HPLC-DAD-ESI-MS analysis of the constituents of aqueous preparations of verbena and lemon verbena and evaluation of the antioxidant activity

Verbena and lemon verbena aqueous preparations were investigated for their content of constituents, especially polyphenols by HPLC/DAD/ESI/MS analysis because they are used worldwide as herbal teas. The main class of compounds of these plants were phenylpropanoids (from 16 to 120 mg/g of dried extract), being verbascoside the most abundant in all the preparations up to 97% of the total phenylpropanoids. Also iridoids, hastatoside and verbenalin together with flavonoids, mono- and di-glucuronidic derivatives of luteolin and apigenin were found. These simple preparations, especially that obtained from infusion of lemon verbena, could be lyophilized to obtain a powder having interesting technological properties to be used as ingredients of cosmetics, food supplements and herbal medicinal products do to the many biological properties of verbascoside. In addition, the antioxidant property of the lemon verbena infusion was evaluated by the DPPH test using Trolox as the reference compound.     

藏药脉花党参的化学成分(英文)

目的:研究藏药脉花党参 Codonopsis nervosa ( Chipp.) Nannf.地上部分的化学成分。方法:采用 D101 大孔树脂柱、硅胶柱、ODS 柱、凝胶柱等色谱手段进行化学分离和纯化, 并利用各种波谱技术进行结构鉴定。结果:分离并鉴定了 15 个化合物, 分别为柯伊利素(1), 苜蓿素(2), 芹菜素(3), 琥珀酸(4), β-胡萝卜苷(5), 木犀草素(6), 木犀草素-7-O-β-D-葡萄糖苷(7),ethylsyringin (8), 芹菜素-7-O-β-D-葡萄糖苷(9), 木犀草素-7-O-β-D-葡萄糖基-(1→6)-[(6’’’-O-咖啡酸)-β-D-葡萄糖苷](10), 木犀草素-7-O-β-D-龙胆二糖苷(11), 丁香苷(12), 绿原酸(13), 新绿原酸(14), 对羟基苯甲酸葡萄糖苷(15)。结论:化合物 1 5, 8, 9, 12, 14,15 均首次从该植物中分离得到。     

大高良姜根茎中的两个新苯丙素化合物(英文)

目的:研究大高良姜的化学成分及活性。方法:运用各种柱色谱方法和重结晶手段分离纯化化合物, 并通过波谱数据鉴定化合物结构。此外, 运用 MTT 法测定了化合物对四种肿瘤细胞株（HepG2, EC109, A549 和 Vero）的细胞毒活性。结果:从大高良姜中分离得到 6 个苯丙素类化合物, 其结构分别鉴定为（S）-1’-ethoxy chavicol acetate （1）, （E）-4-acetoxy cinnamyl ethylether （2）, （E）-4-hydroxy-cinnamaldehyde （3）, （E）-4-acetoxy cinnamyl alcohol （4）, 4-acetoxy cinnamyl acetate （5） 和 4, 4’[（2E, 2’E）-bis（prop-2-ene）-1, 1’-oxy]-diphenyl-7, 7’-diacetate （6）. 结论:化合物 1 和 2 为新化合物。化合物 5 对 A549 肿瘤细胞有一定的细胞毒活性, IC₅0为 19.35 μmol·L¹。     

黄腊果根的化学成分研究

目的 研究黄腊果Stauntonia brachyanthera根的化学成分.方法 利用各种色谱学方法,对药材提取物进行分离纯化,采用核磁共振技术鉴定结构.结果 从黄蜡果根70％乙醇提取物中分离得到13个化合物,分别为3-甲氧基-4-羟基-桂皮醛(Ⅰ)、tortoside F(Ⅱ)、酪醇1-O-β-木糖基-(1→6)-O-β-葡萄糖苷(Ⅲ)、香草酸(Ⅳ)、丁香酸(Ⅴ)、saccharumoside B(Ⅵ)、甘草查儿酮A(Ⅶ)、芦丁(Ⅷ)、异槲皮苷(Ⅸ)、木犀草素-7-O-葡糖糖苷(Ⅹ)、荭草苷(Ⅺ)、6”-O-(3'-羟基-3'-甲基戊二酰)牡荆素(Ⅻ)、槲皮素(Ⅻ).结论 化合物Ⅰ、Ⅲ～Ⅵ、Ⅸ、Ⅺ～)ⅩⅢ均为首次从野木瓜属植物中分离得到.     

Antimicrobial phenylpropanoids from the Argentinean highland plant Parastrephia lucida (Meyen) Cabrera

Ethnopharmacological relevance

The Argentinean highland plant Parastrephia lucida (Meyen) Cabrera is used in traditional medicine as an antiseptic and anti-inflammatory crude drug.

Aim of the study

To relate the antimicrobial effect of the crude drug with the constituents of the active fractions and traditional use.

Materials and methods

Assay-guided isolation of the methanol (MeOH) plant extract was carried out using bacteria and yeasts as target organisms. Both ATCC and local strains were included in the study. The antimicrobial fractions and compounds were detected by bioautographic assays. Minimum inhibitory concentrations (MIC) of each extract and fraction were determined and compared with reference antibiotics. Fractions were analyzed by HPLC–DAD, GC–MS, ¹H NMR and ¹³C NMR.

Results

From the MeOH extract of the plant, assay-guided isolation of the antimicrobial constituents led to 12 phenylpropanoids and two simple phenolics. Most of the compounds occurring in the active fractions were E-caffeoyl or E-cinnamoyl esters including prenyl and phenethyl derivatives. The MIC values of the most active fractions ranged between 12.5 and 200 μg/mL against reference strains and local isolates of Staphylococcus aureus and Enterococcus faecalis.

Conclusions

The antimicrobial effect found in the crude drug was associated with mixtures of phenylpropanoids, including prenyl and phenethyl esters of caffeic and cinnamic acids. The results support at least in part the traditional use of the plant as local antiseptic.     

Antimicrobial compounds from Alpinia conchigera

Ethnopharmacological relevance

The rhizome of Alpinia conchigerahas been used as a condiment in the northern states of Peninsular Malaysia and occasionally in folk medicine in the east coast to treat fungal infections. In some states of Peninsular Malaysia, the rhizomes are consumed as a post-partum medicine and the young shoots are prepared into a vegetable dish. This study aimed to investigate the chemical constituents of the pseudostems and rhizomes of Malaysian Alpinia conchigera and to evaluate the antimicrobial activity of the dichloromethane (DCM) extracts of the pseudostems, rhizomes and the isolated compounds against three selected fungi and five strains of Staphylococcus aureus.

Materials and methods

The dried and ground pseudostems (0.8 kg) and rhizomes (1.0 kg) were successively extracted in Soxhlet extractor using n-hexane, dichloromethane (DCM) and methanol. The n-hexane and DCM extracts of the pseudostem and rhizome were subjected to isolation and purification using column chromatography on silica gel using a stepwise gradient system (n-hexane to methanol). Briefly, a serial two fold dilutions of the test materials dissolved in DMSO were prepared prior to addition of 100 μl overnight microbial suspension (108 cfu/ml) followed by incubation at 37 °C (bacteria) or 26 °C (dermatophytes and candida) for 24 h. The highest concentration of DMSO remaining after dilution (5%, v/v) caused no inhibition to bacterial/candida/dermatophytes’ growth. Antibiotic cycloheximide was used as reference for anticandidal and antidermatophyte comparison while oxacilin was used as reference for antibacterial testing. DMSO served as negative control. Turbidity was taken as indication of growth, thus the lowest concentration which remains clear after macroscopic evaluation was taken as the minimum inhibitory concentration (MIC).

Results

The isolation of n-hexane and DCM extracts of the rhizomes and pseudostems of Alpinia conchigera via column chromatography yielded two triterpenes isolated as a mixture of stigmasterol and β-sitosterol: caryophyllene oxide, chavicol acetate 1, p-hydroxy cinnamaldehyde 2, 1′S-1′-acetoxychavicol acetate 3, trans-p-coumaryl diacetate 4, 1′S-1′-acetoxyeugenol acetate 5, 1′-hydroxychavicol acetate 6, p-hydroxycinnamyl acetate 7 and 4-hydroxybenzaldehyde.The DCM extract of the rhizome of Alpinia conchigera indicated potent antifungal activity against Candida albicans, Microsporum canis and Trycophyton rubrum with MIC values of 625 μg/ml, 156 μg/ml and 156 μg/ml, respectively. It also showed significant inhibitory activity with MIC values between 17.88 and 35.75 μg/ml against the mutant Staphylococci isolates MSSA, MRSA and Sa7.Amongst the isolated compounds, the lowest inhibition observed were of 1′S-1′-acetoxyeugenol against the dermatophytes (MIC 313 μg/ml) followed by trans-p-coumaryl diacetate against both dermatophytes and candida (MIC 625 μg/ml). The compound p-hydroxycinnamyl acetate strongly inhibited Staphylococcusaureus strain VISA (MIC 39 μg/ml) followed by trans-p-coumaryl diacetate and 1′-hydroxychavicol acetate with MIC value of 156 μg/ml.

Conclusion

In conclusion, the observed antibacterial, anticandidal and antidermatophyte activity of the extracts and compounds obtained from the rhizome confirm the traditional use of Alpinia cochigera rhizome in the treatment of skin infection.     

苯丙素类化合物的抗血管生成的研究概况

血管生成是肿瘤发生发展的重要因素,新生血管不仅为肿瘤提供营养和氧气,还为其恶性转移提供必要条件;抗血管生成疗法治疗肿瘤已得到广泛的研究.近年来发现许多苯丙素类化合物具有显著的抗血管生成特性,从而为抗肿瘤血管生成提供了新的药物来源.本文综述了一些得到最为广泛研究的几种苯丙素类抗血管生成化合物的研究概况,并总结归纳了其作用的分子机理.     

Two new phenylpropanoid esters of rhamnose from Lagotis yunnanensis

Two new phenylpropanoid esters of rhamnose, lagotoside B (1) and lagotoside C (2), together with three known compounds (3–5), were isolated from Lagotis yunnanensis. The structures of 1 and 2 were elucidated by spectroscopic methods. Compounds 3–5 have been obtained from this species for the first time.     

藏药云南兔耳草的化学成分研究

从云南兔耳草中分离得到6个化合物,分别鉴定为槲皮素-3-O-β-D-葡萄糖苷(quercetin-3-O-β-D-glucoside,1),芹菜素-7-甲醚(apigenin-7-methyl ether,2),反式-肉桂酸(E-cinnamic acid,3),顺式-肉桂酸(Z-cinnamic acid,4),反式-对香豆酸(E-p-coumatic acid,5),顺式-对香豆酸(Z-p-coumatic acid,6).以上化合物均为首次从该植物中分离得到.     

Comparative study on the production and accumulation of unusual phenylpropanoids in plants andin vitro cultures ofCoreopsis tinctoria andC. lanceolata

Callus and root organ cultures ofCoreopsis tinctoria andC. lanceolata have been established in liquid nutrition medium. Their capacity to accumulate unusual phenylpropanoids was compared with that of seedlings and whole plants. Corresponding callus cultures accumulated the phenylpropanoids only in traces. In contrast to the unorganized callus cultures the root organ cultures accumulated the same pattern of phenylpropanoids as their parent plants. A root organ culture ofC. tinctoria accumulated the compounds up to the same amounts as the root of the whole plant.