Polyphenolic constituents of Actaea racemosa

A new lignan, actaealactone (1), and a new phenylpropanoid ester derivative, cimicifugic acid G (2), together with 15 known polyphenols, protocatechuic acid, protocatechualdehyde, p-coumaric acid, caffeic acid, methyl caffeate, ferulic acid, ferulate-1-methyl ester, isoferulic acid, 1-isoferuloyl-beta-d-glucopyranoside, fukinolic acid, and cimicifugic acids A, B, and D-F, were isolated from an extract of the rhizomes and roots of black cohosh (Actaea racemosa). The structures of the new compounds were determined on the basis of NMR spectroscopic analysis. Compounds 1 and 2 displayed antioxidant activity in the 1,1-diphenyl-2-picrylhydrazyl (DPPH) free-radical assay with IC(50) values of 26 and 37 microM, respectively. Other antioxidants identified from A. racemosa include cimicifugic acid A (3), cimicifugic acid B (4), and fukinolic acid (5). Compounds 1 and 2 also exhibited a small stimulating effect on the growth of MCF-7 breast cancer cell proliferation 1.24-fold (14 microM) and 1.14-fold (10 microM), respectively, compared to untreated cells.     

Actaeaepoxide 3-O-beta-D-xylopyranoside, a new cycloartane glycoside from the rhizomes of Actaea racemosa (Cimicifuga racemosa)

A new cycloartane glycoside (1) was obtained from a minor triterpene fraction of the rhizome extract of Actaea racemosa (synonym: Cimicifuga racemosa) along with a known compound, cimigenol 3-O-beta-D-xylopyranoside. The structure of 1 was elucidated as 20(S),22(R),23(R),24(S)-12beta-acetoxy-16beta:23,23alpha:24-diepoxy-3beta,22beta,25-trihydroxy-9,19-cyclolanost-7-ene 3-O-beta-D-xylopyranoside (actaeaepoxide 3-O-beta-D-xylopyranoside) on the basis of spectral and chemical evidence.     

陕西产秦艽的化学成分研究

目的:对陕西产秦艽Gentiana macrophylla根的化学成分进行系统研究。方法:利用多种色谱手段对秦艽的脂溶及水溶部分进行分离;用UV,IR,MS,¹H-,¹³C-NMR等技术及对照品对照进行鉴定。结果:鉴定了8个化合物,其中脂溶部位4个,分别是:5-羧基-3,4-二氢-1H-2-苯并吡喃-1-酮(5-carboxyl-3,4-dihydrogen-1H-2-benzopyran-1-one1),红白金花内酯(erythrocentaurin 2),栎瘿酸(roburic acid 3),齐墩果酸(oleanolic acid 4)。水溶部位4个:龙胆苦苷(gentiopicroside 5),獐牙菜苦苷(swertiamarine 6),獐牙菜苷(sweroside 7),6′-O-β-D-葡萄糖基龙胆苦苷(6′-O-β-D-gluco-sylgentiopicroside 8)。结论:1为新化合物,命名为红白金花酸,2为首次从本属植物中分得,8为首次从秦艽中分得。     

3-Hydroxy-3-methylglutaryl flavonol glycosides from Oxytropis falcata

Five new 3-hydroxy-3-methylglutaryl (HMG) flavonol 3-O-glycosides, named oxytroflavosides A-E (1-5), and two new rhamnocitrin 3-O-glycosides, oxytroflavosides F and G (6 and 7) were isolated from the n-BuOH-soluble fraction of an EtOH extract of Oxytropis falcata together with seven known kaempferol glycosides (8-14), of which six were isolated from the genus Oxytropis for the first time. The structures of these compounds were elucidated by spectroscopic techniques and chemical methods. The absolute configuration of HMG in compounds 1-5 was determined to be S through spectroscopic analysis of the mevalonamide obtained by amidation and reduction of the HMG moiety. Compounds 1-10 were evaluated for anti-inflammatory activities using lipopolysaccharide-induced RAW 264.7 cells, but none of them showed inhibitory effects on NO production.     

In vitro 12(S)-HETE inhibitory activities of naphthoquinones isolated from the root bark of Euclea racemosa ssp. schimperi

Platelet 12-lipoxygenase is believed to play a role in cancer and other pathological conditions, such as psoriasis, atherosclerosis and arthritis. The inhibition of 12-LOX is a potential therapeutic approach in the treatment of tumor metastasis. The extracts of Euclea racemosa Murr. ssp. schimperi (A. DC.) F. White (Ebenaceae) obtained by maceration and naphthoquinones isolated from the dichloromethane extract have been investigated for their 12(S)-HETE inhibitory activity using human platelets. At 100 microg/ml, the dichloromethane extract inhibited the formation of 12(S)-HETE by 88.7% and compounds 7-methyljuglone (2), isodiospyrin (3), neodiospyrin (4) and mamegakinone (5), isolated from this extract, exhibited significant activities with IC(50) values ranging from 4 to 58 microg/ml (22.2-155.7 microM). Of these the most abundant compound, 7-methyljuglone displayed a potent inhibitory activity with an IC(50) value of 4.18 microg/ml (22.2 microM), which was comparable to the positive control baicalein with an IC(50) value of 5 microg/ml (18.5 microM). In contrast, 4(S)-shinanolone (1), the reduced form of compound 2, did not show any significant inhibitory activity even at a concentration of 60 microg/ml.     

Behavioural and biochemical effects of fractions prepared from Banxia Houpu decoction in depression models in mice

Banxia-houpu decoction is widely used in therapy for depression in China. The water-EtOH extract (WE-1) and chloroform-soluble fraction (WE-1-2) of Banxia-houpu decoction reduced the duration of immobility in the tail suspension test (TST) and the forced swimming test (FST), the efficacy of the latter was higher than that of the former. The petroleum-soluble fraction (WE-1-1), ethyl acetate-soluble fraction (WE-1-3) and water-soluble fraction (WE-1-4) tended to possess antiimmobility effects in the TST. After a 21-day treatment, the potency of WE-1-2 was almost equivalent to that of fluoxetine, a selective serotonin reuptake inhibitor (SSRI), in the TST, but WE-1-2 showed a lower efficiency than fluoxetine in the FST. WE-1, as well as WE-1-3, was found to increase serotonin (5-HT) and 5-hydroxyindoleacetic acid (5-HIAA) levels in mouse hippocampus and striatum, the activities of WE-1 and WE-1-3 were much stronger than that of fluoxetine. Moreover, WE-1-1, WE-1-2 and WE-1-4 significantly elevated 5-HT and 5-HIAA levels only in the striatum, the degrees of increase of 5-HT and 5-HIAA levels were comparable to that of fluoxetine, which significantly enhanced the levels in all regions of animal brains. Neither fractions or fluoxetine affected norepinephrine (NE) and dopamine (DA) levels in the animal brains. It was found that WE-1, WE-1-2 and fluoxetine significantly decreased serum and liver malondialdehyde (MDA) levels in the study. These results provide evidence for a potential role of antidepressive activities in the therapeutic effects of the Banxia-houpu decoction.     

Complement-inhibiting iridoids from Morinda morindoides

Morinda morindoides (Baker) Milne-Redhead (syn. Gaertnera morindoides Bak.) is one of the most popular medicinal plants in the Democratic Republic of Congo. In relation to its traditional use against rheumatic pains, fractionation of both the EtOAc- and the n-BuOH-soluble fraction of the 80% MeOH extract of the leaves, guided by the anticomplementary activity on the classical activation pathway, yielded eight novel iridoids (1-8), all containing a spirolactone functionality. Their structure was elucidated using spectroscopic methods. Gaertneroside 1, acetylgaertneroside 2, and gaertneric acid 5 were found to inhibit the activation of the classical pathway of the complement system, with IC(50) values between 58 and 69 microM. In addition to the biologically active flavonoids reported before from the same plant, these complement-inhibiting iridoids may contribute at least in part to the traditional use against rheumatic pains.     

污叉丝孔菌菌丝培养物中二酮哌嗪和核苷类化合物

目的：研究污叉丝孔菌（Dichomitus squalens，一种常见的白腐病担子菌）菌丝培养物中化学成分。方法：从广东省鼎湖山采集污叉丝孔菌子实体，通过组织培养分离获得菌丝体，菌丝体用多个含有YMG培养基和小麦的10．5L三角瓶进行大量培养。菌丝体培养物用乙醇提取和溶剂分部，正丁醇溶解部位经柱层析和高效液相色谱分离纯化，用光谱分析法鉴定化合物结构。结果：分离获得7个化合物，分别鉴定为环-（S-脯氨酸-R-缬氨酸）（1），环-（S-月甫氨酸-R-异亮氨酸）（2），环-（S-脯氨酸-R-亮氨酸）（3），环-（S-脯氨酸-R-苯丙氨酸）（4），尿嘧啶（5），尿苷（6），胸苷（7）。结论：以上化合物均系首次从污叉丝孔菌中分离获得。     

Abrusosides A-D, four novel sweet-tasting triterpene glycosides from the leaves of Abrus precatorius

In addition to abrusoside A [1], abrusosides B [2], C [3], and D [4], three further sweet glycosides based on the novel cycloartane-type aglycone, abrusogenin [5], were isolated from an n-BuOH-soluble extract of the leaves of Abrus precatorius. Using a combination of spectral methods, the structures of compounds 1-4 were assigned, respectively, as the 3-O-beta-D-glucopyranosyl, the 3-O-beta-D-glucopyranosyl-(1----2)-beta-D-6-methylglucuronopyranosyl+ ++, the 3-O-beta-D-glucopyranosyl-(1----2)-beta-D-glucopyranosyl, and the 3-O-beta-D-glucopyranosyl-(1----2)-beta-D-glucuronopyranosyl derivatives of compound 5. After it established that compounds 1-4 were neither acutely toxic with mice nor mutagenic with Salmonella typhimurium strain TM677, they were found by a human taste panel to exhibit sweetness potencies in the range 30-100 times greater than sucrose.     

橘叶提取物对小鼠自身免疫性睾丸炎的影响

目的研究橘叶提取物对实验性自身免疫性睾丸炎(EAO)模型小鼠睾丸组织形态及血清白细胞介素-1β(IL-1β)和肿瘤坏死因子-α(TNF-α)含量的影响。方法采用单侧睾丸注射冰醋酸法建立小鼠EAO模型,随机分为空白组、模型组、橘叶乙醇提取物组、环己烷组、乙酸乙酯组、正丁醇组和水部位组。光镜下观察睾丸组织结构变化,ELISA法检测血清IL-1β和TNF-α浓度。结果给药3周后,橘叶乙醇提取物、正丁醇部位和水部位组能明显改善睾丸组织病变,减轻炎症反应。橘叶给药组除环己烷部位外,其余各组均能明显降低EAO小鼠血清中炎症因子IL-1β水平,与模型组比较,差异有统计学意义(P <0. 01)。此外,乙醇提取物组、正丁醇部位组中TNF-α含量也明显降低(P <0. 05,P <0. 01)。结论橘叶乙醇提取物、乙酸乙酯、正丁醇及水部位对小鼠EAO的发生均具有拮抗作用,其中,正丁醇部位抗EAO活性较明显,这可能与抑制炎性因子IL-1β和TNF-α释放有关。     

两面针的化学成分研究

目的：对两面针根的化学成分进行分离和鉴定。方法：采用硅胶柱色谱、Sephadex LH-20柱色谱及重结晶等方法进行成分分离及精制,并利用¹H-NMR,¹³C-NMR,MS等光谱技术鉴定其化学结构。结果：从两面针根乙醇提取液的氯仿部分和正丁醇部分分离得到10个单体化合物,分别鉴定为2,4-二羟基嘧啶(2,4-dihydroxypyrimidine,1),紫丁香酸(syringic acid,2),2,6-二甲氧基对苯醌(2,6-dimethoxy-1,4-benzoquinone,3),对羟基苯甲酸(4-hydroxybenzoic acid,4),对羟基苯甲酸乙酯(ethylparaben,5),顺-3-(2,3,4-三甲氧基苯基)丙烯酸［(Z)-3-(2,3,4-trimethoxyphenyl)acrylic acid,6］,5,6,7-三甲氧基香豆素(5,6,7-trimethoxycoumarin,7),stigmast-9(11)-en-3-ol(8),胡萝卜苷(9),β-谷甾醇(10)。结论：化合物1～9为首次从两面针中分离得到,化合物6是新天然产物。     

蝉翼藤根茎化学成分研究

目的:研究蝉翼藤根茎氯仿部分化学成分。方法:采用各种色谱法分离,运用多种波谱技术鉴定结构,并对部分化合物进行了体外DPPH抗氧化试验。结果:分离鉴定出7个化合物,经鉴定为:3,4-二羟基苯甲酸(1),3-羟基-4-甲氧基苯甲酸(2),4-羟基-3-甲氧基-1-烯丙醛基苯(3),7-羟基-1,2,3,8-四甲氧基酮(4),1,3,8-三羟基-4-甲氧基酮(5),1,3,8-三羟基-2-甲氧基酮(6),1,3,6-三羟基-2,7-二甲氧基酮(7)。结论:化合物1～6为首次从该属中得到,化合物3表现出良好的抗氧化能力IC₅₀=4.14μg·mL^-1。     

土荆皮抗真菌化学成分研究

目的对土荆皮Pseudolaricis Cortex抗真菌活性部位进行化学成分研究。方法土荆皮粗粉以95%乙醇回流提取,所得浸膏采用溶剂法分为不同提取部位,体外抗真菌活性测试显示其醋酸乙酯部位对白色念珠菌具有显著的抑制作用。采用硅胶、Sephadex LH-20、制备高效液相色谱对土荆皮醋酸乙酯部位进行分离纯化,并通过波谱数据分析对化合物进行结构鉴定。结果从土荆皮醋酸乙酯部位分离得到5个化合物,分别鉴定为土荆皮酸B(1)、土荆皮酸C(2)、香草酸(3)、香草酸-4-O-β-D-阿洛糖苷(4)、17-羟基土荆皮酸B(5)。结论化合物5为一新化合物,命名为土荆皮酸I;化合物4为首次从该植物中分离得到。体外抗真菌活性测试显示,化合物1对白色念珠菌生长具有显著的抑制作用,化合物2和5仅显示微弱的抑菌活性。     

Alkaloids from Eschscholzia californica and their capacity to inhibit binding of [3H]8-Hydroxy-2-(di-N-propylamino)tetralin to 5-HT1A receptors in Vitro

A 70% ethanol extract of California poppy (Eschscholzia californica) was able to bind to 5-HT(1A) and 5-HT(7) receptors at 100 mug/mL. The subsequent isolation procedure yielded the known alkaloids californidine (1), escholtzine (2), N-methyllaurotetanine (3), caryachine (4), and O-methylcaryachine (5), along with a new pavine alkaloid, 6S,12S-neocaryachine-7-O-methyl ether N-metho salt (7). The structure of 7 was determined by spectroscopic data interpretation, while the absolute stereochemistry was determined by means of circular dichroism. From the results obtained from the radioligand-binding assay of the pure compounds, including the commercially available protopine (6), it was evident that the activity on the 5-HT(1A) receptor was at least partly due to the presence of the aporphine alkaloid 3, which showed the highest inhibition of [(3)H]8-hydroxy-2-(di-N-propylamino)tetralin ([(3)H]8-OH-DPAT) binding with an EC(50) value of 155 nM and a K(i) of 85 nM.     

野菊花心血管活性部位化学成分的研究

目的:研究菊科植物野菊花心血管活性部位中的主要化学成分.方法:采用多种色谱方法进行分离纯化,通过波谱方法结合文献对照鉴定化合物结构.结果:从野菊花心血管活性部位中分离并鉴定了12个化合物,包括7个黄酮类化合物(1～7),5个苯丙素类化合物(8～12),分别鉴定为(2S)-圣草酚-7-O-β-D-吡喃葡萄糖醛酸苷(1),(2S)-圣草酚-7-O-β-D-吡喃葡萄糖苷(2),(2S)-橙皮素-7-O-β-D-吡喃葡萄糖醛酸苷(3),木犀草素-7-O-β-D-吡喃葡萄糖苷(4),木犀草素-7-O-β-D-吡喃葡萄糖醛酸苷(5),香叶木素-7-O-β-D-吡喃葡萄糖醛酸苷(6),槲皮素-7-O-β-D-呲喃葡萄糖苷(7),3,5-二咖啡酰奎宁酸甲酯(8),3,5-二咖啡酰奎宁酸(9),3,5-二顺式咖啡酰奎宁酸(10),1,5-二咖啡酰奎宁酸(11),1,3-二咖啡酰奎宁酸(12).结论:野菊花心血管活性部位中主要成分为黄酮类化合物,共5个化合物分别为2～3,7～8,10;共10个化合物分别为2～3,5～12系首次从该种植物分离得到.     

污叉丝孔菌菌丝体培养物中烷基苷类化合物

目的：研究污叉丝孔菌Dichomitus squalens（Karst）Reid菌丝培养物中的化学成分。方法：在广东省鼎湖山采集污叉丝孔菌子实体,通过组织培养分离获得菌丝体,然后用多个含有YMG培养基和小麦的10．5L三角瓶进行培养。菌丝体培养物用乙醇提取和溶剂分部,正丁醇溶解部位经柱层析和高效液相色谱分离纯化,用光谱分析法鉴定化合物结构。结果：分离获得了9个化合物,分别鉴定为乙基β-D-吡喃木糖苷（1）,乙基β-D-吡喃木糖（1→4）-β-D-吡喃木糖苷（2）,正丁基β-D-吡喃木糖苷（3）,正丁基β-D-吡喃木糖（1→4）-β-D-吡喃木糖苷（4）,乙基β-D-吡喃葡萄糖苷（5）,乙基α-L-呋喃阿拉伯糖苷（6）,正丁基α—L-呋喃阿拉伯糖苷（7）,2-去氧-D-核糖-1,4-内酯（8）,2-去氧-D-核酸甲酯（9）。结论：以上化合物系首次从污叉丝孔菌菌丝体培养物中分离获得。     

Metabolite profiling and chemopreventive bioactivity of plant extracts from Bidens pilosa

Bidens pilosa has been used as a folk medicine in various medications and as a popular ingredient in herb teas. Chemopreventive activities of crude and fractionated plant extracts of Bidens pilosa were evaluated in this study. Ethyl acetate and butanolic fractions, partitioned from the total crude extract of Bidens pilosa, exhibited significant scavenging free radical activity (IC(50) values approximately = with 14-17 microg/mL) comparable to that of alpha-tocopherol. Strong effects on the inhibition of LPS-mediated nitric oxide production in RAW 264.7 cells were also observed for the EA and BuOH fractions. Detectable cytotoxicity on RAW 264.7 cells, however, was observed for the EA fraction at a dose >100 microg/ml. The metabolite profile and major constituents of the BuOH fraction were studied and characterized using various spectroscopic analyses. A new compound, heptanyl 2-O-beta-xylofuranosyl-(1-->6)-beta-glucopyranoside (1), and eight phenolic compounds, namely quercetin 3-O-rabinobioside (2), quercetin 3-O-rutinoside (3), chlorogenic acid (4), 3,4-di-O-caffeoylquinic acid (5), 3,5-di-O-caffeoylquinic acid (6), 4,5-di-O-caffeoylquinic acid (7), jacein (8), centaurein (9) were for the first time isolated from Bidens pilosa. Compounds 2-7 are the major antioxidative constituents in the Bidens pilosa extract.     

小紫金牛的化学成分研究

对瑶族草药小紫金牛的化学成分进行研究,从小紫金牛乙醇提取物的乙酸乙酯萃取部位中分离得到7个化合物,采用光谱分析和文献对照的方法,确定它们的结构分别为:水杨酸(1),对羟基间甲氧基苯甲酸(2),没食子酸乙酯(3),4-羟基-3,5-二甲氧基苯甲酸(4),原儿茶酸(5),没食子酸(6)和儿茶素(7)。以上化合物均为首次从该植物中分离得到,其中化合物7首次从该属植物中得到。     

冬凌草中的一个新生物碱

目的:研究冬凌草(Rabdosia rubescens (Hemls.) Hara)地上部分的化学成分。方法:利用大孔吸附树脂色谱进行分离纯化,根据化合物的理化性质和光谱数据鉴定结构。结果:从冬凌草地上部分分离得到7个化合物,分别为:冬凌草碱(1),黄嘌呤(2),芹菜素-6,8-二-C-β-D-葡萄糖苷(3),7-羟基-4(1H)-喹啉酮(4),1,5-二-(3,4-二羟基苯基)-乙烯醚(5),3-(3,4-二羟基苯基)-2-异丙氧基-丙酸(6),邻苯二甲酸双-(2-乙基己基)酯(7)。结论:化合物1为新化合物,其余化合物均为首次从该属植物中分离得到。     

Acetylenic acids from the aerial parts of Nanodea muscosa

The aerial parts of Nanodea muscosa, collected in Chile, yielded two new acetylenic acids. Their structures were elucidated by spectroscopic analyses, including 2D NMR techniques, as (13E)-octadec-13-en-11-ynoic acid (1) and (2E)-octadec-2-en-4-ynedioic acid (2). Compound 2 constitutes the first example of a conjugated ene-yne fatty diacid isolated from a natural source. Compounds 1 and 2 did not exhibit toxicity toward a panel of DNA damage checkpoint defective yeast mutants or show affinity for the 5-HT(1A), 5-HT(2A), D(2), and H(1) receptors.