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Phenolic Compounds from the Leaves of Castanopsis Fargesii

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Phenolic Compounds from the Leaves of Castanopsis Fargesii molecules Article Phenolic Compounds from the Leaves of Castanopsis fargesii Yong-Lin Huang 1,*, Ya-Feng Wang 1, Jin-Lei Liu 1, Lei Wang 1, Takashi Tanaka 2, Yue-Yuan Chen 1, Feng-Lai Lu 1 and Dian-Peng Li 1 1 Guangxi Key Laboratory of Functional Phytochemicals Research and Utilization, Guangxi Institute of Botany, Guangxi Zhuang Autonomous Region and Chinese Academy of Sciences, Guilin 541006, China; [email protected] (Y.-F.W.); [email protected] (J.-L.L.); [email protected] (L.W.); [email protected] (Y.-Y.C.); [email protected] (F.-L.L.); [email protected] (D.-P.L.) 2 Department of Natural Product Chemistry, Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan; [email protected] * Correspondence: [email protected]; Tel.: +86-773-355-0829; Fax: +86-773-355-0067 Academic Editor: Derek J. McPhee Received: 6 October 2016; Accepted: 13 January 2017; Published: 19 January 2017 Abstract: In the course of a phytochemical and chemotaxonomical investigation of Castanopsis species 0 0 00 (Fagaceae), three new phenolic compounds, (3R,1 S)-[1 -(6 -O-galloyl-β-D-gluco-pyranosyl)oxyethyl]- 3-hydroxy-dihydrofuran-2(3H)-one (1), (2R,3S)-2-[20-(galloyl)oxyethyl]-dihydroxybutanoic acid (2), and (3S,4S)-3-hydroxymethyl-3,4-dihydro-5,6,7-trihydroxy-4-(40-hydroxy-30-methoxyphenyl)-1H-[2]- benzopyran-1-one (3) were isolated from the fresh leaves of Castanopsis fargesii. In addition, a known phenolic glycoside, gentisic acid 5-O-α-L-rhamnopyranosyl-(1!2)-β-D-glucopyranoside (4) was also isolated and identified. Their structures were elucidated by means of spectroscopic methods including one- and two-dimensional NMR techniques. Keywords: Castanopsis fargesii; Castanopsis; phenolic; cytotoxicity 1. Introduction The genus Castanopsis belongs to the Fagaceae family and is commonly found in the evergreen forests of East Asia. There are about 120 species of Castanopsis, however, the classical plant taxonomy of the species is very complicated and sometimes confusing [1], thus, the application of other auxiliary methods and technologies, such as chemotaxonomy and cytotaxonomy, is necessary to identify species within this genus [2]. Previous phytochemical investigations on the plants of this genus C. fissa, C. cuspidata var. seiboldii, and C. hystrix have led to the isolation of triterpene hexahydroxydiphenoyl (HHDP) esters, HHDP glucoses, galloyl, acylated quinic acids, phenol glucosides, condensed tannins, and flavonol glycosides [3–8]. In this study, we investigated C. fargesii, which is widely distributed in southern China, where it is usually used as a traditional medicine for the treatment of diarrhea, hemorrhage, and chronic ulcers [1]. Our preliminary analysis by HPLC and TLC indicated that the leaves are rich in tannins. Subsequent chromatographic separation of the extract yielded two metabolites 1 and 2, which were identified as 2,3-dihydroxy-2-(2-hydroxyethyl)-butanoic acid derivatives, and two phenolic compounds 3 and 4. This paper reports the isolation and structural characterization of the new compounds 1–3 and an assessment of the cytotoxicity of these molecules. 2. Results and Discussion The fresh leaves of C. fargesii were extracted with 80% aqueous ethanol, and the extract was partitioned between Et2O and water. The Et2O and aqueous fractions were separated by a combination Molecules 2017, 22, 162; doi:10.3390/molecules22010162 www.mdpi.com/journal/molecules Molecules 2017, 22, 162 2 of 8 Molecules 2017, 22, 162 2 of 8 of Sephadexof Sephadex LH-20, LH-20, MCI MCI gel gel CHP CHP 20P, 20P,Toyopearl Toyopearl Butyl-650C, Chromatorex Chromatorex ODS, ODS, and and Diaion Diaion HP20SS HP20SS columncolumn chromatography chromatography and and semi-preparative semi-preparative reverse-phase reverse-phase HPLC, HPLC, to to yield yield three three new new compounds compounds1 – 3 and1– one3 and known one known phenolic phenolic compound compound gentisic gentisic acid acid 5-O -5-αO-L--rhamnopyranosyl-(1α-L-rhamnopyranosyl-(1!→2)-2)-β-βD--glucosideD-glucoside [ 9] (4)[9] (Figure (4) (Figure1). 1). OH HO O O O O 2 OH 2' 6" HO O 1 O OH HO O O O 3 HO 2 1' HO 1' 1" HO OH HO HO OH 2' 3 1 2 OH O HOOC HO 9 1 1 O A B OH 5 HO 10 5 3a HO O O OH HO 1' C HO O 3' OCH 3 O 1" OH HO HO OH 3 4 FigureFigure 1.1. StructuresStructures of compounds 11––44. Compound 1 was isolated as a brown amorphous powder and gave a positive FeCl3 test (dark blue), Compound 1 was isolated as a brown amorphous powder and gave a positive FeCl test (dark blue), which suggested the presence of phenol moieties in the molecule. The molecular formula3 C19H24O13 whichwas suggesteddetermined the based presence on the of phenolliquid chromatograp moieties in thehy-mass molecule. spectrometry The molecular IT-TOF formula (LC-MS/IT-TOF), C19H24O13 was determinedwhich showed based [M on − theH]− liquidand [M chromatography-mass + Na]+ ion peaks at m/ spectrometryz 459.1143 (calcd. IT-TOF for C (LC-MS/IT-TOF),19H23O13, 459.1144) whichand − + showed483.1118 [M (calcd.− H] for Cand19H24 [MO13Na, + Na] 483.1109),ion peaks respectively. at m/ zIn459.1143 the 1H- and (calcd. 13C-NMR for spectra C19H23 (TableO13, 459.1144)1), two 1 13 andproton 483.1118 singlets (calcd. at δH for7.13 C (2H,19H24 s)O and13Na, four 483.1109), aromatic respectively.carbon signals Inat δ theC 109.1H- and and 145.2,C-NMR along spectrawith (Tablean ester1), two carbonyl proton signal singlets at δC at166.4δH suggested7.13 (2H, the s) presence and four of aromatic a galloyl carbongroup [10].The signals hydrolysis at δC 109.1 of and1 145.2,produced along D with-glucose, an ester which carbonyl was identified signal by at GCδC 166.4 analysis. suggested The coupling the presence constant of the a galloyl anomeric group sugar [10 ]. Theproton hydrolysis was 7.8 of Hz,1 produced indicatingD -glucose,that the sugar which moiety was identifiedwas in the byβ configuration. GC analysis. TheThe couplinglarge downfield constant of theshift anomeric of the glucose sugar H-6” proton protons was ( 7.8δH 4.32 Hz, indicatingand 4.58) suggested that the sugaresterifica moietytion with was inthe the galloylβ configuration. moiety at this position. This was confirmed by the HMBC00 correlation between H-6” and the carboxy carbon The large downfield shift of the glucose H-6 protons (δH 4.32 and 4.58) suggested esterification with(δC the166.4) galloyl (Figure moiety 2). A second at this HMBC position. correlation This was between confirmed H-1” and by C-1’ the HMBCsuggested correlation that the glycosyl between group00 is linked to C-1′. HSQC experiment showed that the remaining moiety was composed of six 00 H-6 and the carboxy carbon (δC 166.4) (Figure2). A second HMBC correlation between H-1 andcarbons: C-10 suggested a carboxy carbon that the (δC glycosyl178.6, C-2), group an oxygenated is linked methine to C-1 (0δ.C HSQC77.8, C-1’), experiment an oxygenated showed quaternary that the carbon (δC 76.6, C-3), an oxygenated methylene (δC 65.8, C-5), a methylene (δC 29.9, C-4), and a methyl remaining moiety was composed of six carbons: a carboxy carbon (δC 178.6, C-2), an oxygenated (δC 15.6, C-2’) carbon.0 The presence of a γ-lactone structure in the remaining moiety was suggested methine (δC 77.8, C-1 ), an oxygenated quaternary carbon (δC 76.6, C-3), an oxygenated methylene by the lower field shift of the carboxy carbon (δC 178.6) and the unsaturation index (eight). This was (δ 65.8, C-5), a methylene (δ 29.9, C-4), and a methyl (δ 15.6, C-20) carbon. The presence of a Calso confirmed by HMBC correlationsC shown in Figure 2, in whichC the oxygenated methylene protons γ-lactone structure in the remaining moiety was suggested by the lower field shift of the carboxy (δH 4.31–4.34, H-5) correlated with C-2. Furthermore, the 1H-1H COSY correlations of H-4 (δH 2.10) with carbon (δ 178.6) and the unsaturation index (eight). This was also confirmed by HMBC correlations H-5 (δHC 4.32) and H-1′ with H-2′ and the HMBC correlations of H-1’ with C-3 and C-4 and H-4 with shownC-2, C-3, in Figure and C-52, indicated in which that the oxygenatedthe remaining methylene moiety is 3-hydroxy-3-(1’- protons ( δH 4.31–4.34,hydroxyethyl)dihydrofuran- H-5) correlated with 1 1 0 C-2.2(3 Furthermore,H)-one. Consequently, the H- Hthe COSY structure correlations of compound of H-4 1 was (δH 2.10)established with H-5 as 3-[1’-(6”- (δH 4.32)O-galloyl- and H-1β-withD- 0 0 H-2glucopyranosyl)oxyethyl]-3-hydroxy-dihydrofuran-2(3and the HMBC correlations of H-1 with C-3 and C-4H)-one. and H-4 with C-2, C-3, and C-5 indicated 0 that theCompound remaining 2 moietywas isolated is 3-hydroxy-3-(1 as a yellow amorphous-hydroxyethyl)dihydrofuran-2(3 powder and gave a positiveH FeCl)-one.3 test Consequently, (dark blue). 0 00 theThe structure presence of of compound a galloyl group1 was was established deduced from as 3-[1 the-(6 13C-NMR-O-galloyl- signalsβ- D(Table-glucopyranosyl)oxyethyl]- 1) [6]. The molecular 3-hydroxy-dihydrofuran-2(3formula of C13H16O9 was establishedH)-one. based on the LC-MS/IT-TOF (m/z 339.0672 [M + Na]+, calcd.
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