驱虫斑鸠菊中咖啡酰基奎宁酸类化学成分

目的:采用大孔吸附树脂、Sephadex LH-20以及制备HPLC等色谱方法对驱虫斑鸠菊Vernonia anthelmintica成熟种子进行分离纯化,分离得到6个化合物。通过1H,13C-NMR及MS等波谱技术鉴定化合物的结构,分别为咖啡酸(1),3-O-咖啡酰基奎宁酸(2),4-O-咖啡酰基奎宁酸(3),5-O-咖啡酰基奎宁酸(4),表-3,4-O-双咖啡酰基奎宁酸(5),3,4-O-双咖啡酰基奎宁酸(6)。其中,化合物1～6均为首次从该植物中分离得到,其中3～5为首次从该属植物中分离得到。     

Anti-ulcer polysaccharides from Cola cordifolia bark and leaves

Ethnopharmacological relevance

Aqueous extracts of bark and leaves of C. cordifolia are traditionally used in Mali (West Africa) in the treatment of wounds and gastric ailments like abdominal pain, gastritis and gastric ulcers.

Aim of the study

To evaluate and compare the anti-ulcer and immunological activities, as well as the toxicity of polysaccharide rich water extracts from the bark and leaves of C. cordifolia.

Materials and methods

Gastric ulcers were induced in rats and the inhibition of ulcer formation was calculated based on lesion index. Immunological activities were measured by complement fixation and macrophage activation. Toxicity was tested on brine shrimps. The two extracts were characterised by GC, Yariv-precipitation and quantification of phenolic compounds. An ethnomedical survey on C. cordifolia was carried out in Siby (Mali, West-Africa) to generate more knowledge about the traditional use.

Results

Bark and leaf extracts from C. cordifolia significantly inhibited the formation of gastric lesions in rodents in a dose depending manner. CCbark50 showed a high complement fixation activity in vitro. No toxicity was found. The ethnomedical survey showed that C. cordifolia was mainly used for treating pain and wounds.

Conclusions

Our results shows that the bark and the leaves comprise a dose dependant anti-ulcer activity in an experimental rat model (no statistical difference between the plant parts). Clinical studies should be performed to evaluate the effect of both bark and leaves of C. cordifolia as a remedy against gastric ulcer in human.     

Toxicity,antimicrobial and anthelmintic activities of Vernonia guineensis Benth. (Asteraceae) crude extracts

Ethnopharmacological relevance

This study examined the antibacterial, antifungal, and anthelmintic properties of extracts obtained from the plant Vernonia guineensis, a plant commonly used in traditional Cameroonian medicine.

Materials and methods

For in vitro studies, 10 g of leaf and tuber powder from V. guineensis was extracted separately using dichloromethane, methanol and distilled water. The extracts were dried in vacuo and used for antimicrobial and anthelmintic activity studies. In the antimicrobial assay, extracts were tested against bacterial and fungal organisms including; Staphylococcus aureus, Staphylococcus epidermidis, Acinetobacter baumannii, Aspergillus fumigatus, Candida albicans and Trichophyton mentagrophytes. In the anthelmintic assay, larval and adult stages of the hookworm Ancylostoma ceylanicum and the mouse nematode Trichuris muris were used. For the acute toxicity test, male and female rats of 150–200 g body weight were used in the experiment. The aqueous extract of V. guineensis tubers was administered in 4 doses of 500, 1000, 2000 and 4000 mg/kg per group (n=6), respectively, and the control group received distilled water.

Results

The crude extracts exhibited weak antibacterial and antifungal activity except for the dichloromethane extract, which showed moderate activity against A. fumigatus (MIC=200 μg/ml). In the anthelmintic assay, the organic extracts of the tubers had 100% killing efficacy against T. muris at 2 mg/ml in 48 h, while the aqueous extract showed no activity. The organic leaf extracts demonstrated potent activity killing 100% of the adult worms 1 mg/ml in 24 h. The aqueous leaf extract was active at 2 mg/ml in 72 h, killing 100% of the adult worms. In the acute toxicity test, V. guineensis did not produce any toxic signs or death at the maximum concentration of 4000 mg/kg.

Conclusion

Crude extracts from V. guineensis possess anthelmintic activity against T. muris with only weak antibiotic activity. Acute administration of aqueous extract from V. guineensis tubers did not produce toxic effects in rats. The absence of acute toxicity at the highest concentration tested indicates that the tea decoction from V. guineensis extract is safe at concentrations ≤4000 mg/kg.     

毒根斑鸠菊茎皮的化学成分研究

目的:研究毒根斑鸠菊茎皮的化学成分。方法:应用硅胶柱色谱、Sephadex LH-20柱色谱、ODS柱色谱、HPLC等各种色谱技术进行分离纯化,用NMR等谱学方法分析确定化合物结构。结果:从毒根斑鸠菊茎皮的95%乙醇提取物中分离得到12个化合物,分别鉴定为:3,5-二咖啡酰基奎尼酸甲酯(1),3,4-二咖啡酰基奎尼酸甲酯(2),3,4-二咖啡酰基奎尼酸乙酯(3),3,4,5-三咖啡酰基奎尼酸甲酯(4),豆甾醇(5),α-菠甾醇(6),β-谷甾醇(7),24-亚甲基-羊毛甾烷-9(11)-烯-3β-乙酯(8),没食子酸乙酯(9),邻苯二甲酸二正丁酯(10)。结论:化合物1~10均为首次从该植物中获得。     

The anti-ulcer activities of bisabolangelone from Angelica polymorpha

Aim of the study

Evaluate the anti-ulcer effects of bisabolangelone from Angelica polymorpha Maxim and provide the basic data to further study for the Angelica polymorpha and bisabolangelone.

Materials and methods

Bisabolangelone was isolated from Angelica polymorpha Maxim collected from Shennongjia Forest District of China. The structure of bisabolangelone was elucidated by NMR and MS spectrums. The anti-ulcer effects were evaluated with length of lesion (mm) and activity of H⁺/K⁺-ATPase in two models induced by ethanol and Pylorus ligation. Experimental groups were administered with different doses of bisabolangelone (3.8, 7.6 and 15.3 mg/kg). The positive control group was administered omeprazole with a dose of 3.3 mg/kg.

Results

Bisabolangelone significantly reduced the length of lesion (3.8, 7.6 and 15.3 mg/kg, P < 0.01), inhibited the activity of H⁺/K⁺-ATPase (3.8, 7.6 and 15.3 mg/kg, P < 0.01), decreased the volume of gastric juice (7.6 and 15.3 mg/kg, P < 0.05), and increased the pH value of gastric juice (7.6 and 15.3 mg/kg, P < 0.01, 3.8 mg/kg, P < 0.05).

Conclusions

Bisabolangelone is the main anti-ulcer active compound of Angelica polymorpha, and remarkably preventive and therapeutic action on gastric ulcer. It is possible that bisabolangelone inhibited the activity of the H⁺/K⁺-ATPase, then reducing the secretion of H⁺, and the anti-ulcer mechanism of bisabolangelone was deserved to be further studied.     

Antiplasmodial activity of sesquiterpene lactones and a sucrose ester from Vernonia guineensis Benth. (Asteraceae)

Ethnopharmacological relevance

Aqueous preparations of Vernonia guineensis Benth. (Asteraceae) are used in Cameroonian folk medicine as a general stimulant and to treat various illnesses and conditions including malaria, bacterial infections and helminthic infestations.

Materials and methods

Ten gram samples of the leaf and tuber powders of Vernonia guineensis were extracted separately using dichloromethane, methanol and distilled water. The extracts were dried in vacuo and used in bioassays. These extracts and three compounds previously isolated from Vernonia guineensis [vernopicrin (1), vernomelitensin (2) and pentaisovalerylsucrose (3)] were screened for antiplasmodial activity against chloroquine (CQ)-sensitive (Hb3) and CQ-resistant (Dd2) Plasmodium falciparum lines.

Results

Crude extracts and pure compounds from Vernonia guineensis showed antiplasmodial activity against both Hb3 and Dd2. The IC₅₀ values of extracts ranged from 1.64 to 27.2 µg/ml for Hb3 and 1.82–30.0 µg/ml for Dd2; those for compounds 1, 2 and 3 ranged from 0.47 to 1.62 µg/ml (1364–1774 nM) for Hb3 and 0.57–1.50 µg/ml (1644–2332 nM) for Dd2. None of the crude extracts or pure compounds was observed to exert toxic effects on the erythrocytes used to cultivate the Plasmodium falciparum lines.

Conclusion

In Cameroonian folk medicine, Vernonia guineensis may be used to treat malaria in part due to the antiplasmodial activity of sesquiterpene lactones (1, 2), a sucrose ester (3) and perhaps other compounds present in crude plant extracts. Exploring the safety and antiplasmodial efficacy of these compounds in vivo requires further study.     

Cytotoxic sesquiterpene lactones from the leaves of Vernonia guineensis Benth. (Asteraceae)

Ethnopharmacological relevance

Vernonia guineensis Benth. (Asteraceae) preparations are used in folk medicine in Cameroon to treat a number of ailments, including prostate cancer and malaria, and is used as an anthelmintic, adaptogen and antidote. The aim of this study was to continue the validation of the activity of Vernonia guineensis Benth. extracts and isolated molecules against cancer cell lines following the previous isolation of an anti-prostate cancer sugar ester from the root extract.

Materials and methods

Acetone extracts of Vernonia guineensis Benth. leaves were tested for activity against 10 cancer cell lines (Breast—MDA-MB-231, Breast—MCF-7, Colon—HCT-116, Leukemia—HL-60, Lung—A549, Melanoma—A375, Ovarian—OVCAR3, Pancreas—Mia-paca, Prostate—PC-3 and Prostate—DU-145). The acetone extract was subjected to bioactivity guided fractionation. Anti-proliferation and clonogenic activity of the isolated compounds were tested. The WST-1 assay was used for the anti-proliferation activity, while the standard clonogenic test was used to determine the clonogenic activity.

Results

The acetone extract of Vernonia guineensis Benth. demonstrated in vitro activity ranging from IC₅₀ 4–26 μg/mL against the 10 cell lines. Activity guided fractionation of this extract yielded two sesquiterpene lactones, isolated for the first time from the genus Vernonia. The compounds were characterized using spectroscopic experiments, including a combination of 1D and 2D NMR data. Vernopicrin (1) and Vernomelitensin (2) demonstrated in vitro activity against human cancer cell lines with IC₅₀ ranging from 0.35–2.04 μM (P<0.05) and 0.13–1.5 μM (P<0.05), respectively, between the most and least sensitive cell lines for each compound. Vernopicrin was most active against the human melanoma (A375) cell line and least active against the lung cancer (A549) cell line, while Vernomelitensin was also most active against the human melanoma (A375) cell line and least active against the breast cancer (MCF-7) cell line. Both compounds also demonstrated anticlonogenic activity.

Conclusion

The cytotoxicity demonstrated by the crude extract and isolated sesquiterpenes against cancer cell lines highlights the medicinal potential of V. guineensis. The selective anti-proliferation and dose dependent anticlonogenic activities suggest that the identified sesquiterpenes could be potential antitumor agents.     

红药根的化学成分研究

采用硅胶、Sephadex LH-20、高效制备液相等方法,对红药根的甲醇提取物进行分离纯化,通过质谱（MS）、波谱数据分析（¹H,¹³C-NMR）进行结构鉴定。从红药根的甲醇提取物中分离7个化合物,分别鉴定为plantainoside A（1）,plantainoside B（2）,calcedarioside C（3）,calcedarioside D（4）,platyphylloside（5）,hirsutanonol（6）和hirsutanonol-5-O-β-D-glucopyranoside（7）。化合物均5~7为首次从该科物中分离得到。     

瑶山润楠根的化学成分研究

对樟科润楠属植物瑶山润楠Machilus yaoshansis根乙醇提取物的化学成分进行研究。利用多种色谱技术从瑶山润楠的醋酸乙酯萃取物中分离得到15个化合物;通过理化性质和波谱数据鉴定其结构为12个木脂素类(+)-愈创木素(1),kadsuralignan C(2),(+)-异落叶松脂素(3),(+)-5’-甲氧基异落叶松脂素(4),南烛木树脂酚(5),内消旋-裂环异落叶松树脂酚(6),异落叶松脂素-9’-O-β-D-吡喃木糖苷(7),5’-甲氧基-异落叶松脂素-9’-O-β-D-吡喃木糖苷(8),南烛木树脂酚9’-O-β-D-吡喃木糖苷(9),(2R,3R)-2,3-二氢-2-(4-羟基-3-甲氧基苯基)-7-甲氧基-3-甲基-5-(E)-丙烯基苯并呋喃(10),3,5’-二甲氧基-4’,7-环氧-8,3’-新木脂素-4,9,9’-三醇(11),甘密树皮素B(12),和3个黄烷类(+)-儿茶素(13),(-)-表儿茶素(14),bis-8,8’-catechinylmethane(15)。化合物1～15均为首次从该植物中分离得到。     

驱虫斑鸠菊提取物指纹图谱与其对人A375黑素瘤细胞增殖作用的灰关联度分析

目的:建立驱虫斑鸠菊不同乙醇浓度提取物指纹图谱,考察各醇提物共有峰成分对人A375黑素瘤细胞增殖作用的影响;探讨驱虫斑鸠菊醇提物指纹图谱与药效的相关性,为建立驱虫斑鸠菊谱效结合的中药质量控制模式提供理论依据和数据支持。方法:采用HPLC建立驱虫斑鸠菊不同乙醇浓度提取物指纹图谱,并对其进行相似度评价;用四甲基偶氮唑蓝(MTT)比色法研究人A375黑素瘤细胞增殖作用;用灰关联度分析法研究"谱效关系"。结果:驱虫斑鸠菊醇提物指纹图谱有13个共有峰,其对人A375黑素瘤细胞有增殖作用,其中4号峰对其增殖作用贡献最大,灰关联度最高。结论:驱虫斑鸠菊不同乙醇浓度提取物的指纹图谱存在一定差异,指纹图谱共有峰与其对细胞增殖的作用之间有一定的关联性。     

云木香化学成分研究Ⅱ

目的:为了研究菊科风毛菊属植物云木香的化学成分.方法:采用硅胶柱色谱、Sephadex LH-20和反相RP-18柱色谱等手段进行分离纯化,并通过波谱数据鉴定结构.结果:分离鉴定了8个化合物,1β-hydroxycolartin(1),5α-hydroxy-β-costic acid(2),11α,13-dihydroxydehidrocostuslactone(3),11,13-dihydro-7,11-dehydro-13-hydroxy-3-desoxyzaluzanin C(4),8α-hydroxyl-11β-11,13-dihydrodehydrocostuslactone(5),soulangianolide A(6),丁香树酯醇(syringaresinol,7),东莨菪内酯(scopoletin,8).结论:化合物1～4,6～8为首次从该属植物中分离,化合物5为首次从该植物中分离.     

齿叶地不容的生物碱成分研究

目的:研究齿叶地不容Stephania dentifolia的化学成分.方法:应用氧化铝、硅胶和葡聚糖凝胶LH-20等柱色谱方法分离化合物,根据理化性质测试和波谱分析鉴定化合物结构.结果:从齿叶地不容新鲜块茎的稀硫酸提取物中,分离得到8个生物碱成分,分别为青风藤碱(sinoacutine,1)、青藤碱(sinomenine,2)、8-甲氧基青藤碱(cephamonine,3)、四氢巴马汀(tetrahydropalmatine,4)、卡巴任(capaurine,5)、千金藤宁碱(stepharanine,6)、(+)-stepharine(7)、巴马汀(palmatine,8).结论:所有化合物均为首次从齿叶地不容中分离得到.     

Alpha-amylase inhibitory activity of two Anthocleista species and in vivo rat model anti-diabetic activities of Anthocleista djalonensis extracts and fractions

Ethnopharmacological relevance

Anthocleista djalonensis (A. Chev) and Anthocleista vogelii Planch are plants being used in West Africa traditionally to treat various diseases such as malaria, hernia, hypertension, stomach aches, hemorrhoids, syphilis, and diabetes. Diabetes causes about 5% of all deaths globally each year. Chemotherapeutic agents such as biguanides, sulfonylureas, and thiozolidinediones are available for the treatment of diabetes, however, they have undesirable side effects. The need for newer, more effective and less toxic drugs is imperative and the biodiversity of Nigeria has a high potential for drug discovery based on plants used in the ethnomedicine.

Aim of the study

To investigate the leaves, stem bark and roots of these plants for their probable alpha-amylase inhibitory activities and establish their anti-diabetic activities. The overall goal is do bioassay-guided fractionation and isolation of active anti-diabetic compounds.

Materials and methods

Powdered samples (leaves, stem bark and roots) macerated with 80% aqueous methanol were evaluated in vitro using alpha-amylase inhibitory assay while in vivo investigations were carried out on hyperglycemic rats. Diabetes was induced in albino rats by an intraperitoneal injection of alloxan monohydrate (80 mg/kg). Plant extracts (1 g/kg) were given orally for 7 days, while blood glucose levels were monitored using a one touch glucometer. The crude methanol extracts found to be most active were further partitioned into hexane and ethyl acetate fractions which were also tested in vivo on the diabetic animals.

Results

The leaves and stem bark crude methanol extracts of Anthocleista djalonensis gave comparable α-amylase inhibition of 73.66% and 72.90%, respectively which were quite higher than the 38.93% and 22.90% of the same plant parts given by Anthocleista vogelii. The crude stem bark extract of Anthocleista djalonensis exhibited significant peak blood glucose reduction on day 6 (72.59%, p<0.05) which was higher than the leaves or roots which gave 45.73% and 47.46% (p<0.05), respectively The stem bark ethyl acetate fraction of Anthocleista djalonensis gave reduction in blood glucose level of 60.86% (p<0.05).

Conclusion

From our results, the leaves, stem bark and whole root of both plants exhibited α-amylase inhibitory activities with Anthocleista djalonensis also showing good anti-diabetic activities in vivo indicating that they contain active principles for the management of diabetes. There is justification for the use of the plants traditionally to manage diabetes.     

金铁锁化学成分研究

采用硅胶、凝胶柱色谱等多种分离手段从金铁锁Psammosilene tunicoides中分离得到3个化合物。根据化合物的理化性质和光谱数据鉴定其结构分别为 3,3'-(4,5-dimethoxynaphthalene-2,7-diyl) bis(1-nitropropan-1-one)(1),α-菠甾醇-3-O-β-D-葡萄糖苷(2) 和α-菠甾醇-3-O-β-D-葡萄糖苷-6'-O-棕榈酸酯(3)。1为含硝基的新化合物,2和3为从本属植物中首次分离得到。     

中华苦荬菜根部化学成分研究

采用硅胶柱色谱,HPLC 等方法对中华苦荬菜根部化学成分进行分离纯化,得到 15 个化合物,依据理化性质和波谱数据分析鉴定它们的结构分别为 chinensioide G（1）,chinensioide B（2）,10α-羟基-愈创木烷-12,6-内酯-3-酮（3）,chinensioide C（4）,10α-羟基-11βH-4（5）-愈创木烯-12,6-内酯（5）,3β,10α-二羟基-4βH-11（13）-愈创木烯-12,6-内酯（6）,3β,10α-二羟基-4βH,11βH-愈创木-12,6-内酯（7）,3β,10α-二羟基-4（15）,11（13）-愈创木二烯-12,6-内酯（8）,咖啡酸（9）,对羟基苯乙酸（10）,对羟基苯乙酸甲酯（11）,对羟基苯乙酸乙酯（12）,β-谷甾醇（13）,胡萝卜苷（14）,ixerin D（15）。其中化合物 1 为新化合物,命名为chinensioide G,化合物 6,7 首次从该植物中分离得到。     

大八角根化学成分研究

采用硅胶、Sephadex LH-20、ODS及制备型HPLC等多种色谱技术,从大八角根中分离得到10个化合物,根据理化性质及波谱数据（MS,¹H,¹³C-NMR）分析分别鉴定为cycloparviflorolide（1）,cycloparvifloralone（2）,tashironin（3）,tashironin A（4）,anislactone A（5）,anislactone B（6）,pseudomajucin（7）,syringaldehyde（8）,methyl-4-hydroxy-3,5-dimethoxybenzoate（9）和（E）-3-methoxy-4,5- methylenedioxycinnamic alchol（10）。其中化合物 1~4,8~10 为首次从该植物中分离得到。在1.0×10^-5 mol·L^-1下,在LPS刺激小鼠小胶质细胞释放NO抑制模型上,化合物 5,6 抑制率分别为75.31%,53.7%。     

Antinociceptive activity of fractions from Couroupita guianensis Aubl. leaves

Ethnopharmacological relevance

Couroupitaguianensis Aubl. (Lecythidaceae) is popularly known in Brazil as “abricó-de-macaco”. Infusions or teas obtained from its leaves, flowers, and barks are used in South America for the treatment of several disorders such as pain and inflammatory processes.

Aim of the study

Evaluate antinociceptive effects of crude ethanol extract (CEE) and its fractions in three analgesic models (acetic acid-induced contortions, tail flick, and hot plate) and study the possible mechanism of their action.

Materials and methods

CEE, hexane, dichloromethane, ethyl acetate, and butanol fractions (10, 30, and 100 mg/kg, p.o.) and the reference drug morphine (5 mg/kg, s.c.) were evaluated. To elucidate the mechanism of action from the fractions, animals were pre-treated (30 min) with atropine (muscarinic receptor antagonist, 1 mg/kg, s.c.), mecamylamine (nicotinic receptor antagonist, 2 mg/kg, s.c.), naloxone (opioid receptor antagonist, 1 mg/kg, s.c.) or l-nitro arginine methyl ester (l-NAME, nitric oxide synthase inhibitor, 3 mg/kg, s.c.).

Results

CEE and fractions significantly inhibited the number of contortions induced by acetic acid. All fractions showed antinociceptive activity in the tail flick model, being the hexane and ethyl acetate the most potent and long acting fractions. In the hot plate method the highest effect observed was at the dose of 100 mg/kg from all fractions. Administration of naloxone inhibited the antinociceptive effect of fractions. Pre-treatment of mice with atropine reduced the antinociceptive activity of CEE and its fractions, the exception being the dichloromethane fraction. Mecamylamine did not inhibited the effect of dichloromethane fraction. l-NAME reduced the anti-hyperalgesic effect of all fractions, but the most prominent effect was observed in the antinociceptive activity caused by CEE and butanol fraction.

Conclusions

Results obtained demonstrated that Couroupita guianensis CEE and its fractions have antinociceptive activity that is mediated, at least in part, by opioid and cholinergic systems and nitric oxide pathway.     

The in vivo expectorant and antitussive activity of extract and fractions from Reineckia carnea

Aim of study

To evaluate the potential expectorant and antitussive activity of a traditional Chinese medicine.

Materials and methods

The water extract and four fractions of the aerial part of Reineckia carnea were orally administrated to coughing mice induced by ammonium hydroxide and mice injected with phenol red, respectively, to investigate their medification effect on coughing and mucus scretion.

Results and discussion

90% Ethanol fraction significantly lengthened the latent period of cough and decreased cough frequency caused by ammonium hydroxide at the dose of 0.372 g/kg (p < 0.05). Sixty percent ethanol fraction reduced the cough frequency as well as the mucus secretion from mouse tracheas obviously at the dose of 0.570 g/kg (p < 0.05) by measuring the tracheal output of phenol red in mice. The medication effects in multiple doses of the active fractions were then performed and it has been proved that the 60% ethanol and 90% ethanol fraction were curatively effective on expectoration and coughing, respectively both at the high and middle dose, which supplied proofs for the further research on chemical constituents in both of two effective fractions.