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(2-Phenylethyl)-4H-Chromen-4-One Derivative, and Anti-Inflammatory Constituents from the Stem Barks of Aquilaria Sinensis

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(2-Phenylethyl)-4H-Chromen-4-One Derivative, and Anti-Inflammatory Constituents from the Stem Barks of Aquilaria Sinensis Article New Flavones, a 2-(2-Phenylethyl)-4H-chromen-4-one Derivative, and Anti-Inflammatory Constituents from the Stem Barks of Aquilaria sinensis Sin-Ling Wang 1,†, Tsong-Long Hwang 2,3,4, Mei-Ing Chung 1,†, Ping-Jyun Sung 5, Chih-Wen Shu 6, Ming-Jen Cheng 7 and Jih-Jung Chen 8,* Received: 14 October 2015 ; Accepted: 16 November 2015 ; Published: 24 November 2015 Academic Editors: Nancy D. Turner and Isabel C. F. R. Ferreira 1 School of Pharmacy, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 80708, Taiwan; [email protected] (S.-L.W.); [email protected] (M.-I.C.) 2 Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan 33302, Taiwan; [email protected] 3 Research Center for Industry of Human Ecology and Graduate Institute of Health Industry Technology, Chang Gung University of Science and Technology, Taoyuan 33302, Taiwan 4 Immunology Consortium, Chang Gung Memorial Hospital, Taoyuan 33302, Taiwan 5 National Museum of Marine Biology and Aquarium, Pingtung 94450, Taiwan; [email protected] 6 Department of Medical Education and Research, Kaohsiung Veterans General Hospital, Kaohsiung 81362, Taiwan; [email protected] 7 Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu 30062, Taiwan; cmj@firdi.org.tw 8 Department of Pharmacy, Tajen University, Pingtung 90741, Taiwan * Correspondence: [email protected]; Tel.: +886-8-7624-002 (ext. 2827); Fax: +886-8-7624-002 (ext. 5121) † These authors contributed equally to this work. Abstract: In the current study, two new flavones, 41-O-geranyltricin (1) and 31-O-geranylpolloin (2), and a new 2-(2-phenylethyl)-4H-chromen-4-one derivative, 7-hydroxyl-6- methoxy-2-(2-phenylethyl)chromone (3), have been isolated from the stem barks of A. sinensis, together with 21 known compounds 4–24. The structures of new compounds 1–3 were determined through spectroscopic and MS analyses. Compounds 2, 3, 5, 6, and 8–10 exhibited inhibition (IC50 ¤ 12.51 µM) of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). Compounds 3, 6, 8, 10, and 19 inhibited fMLP/CB-induced elastase release with IC50 values ¤ 15.25 µM. This investigation reveals bioactive isolates (especially 2, 3, 5, 6, 8, 9, 10, and 19) could be further developed as potential candidates for the treatment or prevention of various inflammatory diseases. Keywords: Aquilaria sinensis; Thymelaeaceae; structure elucidation; flavone; 2-(2-phenylethyl)- 4H-chromen-4-one; anti-inflammatory activity 1. Introduction Aquilaria sinensis (Lour.) Gilg. (Thymelaeaceae) is an evergreen tree, distributed in southern China [1]. A. sinensis, locally called “Chen Xiang”, is used in China as a folk medicine for treatment of circulatory disorders, abdominal pain, vomiting, and dyspnea [1]. Its leaf has been commercially used as a functional tea with anti-diabetes activity [2]. Benzenoids [3–7], flavonoids [8–13], 2-(2-phenyl-ethyl)-4H-chromen-4-ones [4,10,14–19], steroids [19–22], sesquiterpenoids [21,23], triterpenoids [4], and their derivatives were isolated from this plant in previous studies. Molecules 2015, 20, 20912–20925; doi:10.3390/molecules201119736 www.mdpi.com/journal/molecules Molecules 2015, 20, 20912–20925 Molecules 2015, 20, page–page OCH3 8'' O 1'' 3'' 5'' 7'' 5' 2'' 4'' 6'' 6' 4' 1' 3' 2' H3CO O 9'' 8 10'' 7 2 OCH3 6 3 5 4 OH O 1 OCH3 10'' 9'' 5' 6' 4' 1' 3' H3CO O 2' 2'' 4'' 6'' 8 1" 3'' 5'' 7'' 8'' 7 2 O 6 3 5 4 OH O 2 3' 2' 4' 1' 5' HO O 7' 6' 8 8' 7 2 6 3 5 4 H3CO O 3 R OH OCH3 H3CO O H3CO O OCH3 R OH O OH O 4 R = OCH3 5 R = OCH3 6 R = H 7 R = H OH OH H3CO O H3CO O OH OH O OH O 89 FigureFigure 1. Cont. 2 20913 Molecules 2015, 20, 20912–20925 Molecules 2015, 20, page–page OCH3 OH H3CO O O OCH3 H H H3CO H3CO O O 10 HO 11 OCH3 N HO HO OCH3 OH N OCH3 HO H CO H 3 O O 12 13 14 O R (CH2)21CH3 O HO 15 R = OH 16 R = OCH3 O 17 HO 18 O 19 H CH2OH OH 20 OH HO O 23 O 21 O O H CO OCH OH 3 3 O O O 22 24 FigureFigure 1. 1.The The chemical chemical structures structures ofof newnew compoundscompounds 1–3 andand known known compounds compounds 4–424–24 isolatedisolated from from A.A. sinensis sinensis. 3 20914 Molecules 2015, 20, 20912–20925 Many of these compounds were found to exhibit antitumor [5,18], nitrite scavenging [13], anti-acetylcholinesteraseMolecules 2015, 20, page–page [23], and anti-inflammatory [12,19] activities. In our studies on the anti-inflammatory constituents of Formosan plants and Chinese herbal medicines, many species Many of these compounds were found to exhibit antitumor [5,18], nitrite scavenging [13], have been screened for in vitro inhibitory activity on neutrophil pro-inflammatory responses, and anti-acetylcholinesterase [23], and anti-inflammatory [12,19] activities. In our studies on the A. sinensisanti-inflammatorywas found constituents to be an active of Formosan species. Theplants MeOH and extractChinese ofherbal stem medicines, barks of A. many sinensis speciesshowed potenthave inhibitory been screened effects for on in superoxide vitro inhibitory anion activity generation on neutrophil and elastase pro-inflammatory release by human responses, neutrophils and in responseA. sinensis to was formyl- foundL to-methionyl- be an activeL-leucyl- species.L The-phenylalanine/cytochalasin MeOH extract of stem barks Bof (fMLP/CB).A. sinensis showed Figure 1 illustratespotent inhibitory the structures effects of on two superoxide new flavones, anion gene 41ration-O-geranyltricin and elastase ( rele1) andase by 31 -humanO-geranylpolloin neutrophils (2), andin a newresponse 2-(2-phenylethyl)-4 to formyl-L-methionyl-H-chromen-4-oneL-leucyl-L-phenylalanine/cytochalasi derivative, 7-hydroxyl-6-methoxy-2-(2-phenylethyl)-n B (fMLP/CB). Figure 1 chromoneillustrates (3) the isolated structures from of this two extract. new flavones, Twenty-one 4′-O-geranyltricin known compounds (1) and 3′4-O–24-geranylpolloin, have also been (2), isolatedand anda identified new 2-(2-phenylethyl)-4 from the stemH barks-chromen-4-one of A. sinensis derivative,and their 7-hydroxyl-6-methoxy-2-(2-phenylethyl)- structures are depicted in Figure1. This paperchromone describes (3)the isolated structural from this elucidation extract. Twenty-one of the compounds known compounds numbered 41–through24, have also3, and been the isolated inhibitory activitiesand identified of all isolates from onthe superoxide stem barks generation of A. sinensis and and elastase their releasestructures by neutrophils.are depicted in Figure 1. This paper describes the structural elucidation of the compounds numbered 1 through 3, and the 2. Resultsinhibitory activities of all isolates on superoxide generation and elastase release by neutrophils. 2.Chromatographic Results purification of the EtOAc-soluble fraction of a MeOH extract of stem barks of A. sinensis on a silica gel column and preparative thin-layer chromatography (TLC) afforded three Chromatographic purification of the EtOAc-soluble fraction of a MeOH extract of stem barks of newA. compounds sinensis on a1 –silica3 and gel twenty-one column and known preparative compounds thin-layer4–24 chromatography. (TLC) afforded three 1 new4 -O compounds-Geranyltricin 1–3 and (1) wastwenty-one isolated known as yellowish compounds needles. 4–24. Its molecular formula, C28H32O7, was + determined4′-O-Geranyltricin on the basis of (1 the) was positive isolated HRESIMS as yellowish peak needles. at m/z Its481.22185 molecular [M formula, + H] (calcdC28H32O 481.22208)7, was anddetermined this was supported on the basis by theof the1H-, positive13C-, andHRESIMS DEPT-NMR peak at data. m/z 481.22185 The IR spectrum [M + H]+ showed (calcd 481.22208) the presence of OHand (3408 this was cm´ supported1) and carbonyl by the 1 (1657H-, 13C-, cm and´1) DEPT-NMR groups. Comparison data. The IR of thespectrum1H-NMR showed data the of presence1 with those of tricinof OH (4 (3408)[24, 25cm]− suggested1) and carbonyl that (1657 their cm structures−1) groups. were Comparison closely related,of the 1H-NMR except data that of the 1 4with1-geranyloxy those groupof tricin signals (4)at [24,25]δ 1.59 suggested (3H, br s, that H-9 their11), 1.67 structures (3H, br were s, H-8 closely11), 1.68 related, (3H, brexcept s, H-10 that11 ),the 2.03 4′-geranyloxy (2H, m, H-4 11), 2.08group (2H, m,signals H-511 at), δ 4.64 1.59 (2H,(3H, br d, s,J H-9= 7.2′′), Hz,1.67 (3H, H-1 11br), s, 5.07 H-8 (1H,′′), 1.68 br (3H, t, J br= s, 7.2 H-10 Hz,′′), H-6 2.0311 (2H,), and m, 5.56H-4′′), (1H, 2.08 br t, J = 7.2(2H, Hz, m, H-2H-5′′11),) 4.64 of 1 (2H,replaced d, J = 7.2 the Hz, 41-hydroxy H-1′′), 5.07 group (1H, br of t, 4J .= This 7.2 Hz, was H-6 supported′′), and 5.56 by (1H, HMBC br t, J correlations= 7.2 Hz, H-2′′) of 1 replaced the11 4′-hydroxy group 1of 4. This was supported11 by HMBC correlations11 observed observed between H-1 (δH 4.64) and C-4 (δC 140.4), C-2 (δC 119.9), and C-3 (δC 142.1), and by between H-1′′ (δH 4.64) and C-4′ (δC 140.4),11 C-2′′ (δC 119.9), and C-31 ′′1 (δC 142.1), and11 by NOESY NOESY correlations observed between H-1 (δH 4.64) and OMe-3 /5 (δH 3.95), H-2 (δH 5.56), and correlations observed between H-1′′ (δH 4.64) and OMe-3′/5′ (δH 3.95), H-2′′ (δH 5.56), and H-10′′ H-1011 (δ 1.68).
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