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Bioactive Constituents from the Aerial Parts of Pluchea Indica Less

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Bioactive Constituents from the Aerial Parts of Pluchea Indica Less molecules Article Bioactive Constituents from the Aerial Parts of Pluchea indica Less Jingya Ruan 1, Zheng Li 1, Jiejing Yan 1, Peijian Huang 2, Haiyang Yu 2, Lifeng Han 2, Yi Zhang 1,2,* and Tao Wang 1,2,* 1 Tianjin State Key Laboratory of Modern Chinese Medicine, Tianjin University of Traditional Chinese Medicine, 312 Anshanxi Road, Nankai District, Tianjin 300193, China; [email protected] (J.R.); [email protected] (Z.L.); [email protected] (J.Y.) 2 Tianjin Key Laboratory of TCM Chemistry and Analysis, Institute of Traditional Chinese Medicine, Tianjin University of Traditional Chinese Medicine, 312 Anshanxi Road, Nankai District, Tianjin 300193, China; [email protected] (P.H.); [email protected] (H.Y.); [email protected] (L.H.) * Correspondence: [email protected] (Y.Z.); [email protected] (T.W.); Tel./Fax: +86-22-5959-6163 (Y.Z.); +86-22-5959-6168 (T.W.) Received: 8 August 2018; Accepted: 21 August 2018; Published: 21 August 2018 Abstract: Four new thiophenes, (300R)-pluthiophenol (1), (300R)-pluthiophenol-400-acetate (2), 300-ethoxy- (300S)-pluthiophenol (3), 300-ethoxy-(300S)-pluthiophenol-400-acetate (4), together with twenty-five known compounds were obtained from the 70% ethanol-water extract of the aerial parts of Pluchea indica Less. Their structures were elucidated by spectroscopic methods. Among the known isolates, compounds 7, 8, 11, 14, 15, 18, 20, 23, 25–27 were isolated from Asteraceae family firstly, while compounds 6, 9, 10, 12, 13, 16, 19, 21, 28 were isolated from Pluchea genus for the first time. Meanwhile, compounds 1, 2, 10, 13, 18, 23 displayed significant inhibitory activities on LPS-induced NO production at 40 µM from RAW 264.7 macrophages, while compounds 3, 4, 26–29 possessed moderate inhibitory effects. Keywords: Pluchea indica Less.; chemical compositions; RAW 264.7 cells; anti-inflammatory activities 1. Introduction As one of the largest families, the Asteraceae (Compositae) family contains about 1600–1700 genera and 24,000–30,000 species. Most of the Asteraceae family plants are herbs and shrubs, and have been widely used as herbal medicines since ancient times all over the world [1]. Pluchea indica Less., belongs to Pluchea genus, Asteraceae family, is a 1 to 2 meters high shrub. It mainly distributes in the tropical and subtropical regions of Africa, Asia, America, Australia, and China’s southern provinces. As an amphibious woody semi-mangrove plant, it plays an important role in maintaining the ecological balance in the coastal areas of Southeast Asia in China [2]. As a folk medicine in Guangxi, it exhibits the function of softening hardness and dissolving lump [3]. As a type of food, it possesses the activity of warming the stomach [4]. Its main chemical compositions are thiophenes, quinic acids, sesquiterpenes, lignans, flavonoids, and sterols [2]. Pharmacological studies have shown that the plant exhibits many pharmacological functions such as anti-inflammatory [5], anti-cancer [6], anti-oxidant [7], anti-microbial [8], and insecticidal activities [9]. Through the summary of relevant literature, it is found that the pharmacodynamic material basis is not yet clear for the lack of systematic research on the plant. In the course of studying the anti-inflammatory activity of various medicinal plants, 70% EtOH extract of P. indica was found to possess significant in vitro anti-inflammatory bioactivity. Based on the anti-inflammatory activity on LPS-induced NO production from RAW 264.7 macrophages, a systematic chemical component study of P. indica aerial parts was carried out. In this paper, the isolation and identification of constituents were described as well as their inhibitory effect on the production of NO in RAW 264.7 cells induced by LPS. Molecules 2018, 23, 2104; doi:10.3390/molecules23092104 www.mdpi.com/journal/molecules Molecules 2018, xx, x 2 of 11 Molecules 2018, xx, x 2 of 11 study of P. indica aerial parts was carried out. In this paper, the isolation and identification of study of P. indica aerial parts was carried out. In this paper, the isolation and identification of constituents were described as well as their inhibitory effect on the production of NO in RAW 264.7 constituents were described as well as their inhibitory effect on the production of NO in RAW 264.7 Moleculescells induced2018, 23 by, 2104 LPS. 2 of 11 cells induced by LPS. 2. Results and Discussion 2.2. Results Results and and Discussion Discussion In the course of our investigation of the bioactive constituents from the 70% ethanol-water In the course of our investigation of the bioactive constituents from the 70% ethanol-water (EtOH)In theextract course of the of aerial our investigation parts of P. indica of the, four bioactive new thiophenes, constituents named from theas (3 70%′′R)-pluthiophenol ethanol-water (EtOH) extract of the aerial parts of P. indica, four new thiophenes, named as00 (3′′R)-pluthiophenol (EtOH)(1), extract(3′′R of)-pluthiophenol the aerial parts-4′′ of-acetateP. indica , four( new2), thiophenes,3′′-ethoxy named-(3′′S as)-pluthiophenol (3 R)-pluthiophenol ( 31), (1),00 (3′′R)-pluthiophenol00 -4′′-acetate00 00(2), 3′′-ethoxy-(300′′S)-pluthiophenol00 (3), (33′′-ethoxyR)-pluthiophenol-4-(3′′S)-pluthiophenol-acetate- (42′′),-acetate 3 -ethoxy-(3 (4) (FigureS)-pluthiophenol 1) as well as (3 twenty), 3 -ethoxy-(3-five knownS)-pluthiophenol- compounds, 3′′00-ethoxy-(3′′S)-pluthiophenol-4′′-acetate (4) (Figure 1) as well as twenty-five known compounds, 43,4-acetate-dihydroxy (4) (Figure benzaldehyde1) as well as(5) twenty-five [10], vanillin known (6) compounds,[11], 3,4-dihydroxy 3,4-dihydroxy-5-methoxybenzaldehyde benzaldehyde ( 5)[ 10(7],) 3,4-dihydroxy benzaldehyde (5) [10], vanillin (6) [11], 3,4-dihydroxy-5-methoxybenzaldehyde (7) vanillin[12], syringicaldehyde (6)[11], 3,4-dihydroxy-5-methoxybenzaldehyde (8) [13], dibutylphthalate (9) (7)[[1412], ],e syringicaldehydethyl caffeate (10 (8) )[[1513], [12], syringicaldehyde (8) [13], dibutylphthalate (9) [14], ethyl caffeate (10) [15], dibutylphthalate2,3-dihydroxy-1-(4 (9-hydroxy)[14], ethyl-3-methoxyphenyl) caffeate (10)[15-propan], 2,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)--1-one (11) [16], trans-coniferyl aldehyde (12) 2,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)-propan-1-one (11) [16], trans-coniferyl aldehyde (12) propan-1-one[17], esculetin ( 11(13)[)16 [18], trans], threo-coniferyl-2,3-bis(4 aldehyde-hydroxy (12-3-)[methoxyphenyl)17], esculetin (13-3)[-ethoxypropan18], threo-2,3-bis(4-hydroxy--1-ol (14) [19], [17], esculetin (13) [18], threo-2,3-bis(4-hydroxy-3-methoxyphenyl)-3-ethoxypropan-1-ol (14) [19], 3-methoxyphenyl)-3-ethoxypropan-1-olerythro-2,3-bis(4-hydroxy-3-methoxyphenyl) (14-)[3-ethoxypropan19], erythro-2,3-bis(4-hydroxy-3-methoxyphenyl)-3--1-ol (15) [20], (+)-isolariciresinol (16) erythro-2,3-bis(4-hydroxy-3-methoxyphenyl)-3-ethoxypropan-1-ol (015) [200 ], (+)-0isolariciresinol 0 (16)0 ethoxypropan-1-ol[16,21], (–)-(7S,7 (15′S,8)[R20,8],′R (+)-isolariciresinol)-4,4′-dihydroxy-3,3 (16′,5,5)[16′-pentamethoxy,21], (–)-(7S,7 S-,87,9R′,8:7′R,9)-4,4-diepoxylignane-dihydroxy-3,3 ,5,5(17)- [16,21], (–)-(7S0,7′0S,8R,8′R)-4,4′-dihydroxy-3,3′,5,5′-pentamethoxy0 -7,9′:7′,9-diepoxylignane (17) pentamethoxy-7,9[22,23], (+)-9′-isovaleryllariciresinol:7 ,9-diepoxylignane ( 17)[22(18,23) ], (+)-9[24–-isovaleryllariciresinol26], caryolane-1,9β (-18diol)[24 –26(],19 caryolane-) [27], [22,23], (+)-9′-isovaleryllariciresinol (18) [24–26], caryolane-1,9β-diol (19) [27], 1,9(8Rβ,9-diolR)-isocaryolane (19)[27], (8R-,98,9R-)-isocaryolane-8,9-dioldiol (20) [28], clovane (20-2α,9β)[28],-diol clovane-2 (21) [α27,9],β -diolvalenc (21-1(10))[27-],ene valenc-1(10)-ene--8,11-diol (22) (8R,9R)-isocaryolane-8,9-diol (20) [28], clovane-2α,9β-diol (21) [27], valenc-1(10)-ene-8,11-diol (22) 8,11-diol[2], fraxinellone (22)[2], fraxinellone(23) [29], stigmasterol (23)[29], stigmasterol (24) [30], methyl (24)[30 ],9- methylhydroxynonanoate 9-hydroxynonanoate (25) [31], (25triethyl)[31], [2], fraxinellone (23) [29], stigmasterol (24) [30], methyl 9-hydroxynonanoate (25) [31], triethyl triethylcitrate (26 citrate) [32], ( 269,12,13)[32],-trihydroxyoctadeca 9,12,13-trihydroxyoctadeca-10(-10(E),15(Z)-Edienoic),15(Z)-dienoic acid (27) acid[33], (pinellic27)[33], acid pinellic (28) acid[34], citrate (26) [32], 9,12,13-trihydroxyoctadeca-10(E),15(Z)-dienoic acid (27) [33], pinellic acid (28) [34], (adenosine28)[34], adenosine (29) [35] ( (Figure29)[35 ]2 (Figure) were obt2) wereained. obtained. adenosine (29) [35] (Figure 2) were obtained. Figure 1. The new compounds 1–4 obtained from the aerial parts of P. indicaindica.. Figure 1. The new compounds 1–4 obtained from the aerial parts of P. indica. Figure 2. Cont. Molecules 2018, 23, 2104 3 of 11 Molecules 2018, xx, x 3 of 11 FigureFigure 2 2.. TheThe known known compounds compounds 55––2929 obtainedobtained from from the the aerial aerial parts parts o off P.P. indica . (3′′R)-Pluthiophenol (1) was isolated as yellow oil. Its molecular formula was revealed to be (300R)-Pluthiophenol (1) was isolated as yellow oil. Its molecular formula was revealed to be C13H10O2S by positive ESI-Q-Orbitrap MS analysis (m/z 231.04726 [M + H]+, calcd for C13H11O2S, C H O S by positive ESI-Q-Orbitrap MS analysis (m/z 231.04726 [M + H]+, calcd for C H O S, 231.04743).13 10 2 The characteristic absorptions in its IR spectrum suggested the presences of 13hydroxyl11 2 231.04743). The characteristic absorptions in its IR spectrum suggested the presences of hydroxyl (3312 −1 −1 −1 1 (3312−1 cm ), thiophene ring (3105, 1448−1 cm ), and alkynyl (2222−1 cm 1). Its H-NMR (CD3OD, 500 cm ), thiophene ring (3105, 1448 cm ), and alkynyl (2222 cm ).
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