Diterpenoids from the roots of Suregada glomerulata

Six new diterpenoids, 7beta,8alpha-dihydroxy-12-oxo- ent-abietan-16,14-olide ( 1), 3,4,18beta-cyclopropa-7beta,17-dihydroxy- ent-abieta-8(14),13(15)-dien-16,12-olide ( 2), 3alpha,7beta-dihydroxy- ent-abieta-8(14),13(15)-dien-16,12-olide ( 3), 3-oxo-8beta,14beta-epoxy- ent-abieta-11,13(15)-dien-16,12-olide ( 4), 17-hydroxy- ent-pimara-8(14),15-dien-3-one ( 5), and 3alpha,6beta-dihydroxy- ent-kaur-16-ene ( 6), and two known compounds, 7beta-hydroxy- ent-abieta-8(14),13(15)-dien-16,12-olide ( 7) and jolkinolide B, were isolated from roots of Suregada glomerulata. The structures of the new compounds were elucidated on the basis of 1D and 2D NMR and other spectroscopic studies. The structure of compound 1 was confirmed by X-ray crystallography. Cytotoxic activities were evaluated against five human tumor cell lines.     

Six new diterpenoids from Suregada multiflora

Six new diterpenoids were isolated from a CH(2)Cl(2)-MeOH extract of the bark of Suregada multiflora. The structures were established on the basis of one- and two-dimensional NMR and other spectroscopic studies and chemical derivatizations. Two compounds, suregadolides C (1) and D (2), were identified as new diterpene lactones of two antipodal series, containing a cyclopropane ring bridging C-3 and C-4 of the basic abietane skeleton. Suremulide A (3) was found to be a new abietene diterpene lactone. Bannaringaolide A (4), a diterpene lactone, based on a novel carbon skeleton with a seven-membered ring, possibly formed by the rearrangement of the exocyclic C-17 in ring C of an ent-pimarane framework, has also been isolated. A kaurane triol, suremulol A (5), and a kaurane diol, suremulol B (6), were also identified as new metabolites.     

Novel diterpene lactones from Suregada multiflora

Two new diterpene lactones, suregadolides A (1) and B (2), were isolated from a dichloromethane extract of Suregada multiflora bark. These compounds possess a novel skeleton, which contains a cyclopropane ring bridging C-3 and C-4 of the abietane skeleton. The structures were established on the basis of one- and two-dimensional NMR and other spectroscopic studies. Compound 1 showed moderate inhibitory activity in a mutant yeast strain bioassay.     

Lignans from Kadsura angustifolia

Phytochemical investigation of Kadsura angustifolia led to the isolation and identification of 26 lignans and two triterpenoids, including 11 new lignans named kadangustins A-K ( 1- 11). The structures and stereochemistry of 1- 11 were elucidated by analysis of spectroscopic data. Except for 11 and 20, all the lignans were evaluated for their inhibitory activity against HIV-1. Binankadsurin A ( 19) showed anti-HIV activity with an EC 50 value of 3.86 microM.     

狭叶薰衣草化学成分的研究

目的研究狭叶薰衣草Lavandula angustifolia Mill.的化学成分。方法狭叶薰衣草95%乙醇提取物乙酸乙酯部位采用RP-HPLC、TLC、硅胶、MCI树脂等进行分离纯化,根据理化性质及波谱数据鉴定所得化合物的结构。结果从中分离得到11个化合物,分别鉴定为(-)-isolariciresinol-9-O-glucopyranoside (1)、threo-3,3′-dimethoxy-4,8′-oxyneoligna-9,4′,7′,9′-tetraol-7(8)-ene (2)、1-(4-hydroxy-3-meth-oxyphenyl)-2-[4-(3-hydroxy-propyl)-2-methoxyphenoxy]-propane-1,3-diol (3)、(E)-ferulic acid 4-O-β-D-glucoside (4)、eugenyl-O-β-apiofuranosyl(1″-6′)-O-β-glucopyranoside (5)、2-methoxy-4-(2-propen-1-yl)penyl-β-D-glucopyranoside (6)、 4...     

藏荆芥化学成分的研究

目的研究藏荆芥Nepeta angustifolia C.Y.Wu的化学成分。方法采用硅胶、Sephadex LH-20、ODS、半制备HPLC色谱柱,对藏荆芥70%乙醇提取物的乙酸乙酯部位进行分离纯化,根据理化性质和波谱数据对所得化合物的结构进行鉴定。结果从中分离得到10个化合物,分别鉴定为齐墩果酸(1)、白桦酸(2)、熊果酸(3)、β-谷甾醇(4)、异香柠檬烯(5)、补骨脂酚(6)、布卢门醇C葡糖苷(7)、补骨脂素(8)、迷迭香酸甲酯(9)、橙皮苷(10)。结论化合物5~8为首次从荆芥属植物中分离得到,化合物1、4~10为首次从该植物中分离得到。     

白树的化学成分研究Ⅱ

目的：研究白树Suregada glomerulata的化学成分。方法：采用硅胶,Sephadex LH-20,大孔树脂D101,ODS等柱色谱及重结晶等方法分离纯化,通过理化常数测定和光谱分析鉴定化合物的结构。结果：从中分离得到9个已知化合物分别为Jolkinolide B(1),8α,14-dihydro-7-oxo-jolkinolide E(2),泽漆内酯乙(3),ent-kauran-16β,17-diol(4),7-羰基-β-谷甾醇(5),东莨菪内酯(6),腺苷(7),1′-sinapoylglucose(8),蔗糖(9)。结论：化合物2～9为首次从该属植物中得到。     

番泻叶的化学成分研究

采用反复的硅胶柱色谱进行分离、纯化,根据理化性质和波谱数据进行结构鉴定。从番泻叶中分离鉴定了8个化合物:Tinnevellin glycoside(Ⅰ)、异鼠李素-3-O-β-龙胆二糖苷(Ⅱ)、芹菜素-6,8-二-C-葡萄糖苷(Ⅲ)、大黄素-8-O-β-D-吡喃葡萄糖苷(Ⅳ)、山柰酚(Ⅴ)、芦荟大黄素(Ⅵ)、D-3-O-甲基肌醇(Ⅶ)、蔗糖(Ⅷ)。结论:化合物Ⅲ、Ⅶ、Ⅷ为首次从该植物中分离得到。     

An ethnopharmacological survey for potential angiotensin converting enzyme inhibitors from Indian medicinal plants.

Plants used in different traditional systems of Indian medicine and some relatives/substitutes have been investigated for their angiotensin converting enzyme (ACE) inhibitory activity. They were selected on the basis of their usage as cardiotonics, diuretics and other uses related to the symptoms of hypertension. Out of the 73 species investigated, 22 showed more than 50% ACE inhibitory activity.     

Antibacterial potential of Antarctic lichens against human pathogenic Gram-positive bacteria

Extracts from five Antarctic lichens (L3, Stereocaulon alpinum; L5, Ramalina terebrata; L6, Caloplaca sp.; L8, Lecanora sp.; and L17, Caloplaca regalis) were tested for antimicrobial activities against several clinically important microbes by disk diffusion. The minimum inhibitory concentration (MIC) of each extract was determined by a broth dilution method. Extracts from L3, L5, L6 and L8 were active against two Gram(+) strains. B. subtilis was more sensitive to lichen extracts (except L5) than S. aureus. The MIC of lichen extracts against B. subtilis and S. aureus was observed from 36.7 +/- 0.3 to 953.8 +/- 85.8 microg/mL and 68.5 +/- 0.6 to >1000 microg/mL, respectively. Comparisons of MIC values of Antarctic lichen crude extracts to previously published MIC values of some reported lichen metabolites against Gram(+) bacteria indicated that Antarctic lichens might be an enriched source of effective antibacterial agents against clinically relevant Gram(+) species.     

Antibacterial constituents from Melodinus suaveolens

To investigate the non-alkaloidal chemical constituents of the stems and leaves of Melodinus suaveolens and their antibacterial activities. Compounds were isolated and purified by repeated silica gel, Sephadex LH-20, RP18, and preparative HPLC. Their structures were elucidated by comparison with published spectroscopic data, as well as on the basis of extensive spectroscopic analysis. The antibacterial screening assays were performed by the dilution method. Fourteen compounds were isolated, and identified as lycopersene(1), betulinic aldehyde(2), 3β-acetoxy-22,23,24,25,26,27-hexanordammaran-20-one(3), 3a-acetyl-2, 3, 5-trimethyl-7ahydroxy-5-(4,8,12-trimethyl-tridecanyl)-1,3a,5,6,7,7a-hexahydro-4-oxainden-1-one(4), 3β-hydroxy-28-norlup-20(29)-ene-17β-hydroperoxide(5), 3β-hydroxy-28-norlup-20(29)-ene-17α-hydroperoxide(6), β-sitosterol(7), 28-nor-urs-12-ene-3β, 17β-diol(8), α-amyrin(9), ergosta-4,6,8(14),22-tetraen-3-one(10), 3β-hydroxy-urs-11-en-28,13β-olide(11), betulin(12), obtusalin(13), and ursolic acid(14). Among the isolates, compounds 1, 2, 6, 8, 10, and 14 showed potent antibacterial activities against the four bacteria. This is the first report of the antibacterial activity of the constituents of Melodinus suaveolens.     

Antibacterial diterpenes from Calceolaria pinifolia

Two new isopimaranes, 19-methylmalonyloxy-ent-isopimara-8(9),15-diene (5) and 19-malonyloxy-ent-isopimara-8(9),15-diene (6), were isolated using bioassay-guided fractionation of the CH(2)Cl(2)-MeOH (1:1) extract of the aerial part of Calceolaria pinifolia along with eight other diterpenes (1-4, 7-10) and two triterpenes (11, 12). All compounds were assayed against Staphylococcus aureus (SA), methicillin-resistant S. aureus (MRSA), Bacillus subtilis (BS), and Escherichia coli (EC). 4-Epi-dehydroabietinol (2) and ent-isopimara-9(11),15-diene-19-ol (8) were found to be active against MRSA with MIC values of 8 and 2 microgram/mL, respectively. Mechanistic studies of 8 in BS suggested rapid and nonspecific inhibition of uptake and incorporation of radiolabeled precursors into DNA, RNA, and protein consistent with membrane-damaging effects in bacteria. Compound 8 did not afford protection against an acute infection with SA in mice.     

Antibacterial acylphloroglucinols from Hypericum olympicum

New antibacterial acylphloroglucinols (1-5) were isolated and characterized from the aerial parts of the plant Hypericum olympicum L. cf. uniflorum. The structures of these compounds were confirmed by extensive 1D- and 2D-NMR experiments to be 4,6-dihydroxy-2-O-(3″,7″-dimethyl-2″,6″-octadienyl)-1-(2'-methylbutanoyl)benzene (1), 4,6-dihydroxy-2-O-(7″-hydroxy-3″,7″-dimethyl-2″,5″-octadienyl)-1-(2'-methylbutanoyl)benzene (2), 4,6-dihydroxy-2-O-(6″-hydroxy-3″,7″-dimethyl-2″,7″-octadienyl)-1-(2'-methylbutanoyl)benzene (3), 4,6-dihydroxy-2-O-(6″-hydroperoxy-3″,7″-dimethyl-2″,7″-octadienyl)-1-(2'-methylbutanoyl)benzene (4), and 4,6-dihydroxy-2-O-(6″,7″-epoxy-3″,7″-dimethyloct-2″-enyl)-1-(2'-methylbutanoyl)benzene (5). These new natural products have been given the trivial names olympicins A-E (1-5). All compounds were evaluated against a panel of methicillin-resistant Staph. aureus and multidrug-resistant strains of Staph. aureus. Compound 1 exhibited minimum inhibitory concentrations (MICs) of 0.5-1 mg/L against the tested Staph. aureus strains. Compounds 2 to 5 were also shown to be active, with MICs ranging from 64 to 128 mg/L. Compound 1 was synthesized using a simple four-step method that can be readily utilized to give a number of structural analogues of 1.     

Antibacterial pterocarpans from Erythrina subumbrans

Seven pterocarpans, erybraedin B (1), erybraedin A (2), phaseollin (3), erythrabyssin II (4), erystagallin A (5), erythrabissin-1 (6) and erycristagallin (7), two flavanones, 5-hydroxysophoranone (8) and glabrol (9), and one isoflavone, erysubin F (10), were isolated from the stems of Erythrina subumbrans (Leguminosae). Their structures were identified by means of spectroscopy. This is the first report of the isolation of the non-alkaloidal compounds from Erythrina subumbrans and the observed dehydration of 6a-hydroxypterocarpans 5 and 6 in CDCl(3) to the corresponding pterocarpenes 11 and 12, respectively. Compounds 8 and 9 were isolated for the first time from the genus Erythrina. Compounds 2 and 4 exhibited the highest degree of activity against Streptococcus strains with an MIC range of 0.78-1.56 microg/ml, whereas compound 7 exhibited the highest degree of activity against Staphylococcus strains, including drug-resistant strains (MRSA and VRSA), with an MIC range of 0.39-1.56 microg/ml. Interestingly, compounds 2, 4, 5 and 7 were more active against several strains of Streptococcus and Staphylococcus than the standard antibiotics vancomycin and oxacillin. Compound 7 showed the highest level of activity against all VRSA strains tested, with an MIC range of 0.39-1.56 microg/ml, which were resistant to both antibiotics. These compounds may prove to be potent phytochemical agents for antibacterial activity, especially against the MRSA and VRSA strains.     

Antibacterial compounds from Glycyrrhiza uralensis

From the roots of Glycyrrhiza uralensis, two new pterocarpenes, glycyrrhizol A (1) and glycyrrhizol B (2), along with four known isoflavonoids, 5-O-methylglycryol (3), isoglycyrol (4), 6,8-diisoprenyl-5,7,4'-trihydroxyisoflavone (5), and gancaonin G (6), were isolated using a bioassay-guided fractionation method. The structures of the new compounds (1and 2) were elucidated by spectroscopic data interpretation. The known compounds (3-6) were identified by comparison of their spectroscopic data with reported values in the literature. Glycyrrhizol A (1) and 6,8-diisoprenyl-5,7,4'-trihydroxyisoflavone (5) exhibited potent antibacterial activity against Streptococcus mutans with minimum inhibitory concentrations of 1 and 2 microg/mL, respectively, while glycyrrhizol B (2) and gancaonin G (6) showed more moderate activity.     

沙枣总酚抗炎作用研究

目的:研究沙枣总酚的抗炎作用及其急性毒性.方法:昆明种小鼠60只随机分为模型组、阿司匹林组(200 mg·kg-1),沙枣总酚低、中、高剂量组(90,180,360 mg· kg-),检测药物对二甲苯致小鼠耳肿胀的影响;SD大鼠180只随机分为模型对照组,阿司匹林组(165 mg·kg-1),沙枣总酚低、中、高剂量组(75,150,300 mg· kg-1),分别采用角叉菜胶致大鼠足肿胀模型、大鼠毛细血管通透性模型以及大鼠棉球肉芽肿模型观察沙枣总酚的抗炎作用;采用最大耐受量(MTD)测定其急性毒性.结果:与对照组相比,沙枣总酚对二甲苯所致小鼠耳肿胀有显著性抑制作用(P＜0.05),其低、中、高剂量组的抑制率分别为31.30％,33.44％和49.75％;对角叉菜胶致大鼠足肿胀有显著抑制作用(P＜0.01)并呈剂量依赖性;对大鼠棉球肉芽肿有明显抑制作用(P＜0.01),其低、中、高剂量组的抑制率分别为17.86％,32.87％和42.24％;并能显著减少大鼠毛细血管渗出(P＜0.01);其最大耐受量为160 g·kg-1.结论:沙枣总酚具有一定的抗炎活性,其急性毒性小.     

The activity of volatile compounds from Lavandula angustifolia against Psoroptes cuniculi

Previously we demonstrated the acaricidal properties of Lavandula angustifolia Miller essential oil and of linalool, one of its main components, against Psoroptes cuniculi detected following direct contact of the substances with the mites. In the present paper we report the acaricidal activity of volatile linalool and of the lavender essential oil without direct contact of the ectoparasites with these substances. Diethyl ether extracts of dead mites showed linalool was the only detectable substance using this method by gas chromatography. The study confirms the acaricidal properties of lavender essential oil and of linalool by inhalation, indicating an additional route for possible use of these substances both for prophylactic and therapeutic purposes.     

Antibacterial and anti-inflammatory activities of 4-hydroxycordoin: potential therapeutic benefits

4-Hydroxycordoin (1), a natural isopentenyloxychalcone, is a plant secondary metabolite that is relatively rare. Since there are very few reports about the biological activities of 1, its potential benefits for periodontal disease were investigated. A marked and dose-dependent antibacterial activity of 1 was observed against the three major periodontal pathogens, Porphyromonas gingivalis, Fusobacterium nucleatum, and Prevotella intermedia. Moreover, compound 1 showed an antiadhesion effect, since it inhibited attachment of P. gingivalis to oral epithelial cells. Finally, using a macrophage model, the ability of 1 to inhibit the secretion of inflammatory mediators induced by Aggregatibacter actinomycetemcomitans lipopolysaccharide was demonstrated. The anti-inflammatory effect observed was associated with reduced activation of the nuclear factor-κB (NF-κB) p65 and activator protein-1 (AP-1) pathways.     

小桐子抑菌成分粗提工艺及其活性研究

目的 探索小桐子综合开发利用的价值.方法 在不同条件下对小桐子树叶中的抑菌成分进行粗提,以好食脉孢霉和粗糙脉孢霉为对象,检验提取物的最低抑菌浓度(MIC).结果 最佳提取工艺为:纯水作为提取液,料液比为1:15,30℃恒温搅拌提取10 h,此时提取物对供试菌的最低抑菌浓度为1.0g/L,粗提液经醇沉后,最低抑菌浓度下降为0.5 g/L.结论 小桐子提取物有较强的抑菌活性,在植物源抑菌剂的开发方面具有良好的应用前景.     

Antibacterial iridoid glucosides from Eremostachys laciniata

Eremostachys laciniata (L) Bunge (family: Lamiaceae alt. Labiatae; subfamily: Lamioideae) is one of the 15 endemic Iranian herbs of the genus Eremostachys. A decoction of the roots and flowers of E. laciniata has traditionally been taken orally for the treatment of allergies, headache and liver diseases. Three antibacterial iridoid glucosides, phloyoside I (1), phlomiol (2) and pulchelloside I (3) have been isolated from the rhizomes of this plant. The structures of these compounds were elucidated unequivocally by a series of 1D and 2D NMR analyses. The antibacterial activity and brine shrimp toxicity of these compounds were assessed using the resazurin microtitre assay and the brine shrimp lethality assay, respectively. All three iridoid glycosides 1-3 exhibited from low to moderate levels (MIC = 0.05-0.50 mg/mL) of antibacterial activity. Of these compounds, compound 3 was the most active, and displayed antibacterial activity against 9 of 12 different strains tested. The most noteworthy activity of 3 was against Bacillus cereus, penicillin-resistant Escherichia coli, Proteus mirabilis and Staphylococcus aureus with an MIC value of 0.05 mg/mL.