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New Cadinane Sesquiterpenes from the Stems of Kadsura Heteroclita

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New Cadinane Sesquiterpenes from the Stems of Kadsura Heteroclita molecules Article New Cadinane Sesquiterpenes from the Stems of Kadsura heteroclita 1, 1,2, 1,2 1 1 Liang Cao y, Nuzhat Shehla y, Shumaila Tasneem , Mengru Cao , Wenbing Sheng , Yuqing Jian 1, Bin Li 1, Caiyun Peng 1, M. Iqbal Choudhary 1,2,*, Atta-ur-Rahman 2, Duan-fang Liao 1 and Wei Wang 1,2,* 1 TCM and Ethnomedicine Innovation & Development International Laboratory, Innovative Materia Medica Research Institute, School of Pharmacy, Hunan University of Chinese Medicine, Changsha 410208, China; [email protected] (L.C.); [email protected] (N.S.); [email protected] (S.T.); [email protected] (M.C.); [email protected] (W.S.); [email protected] (Y.J.); [email protected] (B.L.); [email protected] (C.P.); dfl[email protected] (D.-f.L.) 2 H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan; [email protected] * Correspondence: [email protected] (M.I.C.); [email protected] (W.W.); Tel.: +86-136-5743-8606 (M.I.C.); +92-21-4824924 or +92-21-4819010 (W.W.) They contributed equally to this work. y Received: 10 March 2019; Accepted: 26 April 2019; Published: 28 April 2019 Abstract: As part of our continual efforts to exploit ‘Tujia Ethnomedicine’ for their pharmacophoric functionalities, we herein investigated Kadsura heteroclita collected from a deep Wulin mountain area in northern Hunan province. The current study resulted in the isolation of three new sesquiterpenes: 6α,9α,15-trihydroxycadinan-4-en-3-one (1), (+)-3,11,12-trihydroxycalamenene (2), (–)-3,10,11,12-tetrahydroxy-calamenene (3), along with four known sesquiterpenes (4–7), and a cytochalasin H (8). Their chemical structures were elucidated by 1D-, and 2D-NMR spectroscopy, and HRESI-MS, CD spectrometry. The antioxidant, and cytotoxic activities of the compounds were evaluated. Compound 8 exhibited a strong antioxidant effect with an IC50 value of 3.67 µM on isolated human polymorphonuclear cells or neutrophils. Keywords: Kadsura heteroclita; Schisandraceae; sesquiterpenes; antioxidant; Tujia ethnomedicine 1. Introduction In the last few decades, phytochemical work on the family Schisandraceae has resulted in a seminal contribution to novel structural frameworks for triterpenoidal skeletons [1–4]. Recently, some promising sesquiterpenes has also been reported from the plants of family Schisandraceae [5–10]. In our previous research, we reported the identification of several bioactive lignanoids from the genus kadsura [11] that highlight the immense diversity in the chemical constituents of these plants as well as in their important biological activities. Herein, we report the identification of three new sesquiterpenoids (1–3) from kadsura heteroclita, amongst compound 1 was a structural analogue of our previously reported compound 4, while compounds 2–3 possess calamenene core skeletons, which are identified for the first time from this species. With the major distribution in China, genus Kadsura (Schisandraceaea) is represented by sixteen species, half of which are mainly distributed in the southwest and southeast part of China [12]. Kadsura heteroclita is a vine plant primarily distributed in the southwest part of China, has been used in Traditional Chinese Medicine (TCM) as “Hai Feng Teng” or “Ji Xue Teng” for the treatment of menstrual irregularities and blood deficiencies [13], by activating the blood circulation, relieving pain, and eliminating dampness. In the “Hu Ping” and “Xue Feng” mountain areas of northwest Hunan Molecules 2019, 24, 1664; doi:10.3390/molecules24091664 www.mdpi.com/journal/molecules Molecules 2019, 24, 1664 2 of 10 Molecules 2019, 24, x 2 of 10 province, the stems of K. heteroclita are used to treat traumatic injuries and rheumatoid arthritis by Hunanone of theprovince, Chinese the ethnic stems minorities of K. heteroclita known are as the used Tujia to peopletreat traumati [14,15].c Traditionallyinjuries and theyrheumatoid named arthritisthe stems by of oneK. heteroclitaof the Chineseas “Xue ethni Tong”c minorities which meansknown“circulating as the Tujia thepeople blood [14,15]. system”, Traditionally which is usedthey namedto treat the blood stems related of K. diseases heteroclita [16 as]. “Xue These Tong” features which triggered means our “circulating research enthusiasmthe blood system”, to explore which the isbioactive used to metabolites treat blood fromrelated this diseases species that[16]. canThes bee relatedfeatures to triggered its clinical our application. research enthusiasm The previous to explorework implied the bioactive that the metabolites plant contains from triterpenoidsthis species that [17 –can19], be lignans related [20 to– its22 ]clinical and sesquiterpenes application. The [6]. previousIn the present work work, implied we reported that the three plant new contains sesquiterpenes triterpenoids (1–3) (Figure [17–19],1) along lignans with [20–22] four known and sesquiterpenes [6]. 6α ,9Inα the-dihydroxycadinan-4-en-3-one present work, we reported three (4)[ 6new], isoepicubenol sesquiterpenes (5 )[(123–3],) (Figure cryptomeridiol 1) along with(6)[24 four], 1β known,4β,7α-trihydroxyeudesmane sesquiterpenes 6α,9α-dihydroxycadinan-4-en-3-one (7)[25,26], and a cytochalasin H(4) ( 8[6],)[27 isoepicubenol,28] isolated from(5) [23], the cryptomeridiolstems and roots ( of6) K.[24], heteroclita 1β,4β,7αas-trihydroxyeudesmane shown in Figure1. (7) [25,26], and a cytochalasin H (8) [27,28] isolated from the stems and roots of K. heteroclita as shown in Figure 1. Figure 1. Structures of compounds 1–8. Figure 1. Structures of compounds 1–8. 2. Results and Discussion 2. Results and Discussion 2.1. Structure Characterization of the Isolated Compounds (1–3) 2.1. Structure Characterization of the Isolated Compounds (1–3) 6α,9α,15-Trihydroxycadinan-4-en-3-one (1) (Figure2) was isolated as a white amorphous powder. + The molecular6α,9α,15-Trihydroxycadinan-4-en-3-one formula was established as C 15(1H) 22(FigureO4 from 2) itswas HRESI-MS isolated (mas/z a289.1419, white amorphous [M + Na] powder.calcd. 289.1410), The molecular indicating formula five degrees was established of unsaturation. as C15H The22O41 fromH-NMR its HRESI-MS spectrum (Table (m/z 1289.1419,) the revealed [M + + 1 Na]presence calcd. of 289.1410), one secondary indicating group fi (δveH 1.00,degrees d, J of= 6.9),unsaturation. a tertiary methylThe H-NMR group (spectrumδH 1.83, s), (Table one olefinic 1) the revealedmethine presence group (δH of6.85, one secondary s), and a terminal group (δ olefinicH 1.00, d, methylene J = 6.9), a tertiary group ( δmethylH 4.77, group 4.90, brs(δH each)1.83, s), in one the olefinicstructure. methine The 13 groupC-NMR (δH and 6.85, DEPT s), and NMR a terminal spectra olefinic of compound methylene1 indicated group (δ fifteenH 4.77, carbon4.90, brs signals each) 13 inattributed the structure. to one The carbonyl C-NMR carbon and (δ CDEPT200.5), NMR four olefinicspectra carbonsof compound (δC 155.2, 1 indicated 146.6, 137.0, fifteen 114.6), carbon and signalsthree oxygenated attributed to carbons one carbonyl (δC 73.3, carbon 71.9, 59.5). (δC 200.5), Apart four from olefinic these carbons signals, three(δC 155.2, methines 146.6, (137.0,δC 37.3, 114.6), 48.6, and50.2), three two methylenesoxygenated (δcarbonsC 36.8, 37.0),(δC 73.3, and 71.9, two methyl59.5). Apart groups from (δC these15.0, 23.0)signals, were three also methines observed. ( BesidesδC 37.3, 48.6,the two 50.2), double two methylenes bonds and one(δC 36.8, carbonyl, 37.0), theand remaining two methyl two groups unsaturation (δC 15.0, degrees23.0) were together also observed. with the Besideschemical the shift two patterns double suggestedbonds and that one the carbonyl, compound the isremaining a bicycle two sesquiterpene unsaturation based degrees on a cadinanetogether withskeleton. the chemical A downfield shift chemical patterns shiftsuggested of an olefinic that the proton compound (δH 6.85, is a s) bicycle conjugated sesquiterpene with carbonyl based carbon on a cadinane(δC 200.5) skeleton. showed the A presencedownfield of chemic an α-βalunsaturated shift of an ketone olefinic moiety proton in the(δH skeleton6.85, s) conjugated of 1. with carbonylBy carefully carbon (δ comparingC 200.5) showed the 1 H-the and presence13C-NMR of anchemical α-β unsaturated shifts data ketone (Table mo1iety) of in1 thewith skeleton that of ofknown 1. compound 6α,9α-dihydroxycadinan-4-en-3-one (4), which was also reported previously from K. heteroclitaBy carefully[6], we comparing revealed the major1H- and di ff13erenceC-NMR between chemical the shifts two structures.data (Table The 1) of chemical 1 with shiftthat of knownC-15 (δ Ccompound15.3, δ3H 1.81, 6α,9α 3H)-dihydroxycadina correspondingn-4-en-3-one to a methyl group(4), which in 4 changedwas also reported to oxygenated previously methylene from K.(δC heteroclita59.5, δ2H [6],4.16, we 2H) revealed in 1. This the deductionmajor difference was supported between bythe HMBC two structures. correlations The of chemical H2-15 with shift C-3 of C-15(δC 200.5), (δC 15.3, C-4 δ3H (δ C1.81,137.0), 3H) and corresponding C-5 (δC 155.2). to a An methyl isopropenyl group in unit 4 changed was also to identified oxygenated in the methylene skeleton (δC 59.5, δ2H 4.16, 2H) in 1. This deduction was supported by HMBC correlations of H2-15 with C-3 (δC 200.5), C-4 (δC 137.0), and C-5 (δC 155.2). An isopropenyl unit was also identified in the skeleton on the basis of the presence of terminal methylene (δC 114.6, δH 4.77, 4.90 brs each), a tertiary methyl Molecules 2019, 24, x 5 of 10 Figure 3. 1H−1H COSY, HMBC and NOESY correlations of compound 2. A: Key 1H−1H COSY (bold ─), and HMBC (→) correlations.
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