葛根的化学成分

目的研究葛根(Pueraria lobata)的化学成分。方法采用硅胶柱色谱、Sephadex LH-20柱色谱、反相ODS柱色谱等方法进行分离纯化,根据理化性质及光谱数据确定化合物的结构。结果分离得到13个化合物,分别鉴定为羽扇豆醇(lupeol,1)、芒柄花素(formononetin,2)、水杨酸(salicylicacid,3)、槲皮素(quercetin,4)、染料木素(genistein,5)、α-棕榈酸单甘油酯(2,3-dihydroxypropylpalmitate,6)、葛香豆雌酚(puerarol,7)、大豆素(daidzein,8)、大豆苷(daidzin,9)、葛根素(puerarin,10)、芒柄花苷(ononin,11)、没食子酸(gallic acid,12)、3′-甲氧基葛根素(3′-methoxy puerarin,13)。结论化合物6为首次从该属植物中分离得到,化合物1为首次从该植物中得到。     

Identification of isoflavones in the roots of Pueraria lobata

The isoflavones of the roots of Pueraria lobata (Willd.) Ohwi (Puerariae Radix) were investigated by high-performance liquid chromatography (HPLC) coupled to photodiode array (PDA) and to mass spectroscopy (MS) using atmospheric pressure chemical ionization (APCI) or electrospray ionization (ESI) in combination with collision-activated decomposition (CAD) (HPLC-APCI-CAD-MS or ESI-CAD-MS) for identification of glycosides and HPLC-APCI-CAD-MS for identification of aglycones. The major glycosides are derived from daidzein ( 9) and most are 8- C-glycosides. 3'-Hydroxypuerarin-4'- O-deoxyhexoside ( 2B) and 3'-methoxy-6'- O- D-xylosylpuerarin ( 6) were identified as new constituents. MS data were obtained for puerarin-4'- O- D-glucoside ( 1), 3'-hydroxypuerarin ( 2A), puerarin ( 3), 3'-methoxypuerarin ( 4), 6'- O- D-xylosylpuerarin ( 5), daidzin ( 7) and 3'-methoxydaidzin ( 8), which were previously characterized by NMR analysis. Isoflavones identified in Puerariae Radix comprise 3'-methoxydaidzein ( 10), genistein ( 12), daidzein-7- O-methyl ether ( 13A), 3'-methoxydaidzein-7- O-methyl ether or 3'-methoxyformononetin ( 13B) and biochanin A ( 15), while previous characterization of daidzein ( 9) and formononetin ( 14) was substantiated by MS data. The structure of compound 11 could not be established by MS techniques. The estrogenic activity was mainly located in the aglycone fraction.     

野葛化学成分研究

目的研究野葛(Pueraria lobata)根的化学成分。方法利用溶剂提取,硅胶柱色谱和凝胶色谱等手段进行分离、纯化,根据理化性质和波谱数据进行结构鉴定。结果分离鉴定了14个化合物,分别为大豆苷元(1),芒柄花苷(2),大豆苷(3), 3′-甲氧基葛根素(4),葛根素(5),葛苷B(6),大豆苷元-8-C-芹菜糖基-(1-6)-葡萄糖苷(7), 3′-羟基葛根素(8),葛根素木糖苷(9),大豆苷元-7,4′-O-二葡萄糖苷(10),葛根素-4′-O-葡萄糖苷(11),美佛辛-4′-O-葡萄糖苷(12), sissotorin(13),葛苷C(14)。结论化合物11和13为首次从野葛的根中分离得到。     

Two new isoflavone glycosides from Pueraria lobata

Two new isoflavone diglycosides, formononetin 8-C-[beta-D-apiofuranosyl-(1 --> 6)]-beta-D-glucopyranoside (1) and formononetin 8-C-[beta-D-xylopyranosyl-(1 --> 6)]-beta-D-glucopyranoside (2), were isolated from the roots of Pueraria lobata, together with four known compounds, 4'-methoxypuerarin (3), daidzin (4), genistin (5), and daidzein (6). The structures of these compounds were elucidated by the spectroscopic methods.     

Two new isoflavone glycosides from Pueraria lobata

Two new isoflavone diglycosides, formononetin 8-C-[beta-d-apiofuranosyl-(1 --> 6)]-beta-d-glucopyranoside (1) and formononetin 8-C-[beta-d-xylopyranosyl-(1 --> 6)]-beta-d-glucopyranoside (2), were isolated from the roots of Pueraria lobata, together with four known compounds, 4'-methoxypuerarin (3), daidzin (4), genistin (5), and daidzein (6). The structures of these compounds were elucidated by the spectroscopic methods.     

Isoflavonoid glycosides from the flowers of Pueraria lobata

Pueraria lobata flower is a medicinal herb for treating intoxication, hepatic, and gastrointestinal tract lesions induced by alcohol. This study aims to investigate the isoflavonoid glycosides in P. lobata flowers. Two new isoflavone compounds were isolated from the extract of P. lobata flowers. Their structures were determined to be 5,6,7,4′-tetrahydroxyisoflavone-6,7-di-O-β-d-glucopyranoside and 5,6,7-trihydroxy-4′-methoxyisoflavone-6,7-di-O-β-d-glucopyranoside on the basis of spectroscopic means including HR-ESI-MS, UV, IR, ¹H, and ¹³C NMR.     

Isoflavonoid glycosides from the flowers of Pueraria lobata

Pueraria lobata flower is a medicinal herb for treating intoxication, hepatic, and gastrointestinal tract lesions induced by alcohol. This study aims to investigate the isoflavonoid glycosides in P. lobata flowers. Two new isoflavone compounds were isolated from the extract of P. lobata flowers. Their structures were determined to be 5,6,7,4'-tetrahydroxyisoflavone-6,7-di-O-β-D-glucopyranoside and 5,6,7-trihydroxy-4'-methoxyisoflavone-6,7-di-O-β-D-glucopyranoside on the basis of spectroscopic means including HR-ESI-MS, UV, IR, 1H, and 13C NMR.     

Anti-inflammatory and antioxidant activities of Jungia paniculata

The present study was conducted to evaluate the antioxidant and anti-inflammatory activities of Jungia paniculata (DC.) A. Gray (Asteraceae), used traditionally in Peru. The dry leaves were extracted with methanol, 50% methanol, and water. The anti-inflammatory activity of this plant was studied using in vitro (nitric oxide production in RAW 264.7 macrophages and sPLA₂ inhibition assay) and in vivo (carrageenan-induced paw edema in rats and TPA-induced ear edema in mice) model systems. The antioxidant activity of extracts was studied using three in vitro model systems (DPPH^? radical-scavenging assay, ABTS^?+ assay, and superoxide radical-scavenging activity). The results have been correlated with total phenolics and total flavonoids contents. In the NO test of the extracts of Jungia paniculata, no significant cytotoxicities were observed at the concentrations determined by MTT assay. Only the MeOH50 extract of Jungia paniculata significantly inhibited PLA₂ enzyme activity (82.3?±?2.6%). At 3?h, the 50% methanol extract of Jungia paniculata at an oral dose of 500?mg/kg showed significant suppression of carrageenan-induced rat paw edema (36.36%). The same extract induced a 93.99% reduction in TPA-induced edema in topical administration. The extracts exhibited a high antioxidant activity and contained high total levels of polyphenols and flavonoids. There was a significant linear correlation between total phenolics and flavonoids contents and antioxidant activity in the three models used. In conclusion, Jungia paniculata possesses anti-inflammatory and antioxidant properties, which confirm the use of this plant in folk medicine as a topical anti-inflammatory herbal.     

Anti-inflammatory activity of two cucurbitacins isolated from Cayaponia tayuya roots

Fractionation of an anti-inflammatory extract from Cayaponia tayuya roots yielded two active compounds, identified as 23,24-dihydrocucurbitacin B (1) and cucurbitacin R (2). Both were evaluated for their anti-inflammatory activity on several experimental models of pain and inflammation. In addition, their cytotoxicity and effects on leukotriene B4 (LTB4) formation were evaluated in rat polymorphonuclear leukocytes. Both compounds showed activity in the following models: carrageenan-induced mouse paw oedema (1, 4 mg/kg p.o., 46% inhibition at 3 h), phospholipase A2-induced mouse paw oedema (2, 3 mg/kg i.p., 61% inhibition at 60 min), serotonin-induced mouse paw oedema (1 and 2, 0.5 mg/kg s.c., 73% and 79% inhibition, respectively), 12- O-tetradecanoylphorbol 13-acetate (TPA)-induced acute ear oedema (2, 36% inhibition at 4 mg/kg p.o., and 87% inhibition at 0.1 mg/ear topically). The compounds were also active against the inflammation induced by repeated application of TPA on mouse ears, affecting both the oedema itself (1 and 2 at 0.1 mg/ear, 44% and 56% inhibition, respectively) as well as cell infiltration (68% and 69%, respectively). The activity of both compounds against oedema induced by serotonin was not modified by the glucocorticoid receptor antagonist mifepristone; however, the protein synthesis inhibitor cycloheximide abolished the anti-inflammatory response in both cases. Neither compound modified the production of LTB4 in rat polymorphonuclear leukocytes, nor did they exhibit analgesic properties at the dose assayed.     

野葛的现代研究概况

野葛是传统的药用植物,其多个药用部位得到了广泛研究。本文对野葛的根、藤、花等部位的化学成分、药理作用、临床应用等方面进行了综述     

野葛根中葛根素的提取及HPTLC测定

采用有机溶剂萃取结合酸水解的方法,直接从野葛根中分离葛根素,并用HPTLC进行纯度分析。产率为1．15％,含量为97．6％。操作简便,产品纯度和产率高,成本低。     

Anti-inflammatory and antioxidant activities of some extracts and pure natural products isolated from Rhus tripartitum (Ucria)

Chromatographic separation of Rhus tripartitum (Anacardiaceae) chemical components revealed the presence of four main natural substances: a new biflavonoid masazinoflavanone (S1), myricetin (S2), (-)-lyoniresinol 3α-O-β-D-glucopyranoside (S3), and (-)-methyl shikimate (S4). The anti-inflammatory activity of the new biflavonoid substance was performed. Compared with the standard drug dexamethasone, the biflavonoid substance masazinoflavanone (S1) inhibited in a dose-related manner carrageenan-induced paw edema in rats. Antiradical scavenging capacities of extracts and natural substances issued from Rhus tripartitum were tested using free radical forms of ABTS and DPPH. The Trolox Equivalent Antioxidant Capacity (TEAC) assay shows values of 1.92, 1.39, 1.25, 2.40, and 1.58 mM Trolox/mg sample respectively for the chloroformic extract, the ethyl acetate extract, (S1), (S2), and (S3). Values revealed form the total phenolic content assay were 299.3, 372.3, 99.1, and 235.7 mg Catechin/g extract respectively for the chloroformic, ethyl acetate, ethyl acetate/methanol, and methanolic extracts.     

Anti-inflammatory and apoptotic activities of pomolic acid isolated from Cecropia pachystachya

The dichloromethane extract and pomolic acid ( 5) obtained from leaves of Cecropia pachystachya both reduced carrageenan-induced paw oedema in mice. Interestingly, while the triterpenoid inhibited the in vivo production of interleukin-1beta by 39 %, it had no effect on tumour necrosis factor-alpha production. We also demonstrated that both the dichloromethane extract and 5 inhibited the viability of human polymorphonuclear (PMN) cells in a time- and dose-dependent fashion. The PMN membrane integrity was determined with the aid of flow cytometry by means of the exclusion of propidium iodide as assay. Although the cell membrane integrity was altered, neither the extract nor 5 produced cellular necrosis. Moreover, the development of hypodiploid nuclei and DNA fragmentation in the PMN cells were both dependent on dose and time. Finally, in the annexin V-FITC binding assay, compound 5 increased the total of apoptotic cells by 42 % at 100 microM and by 71 % at 200 microM with respect to the control group. In conclusion, both the dichloromethane extract of ambay and isolated compound 5 inhibit the viability of PMN cells through apoptosis. Since they can regulate human neutrophil functions in this way, it is likely that these substances can also limit inflammation.     

Anti-inflammatory activities of aqueous extract from Radix Ophiopogon japonicus and its two constituents

To provide some pharmacological evidence for its clinical use in inflammatory diseases, anti-inflammatory effect of the aqueous extract from Radix Ophiopogon japonicus (ROJ-ext), a traditional Chinese herb, was examined in mouse and rat models. ROJ-ext significantly inhibited xylene-induced ear swelling and carrageenan-induced paw edema in mice when given orally at doses of 25 and 50 mg/kg. Moreover, ROJ-ext also remarkably suppressed carrageenan-induced pleural leukocyte migration in rats and zymosan A-evoked peritoneal total leukocyte and neutrophil migration in mice, while had no obvious effect on pleural prostaglandin E2 level. Furthermore, two active compounds were isolated from ROJ-ext and identified as ruscogenin and ophiopogonin D. As the results, ROJ-ext, ruscogenin and ophiopogonin D dose-dependently reduced phorbol-12-myristate-13-acetate (PMA)-induced adhesion of HL-60 cells to ECV304 cells, with IC50 of 42.85 microg/ml, 7.76 nmol/l and 1.38 nmol/l, respectively. However, they showed no inhibitory effect on PMA-induced cyclooxygense-2 (COX-2) mRNA expression in ECV304 cells. Ruscogenin and ophiopogonin D also notably decreased zymosan A-induced peritoneal leukocyte migration, in comparison with ROJ-ext. These results demonstrate that ROJ-ext presents remarkable anti-inflammatory activity and ruscogenin and ophiopogonin D are two of its active components, which supported its traditional use in the treatment of various diseases associated with inflammation.     

葛根总黄酮的HPCE指纹图谱研究

目的:建立葛根总黄酮的高效毛细管电泳(HPCE)指纹图谱。方法:运行缓冲液为30mmol·L-1硼砂溶液,分离电压为13kV,进样时间为5s,检测波长为254nm,柱温为25℃。结果:从葛根总黄酮HPCE指纹图谱中标定了14个共有峰,其总峰面积达到93%以上。结论:所建立的指纹图谱准确、可靠,可用于评价和控制葛根总黄酮的质量。     

Anti-inflammatory and antioxidant activities of phenolic compounds from Desmodium caudatum leaves and stems

Four flavanonols (1–4), one xanthone (5), and three flavonoid glycosides (6–8), were isolated from the leaves and stems of Desmodium caudatum. Their structures were elucidated by comparing spectroscopic data with reported values. The anti-inflammatory activity of the isolated compounds was investigated in lipopolysaccharide (LPS)-stimulated bone marrow-derived dendritic cells. Among them, compounds 1 and 2 exhibited inhibitory effects on LPS-induced IL-6, IL-12 p40, and TNF-α production with IC₅₀ values ranging from 6.0 to 29.4 μM. Compound 5 exhibited 1,1-diphenyl-2-picrylhydrazyl radical and intracellular reactive oxygen species scavenging activity in human HaCaT keratinocytes. These results warrant further studies of the potential anti-inflammatory and antioxidant benefits of compounds from D. caudatum.     

Chemical constituents from the roots of Lindera aggregata and their biological activities

Three new benzylisoquinoline alkaloids, (1′S)-12′-hydroxyl-linderegatine (1), (1S)-5′-O-p-hydroxybenzoyl norreticuline (2), (1R, 1′R)-11,11′-biscoclaurine (3), along with 18 known compounds were isolated from the roots of Lindera aggregata (Sims) Kosterm. Their structures were determined on the basis of extensive spectroscopic analysis (IR, UV, HR-ESI–MS, 1D and 2D NMR). The absolute configurations of three new compounds were determined by comparing their experimental and calculated ECD for the first time. Compounds (4) and (9) showed cytotoxic activities against human colon carcinoma cell line (HCT-116), with IC50 values of 51.4 and 27.1 μM, respectively. Furthermore, compounds (10) and (11) showed inhibitory activities on nitric oxide production induced by lipopolysaccharide in mouse macrophage RAW 264.7 cells, with IC50 values of 37.8 and 38.7 μM, respectively.     

Anti-inflammatory constituents from Perovskia atriplicifolia

Abstract

Context: Perovskia atriplicifolia Benth (Labiantae) has long been used as a traditional herbal medicine for anti-inflammation in Pakistan; this prompted us to isolate anti-inflammatory compounds from this plant.

Objective: The objective of this study was to isolate and characterize the anti-inflammatory principles from Perovskia atriplicifolia.

Materials and methods: The CHCl₃-soluble fraction of the methanol extract of the whole plant on column chromatography yielded compounds 1–6. The anti-inflammatory potential of the compounds 1–6 was evaluated by Leukotriene C4 (LTC₄) Release Assay which was performed according to the established protocol. LTC₄ in the supernatant of each well was measured using an ELISA kit (Cayman Chemical Co., Ann Arbor, MI).

Results: The bioassay-guided phytochemical investigation of the CHCl₃ soluble fraction of the methanol extract of Perovskia atriplicifolia furnished six compounds, abrotanone (1), abrotandiol (2), (+)-pinoresinol (3), (+)-syringaresinol (4), (+)-lariciresinol (5), and (+)-taxiresinol (6). The compounds (1–6) were evaluated for their inhibitory activities on LTC₄ release. Among the tested compounds, (+)-taxiresinol (6) exhibited the most potent inhibition of LTC₄ release with an IC₅₀ value of 3.4?±?0.09?µM followed by compounds 4, 5, 3, and 2 with an IC₅₀ value ranging from 7.9?±?0.04 to 17.2?±?0.07?µM. Abrotanone (1) showed the lowest inhibition of LTC₄ release with an IC₅₀ value of 35.1?±?0.05?µM (the positive control, zileuton, 0.77?±?0.05?µM).

Conclusion: Compounds 1–6 were found to possess inhibitory activity and seem to have potential therapeutic effect on inflammatory diseases.     

Antipyretic, analgesic and muscle relaxant activities of pueraria isoflavonoids and their metabolites from Pueraria lobata Ohwi-a traditional Chinese drug

We evaluated the antipyretic, analgesic, and muscle relaxant activities of Pueraria isoflavonoids and their metabolites in mice. The glycosides daidzin and genistin significantly reduced fever induced by lipopolysaccharide (LPS). Their metabolites, daidzein and p-ethylphenol, also significantly reduced fever induced by LPS. In addition, daidzin, daidzein, dihydrodaidzein, and p-ethylphenol showed analgesic activity as assessed by the acetic acid-induced writhing test. Furthermore, equol and p-ethylphenol showed muscle relaxant activity in the rotarod and horizontal wire test. These results suggest that these compounds play a major role in the therapeutic activity of Pueraria isoflavonoids.