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Chemical Constituents from Flueggea Virosa and the Structural Revision of Dehydrochebulic Acid Trimethyl Ester

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Chemical Constituents from Flueggea Virosa and the Structural Revision of Dehydrochebulic Acid Trimethyl Ester molecules Article Chemical Constituents from Flueggea virosa and the Structural Revision of Dehydrochebulic Acid Trimethyl Ester Chih-Hua Chao 1,2,*, Ying-Ju Lin 3,4, Ju-Chien Cheng 5, Hui-Chi Huang 6, Yung-Ju Yeh 5, Tian-Shung Wu 7,8, Syh-Yuan Hwang 9 and Yang-Chang Wu 1,2,10,11,* 1 School of Pharmacy, China Medical University, Taichung 40402, Taiwan 2 Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 40447, Taiwan 3 School of Chinese Medicine, China Medical University, Taichung 40402, Taiwan; [email protected] 4 Genetic Center, Department of Medical Research, China Medical University Hospital, Taichung 40447, Taiwan 5 Department of Medical Laboratory Science and Biotechnology, China Medical University, Taichung 40402, Taiwan; [email protected] (J.-C.C.); [email protected] (Y.-J.Y.) 6 Department of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung 40402, Taiwan; [email protected] 7 Department of Pharmacy, National Cheng Kung University, Tainan 70101, Taiwan; [email protected] 8 Department of Pharmacy and Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung 90741, Taiwan 9 Endemic Species Research Institute, Council of Agriculture, Nantou 55244, Taiwan; [email protected] 10 Center for Molecular Medicine, China Medical University Hospital, Taichung 40447, Taiwan 11 Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 80708, Taiwan * Correspondence: [email protected] (C.-H.C.); [email protected] (Y.-C.W.); Tel.: +886-4-2205-3366 (ext. 5157) (C.-H.C.) Academic Editor: Derek J. McPhee Received: 9 August 2016; Accepted: 12 September 2016; Published: 16 September 2016 Abstract: In an attempt to study the chemical constituents from the twigs and leaves of Flueggea virosa, a new terpenoid, 9(10!20)-abeo-ent-podocarpane, 3β,10α-dihydroxy-12-methoxy-13- methyl-9(10!20)-abeo-ent-podocarpa-6,8,11,13-tetraene (1), as well as five known compounds were characterized. Their structures were elucidated on the basis of spectroscopic analysis. In addition, the structure of dehydrochebulic acid trimethyl ester was revised as (2S,3R)-4E-dehydrochebulic acid trimethyl ester based on a single-crystal X-ray diffraction study. The in vitro anti-hepatitis C virus (anti-HCV) activity and cytotoxicity against Huh7.5 cells for the isolated compounds were evaluated. Keywords: Flueggea virosa; dehydrochebulic acid trimethyl ester; ent-podocarpane; anti-HCV; HCVcc 1. Introduction Flueggea virosa (Roxb. ex Wild) Baill, belonging to the Euphorbiaceae family, is a common medicinal plant in Africa and China [1,2]. In previous reports, Securinega alkaloids have been widely regarded as a representative group of the genus Flueggea [3], formerly classified as Securinega genus. However, our prior studies have demonstrated that the roots of F. virosa contained a series of non-alkaloids, including ent-podocarpanes [4,5], 9(10!20)-abeo-ent-podocarpanes [6], 3,4-seco-ent-podocarpanes [7], and 3,4-seco-30-nor-friedelanes [6], some of which were endowed with anti-HCV activities and weak toxicities. Among them, 4-hydroxy-12-methoxy-13-methyl-3,4-seco- ent-podocarpa-6,8,11,13-tetraen-3-oic acid was found to be a brand new type anti-HCV Molecules 2016, 21, 1239; doi:10.3390/molecules21091239 www.mdpi.com/journal/molecules Molecules 2016, 21, 1239 2 of 7 MoleculesMolecules 2016 2016, ,21 21, ,1239 1239 22 of of 7 7 podocarpanesMolecules 2016, 21 ,[7], 1239 and 3,4-seco-30-nor-friedelanes [6], some of which were endowed with anti-HCV2 of 7 activitiespodocarpanespodocarpanes and [7], [7],weak andand 3,4-3,4toxicities.‐secoseco-30-‐30 ‐nornorAmong-friedelanes‐friedelanes them, [6],[6], 4-hydroxy-12-methoxy-13-methyl-3,4-somesome ofof whicwhichh werewere endowedendowed withwith anti-HCVantiseco‐HCV-ent- podocarpa-6,8,11,13-tetraen-3-oicactivitiesactivities andand weakweak toxicities.toxicities. acid AmongAmong was found them,them, to be4-hydroxy-12-methoxy-13-methyl-3,4-4‐ hydroxya brand ‐new12‐methoxy type anti-HCV‐13‐methyl agent‐3,4 ‐seco[7].seco -The‐entent-‐ non-alkaloidsagentpodocarpa-6,8,11,13-tetraen-3-oicpodocarpa [7].‐6,8,11,13 Thein the non-alkaloids other‐tetraen parts‐3‐oic of inacidacidthis the plantwaswas other found foundstill partsreceived toto bebe of aa less brand thisbrand attention. plant newnew type stilltype Thus, anti-HCV receivedanti the‐HCV isolation less agentagent attention. of [7].[7]. active TheThe constituentsThus,non-alkaloidsnon‐alkaloids the from isolation in in the the the other other twigs of parts activeparts and ofleavesof constituents thisthis plantofplant F. virosa stillstill fromreceived receivedwas carried the less less twigs attention. out,attention. which and Thus, Thus, leavesresulted the the of isolation inisolation theF. virosaisolation of of active activewas of acarriedconstituentsconstituents new 9(10 out,→ from 20)-from whichabeo the the- resulted ent twigstwigs-podocarpane, andand in leaves leaves the isolation of namelyof F. F. virosa virosa of3β ,10was awasα new -dihydroxy-12-methoxy-13-methyl-9(10carried carried 9(10 out, !out,20)- which whichabeo- entresulted resulted-podocarpane, inin thethe isolationisolation namely→20)- ofof abeo3aaβ newnew,10-entα 9(10-dihydroxy-12-methoxy-13-methyl-9(109(10-podocarpa-6,8,11,13-tetraene→→20)-20)‐abeoabeo-‐entent-podocarpane,‐podocarpane, ( 1 namelynamely), alone! 33 β20)-βwith,10,10abeoαα‐ -dihydroxy-12-methoxy-13-methyl-9(10fivedihydroxy-ent -podocarpa-6,8,11,13-tetraeneknown‐12 co‐methoxympounds.‐13 ‐methylIn addition,‐9(10 (1),→ alone→ 20)-the20)‐ withstructuralabeoabeo-‐ent fiveent-podocarpa-6,8,11,13-tetraene‐podocarpaknown revision compounds. of‐6,8,11,13 dehydrochebulic‐tetraene In addition, (ac(11),),id thealone alonetrimethyl structural withwith ester fivefive revision (Chart knownknown of1, dehydrochebulic originalcocompounds.mpounds. 2) was In Inalso acidaddition,addition, reported trimethyl the thein thisesterstructuralstructural study. (Chart revision revision1, original ofof dehydrochebulicdehydrochebulic2) was also reported acacidid in trimethyltrimethyl this study. esterester (Chart(Chart 1,1, originaloriginal 22)) waswas alsoalso reportedreported inin thisthis study. study. Chart 1. Structures of compounds 1–6. ChartChart 1. 1. Structures Structures of of compounds compounds 1 1––66. 2. Results Results and and Discussion Discussion 2.2. Results Results and and Discussion Discussion The MeOH MeOH extract extract from from the twigs the twigsand leaves and of leaves F. virosa of wasF. concentrated virosa was concentrated and the alkaloids and were the removedalkaloidsTheThe MeOH byMeOH were partition removedextract extract with from from byacidic the the partition twigs twigswater. and and The with leaves leaves result acidic of ingof F. F. water. nonalkaloidvirosa virosa was was The concentrated concentrated layer resulting was separated nonalkaloid and and the the alkaloids alkaloidsrepeatedly layer were were was by → columnseparatedremovedremoved chromatography byby repeatedly partitionpartition with bywith to column afford acidicacidic a water. chromatography water.new 9(10 TheThe result20)-resultingabeoing to- ent nonalkaloid affordnonalkaloid-podocarpane a new layerlayer 9(10 (1 ) was! wasand20)- separatedfiveseparatedabeo known-ent -podocarpane repeatedlyrepeatedly compounds, byby → → which(columncolumn1) and were chromatography chromatography five identified known as compounds, 4 to Eto -dehydrochebulicafford afford a a new new which 9(10 9(10→ wereacid20)-20) trimethyl‐abeo identifiedabeo-‐entent-podocarpane‐ podocarpaneester as (2 4)E [8,9],-dehydrochebulic ( (112-hydroxy-20(101)) and and five five known known acid compounds, compounds,5)- trimethylabeo-4,5- → secoesterwhichwhich-podocarpa-5(10),6,8,11,13-pentaen-3-one ( 2were were)[8, 9identified identified], 12-hydroxy-20(10 as as 4 4EE-dehydrochebulic‐dehydrochebulic!5)-abeo-4,5- acid acid(3seco) trimethyl [10],trimethyl-podocarpa-5(10),6,8,11,13-pentaen-3-one 3β,12-dihydroxy-13-methylpodocarpa-6,8,11,13- ester ester ( (22)) [8,9], [8,9], 12-hydroxy-20(10 12‐hydroxy‐20(10→5)-5)‐abeo (abeo3)[-4,5-‐104,5],‐ tetraene3secosecoβ,12-dihydroxy-13-methylpodocarpa-6,8,11,13-tetraene-podocarpa-5(10),6,8,11,13-pentaen-3-one‐podocarpa (4) [10],‐ betulinic5(10),6,8,11,13 acid ‐3pentaenβ-calfeate‐3‐ (one5) [11], ((33)) and[10],[10], (+) 3 3ampelosinββ,12-dihydroxy-13-methylpodocarpa-6,8,11,13-,12 (4‐)[dihydroxy10], E betulinic (6) [12].‐13‐methylpodocarpa acid 3β-calfeate‐6,8,11,13 (5)[11],‐ andtetraenetetraene (+) ampelosin( (44)) [10], [10], betulinic betulinic E (6)[ 12acid acid]. 3 3ββ‐-calfeatecalfeate ( (55)) [11], [11], and and (+) (+) ampelosin ampelosin E E ( (66)) [12]. [12]. Figure 1. Selected 1H−1H COSY (▬) and HMBC (→) correlations of 1. 1 1 FigureFigureFigure 1.1. 1.Selected Selected Selected 1 H1HH−−11HH COSY COSY ( (▬▬)) and and HMBC HMBC ( ( →→!)) )correlations correlations correlations of of 1 1. Compound 1 was obtained as a colorless oil and a molecular formula of C19H26O3 was deduced for thisCompound compound 1 basedwas obtained on the molecular as a colorless ion peakoil and [M a − molecular H]− at m/z formula 301.1805 of in C the19H (26−O)-HR-APCI-MS3 was deduced Compound 1 was obtainedobtained asas aa colorlesscolorless oiloil andand aamolecular molecular formula formula of of C C1919HH2626O3 was deduced 1 − 13 (calcdforfor this this for compoundcompound compound C19H25O3 based,based based301.1809). on on on the the the
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