The spatial structure of lichen Hypogymnia physodes (L.) Nyl

Structure analysis based on regular morphological variability at organism level is applied to study the shape and spatial construction of lichen Hypogymnia phyzodes (L.) Nyl. Some structural were determined at juvenile stage of development with the use of this approach. Five of them are dominant. Besides, five the most frequent encounter types of thallus branching were described. It is shown that thallus structure at adult stage is usually built from two main elements forming axial dichotomy. Analysis of thallus shape indicates that transformation of dichotomy elements into trichotomy ones may also take place during growth and development of thallus.     

Chemical constituents from Tribulus terrestris and screening of their antioxidant activity

Two oligosaccharides (1, 2) and a stereoisomer of di-p-coumaroylquinic acid (3) were isolated from the aerial parts of Tribulus terrestris along with five known compounds (4–8). The structures of the compounds were established as O-β-d-fructofuranosyl-(2 → 6)-α-d-glucopyranosyl-(1 → 6)-β-d-fructofuranosyl-(2 → 6)-β-d-fructofuranosyl-(2 → 1)-α-d-glucopyranosyl-(6 → 2)-β-d-fructofuranoside (1), O-α-d-glucopyranosyl-(1 → 4)-α-d-glucopyranosyl-(1 → 4)-α-d-glucopyranosyl-(1 → 2)-β-d-fructofuranoside (2), 4,5-di-p-cis-coumaroylquinic acid (3) by different spectroscopic methods including 1D NMR (¹H, ¹³C and DEPT) and 2D NMR (COSY, TOCSY, HMQC and HMBC) experiments as well as ESI-MS analysis. This is the first report for the complete NMR spectral data of the known 4,5-di-p-trans-coumaroylquinic acid (4).The antioxidant activity represented as DPPH free radical scavenging activity was investigated revealing that the di-p-coumaroylquinic acid derivatives possess potent antioxidant activity so considered the major constituents contributing to the antioxidant effect of the plant.     

Phenolic substances of brown algae and their antioxidant activity

The composition and content of phenolic substances were studied in 14 species of marine brown algae of the Canary Islands littoral (Spain). The highest content of phenolic substances was found inCystoseira compressia andSargassum furcatum. A high antioxidant activity was found in florotannin isolated fromCystoseira sp.     

Trait variability in ontogenesis of epiphytic lichen Hypogymnia physodes (L.) Nyl.

Ontogenesis of the foliose lichen Hypogymnia physodes has been described on the basis of the material obtained from natural populations. Ontogenetic dynamics (diameter of thallus and the number of lobes) and the features of reproductive structures (the number and diameter of labelloid and galeated sorales) were studied in ecologically different pine forests. We reasonably rejected the use of the variance analysis and nonparametric criteria for the result processing. It was shown that the median dynamics and trait variance may be either similar or different throughout the ontogenesis. The trait variances in ecologically different ecotopes were shown to be different.     

Phenolic compound profiles and their corresponding antioxidant Capacity of purple pitaya (Hylocereus sp.) genotypes

Folin-Ciocalteu and TEAC (Trolox equivalent antioxidant capacity) assay together with the spectrophotometric determination of betalains were applied to investigate the correlation between phenolics and their contribution to the antioxidant capacity of five different Costa Rican genotypes of purple pitaya (Hylocereus sp.) and of H. polyrhizus fruits. Maximum antioxidant capacity, total phenolic and betalain contents were observed in the genotype 'Lisa'. While non-betalainic phenolic compounds contributed only to a minor extent, betalains were responsible for the major antioxidant capacity of purple pitaya juices evaluated. The phenolic pattern of each genotype was also thoroughly investigated using liquid chromatography coupled to positive electrospray ionization (ESI) tandem mass spectrometry. In addition to the well known betalains previously reported in Hylocereus fruits, several biosynthetic precursors were detected. Notably, decarboxylated and dehydrogenated betalains were identified as genuine compounds of the juices. Some of these compounds were previously described as artifacts upon heat exposure. Moreover, gallic acid was identified for the first time in pitaya fruits. While the phenolic profiles generally differed between genotypes, phenolic compound composition of 'Rosa' resembled that of H. polyrhizus with respect to total contents of betacyanins, betalainic precursors, phyllocactin and cyclo-Dopa malonyl-glucosides.     

Phenolic constituents from the wood of Morus australis with cytotoxic activity

A new methylated flavonol, 5,7,2',4'-tetrahydroxy-3-methoxyflavone (1), had been isolated from the methanol extract of the wood of Morus australis, along with nine known compounds, kuwanon C (2), morusin (3), morachalcone A (4), oxyresveratrol (5), 4'-(2-methyl-2-buten-4-yl)oxyresveratrol (6), moracins M (7) and C (8), alboctalol (9), and macrourin B (10). The structures of these compounds were determined based on spectral evidence, including UV, IR, NMR, and mass spectra. Cytotoxic properties of compounds 1-10 were evaluated against murine leukemia P-388 cells. The prenylated stilbene 6 and 2-arylbenzofuran 8, and morusin (3) were found to have strong cytotoxic effects with IC50 values of 6.9, 8.7, and 10.1 microM, respectively.     

Phenolic compounds and antioxidant activity from red grape marc extracts

The aims of this work were to determine the amounts of the different classes of phenolic compounds in an ethanolic extract from red grape marc and its components, peels and seeds, and to evaluate their antioxidant activities by the beta-carotene bleaching test for their utilization as natural antioxidants. The results showed that red grape marc was rich in polyphenol compounds with a clear antioxidant activity. The extracts, in fact, at very low concentration (20 ppm) in total phenols showed an antioxidant activity (AA) higher than 43% on average, while at higher concentration (80-160 ppm) all the fractions had an AA comparable to that of butlylated-hydroxytoluene. Grape seeds seemed to give the highest contribution to such AA, as they contained high quantities of proanthocyanidines, a type of flavonoid known for its high antioxidant properties.     

Phenolic compounds with antioxidant activity from Anthemis tinctoria L. (Asteraceae)

From the aerial parts of Anthemis tinctoria L. subsp. tinctoria var. pallida DC. (Asteraceae), one new cyclitol glucoside, conduritol F-1-O-(6'-O-E-p-caffeoyl)-beta-D-glucopyranoside (1), has been isolated together with four flavonoids, nicotiflorin (2), isoquercitrin (3), rutin (4) and patulitrin (5). The structures of the isolated compounds were established by means of NMR, MS, and UV spectral analyses. Methanolic extract and pure isolated compounds were examined for their free radical, scavenging activity, using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) free stable radical, and for their inhibitory activity toward soybean lipoxygenase, using linoleic acid as substrate. Compounds 1 and 5 showed a strong scavenging effect in the DPPH radical assay. In addition 5 also exhibited high inhibitory activity on soybean lipoxygenase.     

Phenolic compounds from the roots of Ochna schweinfurthiana and their antioxidant and antiplasmodial activities

An investigation of compounds extracted from Ochna schweinfurthiana roots with ethyl acetate led to the isolation of three new compounds 4⿴-methoxylophirone A (1), 4,4⿲,4⿴⿿trimethoxylophirone A (2) and (4E;7Z)-3,8-dicarboxy-1-(O-β-d-glucopyranosyl-(1 ⿿ 6)-O-β-d-glucopyranosyl-2,9-dihydroxyhexeicosa-4,7-diene (3). Six known compounds were also identified, including Calodenone (4), Calodenine B (5), Lophirone A (6), Gerontoisoflavone A(7), 16α,17-dihydroxy-ent-kauran-19-oic acid (8) and 3β-O-d-glucopyranosyl-β-sitosterol (9). This report describes the first time that compounds 4-8 have been isolated from this plant, while 8 has never been identified in the genus Ochna. Some of the isolated compounds were evaluated for their antiplasmodial activity against the chloroquine-sensitive Plasmodium falciparum strain 3D7 and antioxidant activity using DPPH radical scavenging and Ferric reducing-antioxidant power (FRAP) assays. Compound 5 exhibited prominent radical scavenging and FRAP activities, while 7 had weak activity. Compound 1 showed good in vitro anti-plasmodial activity. The structures of the isolated compounds were elucidated by spectroscopic methods and comparisons with prior data in the literature.     

硬枝树花的化学成分及抗氧化研究

以梯度提取的方法对硬枝树花进行石油醚(30–60)、二氯甲烷、乙酸乙酯提取,浸膏经过色谱柱层析分离纯化得到6个单体化合物,分别为松萝酸(1)、黑茶溃素(2)、巴尔巴地衣酸(3)、去甲环萝酸(4)、地弗地衣酸(5)、藻纹苔酸(6),并且都是首次从硬枝树花中分离得到。通过对清除DPPH?和ABTS?+能力的测定,对这6个化合物体外抗氧化活性进行评价。结果表明:藻纹苔酸在检测浓度范围内的?DPPH的清除率和终浓度呈现一定的量效关系,在55μmol/L时,藻纹苔酸的清除率为57.05%(P0.01)。黑茶溃素、巴尔巴地衣酸、去甲环萝酸在13.75–55μmol/L检测浓度范围内的DPPH自由基清除率与终浓度呈量效关系。松萝酸对DPPH?的清除能力较强,在3.4375μmol/L及27.5μmol/L时,DPPH自由基清除率达到74.78%(P0.01)及74.82%(P0.01),接近对照组BHT浓度为55μmol/L的清除率。地弗地衣酸、藻纹苔酸、巴尔巴地衣酸的ABTS?+自由基清除率与终浓度呈现一定的量效关系,在浓度为55μmol/L时,地弗地衣酸ABTS?+自由基清除率为50.79%(P0.01),藻纹苔酸为44.53%(P0.01),巴尔巴地衣酸为44.34%(P0.01),在13.75–55μmol/L浓度范围内,黑茶溃素ABTS?+自由基的清除率随着浓度的增大而逐渐增大。硬枝树花中含有多样的苯骈呋喃类和缩酚酸类化合物及其衍生物,是具有开发利用潜力的抗氧化剂资源。     

Phenolic constituents from the core of kenaf (Hibiscus cannabinus)

Four lignans, boehmenan H [2-(4-hydroxy-3-methoxyphenyl)-5-[3-(4-hydroxy-3-methoxycinnamoyloxy)propyl]-3-hydroxymethyl-7-methoxybenzodihydrofuran], boehmenan K [2-(4-hydroxy-3-methoxyphenyl)-5-[3-(4-hydroxycinnamoyloxy)-1-propenyl]-3-(4-hydroxy-3-methoxycinnamoyloxymethyl)-7-methoxybenzodihydrofuran], threo-carolignan H [threo-1-(4-hydroxy-3-methoxyphenyl)-2-[4-[3-(4-hydroxy-3-methoxycinnamoyloxy)propyl]-2-methoxyphenoxy]-1,3-propanodiol], and threo-carolignan K [threo-1-(4-hydroxy-3-methoxyphenyl)-3-(4-hydroxy-3-methoxycinnamoyloxy)-2-[4-[3-(4-hydroxycinnamoyloxy)-1-propenyl]-2-methoxyphenoxy]-1-propanol] as well as several other lignans, aldehydes and a tyramine derivative were isolated from the acetone extract of core of kenaf (Hibiscus cannabinus). All the structures were established by spectroscopic methods. The hitherto unreported 13C NMR spectra of some compounds are also presented and discussed. 2D NMR techniques have allowed the revision of certain previously reported 13C NMR assignments of some scarce naturally occurring compounds.     

Phenolic constituents from the roots of Rosa laevigata (Rosaceae)

Chemical investigation of the root of Rosa laevigata led to the isolation of sixteen phenolic compounds, including seven flavonoids (1–7), five condensed tannins (8–12), two stilbenes (13 and 14) and two benzoic acid derivatives (15 and 16). Their structures were identified as (+)-catechin (1), (+)-gallocatechin (2), (2R, 3S, 4S)-cis- leucocyanidin (3), (2R, 3S, 4S)-cis-leucofisetinidin (4), (2S, 3R, 4R)-cis- leucofisetinidin (5), dehydrodicatechin A (6), phloridzin (7), procyanidin B3 (8), fisetinidol-(4α, 8)-catechin (9), guibourtinidol- (4α, 8)-catechin (10), ent- isetinidol -(4α, 6)-catechin (11), fisetinidol-(4β, 8)-catechin (12), (Z)-3-methoxy-5-hydroxy- stilbene (13), (Z)-piceid (14), gallic acid (15) and 4-hydroxybenzoic acid- 4-O-β-D-glucopyranoside (16). Among them, compounds 3–7, 9–14, and 16 were isolated from R. laevigata for the first time, and compounds 3–7, 9, 10, 12–14 and 16 were reported for the first time from the genus Rosa. The chemotaxonomic significance of these compounds was summarized.     

Chemical constituents from Melodinus cochinchinensis (Lour.) Merr. and their chemotaxonomic significance

A phytochemical investigation on the twigs and leaves of Melodinus cochinchinensis (Lour.) Merr. resulted in the isolation and identification of 22 compounds, including seven sesamin-type lignans (1–7), three pentacyclic triterpenes (8–10), one anthraquinone (11), one flavanone (12), two phenolic compounds (13 and 14), five aspidosperma-type indole alkaloids (15–19), and three eburnan-type indole alkaloids (20–22). The structures of these compounds were elucidated by means of spectroscopic analysis, including HREIMS together with 1D and 2D NMR experiments, and comparison with reported data. Among them, compounds 1/4, 2/5, and 3/6 are three pairs epimers at C-7''. Compounds 1–6, 8 and 11 were firstly isolated from the family Apocynaceae, whereas 17 was isolated from Melodinus species for the first time. Compound 8 was only found in Juglans hopeiensis, while 11 was only found in roots of Rubia cordifolia. Compounds 1–6, 8, 11 and 15–22 could be considered as chemotaxonomic markers for M. cochinchinensis. Furthermore, the chemotaxonomic significance and distribution of these isolates in Melodinus genus are discussed in detail.     

马尾伸筋草化学成分及抗骨质疏松活性研究

为研究马尾伸筋草(Lycopodium fargesii Hert.)的化学成分及其抗骨质疏松活性,采用硅胶、MCI、RP-18、Sephadex LH-20柱色谱及半制备高效液相色谱对马尾伸筋草的乙醇提取物进行系统分离,从乙酸乙酯部位中得到18个化合物,综合利用NMR、HR-ESI-MS等技术,分析鉴定化合物的结构,分别鉴定为α-芒柄蜡素(1)、26-去甲-8-氧化-α-芒柄蜡素(2)、serrat-14-en-3β,21α,24-triol(3)、serrat-14-en-3β,21β,24-triol(4)、1,20-eicosanediol(5)、二十三烷(6)、glycerolmonolinoleate(7)、glyceryl linolentate(8)、3-(4′-formylphenoxy)-4-methoxybenzaldehyde(9)、芹菜素(10)、对羟基苯甲醛(11)、香草酸(12)、3-羟基-4-甲氧基苯甲酸(13)、2-羟基-1-(4-羟基-3-甲氧基-苯基)-丙基-1-酮(14)、3-甲氧基-4-羟基桂皮醛(15)、8-acetoxy-5-hydroxyumbelliprenin(16)、trans-4-hydroxy-2-nonenoic acid(17)和正十烷硫醇(18)。化合物1~18均为首次从马尾伸筋草中分离得到,其中化合物16对破骨细胞活性具有显著的抑制作用,其IC₅₀为1.98μM。     

Antidyslipidemic and antioxidant activity of the constituents isolated from the leaves of Calophyllum inophyllum

In continuation of our drug discovery program on Indian medicinal plants, we isolated bioactive compounds (1–5) from the leaves of Calophyllum inophyllum and evaluated their antidyslipidemic activity in triton induced hyperlipidemia model. The calophyllic acid (1A) and isocalophyllic acid (1B) mixture, canophyllic acid (4) and amentoflavone (5) showed dose dependent lipid lowering activity in in vivo experiments. The compounds 1A + 1B mixture and 3 also showed good in vitro antioxidant activity.     

Dependence of the cellulosolytic activity in the lichen <Emphasis Type="Italic">Hypogymnia physodes</Emphasis> (L.) Nyl. on the substrate

Samples of the lichen H. physodes were collected from bark of living trees (pine, spruce, birch, alder, rowan, and willow); from the wood of these trees and of juniper; from bark of dead spruce, alder, and rowan trees; and from the moss Hypnum pallescens. Thalli of this lichen were placed onto medium with carboxylmethyl cellulose (CMC) (water being used as a control). Output of sugars was determined using the Nelson-Somogyi technique. Cellulosolytic activity of samples from the bark of pine and birch was higher than that of samples from the bark of spruce. In thalli of the lichen from wood, from moss, and from bark of living alder and rowan trees, the output of sugars on the medium with CMC was similar to that in the control. The cellulosolytic activity was revealed in samples from the lichen from bark of dead rowan and alder trees. In the lichen from spruce bark, the output of sugars on the medium with CMC was higher in samples from dead trees in comparison with living trees. The results are discussed.     

Phenolic constituents from the rhizomes of Acorus gramineus and their biological evaluation on antitumor and anti-inflammatory activities

On the search for anti-cancer compounds from natural Korean medicinal sources, a bioassay-guided fractionation and chemical investigation of the MeOH extract from the rhizomes of Acorus gramineus resulted in the isolation and identification of thirteen phenolic derivatives (1–13) including two new 8-O-4′-neolignans, named surinamensinols A (1) and B (2) and a new phenolic compound, named acoramol (9). The structures of these new compounds were elucidated on the basis of 1D and 2D NMR spectroscopic data analyses as well as circular dichroism (CD) spectroscopy studies. The cytotoxic activities of the isolates (1–13) were evaluated by determining their inhibitory effects on human tumor cell lines. The new 8-O-4′-neolignans, compounds 1 and 2, showed moderate antiproliferative activities against A549, SK-OV-3, SK-MEL-2, and HCT-15 cell lines with IC₅₀ values in the range of 4.17–26.18 μM. On the basis of the expanded understanding that inflammation is a crucial cause of tumor progression, anti-inflammatory activities of these compounds were determined by measuring nitric oxide (NO) levels in the medium using murine microglia BV-2 cells. Compounds 1, 2, 4, 7 and 10 inhibited NO production in BV-2 stimulated by lipopolysaccharide with IC₅₀ values of 8.17–18.73 μM via NO scavenging, inhibition of iNOS activity, and/or suppression of iNOS expression.