广东紫珠中黄酮碳苷的分离与结构鉴定及初步体外抗炎活性研究

利用AB-8大孔树脂、Sephadex LH-20、C18及硅胶等柱色谱法分离纯化了广东紫珠的抗炎活性部位。根据理化性质和波谱方法(1H NMR、13C NMR、HMBC、ESI-MS等)鉴定化合物的结构。结果从中分离鉴定了5个黄酮碳苷化合物,分别为5,7,3’,4’-四羟基-8-C-β-D-葡萄糖黄酮碳苷(Ⅰ)、5,7,3’,4’-四羟基-6-C-[α-L-鼠李糖-(1→2)]-β-D-葡萄糖黄酮碳苷(Ⅱ)、5,7,3’,4v-四羟基-8-甲氧基-6-C-β-D-葡萄糖黄酮碳苷(Ⅲ)、5,4’-二羟基-6,7-二甲氧基-8-C-[β-D-木糖-(1→2)]-β-D-葡萄糖黄酮碳苷(Ⅳ)及5,4’-二羟基-6,7-二甲氧基-8-C-β-D-葡萄糖黄酮碳苷(Ⅴ)。化合物Ⅰ为首次从该植物中分离得到,其余4个化合物均为首次从紫珠属植物中分离得到。考察了5个化合物的抗环氧合酶-2活性,结果化合物Ⅰ、Ⅱ、Ⅲ均显示较强的体外抗炎活性。     

乌药叶中黄酮类成分研究(2)

目的研究乌药叶的抗菌、抗炎有效成分。方法采用多种色谱学 ,化学及波谱学等方法进行分离与结构鉴定。结果在以前研究的基础上 ,又从乌药叶中分离得到 4个黄酮类化合物和 1个倍半萜类化合物 :乌药醇 (5 ) ,4个黄酮类化合物分别被鉴定为nubigenol(1 ) ,山奈酚 3 O (6″ 反式 对 肉桂酰基 ) β D 吡喃葡萄糖苷 (2 ) ,香叶木素 7 O β D 葡萄糖苷 (3 )和芦丁 (4 )。 结论这 4个黄酮类化合物均为属内首次分离得到     

Chemical constituents from Portulaca oleracea and their bioactivities

In the present study, we aimed to intensively study the chemical constituents, especially organic acids from a medicinal plant Portulaca oleracea L., and screen their anti-inflammatory and quinone reductase (QR, a phase II detoxyfication enzyme) inductive activity. A total of 20 compounds were isolated and identified based on spectroscopic methods, as succinic acid (1), mono-methyl succinate (2), L-malic acid (3), L-1-methyl malate (4), L-4-methyl malate (5), L-dimethyl malate (6), L-6-ethyl citrate (7), L-1-methyl citrate (8), L-1,5-dimethyl citrate (9), 4-hydroxy-5-methylfuran-3-carboxylic acid (10), 5-hydroxymethyl-furoic acid (11), stearic acid (12), L-pyroglutamic acid (13), cyclo-(tyrosine-leucine) (14), L-isoleucine (15), (–)-dehydrovomifoliol (16), (–)-epiloliolide (17), 3,4-dihydroxyphenylethanol (18), succinimide (19), and uracil (20). Among them, 14 compounds (2, 4–8, 10, 11, 13–18) were isolated from P. oleracea for the first time. Compound 18 (12.5 μM) exhibited potent anti-inflammatory effect in lipopolysaccharide (LPS)-induced macrophage cells (RAW264.7) by reducing NO production, and it also increased QR activity in Hepa lclc7 cells. Compound 16 (50 μM) showed weak QR inductive activity. None of other compounds showed anti-inflammatory or QR inductive activities.     

Structure-activity relationship study of androstene steroids with respect to local anti-inflammatory activity

A sex hormone, 3beta-acetoxy-17beta-hydroxy-androst-5-ene (1) (CAS 1639-43-6), was isolated from aerial parts of Acacia nilotica. This compound is reported to have anti-inflammatory activity. In view of this, considering this molecule as a lead molecule different androstene compounds were synthesized to study their potency and structure-activity relationship with respect to local anti-inflammatory activity. The experiments indicated that 17 ketonic compounds were more active towards inflammation than their oxime analogues. Similarly, for the compounds containing an acetyl group fixed at C-3 position a decreasing trend of activity was observed in the order of ketonic, hydroxyl, oxime and acetyl group, respectively, when these groups are at C-17 position.     

A new flavan-3-ol and the anti-inflammatory effect of flavonoids from the fruit peels of Wisteria floribunda

A new flavan-3-ol, (+)-afzelechin 5-O-β-d-glucopyranoside (2), together with 13 known flavonoids (1, 3-14), was isolated from the fruit peels of Wisteria floribunda. Their structures were assigned by detailed interpretation of NMR, MS, and CD spectroscopic data, as well as by comparing with published reports. The in vitro anti-inflammatory activity of the isolated compounds (1-14) was examined. Among them, compounds 3, 6, and 9 produced highest inhibitory effects on tumor necrosis factor alpha (TNF-α)-induced nuclear factor kappa-B activation in HepG2 cells with IC(50) values of 14.1, 16.5, and 11.9 μM, respectively. With the exception of compound 6, the compounds significantly inhibited the accumulation of pro-inflammatory inducible nitric oxide synthase and cyclooxygenase-2 proteins in TNF-α-stimulated HepG2 cells at a concentration as low as 0.1 μM.     

翼核果中化学成分的研究Ⅰ

本文从广西产翼核果（ＶｅｎｔｉｌａｇｏｌｅｉｏｃａｒｐａＢｅｎｔｈ．）根茎的抗炎有效部位碱提取酸沉淀中分离得到了６个化合物，其中４个蒽醌类化合物：大黄素（１），大黄素－８－Ｏ－β－Ｄ－葡萄糖甙（ｅｍｏｄｉｎ－８－Ｏ－β－Ｄ－ｇｌｕｃｏｓｉｄｅ）（２），大黄素－６，８－二甲醚（ｅｍｏｄｉｎ－６，８－ｄｉｍｅｔｈｙｌｅｔｈｅｒ）（３），１－羟基蒽醌（１－ｈｙｄｒｏｘｙａｎｔｈｒａｑｕｉｎｏｎｅ）（４），１个酮类化合物：１，６－二羟基－３－甲基酮－８－羧酸（ｃａｌｙｘａｎｔｈｏｎｅ）（５），及１个异黄酮类化合物：鸢尾甙元（ｔｅｃｔｏｒｉｇｅｎｉｎ）（６）．其中化合物（２），（５）为本种植物中首次分离得到，（６）为本属植物中首次分离得到。     

Antiinflammatory constituents from the roots of smilax bockii warb.

From 70% ethanol extract of the roots of Smilax bockii warb., seven flavonoids, kaempferol (1), kaempferol-7-O-beta-D-glucopyranoside (2), quercetin (3), isorhamnetin (4), (+)-dihydro-kaempferol (5), engeletin (6), isoengeletin (7), and n-butyl-beta-D-fructopyranoside (8), caffeic acid n-butyl ester (9) were isolated and identified by means of chemical and spectroscopic. Compounds 2, 4, and 6-9 were isolated for the first time from the roots of S. bockii and compounds 2, 8, and 9 were firstly isolated from the genus Smilax. In addition, using the SEAP (Secreted alkaline phosphatase) assay system, we investigated the in vitro anti-inflammatory activity of the 70% ethanol extract of the roots of S. bockii, which showed moderate activity in inhibiting TNF-alpha-induced NF-kappaB activation with an IC50 value of 166.6 microg/mL.     

Lignans from the rhizomes of Coptis japonica differentially act as anti-inflammatory principles.

Coptis japonica Makino (Ranunculaceae) is known to possess several biological activities such as anti-inflammatory effects. In this study, five lignans, isolariciresinol (1), lariciresinol glycoside (2), pinoresinol (3), pinoresinol glycoside (4) and syringaresinol glycoside (5), isolated from the rhizomes of C. japonica were tested to evaluate their in vitro anti-inflammatory effects. Pinoresinol and isolariciresinol showed higher inhibitory effects on TNF-alpha production, whereas syringaresinol glycoside strongly suppressed lymphocyte proliferation. The results indicate that the lignans may differentially modulate inflammatory cell responses, suggesting that these compounds may participate in anti-inflammatory processes by C. japonica.     

Three new stilbene trimers from the lianas of Gnetum hainanense

Three new stilbene trimers, gnetuhainins M-O (1-3), were isolated from the lianas of Gnetum hainanense. Their structures and relative configurations were determined by spectroscopic evidence, especially on 2D NMR analysis. The anti-inflammatory activity has been tested for the isolated compounds.     

Geranyl flavonoid derivatives from the fresh leaves of Artocarpus communis and their anti-inflammatory activity

Breadfruit (Artocarpus communis) is a widely distributed crop in tropical and subtropical regions of the world. It is used in Southeast Asia and India to treat several inflammatory disorders. The aim of this study was to investigate the presence of anti-inflammatory flavonoids in A.?communis leaves. Three new geranyl flavonoids, arcommunol C (1), arcommunol D (3), and 5'-geranyl-3,4,2',4'-tetrahydroxychalcone (5), together with four known compounds, prostratol (2), arcommunol E (4), 3'-geranyl-3,4,2',4'-tetrahydroxydihydrochalcone (6), and 3'-geranyl-3,4,2',4'-tetrahydroxychalcone (7), were isolated from the leaves of A.?communis. Compound 4 was isolated for the first time from natural sources. The anti-inflammatory activity of the isolated compounds (1-7) was evaluated by determining their inhibitory activity on the production of proinflammatory mediators in lipopolysaccharide (LPS)-activated RAW 264.7 murine macrophage cells. Compounds 2, 3, and 4 suppressed the LPS-induced production of nitric oxide (NO) in RAW 264.7 cells with IC50 values of 8.13 ± 0.17, 18.45 ± 2.15, and 22.74 ± 1.74 μM, respectively. Furthermore, 2 decreased lipopolysaccharide (LPS)-mediated induction of protein expressions of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in RAW 264.7 cells. It was also found that 2 suppressed LPS-induced phosphorylation of JNK and p38 mitogen-activated protein kinase (MAPK) signaling.     

Phytochemical and biological studies of Adiantum capillus-veneris L.

Chromatographic fractionation of the alcoholic extract of the dried fronds of Adiantum capillus-veneris L. (Adiantaceae) yielded seven compounds: four triterpenoidal compounds belonging to adiantane and filicane groups were isolated from the hexane fraction and identified as isoadiantone (1); isoadiantol-B (2); 3-methoxy-4-hydroxyfilicane (3) and 3,4-dihydroxyfilicane (4) and three flavonoids were isolated from the ethyl acetate fraction and identified as: quercetin (5), quercetin-3-O-glucoside (6) and quercetin-3-O-rutinoside (rutin) (7). The identification of the isolated compounds has been established through their physical, chemical and spectroscopic methods including IR, ¹H NMR, ¹³C NMR, HSQC, HMBC, NOESY and MS. Biological studies of the total alcoholic extract, hexane fraction and some of the isolated compounds showed an anti-inflammatory activity while the hypoglycemic study of the total alcoholic extract showed a significant activity.     

Anti-inflammatory xanthones from the twigs of Hypericum oblongifolium wall

Two new xanthonolignoids, hypericorin A (1) and hypericorin B (2), along with five known new source compounds, a xanthonolignoid, kielcorin (3), 4-hydroxy-2,3-dimethoxyxanthone (4), 3,4,5-trihydroxyxanthone (5), 1,3-dihydroxy-5-methoxyxanthone ( 6) and 1,3,7-trihydroxyxanthone (7), were isolated from the stems (twigs) of Hypericum oblongifolium Wall. The structures of the new compounds were deduced on the basis of spectroscopic techniques (EI-MS, HREI-MS, (1)H NMR, (13)C NMR, HMQC, HMBC, and NOESY). We also report herein for the first time the single crystal X-ray structure of compound 6. Compounds 1- 7 were screened for their IN VITRO anti-inflammatory (respiratory burst) inhibiting activities using isolated human neutrophils; compounds 1, 2, 3, 5, and 7 showed significant activities (IC (50)?=?816.23?±?73.30, 985.20?±?55.80, 965.21?±?65.80, 907.20?±?50.80, 975.20?±?81.10?μM, respectively), compound 6 showed moderate activity (IC (50)?=?2500.85?±?50.50?μM), while compound 4 was totally inactive at 1000?μg/mL as compared to the positive control used, indomethacin (IC (50)?=?757.99?±?5.90?μM), and aspirin (IC (50)?=?279.44?±?4.40?μM). Compound 4 was also inactive in comparison with other tested Hypericum compounds.     

Two new α-pyrones and other components from the cladodes of<Emphasis Type="Italic">Opuntia dillenii</Emphasis>

The aqueous ethanolic extract from the fresh cladodes of Opuntia dillenii HAW. was found to show anti-inflammatory activity. Two new alpha-pyrones, named opuntioside II (1) and opuntioside III (2), were isolated from the extract together with six known compounds. The structures of the new compounds were determined on the basis of chemical and physicochemical evidence.     

Antinociceptive activities of alpha-truxillic acid and beta-truxinic acid derivatives

Our recent study demonstrated that the dimeric structure of alpha-truxillic acid derivatives played an important role in the expression of their anti-inflammatory activities. In the present report, to investigate the correlation between the structure and anti-inflammatory activity, alpha-truxillic acid (1) and its derivatives (2-6), beta-truxinic acid (7) and its derivatives (8-10) were prepared, and their activities were evaluated in the formalin test. All compounds showed only weak or no activities against the neurogenic pain response, but demonstrated significant activities against the inflammatory pain response induced by formalin. The highest anti-inflammatory activities were observed for alpha-truxillic acid (1) and its derivative 4,4'-dihydroxy-alpha-truxillic acid (2). In addition, alpha-truxillic acid (1) and its derivative, alpha-truxillic acid bis(p-nitrophenyl)ester (5), showed higher anti-inflammatory activities than beta-truxinic acid (7) and the corresponding derivative (10). Furthermore, free carboxylic acids (1, 2) showed higher activities than their dimethyl esters (3, 4) and bis(p-nitrophenyl)ester (5). These results confirmed that the alpha-formation of dimeric structure and the free carboxylic acid were also important for the expression of anti-inflammatory activities. Otherwise, 4,4'-dichloro-beta-truxinic acid (8) had higher activity than its parent compound 7; furthermore, 1,3-dibenzoyl-2,4-di(4-chlorophenyl)cyclobutane (6) also showed strong anti-inflammatory activity. These results suggested that substituents in the phenyl groups were also important for the expression of anti-inflammatory activity. In order to gain information about their activity intensity, the anti-inflammatory activities of 2 and 4,4'-dichlorolated derivatives (6, 8) were compared with that of indomethacin (a nonsteroidal anti-inflammatory drug) in the formalin test. As a result, compounds 2, 6 and 8 showed stronger anti-inflammatory activities than indomethacin. These results suggested that alpha-truxillic acid and beta-truxinic acid derivatives might be developed into a new type of anti-inflammatory drug.     

N-Acyl-N-phenyl ureas of piperidine and substituted piperidines endowed with anti-inflammatory and anti-proliferative activities.

Six series of N-acyl-N-phenyl ureas 1-6 of piperidine (1), and 2-ethyl- (2), 3-methyl- (3), 4-methyl- (4), 4-phenyl- (5), cis-2,6-dimethyl- (6) piperidine were synthesised and evaluated for their anti-inflammatory, anaesthetic, anti-pyretic properties. Some derivatives of series 1 and 5 were also assayed for anti-proliferative activity. Several compounds showed an anti-inflammatory activity comparable or slighty inferior to that of indomethacin in rats (1c,d, 2a,b,g,h, 3b, 4h, 5d,e). Moreover, an appreciable anti-inflammatory activity was also found in 2c,e, 3e,f,g, 4g, 5a,b,c,f,h, and 6a,b,d. All the compounds were devoid of anti-pyretic activity and only a few of them exhibited a low level of infiltration anaesthesia in mice. Compound 5a showed a broad spectrum anti-cancer activity (at low micromolar concentrations), particulary significant against leukemia subpanel.     

Protected effect of Esenbeckia leiocarpa upon the inflammatory response induced by carrageenan in a murine air pouch model

This study was conducted to investigate the anti-inflammatory efficacy of Esenbeckia leiocarpa against the inflammation caused by the carrageenan using a murine air pouch model. Material and methods: The effects of the crude hydroalcoholic extract (CHE), fractions (n-hexane (Hex) and ethyl acetate (AcOEt)), subfractions (polar (Pol) and nonpolar (Nonpol)), or isolated compounds (dihydrocorynantheol (DHC) and beta-sitosterol (β-Sit)) isolated from CHE upon leukocytes, exudate, myeloperoxidase (MPO) adenosine-deaminase (ADA), nitrate/nitrite (NO_x), interleukin-1 beta (IL-1β), tumor necrosis factor-alpha (TNF-α), and inhibitory kappa-B-alpha (IκB-α) degradation were evaluated. The CHE, Alk, Pol, Nonpol, DHC and β-Sit, inhibited leukocytes, exudate, MPO and ADA, NO_x, IL-1β, and TNF-α (P < 0.05). The Hex and AcOEt fractions inhibited all of the proinflammatory parameters, except the exudate. The compound DHC prevented the IκB-α degradation. Conclusion: E. leiocarpa possesses important anti-inflammatory properties. These inhibitory effects occurred along with the downregulation of nitric oxide, IL-1β and TNF-α levels. The isolated compounds DHC and β-Sit may be partially responsible for these anti-inflammatory effects.     

Coumarinic derivatives show anti-inflammatory effects on alveolar macrophages, but their anti-elastase activity is essential to reduce lung inflammation in vivo

We have previously demonstrated the potency of coumarinic derivatives to inhibit human leukocyte elastase. Given the anti-inflammatory activities of some coumarins, we investigated the capacity of our coumarinic derivatives to inhibit inflammation and whether their anti-elastase activity was essential for their anti-inflammatory functions. All compounds studied were coumarinic derivatives displaying differential anti-proteinase activity. Coumarinic derivatives 1, 2, and 3 efficiently inhibited human leukocyte elastase in vitro, whereas the coumarinic derivative 4 did not show inhibitory activity. The anti-inflammatory effect of these compounds and a coumarin control, scopoletin, on interleukin-6 (IL-6), tumor necrosis factor (TNF), and macrophage chemotactic protein-1 (MCP-1) release was studied using lipopolysaccharide (LPS)-stimulated alveolar macrophages. The in vivo effect of compound 2, that inhibits elastase, and compound 4, that does not show proteinase inhibition, was investigated using a mouse model of LPS-induced lung inflammation and elastase-induced acute lung injury. All investigated coumarinic derivatives, regardless of their anti-proteinase activity, significantly inhibited IL-6 and TNF production by LPS-stimulated alveolar macrophages. However, only compounds 2, 3, and 4 significantly reduced MCP-1 release. Compound 2 attenuated LPS-induced leukocyte recruitment in bronchoalveolar lavage, whereas no inhibition was observed with compound 4 devoid of elastase inhibitory capacity. Interestingly, MCP-1 level was reduced in bronchoalveolar lavage of compound 4 treated mice, whereas TNF and IL-6 levels were not modulated by coumarins. Furthermore, compound 2, but not 4, reduced elastase induced lung injury. Our data suggest that although coumarinic derivatives have anti-inflammatory properties, their anti-elastase activity is essential to reduce lung inflammation in vivo.     

Protective effect of phlorotannins from Eisenia bicyclis against lipopolysaccharide-stimulated inflammation in HepG2 cells

In this study, four bioactive phloroglucinol derivates including phloroglucinol (1), eckol (2), dioxinodehydroeckol (3), and dieckol (4) were isolated from Eisenia bicyclis and characterized by nuclear magnetic resonance (NMR) spectroscopic methods. Moreover, the anti-inflammatory activity of these compounds was investigated on human hepatoma cell line HepG2 cells stimulated by lipopolysaccharide (LPS). It was demonstrated that LPS can induce the production of pro-inflammatory cytokines such as interleukin-1β (IL-1β), interleukin-6 (IL-6), and tumor necrosis factor-α (TNF-α) as well as the expression of inflammatory mediators as cyclooxygenase-2 (COX-2), and inducible nitric oxide synthases (iNOS) from HepG2 cells. Among isolated compounds, compound (1) exhibited significant inhibition on LPS-stimulated inflammatory responses in HepG2 cells without any cytotoxicity. Herein, compound (1) suppresses the production of pro-inflammatory cytokines such as IL-1β, IL-6, and TNF-α and the expression of COX-2 and iNOS. Thus, these results indicated that phlorotannins isolated from E. bicyclis, especially compound (1), can be used as a beneficial source for preventing and treating inflammation response.     

Anti-inflammatory activity of phenylpropanoids and phytoquinoids from Illicium species in RBL-2H3 cells

Two phenylpropanoids, 1-allyl-3,5-dimethoxy-4-(3-methyl-but-2-enyloxy)benzene ( 4) and 4-allyl-2,6-dimethoxy-3-(3-methyl-2-butenyl)phenol ( 6), and two phytoquinoids, 4 R-(-)-illicinone-A ( 7) and 2 S,4 R-(-)-illicinone-B ( 8), isolated from plants of the ILLICIUM species significantly inhibited histamine release from rat basophilic leukemia (RBL-2H3) cells stimulated with A23187. Furthermore, these compounds caused a decline in TNF-alpha levels in culture supernatants of RBL-2H3 cells following treatment with A23187. The results indicate that these compounds might be useful as anti-inflammatory agents against mast cell-mediated inflammatory diseases.     

A new auronol from Cudrania cochinchinensis

A new auronol, cudrauronol (1), was isolated from the roots of Cudrania cochinchinensis along with 10 known compounds, 1,3,5-trihydroxy-4-prenylxanthone (2), 1,3,7-trihydroxy-4-prenylxanthone (3), 3,4',5,7-tetrahydroxydihydroflavonol (4), kaempferol (5), 3,6-dihydroxy-1,5-dimethoxyxanthone (6), 2',4',5,7-tetrahydroxyflavanolol (7), 3,7-dihydroxy-1-methoxyxanthone (8), 1,3,5-trihydroxyxanthone (9), cudraflavone B (10), and 2'-oxyresveratrol (11). Compounds 1-8 were evaluated for anti-inflammatory activity on lipopolysaccharide-induced nitric oxide production in RAW 264.7 macrophages. Compounds 2-5 were more active than aminoguanidine, with IC(50) values of 8.8, 23.2, 27.1, and 11.9?μM, respectively.