Immunomodulatory triterpenoids from the oleogum resin of Boswellia carterii Birdwood

The immunomodulatory bioassay-guided fractionation of the oleogum resin of frankincense (Boswellia carterii Birdwood) resulted in the isolation and identification of 9 compounds; palmitic acid and eight triterpenoids belonging to lupane, ursane, oleanane, and tirucallane skeleta were isolated form the resin. These triterpenoids are lupeol, beta-boswellic acid, 11-keto-beta-boswellic acid, acetyl beta-boswellic acid, acetyl 11-keto-beta-boswellic acid, acetyl-alpha-boswellic acid, 3-oxo-tirucallic acid, and 3-hydroxy-tirucallic acid. The structures of the isolated compounds were deduced based on spectroscopic evidences. The lymphocyte transformation assay of the isolated compounds proved that the total extract retained more activity than that of any of the purified compounds.     

Lack of Specificity in Plant Extracts and Chemicals as Inducers of Systemic Resistance in Cucumber Plants to Anthracnose

Canoia, lettuce, green bean, dwarf pea, tobacco, tomato, poplar, corn, wheat, and cucumber leaves were extracted by boiling with 95% ethanol. The ethanol was removed from the ethanol-water extract, and the water-soluble fraction was centrifuged and filtered to remove compounds with a molecular weight > 1 000 D. The undersides of the first true leaf of a cucumber plant (leaf 1) and the leaf above (leaf 2) were sprayed with each plant extract (induction), and 7 days later leaf 3 was inoculated with a conidial suspension of Colletotrichym lagenarium (challenge). Extracts from all plants tested induced systemic resistance in leaf 3 to C. lagenarium . Commercially available compounds were screened to determine structural similarities among the compounds which can induce systemic resistance. All compounds which induced resistance in leaf 3 caused some damage to leaves 1 and 2. but not all compounds which damaged leaves 1 and 2 induced resistance in leaf 3. Galacturonic acid, glucuronic acid, salicyhc acid, m-hydroxybenzoic acid, p-hydroxybenzoic acid, y-resorcylic acid, protocatecbuic acid, gallic acid, hemimelletic acid, trimelletic acid, trimesic acid, phloroglucinol, and glycine induced systemic resistance, whereas catechol, resorcinol, hydroquinone, pyrogaLol, hydroxyhydroquinone, benzoic acid, phthalic acid, α-resorcylic acid, β-resorcylic acid, gentisic acid. 2, 3-dihydroxybenzoic acid, benzaldehyde, 2,3-dihydroxybenzaldehyde, β-resorcaldehyde, protocatechuic aldehyde, benzyl alcohol, salicyl alcohol, myo-inositol, phytic acid, pinitol, and quebrachitol did not. Structural similarities were not evident among either compounds which induced systemic resistance or those that did not.     

Production of Tricarboxylic Acid Anhydrides from Fatty Acids by a Lipase-producing Strain of Pseudomonas cepacia

A lipase-producing strain of Pseudomonas cepacia isolated from a soil sample was found to produce five compounds when oleic acid was added to the culture medium as lipase inducer. The five compounds were isolated by solvent extraction, silicagel column chromatography and preparative HPLC, and their structural elucidation was performed by mass spectrometry, and infrared and nuclear magnetic resonance spectroscopies. The products were identified as dec-3-ene-1,3,4-tricarboxylic acid 3,4-anhydride (product 1 ), undec-3-ene-1,3,4-tricarboxylic acid 3,4-anhydride (product 2 ), dodec-3-ene-I,3,4-tricarboxylic acid 3,4-anhydride (product 3 ), dodec-3,8-diene-1,3,4-tricarboxylic acid 3,4-anhydride (product 4 ) and dodec-3,6-diene-I,3,4-tricarboxylic acid 3,4-anhydride (product 5 ). Accumulation of these compounds in the culture medium started after oleic acid consumption and followed a pattern similar to that found for cell growth and for lipase production. The five compounds were radioactively labeled when [U- 14 C]oleic acid was supplied to the culture medium, thus showing that they were produced by transformation of the acid. When isolated from cultures containing [1,2- 13 C]acetic acid and oleic acid as the sole sources of carbon, the compounds showed to contain the 13 C isotope only in the first five atoms of carbon of the molecule. Several long chain fatty acids also acted as precursors of these compounds, with maximal yields for chain lengths between 11 and 18 atoms of carbon. None of the five compounds acted as lipase inducer when added to the culture medium instead of oleic acid. The compounds showed moderate antibacterial and antifungal activities when tested in solid media bioassays.     

Production of Tricarboxylic Acid Anhydrides from Fatty Acids by a Lipase-producing Strain of Pseudomonas cepacia

A lipase-producing strain of Pseudomonas cepacia isolated from a soil sample was found to produce five compounds when oleic acid was added to the culture medium as lipase inducer. The five compounds were isolated by solvent extraction, silicagel column chromatography and preparative HPLC, and their structural elucidation was performed by mass spectrometry, and infrared and nuclear magnetic resonance spectroscopies. The products were identified as dec-3-ene-1,3,4-tricarboxylic acid 3,4-anhydride (product 1 ), undec-3-ene-1,3,4-tricarboxylic acid 3,4-anhydride (product 2 ), dodec-3-ene-I,3,4-tricarboxylic acid 3,4-anhydride (product 3 ), dodec-3,8-diene-1,3,4-tricarboxylic acid 3,4-anhydride (product 4 ) and dodec-3,6-diene-I,3,4-tricarboxylic acid 3,4-anhydride (product 5 ). Accumulation of these compounds in the culture medium started after oleic acid consumption and followed a pattern similar to that found for cell growth and for lipase production. The five compounds were radioactively labeled when [U- 14 C]oleic acid was supplied to the culture medium, thus showing that they were produced by transformation of the acid. When isolated from cultures containing [1,2- 13 C]acetic acid and oleic acid as the sole sources of carbon, the compounds showed to contain the 13 C isotope only in the first five atoms of carbon of the molecule. Several long chain fatty acids also acted as precursors of these compounds, with maximal yields for chain lengths between 11 and 18 atoms of carbon. None of the five compounds acted as lipase inducer when added to the culture medium instead of oleic acid. The compounds showed moderate antibacterial and antifungal activities when tested in solid media bioassays.     

The Relationships between Chemical and Genetic Differentiation and Environmental Factors across the Distribution of Erigeron breviscapus (Asteraceae)

Aims

Erigeron breviscapus (Vant.) Hand.-Mazz. is an important, widely used Chinese herb with scutellarin, 1,5-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid and erigoster B being its major active compounds. We aimed to resolve the influence of biotic and abiotic factors on the concentrations of these compounds and to determine appropriate cultivation methods to improve the yields of the four compounds in this herb.

Methods

In order to detect the major genetic and natural environmental factors affecting the yields of these four compounds, we applied AFLP markers to investigate the population genetic differentiation and HPLC to measure the concentrations of four major active compounds among 23 wild populations which were located across almost the entire distribution of this species in China. The meteorological data including annual average temperature, annual average precipitation and annual average hours of sunshine were collected. The relationships among the concentrations of four compounds and environmental factors and genetic differentiation were studied.

Important Findings

Low intraspecific genetic differentiation is detected, and there is no obvious correlation between the genetic differentiation and the contents of the chemical compounds. We investigated the correlation between the concentrationsof four compounds (scutellarin, 1,5-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid and erigoster B) and environmental factors. Concentrations of two compounds (1,5-dicaffeoylquinic acid and 3,5-dicaffeoylquinic acid) were correlated with environmental factors. The concentration of 1,5-dicaffeoylquinic acid is positively correlated with latitude, and is negatively correlated with the annual average temperature. The concentration of 3,5-dicaffeoylquinic acid is positively correlated with annual average precipitation. Therefore, changing cultivation conditions may significantly improve the yields of these two compounds. We found the concentration of scutellarin positively correlated with that of erigoster B and 3,5-dicaffeoylquinic acid, respectively. We inferred that the synthesis of these two pairs of compounds may share similar triggering mechanism as they synthesized in a common pathway.     

横断山区莎草科新分类群（一）

作者于1981—1983年随中国科学院青藏综合科学考察队赴横断山区考察,采集到不少莎草科植物标本。近年来、在承担《横断山区植物》一书莎草科的编著任务中,除鉴定了青藏队采集的该科标本外,还鉴定了我所标本馆收藏的该科部分标本,发现了一些新分类群,现在本文发表.     

Diosgenin glucuronides from Solanum lyratum and their cytotoxicity against tumor cell lines

Bioassay-directed fractionation of the cytotoxicity active fraction of the whole plant from Solanum lyratum led to the isolation of a new steroidal saponin, diosgenin 3-O-beta-D-glucopyranosiduronic acid methyl ester (2), as well as four known compounds, diosgenin (1), diosgenin 3-O-beta-D-glucopyranosiduronic acid (3), diosgenin 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosiduronic acid (4), diosgenin 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucuroniduronic acid methyl ester (5). The structures of the isolated compounds were elucidated on the basis of their spectral data and chemical evidences. Compound 1 was isolated for the first time from this plant, and compound 3 was isolated as a new natural product. Cytotoxic activities of the isolated compounds were evaluated and the cytotoxicities of compounds 2-5 reported for the first time.     

Functional studies of newly synthesized benzoic acid derivatives: identification of highly potent retinoid-like activity

Three newly synthesized benzoic acid derivatives (terephthalic acid anilides, chalcone carboxylic acid, and azobenzene carboxylic acid), with a certain structural similarity to retinoic acid, were examined for their retinoid-like bioactivity and their capacity to bind to cellular retinoid binding proteins. Two in vitro systems were used to evaluate their retinoid-like bioactivity: inhibition of adipose conversion of ST 13 murine preadipose cells and growth promotion of murine sarcoma virus (MSV)-transformed 3T3 cells in serum-free culture. All three compounds tested inhibited ST 13 adipose conversion at nanomolar concentrations in a manner similar to classical retinoids such as retinoic acid. The growth-stimulating activity of these compounds on MSV-transformed 3T3 cells was one to two orders of magnitude greater than that of retinoic acid. Simultaneous treatment with these compounds and retinoic acid produced only a barely detectable additive effect, suggesting a common mechanism of action, whereas unrelated mitogens, thrombin, and insulin worked synergistically in combination with retinoic acid. None of the compounds competed with retinol for binding to cellular retinol binding protein. However, two of the three competed with retinoic acid for binding to cellular retinoic acid binding protein. This study provides evidence that the newly synthesized compounds should be included among the retinoids and that their strong biological activity will undoubtedly contribute to the biological and medical application of retinoids.     

Studies on the Chemical Constituents of the Spores from Ganoderma lucidum Leyss et Fr,Karst

Two and ten compounds were isplated from the water portion and the ethereal soluble lipophilic fraction of Ganoderma lucidum respectively. On the basis of their chemical properties and co-TLC and IR spectral analysis, the two compounds from the water portion were identified as choline (Ⅰ) and betains (Ⅱ), ten compounds from thereal soluble fraction as tetra- cosanoic acid, stearic acid, palmitic acid, ergosta-7, 22-diene-3β-ol, nonadecanoic acid, benenic acid, tetracosane, hentriacontane, ergosterol and β-sitosterol. In addition, there are two compounds not be purified as contaminated by a small amount of ergosta-7, 22-diene-3β-ol.     

Tyrosine kinase inhibitors from the rainforest tree Polyscias murrayi

A series of 3-(4-hydroxyphenyl) propanoic acid derivatives, which inhibit Itk (interleukin-2 inducible T-cell kinase), a Th2-cell target, were isolated from the Australian rainforest tree Polyscias murrayi. The new compound 3-(4-hydroxyphenyl) propionyl choline and a 2:1 mixture of the new compounds 3,4-di-O-3-(4-hydroxyphenyl) propionyl-1,5-dihydroxycyclohexanecarboxylic acid and 3,5-di-O-3-(4-hydroxyphenyl) propionyl-1,4-dihydroxycyclohexanecarboxylic acid were isolated along with two known compounds 3-(4-hydroxyphenyl) propanoic acid and 3-(3,4-hydroxyphenyl) propanoic acid. Their structures were determined by 1D and 2D NMR spectroscopy. The assay results suggest that both the 3-(4-hydroxyphenyl) propanoate and carboxyl moieties contribute to Itk activity of the compounds.     

Furanyl-1,3-thiazol-2-yl and benzoxazol-5-yl acetic acid derivatives: novel classes of heparanase inhibitor

Using a furanylthiazole acetic acid as a starting point, a novel series of benzoxazol-5-yl acetic acid derivatives have been identified as heparanase inhibitors. Several compounds possess an IC50 of approximately 200 nM against heparanase, for example, trans 2-[4-[3-(3,4-dichlorophenylamino)-3-oxo-1-propenyl]-2-fluorophenyl]benzoxazol-5-yl acetic acid (16e). Several of the compounds show anti-angiogenic properties. Improvement to the DMPK profile of compounds has provided compounds of potential use in in vivo models.     

Biochemical effects of the hypoglycaemic compound pent-4-enoic acid and related non-hypoglycaemic fatty acids. Oxidative phosphorylation and mitochondrial oxidation of pyruvate, 3-hydroxybutyrate and tricarboxylic acid-cycle intermediates

1. The effects of the hypoglycaemic compound pent-4-enoic acid, and of four structurally related non-hypoglycaemic compounds (pent-2-enoic acid, pentanoic acid, cyclopropanecarboxylic acid and cyclobutanecarboxylic acid), on several reactions in rat liver mitochondria were determined. 2. The use of manometric techniques for measurements of oxidations and of phosphorylation is critically discussed. 3. Pent-4-enoic acid and pentanoic acid uncoupled oxidative phosphorylation at low concentrations, but usually by not more than about 50%. 4. All the compounds, except cyclobutanecarboxylic acid, strongly inhibited the oxidation of pyruvate and 2-oxoglutarate, but the oxidations of succinate, citrate and 3-hydroxybutyrate were not strongly inhibited. 5. All the compounds, except cyclobutanecarboxylic acid, inhibited decarboxylation of [1-(14)C]pyruvate with ferricyanide as electron acceptor. 6. All the compounds, except pent-2-enoic acid, caused mitochondrial swelling after a time-lag.     

一氧化氮参与盐胁迫下长春花酚类代谢的调控研究

为研究外源一氧化氮(NO)调控盐胁迫下长春花中酚类化合物的响应,采用液相色谱—质谱联用(LCMS)技术靶向分析梯度浓度硝普纳(SNP)处理对盐胁迫下长春花幼苗根、茎、花、叶4个部位中酚类化合物组分及含量水平的变化。结果共鉴定出L-苯丙氨酸和18种酚类物质,C6C1类5种、C6C3类5种、C6C3C6类8种,其中原儿茶酸、绿原酸、槲皮素在长春花根、茎、花、叶4个部位中均存在;不同浓度SNP处理后长春花不同部位酚类化合物响应积累明显不同,其中C6C1和C6C3小分子酚酸类化合物主要积累在根和茎中,C3C6C3类主要富集在花和叶中;L-苯丙氨酸在茎、叶中相对含量较高,盐胁迫下茎中含量显著升高,且随外源NO浓度增大呈下降趋势。外源NO影响盐胁迫下植物器官中酚类化合物的积累和变化,其中根和茎响应敏感,从种类和相对含量的角度,茎和叶更适合检测酚类化合物。     

Synthesis of Some New Halogenated N-Thiazolyl Substituted 2-Mercapto Benzoic Acid Amides and Their Use as Possible Fungicides

One hundred and four acid amido compounds have been prepared by condensing 2-mercapto benzoic acid and its 5-bromo, 3, 5-dibromo and 3, 5-dichloro derivatives with 2-amino-4-substituted thiazoles and their 5-halogenated derivatives via the acid chloride. All these compounds have been tested against Helminthosporium. Four of the compounds were tested for their antibacterial, antihelminthic activities and also for their hypoglycemic activity.     

Flavonoid glycosides and phenolic acids from Ehretia thyrsiflora

Chemical constituents of the leaves of Ehretia thyrsiflora were continuously investigated. Twelve compounds including six flavonoids and six phenolic acids, isoquercetrin, hyperoside, trifolin, astragalin, kaempferol 3-O-arabinosylgalactoside, quercetin 3-O-arabinosylgalactoside, rosmarinic acid, cinnamic acid, icariside E5, ferulic acid, α-hydroxydihydrocaffeic acid, lithospermic acid B were first isolated from this species. The considerable phenolic compounds existed in this species have important systematic significance in the argument of the family the Boraginaceae.     

Partial isotope fractionation during high-performance liquid chromatography of deuterium-labelled internal standards in plant hormone analysis: A cautionary note

Deuterium-labelled indole-3-acetic acid, abscisic acid and phthalimido-1-aminocyclopropane-1-carboxylic acid were found to separate from the unlabelled compounds on reverse-phase high-performance liquid chromatography (HPLC). A similar separation was found for the methyl esters of these compounds on normal-phase HPLC. Such separations may lead to substantial errors when these compounds are used as internal standards for quantitation by gas chromatography-mass spectrometry/selective ion detection, unless the complete chromatographic peaks are collected.Abbreviations ABA abscisic acid - ACC 1-aminocyclopropane-1-carboxylic acid - IAA indole-3-acetic acid - GC-MS gas chromatography-mass spectrometry - HPLC high-performance liquid chromatography - Pht-ACC phthalimido-ACC - SIM selected ion monitoring     

Metabolism of sinapic acid and related compounds in the rat

1. Administration of sinapic acid to the rat results in the excretion of 3-hydroxy-5-methoxyphenylpropionic acid, dihydrosinapic acid, 3-hydroxy-5-methoxycinnamic acid and unchanged sinapic acid in the urine. The sinapic acid conjugate sinalbin is also catabolized to free sinapic acid and 3-hydroxy-5-methoxyphenylpropionic acid in the rat. 2. 3,4,5-Trimethoxycinnamic acid is metabolized in part to sinapic acid and 3-hydroxy-5-methoxyphenylpropionic acid. 3. 3,5-Dimethoxycinnamic acid is metabolized to 3-hydroxy-5-methoxycinnamic acid and 3-hydroxy-5-methoxyphenylpropionic acid. 4. The metabolic interrelationships of these compounds were studied by the administration of intermediates and a metabolic pathway is proposed. 5. The metabolism of the corresponding benzoic acids was studied, but these compounds and their metabolites were shown not to be intermediates or products of the metabolism of the related cinnamic acids.     

紫珠的松香烷型二萜成分研究

从紫殊全草的乙醇提取物的氯仿部分中分得5个松香烷型二萜,经光谱数据分别鉴定为脱氢枞酸(1)、7β-羟基-脱氢枞酸(2)、7α-羟基-脱氢枞酸(3)、7-羰基-脱氢枞酸(4)和18-羧基-6,8,11,13-松香烷酸。以上化台物均为首次从该植物中分得。     

Omega-3 fatty acids and their lipid mediators: towards an understanding of resolvin and protectin formation

Omega-3 polyunsaturated fatty acids (n-3 PUFAs) have long been associated with decreased inflammation and are also implicated in the prevention of tumorigenesis. Conventional thinking attributed this mainly to a suppressive effect of these fatty acids on the formation of arachidonic acid-derived prostaglandins and leukotrienes. Recent years have seen the discovery of a new class of inflammation-dampening and resolution-promoting n-3 PUFA-derived lipid mediators called resolvins and protectins. Chemically, these compounds are hydroxylated derivatives of the parent n-3 PUFA eicosapentaenoic acid (EPA) for the E-resolvins, and docosahexaenoic acid (DHA) for the D-resolvins and protectin D1. While a relatively large number of these compounds have been identified and characterized until now, with differences in the positions of the hydroxyl-groups as well as in the chirality at the different carbon atoms, all compounds share common precursor metabolites, 17-hydroperoxydocosahexaenoic acid (17-H(p)DHA) for the DHA-derived compounds and 18-hydroperoxyeicosapentaenoic acid (18-H(p)EPE) for the EPA-derived compounds. In this review we summarize the current knowledge about EPA- and DHA-derived resolvins and protectins and explore the potential use of the pro-resolvins 17-hydroxydocosahexaenoic acid (17-HDHA) and 18-hydroxyeicosapentaenoic acid (18-HEPE) as indicators of anti-inflammatory n-3 PUFA mediator formation.     

Pentacyclic triterpenoid and saponins from Gambeya boukokoensis

Chemical studies of the EtOAc extract of Gambeya boukokoensis Aubr. et Pellegr. stem bark led to the isolation of eight compounds. Three of them were elucidated as new compounds and designated as: gamboukokoensein A, 1alpha,2alpha,3beta,19alpha,23-pentahydroxyurs-12-en-28-oic acid; gamboukokoenside A, 2beta,3beta,6beta,28-tetrahydroxyolean-12-en-23-oic acid 23-O-alpha-L-arabinopyranosyl ester and gamboukokoenside B, 6beta,28-dihydroxy-3-oxoolean-12-en-23-oic acid 23-O-alpha-L-arabinopyranosyl ester. The other five compounds were known and identified as myrianthic acid, protobassic acid, oleanolic acid, erythrodiol and chondrillasterol. Their structures were elucidated on the basis of one and two dimensional NMR spectroscopic techniques, FABMS, ESMS and chemical evidence.