quercetin 3-O-galacto- al., 2007). side, quercetin 3-O-rutinoside, quercetin 3-O- Davidia involucrata Baill. is endemic to south- arabinoside, quercetin itself, quercetin 7-O-gly- western China (Mabberley, 1997) and is some- coside and kaempferol glycoside. Of their com- times cultivated in the gardens and parks as orna- pounds, the former five glycosides were major mentals. We noticed that the two translucent ones and have been shown to be the important bracts, which bear in spring, put on the inflores- UV shields in this species (Iwashina et al., cence such as a parasol, and presumed that UV- 2004). Quercetin 3-O-[6Љ-(3-hydroxy-3-methyl- absorbing substances, e.g., flavonoids, are accu- glutaroyl)-glucoside] was a new acylated flavonol mulated in the bracts such as Rheum nobile and glycoside. Saussurea involucrata. Saussurea involucrata Karel. et Kir. (Aster- The flavonoid compounds have been isolated aceae) also put the large translucent cream-col- from the leaves of D. involucrata and identified ored bracts concealing the huge inflorescence as quercetin 3-O-glucoside, quercetin 3-O-galac- and grows in the alpine zone of central Asia such toside, quercetin 3-O-arabinoside and kaempfer- UV-absorbing substances in the bracts of Davidia 3 ol 3-O-galactoside (Iwashina and Hatta, 1998). ODS column (I.D. 10.0ϫ250 mm, Senshu Scien- Ouyang and Zhou (2003) have been surveyed the tific Co. Ltd.) at flow-rate: 1.5 ml minϪ1, detec- leaves for flavonoids and isolated kaempferol, tion: 350 nm and eluent: HCOOH/MeCN/H2O kaempferol 3-O-glucoside and quercetin in addi- (1 : 20 : 79). tion to the above flavonoids. Of their compounds, quercetin 3-O-galactoside has also been found in Liquid chromatograph-mass spectra (LC-MS) the bracts as a major flavonoid, together with LC-MS was measured using a PEGASIL ODS minor quercetin 3-O-rhamnoside (Rast, 1968). column (I.D. 2.0ϫ150 mm; Senshu Scientific Co. In this paper, we describe the identification of Ltd.), at flowe-rate of 0.2 ml minϪ1, eluent: ϩ the flavonoid glycosides in the bracts and func- MeCN/H2O/HCOOH (22 : 78 : 1), and ESI tion of their compounds as UV filter. 4.5 kV, ESIϪ 3.5 kV, 250°C. Extraction and isolation of UV absorbing sub- Materials and Methods stances Plant materials Fresh bracts (ca. 39 g) were extracted with Davidia involucrata Baill. is cultivated in the MeOH. After evaporation, the extracts were Tsukuba Botanical Garden, National Museum of applied to preparative paper chromatography Nature and Science, Tsukuba, Japan (Acc. no. (PPC) using solvent systems: BAW (n- ϭ TBG 43668). The fresh bracts were collected in BuOH/HOAc/H2O 4:1:5, upper phase), 15% ϭ May, 2004. HOAc and then BEW (n-BuOH/EtOH/H2O 4:1:2.2). The isolated compounds were finally Measurement of UV radiation in sunshine, and purified by Sephadex LH-20 column chromatog- direct UV-visible spectral survey of bracts raphy using solvent system: 70% MeOH. Of UV-A (355nm) and B (313 nm) radiation in seven compounds (1–7) detected by HPLC sur- sunshine before and after passing the translucent vey, 1 and 3 were obtained as pure solutions, and bract was measured by UV monitor MS-211-I 2 and 3, and 5 and 6 as the mixtures, respectively. (EKO Co. Ltd.). UV-visible spectra of the fresh Compound 4 could not be isolated for the minute bracts were surveyed on a Shimadzu MPS-2000 amount. For further isolation of minor com- multi purpose recording spectrophotometer be- pounds 5 and 6, fresh bracts (136 g) were collect- tween 300 and 700 nm. ed in May, 2005 and extracted with MeOH. After application to PPC, they were isolated by prepar- Qualitative and quantitative HPLC of crude ex- ative HPLC and obtained as pale yellow powder tract and isolated UV absorbing substances (5) and pure solution (6). Qualitative HPLC survey of the crude extracts from the bracts and the isolated UV-absorbing Identification of UV absorbing substances substances were performed with Shimadzu UV absorbing substances were identified by HPLC systems using a Shim-pack CLC-ODS UV spectral survey according to Mabry et al. (I.D. 6.0ϫ150 mm; Shimadzu) at flow-rate: (1970), LC-MS, acid hydrolysis (in 12% aq.HCl, Ϫ 1.0 ml min 1, detection: 190–700 nm and eluent: 100°C, 30 min) and characterization of its prod- 1 13 MeCN/H2O/H3PO4 (22 : 78 : 0.2). Fresh bracts ucts, H and C NMR (in pyridine-d5, 500 MHz (0.1 g) were extracted with MeOH (2 ml) for for 1H NMR and 125 MHz for 13C NMR), direct quantitative HPLC survey. After keeping for 1 TLC and HPLC comparisons with authentic sam- day in room temperature, the extracts were fil- ples. TLC, HPLC, LC-MS, and 1H and 13C NMR tered and analysed by HPLC. data of UV absorbing substances are as follows. Preparative HPLC was performed with Tosoh Quercetin 3-O-sambubioside (1). TLC: Rf HPLC systems using a Senshu-pak PEGASIL 0.42 (BAW), 0.42 (BEW), 0.47 (15% HOAc); 4 Seiko Takemura et al. 262, 297, 373. LC-MS: m/z 477 [MϩH]ϩ and m/z 475 [MϪH]Ϫ. 1H NMR (500 MHz, pyridine- ϭ d5): d 13.43 (1H, s, 5-OH), 8.35 (1H, d, J 2.1 Hz, H-2Ј), 8.20 (1H, dd, Jϭ2.1 and 8.4 Hz, H- 6Ј), 7.30 (1H, d, Jϭ8.6 Hz, H-5Ј), 6.71 (1H, d, Jϭ1.8 Hz, H-8), 6.62 (1H, d, Jϭ2.1 Hz, H-6), 6.29 (1H, d, Jϭ7.6 Hz, galactosyl H-1), 6.27 (1H, d, Jϭ6.7 Hz, galactosyl H-2), 4.64 (1H, d, Jϭ2.7 Hz, galactosyl H-4), 4.39 (1H, m, galacto- syl H-6a), 4.38 (1H, m, galactosyl H-3), 4.27 (1H, dd, Jϭ5.8 and 11.0 Hz, galactosyl H-6b), 4.18 (1H, t, Jϭ12.5 Hz, galactosyl H-5), 2.16 13 (3H, s, acetyl CH3).
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