万花木化学成分的研究(Ⅰ)

本文对菊科蚂蚱腿子属植物万花木(Myripnois dioica Bunge)地上部分进行了化学成分研究。利用葡聚糖凝胶Sephadex LH-20、硅胶柱层析对万花木乙酸乙酯部位进行反复色谱分离,从中分得15个化合物,并采用谱学分析和理化常数对照等方法对所得化合物进行结构鉴定,分别为:阿魏酸(1)、木栓酮(2)、木栓醇(3)、1-无羁萜烯-3-酮(4)、3-乙酰基齐墩果酸(5)、1-无羁萜烯-3-醇(6)、3α-乙酰基木栓醇(7)、槲皮素(8)、5,7,3′,4′-四羟基黄烷酮(9)、花旗松素(10)、ixerin A(11)、14-oxomelampolide(12)、ainsliaside B(13)、β-谷甾醇(14)和β-胡萝卜苷(15)。所有化合物均为首次从该属植物中分离得到。     

火麻仁的化学成分研究

采用硅胶柱色谱和葡聚糖凝胶LH-20,从火麻仁70％乙醇提取物的氯仿和乙酸乙酯萃取部位分离得到6个化合物。经理化鉴定和波谱方法鉴定方法确定为CannabsinA（1）．β-谷甾醇（2）、胡萝卜苷（3）、正二十四烷酸（4）、甘露醇（5）、棕榈酸（6）。     

Chemical Characterization of Leaves,Male and Female Flowers from Spontaneous Cannabis (Cannabis sativa L.) Growing in Hungary

Spontaneous forms of hemp (Cannabis sativa L., often reported as Cannabis sativa var. spontanea Vavilov ) with a low content of psychoactive cannabinoids can be considered as a valuable source of other phytoconstituents to be used in nutraceuticals or for their health promoting properties. Chemical data on this hemp variety are rather scarce. In this article, we report a comprehensive phytochemical characterization of leaves, male and female inflorescences of C. sativa growing wild in Hungary. For the purpose, the essential oil along with polar extracts were analyzed using GC/MS, NMR and LC‐DAD‐MS techniques, respectively. The results indicated that female inflorescence essential oil contains high amounts of the CB2 agonists, (E)‐caryophyllene (28.3 %) and cannabidiol (CBD; 24.9 %), whereas leaves and male inflorescence essential oils contained lower amounts of both compounds. HPLC/MS allowed to quantify cannabidiol (CBD) and cannabidiolic acid (CBD?A) in the ethyl acetate extracts from leaves, male and female inflorescences; they were 0.3, 0.8 and 0.9 %, and 0.2, 0.3 and 0.4 %, respectively. Flavonoids of this spontaneous form of hemp were formed by C‐glycosides and glucuronic acids of kaempferol and apigenin with a total content of 3.8, 6.1 and 7.8 mg/g in methanolic extracts from leaves, male and female inflorescences, respectively. Based on these results, spontaneous C. sativa may represent an important source of CB₂ agonists and bioflavonoids to be used in nutraceuticals, cosmetics and pharmaceuticals.     

Role of Steroids and Amino Acids in Pollen Germination of Eichhornia crassipes Solms.

Detection of amino acids from the pollen grains of Eichhornia crassipes together with isolation of β-sitosterol, stigmasterol and free sugars from the pistil were carried out. The role of the growth potential of the pollen and the growth-influencing compounds of the pistil are discussed. Amino acids and free sugars were detected in pollen and in pistils by paper chromatography. The neutral fractions of the alcohol extract (95%) of the pistil on column chromatography [petroleum ether: benzene (2:1)] gave a crystalline compound (m.p. 136-139°C) with positive Liebermann-Burchard test for sterol. A mass spectrum of the compound showed a mixture of β-sitosterol and stigmasterol, which was confirmed by comparative thin-layer chromatography and gas-layer chromatography.     

Agrobacterium infection of hemp (Cannabis sativa L.): establishment of hairy root cultures

Abstract

Experimental conditions were optimized for hemp, a difficult to transform plant, to be effectively infected with either Ri or Ti plasmid-bearing agrobacteria and to establish stably transformed tissues. Hypocotyl of intact seedlings was the most responsive material and the response depended on both bacterial strain and plant variety. Transformed tissues, hairy roots and tumors, were cultured and stabilized in vitro and showed the characteristic traits of fast and phytohormone-independent growth as well as high incidence of lateral branching and abundance of root hairs in the case of roots. They all contained T-DNA of the corresponding Ri or Ti plasmid as revealed by PCR analysis with specific primers and further hairy roots induced by AR10GUS strain showed normal pattern of β-glucuronidase positive staining. To our knowledge, this represents the first reported protocol for the establishment of Cannabis sativa hairy root cultures.     

中药马骝卵的化学成分研究

从中药马骝卵 (Nephrolepiscordifolia(L .) )的乙酸乙酯萃取部分中分离出 8个成分 ,利用UV、IR、1HNMR、13 CNMR、MS等光谱方法鉴定出 5个化合物 ,它们分别是 :β 谷甾醇、胡萝卜苷、山柰酚 3 O β 葡萄糖苷、槲皮素 3 O β 鼠李糖苷、软脂酸单甘油酯 ,其中 2个黄酮苷、油酸单甘油酯等 3个化合物为首次从该植物中分得。     

Evaluation of Cytotoxicity and Antifungal Activity of Friedelanes from Salacia elliptica Roots

Plants from Salacia genus are used in traditional medicine for a wide range of diseases. Previous studies reported bioactive pentacyclic triterpenoids from S. elliptica leaves and branches. In this study, the novel pentacyclic triterpenoid 7α,15α-dihydroxyfriedelan-3-one ( 1 ) was obtained from the roots of Salacia elliptica, along with seven known compounds: friedelan-3-one ( 2 ), friedelan-3β-ol ( 3 ), friedelan-1,3-dione ( 4 ), friedelan-3,15-dione ( 5 ), 15α-hydroxyfriedelan-3-one ( 6 ), 15α,26-dihydroxyfriedelan-3-one ( 7 ), and 26-hydroxyfriedelan-3,15-dione ( 8 ). Additionally, one steroid, spinasterol ( 9 ), was also identified. The chemical structures of all compounds were established through ¹H and ¹³C-NMR. Compound 1 was analysed by additional 2D experiments (HMBC, HSQC, COSY, and NOESY) for complete elucidation. Furthermore, the cytotoxicity of compounds 2 , 3 , 6 , 7 and 8 against the A549 lung cancer cells model was evaluated. The flow cytometry analysis revealed a significant cytotoxic activity similar to that exhibited by the triterpenoid lupeol. Additionally, compounds 2 , 3 , 6 , and 7 were tested for in vitro antifungal activity against Candida, Cryptococcus and Sporothrix strains. However, all compounds showed no activity at the tested concentrations.     

Phytochemical Profiling by UPLC-ESI-QTOF-MS of Kalaharia uncinata (Schinz) Moldenke,Widely Used in Traditional Medicine in DR Congo

Kalaharia uncinata (Schinz) Moldenke, is a tropical erect bushy shrub or subshrub of the Lamiaceae family. It is an endemic plant species of Southern Africa, widely used in the pharmacopoeia against upper respiratory tract infections. A previously conducted ethnobotanical survey revealed that it is believed to contain bioactive substances. However, no relevant phytochemical information was available. This study aimed to perform a phytochemical characterization of K. uncinata and also to discuss the potential bioactivity of the identified phytochemical constituents based on documented data. Ultra-performance liquid chromatography with electrospray ionization quadrupole time-of-flight mass spectrometry (UPLC-ESI-QTOF-MS) was used for profiling and identification of the main phytochemical constituents from leaf extracts (MeOH 90 %, DCM, AcOEt, BuOH, hexane and residue) of K.uncinata. Twenty-four constituents, representing mainly flavonoids (14), followed by phenylethanoid glycosides (7), phenolic acids (2), and an iridoid glycoside (1) were tentatively identified. Most of the identified compounds are documented to have antiviral and anti-inflammatory properties, which could possibly be the rationale behind the use of K. uncinata against upper respiratory tract infections.     

The Chemical Components of Lobelia davidii Franch.

Some constituents were isolated from the fresh whole plant of Lobelia davidii Franch. collected from Yunnan Province, with silica gel chromatography, ion exchange and preparative TLC. The structures except lelobanonoline, were identified by techniques comparision of their MS, IR, 1NHMR and 13C-NMR with the literature data thereof. They are β-sitosterol, β-amyrin palmitate, β-amyrin, norlelobanidine, norlobelanine, lelobanonoline, lobelanidine and norlobelanidine. Lelobanonoline is a new alkaloid with the structure of l-[6-(2-hydroxy-2-phenple-thyl)-l-methyl-2-piperidinyl ] butan-2-one.     

Identification of some Bioactive Metabolites in a Fractionated Methanol Extract from Ipomoea aquatica (Aerial Parts) through TLC,HPLC, UPLC‐ESI‐QTOF‐MS and LC‐SPE‐NMR Fingerprints Analyses

Introduction

The plant species Ipomoea aquatica contains various bioactive constituents, e.g. phenols and flavonoids, which have several medical uses. All previous studies were executed in Asia; however, no reports are available from Africa, and the secondary metabolites of this plant species from Africa are still unknown.

Objective

The present study aims finding suitable conditions to identify the bioactive compounds from different fractions.

Methodology

Chromatographic fingerprint profiles of different fractions were developed using high‐performance liquid chromatography (HPLC) and then these conditions were transferred to thin‐layer chromatography (TLC). Subsequently, the chemical structure of some bioactive compounds was elucidated using ultra‐performance liquid chromatography‐quadrupole time of flight‐tandem mass spectrometry (UPLC‐QTOF‐MS) and liquid chromatography‐solid phase extraction‐nuclear magnetic resonance (LC‐SPE‐NMR) spectroscopy.

Results

The HPLC fingerprints, developed on two coupled Chromolith RP‐18e columns, using a gradient mobile phase (methanol/water/trifluoroacetic acid, 5:95:0.05, v/v/v), showed more peaks than the TLC profile. The TLC fingerprint allows the identification of the types of chemical constituents, e.g. flavonoids. Two flavonoids (nicotiflorin and ramnazin‐3‐O‐rutinoside) and two phenolic compounds (dihydroxybenzoic acid pentoside and di‐pentoside) were tentatively identified by QTOF‐MS, while NMR confirmed the structure of rutin and nicotiflorin.

Conclusion

The HPLC and TLC results showed that HPLC fingerprints give more and better separated peaks, but TLC helped in determining the class of the active compounds in some fractions. Bioactive constituents were identified as well using MS and NMR analyses. Two flavonoids and two phenolic compounds were tentatively identified in this species for the first time, to the best of our knowledge. Copyright © 2017 John Wiley & Sons, Ltd.     

元宝山冷杉化学成分的研究

采用色谱技术对元宝山冷杉的化学成分进行分离,根据波谱学方法确定化合物的结构。结果从元宝山冷杉中分离得到5个单体化合物,分别鉴定为:3α-甲氧基-9β-羊毛甾-7,24-二烯-26,23R-内酯(1)、β-谷甾醇(2)、6-甲基-3,7-二甲氧基山奈酚(3)、3-氧代-羊毛甾(9,11)-烯-24S,25-二醇(4)、豆甾-4-烯-6β-羟基-3-酮(5)。所有这些化合物均为首次从该植物中分离得到。     

Identification of benzophenanthridine alkaloids from Bocconia arborea by gas chromatography-mass spectrometry

A methanol extract of the bark of Bocconia arborea was fractionated on silica gel and the fractions analysed using gas chromatography coupled with mass spectrometry (GC-MS). Several benzophenanthridine alkaloids were identified including dihydrosanguinarine, oxysanguinarine, 11-acetonyldihydrochelerythrine, dihydrochelerythrine, chelerythrine, chelerythridimerine and angoline as the principal constituents. The results show that the direct GC-MS analysis of these alkaloids is possible with a clear distinction between the compounds. The technique is shown to be a valuable tool and an alternative technique to classical phytochemical procedures permitting the fast analysis of alkaloids mixtures.     

Antifungal constituents isolated from the seeds of Aegle marmelos

Antifungal constituents, 2-isopropenyl-4-methyl-1-oxa-cyclopenta[b]anthracene-5,10-dione and (+)-4-(2′-hydroxy-3′-methylbut-3′-enyloxy)-8H-[1,3]dioxolo[4,5-h]chromen-8-one in addition to known compounds imperatorin, β-sitosterol, plumbagin, 1-methyl-2-(3′-methyl-but-2′-enyloxy)-anthraquinone, β-sitosterol glucoside, stigmasterol, vanillin and salicin were isolated during phytochemical investigation on seeds of Aegle marmelos Correa.     

Lipid components of olive oil from Tunisian Cv. Sayali: Characterization and authenticity

The analysis of the total lipid fraction from the Sayali variety of olive oil was accomplished in the present investigation. Glyceridic, unsaponifiable and flavour fractions of the oil were isolated and identified using several analytical methods. Chromatographic techniques have proven to be suitable for these determinations, especially capillary gas chromatography. Gas chromatography coupled to mass spectrometry was successfully used to identify sterols, triterpenes alcohols, 4-monomethylsterols, aliphatic alcohols and aroma compounds in our samples. Furthermore, solid phase microextraction was used to isolate volatiles from the total lipid fraction. Results from the quantitative characterization of Sayali olive oil showed that oleic acid (77.4%) and triolein (47.4%) were the dominant glyceridic components. However, the main compounds of the unsaponifiable fraction were β-sitosterol (147.5 mg/100 g oil), 24-methylene cycloartenol (146.4 mg/100 g oil) and hexacosanol (49.3 mg/100 g oil). Moreover, results showed that the aldehydic compounds were the major flavours present in Sayali olive oil.     

Phytochemical Screening,Antioxidant Assay and Cytotoxic Profile for Different Extracts of Chrysopogon zizanioides Roots

The Chrysopogon zizanioides plant possesses multiple traditional uses, especially in therapeutics, but only a few articles have reported its biological activity. Hence, the present study was planned to explore the phytochemical constituents, cytotoxic potential, radical scavenging activity, and GC/MS (Gas chromatography & Mass spectrometry) analysis of the vetiver root extracts. The roots extracted with different solvents exhibited more significant phytochemical constituents in polar solvents in comparison to non-polar ones, favoring the extraction of a greater number of components in highly polar solvents. All the extracts were tested for their cytotoxicity using SRB (Sulforhodamine B) assay. They confirmed ethanolic extract as a potent extract with GI₅₀ 56±0.5 μg/ml in oral cancer (SCC-29B) along with no cytotoxicity in healthy cells (Vero cells), making it a safer therapeutic option in comparison to standard Adriamycin. This extract was also analyzed for its antioxidant potential by DPPH (1,1-Diphenyl-2-picrylhydrazyl) assay with IC₅₀ value 10.73 μg/ml, which was quite comparable to Ascorbic acid having IC₅₀ value 4.61 μg/ml. The quantitative analysis of ethanolic extract exhibited 107 compounds amongst which Khusenic acid, Ascorbic acid, Junipen, gamma-Himachalene, alpha-Guaiene were the majorly occurring compounds that can be explored further for their cytotoxic activity.     

滇南蛇根草化学成分的研究

采用柱色谱技术从药用植物滇南蛇根草Ophiorrhiza austroyunanensis Lo.全草的甲醇提取物分离得到9个化合物,利用理化性质及波谱方法分别鉴定为β-谷甾醇(1)、β-豆甾醇(2)、β-胡萝卜苷(3)、白桦脂醇(4)、叶黄素(5)、东莨菪素(6)、熊果酸(7)、茜根酸-1-甲醚(8)和豆甾醇-3-O...     

硬孔灵芝的化学成分研究

采用硅胶柱层析法进行分离纯化,从硬孔灵芝Ganoderma duropora的氯仿萃取物中分离得到甾类化合物8种。根据波谱数据,化合物1-8结构分别被鉴定为:麦角甾醇、麦角甾-7,22-二烯-3β-醇、麦角甾-7,22-二烯-3-酮、6,9-环氧麦角甾-7,22-二烯-3β-醇、过氧麦角甾醇、3,5-二羟基麦角甾-7,22-二烯-6-酮、β-谷甾醇和胡萝卜苷。     

Biochemical composition of Tunisian Nigella sativa L. at different growth stages and assessment of the phytotoxic potential of its organic fractions

The present study was conducted to study some biochemical characteristics of Tunisian Nigella sativa at different developmental stages of plant growth (vegetative, flowering and fruiting stages) and to screen the chemical constituents and the phytotoxic activity of their organic extracts on lettuce (Lactuca sativa L.). The GC–MS analysis of petroleum ether fractions revealed that N. sativa seeds were rich in linoleic acid (58% of total fatty acids), oleic acid (22% of total fatty acids) and palmitic acid (12% of total fatty acids). The fatty acid composition of aerial parts showed an increase in the level of saturated fatty acids accompanied by a concomitant decrease of polyunsaturated fatty acids levels during the developmental stage. The phytochemical investigation showed that among the organic extracts, the methanolic extract from aerial parts harvested at the fruiting stage contained the highest amounts of phenolic and flavonoid compounds. The phytotoxic study revealed that N. sativa negatively affected the growth of lettuce plants. This effect was largely dependent on the developmental stage at which material was collected and the nature of extracting solvent. The methanolic extract of aerial parts harvested at the vegetative stage was the most active on seedling growth of lettuce.     

Volatile constituents in mosses (Musci)

The essential oils of mosses of the genera Mnium, Plagiomnium, Homalia, Plagiothecium and Taxiphyllum (Musci) have been investigated by gas chromatography and mass spectrometry. The new sesquiterpenes (+)-10-epi-muurola-4,11-diene and 10,11-dihxdro-alpha-cuparenone were isolated by preparative gas chromatography and identified as major constituents of the hydrodistillation products of Mnium hornmum (Hedw.) using NMR and mass spectrometry. In addition, (+)-dauca-8,11-diene and two new butenolides, 3,4,5-trimethyl-5-pentyl-5H-furan-2-one and 3.4-dimethyl-5-pentyl-5H-furan-2-one were identified as constituents in Plagiomnium undulatum (Hedw.) T. Kop. Although the amounts of volatiles present in the investigated mosses are generally smaller than in liverworts, the spectrum of terpenoid compounds is similar. The investigated mosses also generate aliphatic compounds of greater abundance and structural variety.