Chemical constituents from the Moutan Cortex charcoal and their potential coagulation activities

The chemical constituents of Cortex Moutan charcoal were studied in depth, and their coagulation activity was screened. The chemical constituents were isolated by polyamide, silica gel and Sephadex G-Sepharose chromatography purification,and their structures were identified by NMR spectroscopy and other analyses. A total of 10 compounds were obtained and identified as follows: 3-(2-furan)-1-(2-hydroxy-4-methoxy-phenyl)-2-propylene ketone (1), 2-(2,5-hydroxy-4-methyl phenyl) propionate ethyl ester (2), methyl tetradec-5-enoate (3), 1,4-diethylcyclohexane (4), catechol (5), methyl-4-hydroxybenzoate (6), 3-hydroxy-2-methyl-4-pyrone (7), 3,8-dihydroxy-2-metyl-chromone (8), 3β-hydroxy-olean-12-en (9), 1-monolinolein (10). Among them, compounds 1 and 2 were new natural products, and 3–10 were isolated from the Cortex Moutan charcoal for the first time. The potential coagulation activities of compounds were evaluated, and compounds 2, 9 and 10had strong hemostatic effects. While compounds 1 and 8 could significantly activate blood circulation.     

Effects of ginsenosides from Panax ginseng on cell-to-cell communication function mediated by gap junctions

Gap junctions have been shown or are believed to be involved in the pathogenesis of many inherited and acquired human diseases. Agents that regulate the gap junction-mediated intercellular communication (GJIC) function may facilitate prevention and treatment of GJIC-involved diseases. In the present study we examined the effects of 27 ginsenosides isolated from Panax ginseng on GJIC. The results show that compounds 1 (oleanolic acid), 2 (ginsenoside-R0), 3 (ginsenoside-Rb1), 5 (ginsenoside-Rb2), 7 (ginsenoside-Rd), 8 (ginsenoside-Rg3), 12 (panaxadial), 13 (notoginsenoside-R4), 17 [ginsenoside-Rg2 (20S)], 18 (ginsenoside-Rf), and 26 (ginsenoside-F3) did not obviously affect GJIC, whereas compounds 4 (ginsenoside-Rc), 6 (ginsenoside-Rb3), 9 (ginsenoside-Rd2), 10 (notoginsenoside-Fe), 11 (ginsenoside-Rh2),14 (ginsenoside-Ra1), 15 (ginsenoside-Re), 16 [ginsenoside-Rg2 (20R)], 19 (ginsenoside-Ia), 20 [ginsenoside-Rh1 (20S)], 21 [ginsenoside-Rh1 (20R)], 22 (ginsenoside-F1), 23 (protopanaxatriol), 24 (panaxatriol), 25 (ginsenoside-Rg1), and 27 (chikusetsaponin-L8) induced GJIC reductions at various degrees. Compounds 2, 7, and 8 protected against the tyrosine phosphatase inhibitor vanadate-induced GJIC reduction, while compounds 1, 5, 7, and 17 inhibited the cytokine interleukin 1 alpha (IL-1alpha)-induced reduction in GJIC. Nevertheless, no compounds protected against the protein kinase C (PKC) activator 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced GJIC inhibition. On the other hand, GJIC reductions induced by compounds 6, 9,10, 20, 21, 22, 24, and 25 were inhibited by the tyrosine kinase (TK) inhibitor genistein, while GJIC reductions induced by compounds 6, 9, 14, 16, 19, 21, and 24 were attenuated in the presence of the PKC inhibitor calphostin C. However, GJIC reductions induced by compounds 4, 23, and 27 were not inhibited either by genistein or by calphostin C. These data indicate that various mechanisms are responsible for effects of ginsenosides on GJIC.     

海洋放线菌KSC2-1次级代谢产物化学成分的分离与鉴定

目的研究海洋放线菌KSC2-1次级代谢产物,以期得到有活性的先导化合物。方法利用硅胶柱色谱,凝胶柱色谱(Sephadex LH-20),制备高效液相色谱(PRE-HPLC)等手段进行分离纯化,通过理化性质和光谱数据对化合物进行了结构鉴定。结果从海洋放线菌KSC2-1的发酵液的正丁醇萃取物中分离得到10个化合物,分别鉴定为:3-(α-羟丙酰基)-1H-吲哚(3-(α-hydroxypropionyl)-1H-indole,1)、3-乙酰基-1H-吲哚(3-acetyl-1H-indole,2)、1H-吲哚-3-醛(1H-indole-3-carbaldehyde,3)、1H-吲哚-3-羧酸(1H-indole-3-carboxylic acid,4)、2-(1H-吲哚-3-基)乙醇(2-(1H-indol-3-y1)eth-anol,5)、3-乙基-3-羟基-1-甲基吲哚啉-2-酮(3-ethyl-3-hydroxy-1-methylindolin-2-one,6)、2-羟基-1-(4-羟苯基)乙酮(2-hydroxy-1-(4-hydroxyphenyl)ethanone,7)、4-羟基苯乙醇(4-(2-hydroxyethyl)phenol,8)、胸腺嘧啶脱氧核糖核苷(thymine nucleoside deoxyribose,9)、尿嘧啶核糖核苷(uracil nu-cleoside,10)。结论化合物1-10均为首次从海洋放线菌KSC2-1次级代谢产物中分离得到。     

Characterization of odor-active compounds in cooked meat of farmed obscure puffer (Takifugu obscurus) using gas chromatography–mass spectrometry–olfactometry

The volatile and odor-active compounds in cooked meat of farmed obscure puffer (Takifugu obscurus) were analyzed by gas chromatography–mass spectrometry–olfactometry (GC–MS–O). The volatile compounds were extracted by the simultaneous distillation–extraction (SDE) method, then separated and identified by GC–MS. Odor-active compounds in the SDE extract were characterized by GC–MS–O. A total of 68 volatile compounds were found, including 23 aldehydes, 10 alcohols, nine ketones, 17 N- or S-containing compounds and aromatics, three acids, three alkanes, and three esters. Of these, 31 odor-active compounds were detected and identified. Trimethylamine (fishy), octanal (grassy, leafy, green), (E)-2-octenal (roast, fatty), 1-octen-3-ol (fishy, fatty, mushroom, grassy), 2-ethyl-1-hexanethiol (cooked fish), (E,E)-2,4-octadienal (cooked meat, sweet), 2-acetylthiazole (meaty, roast, nutty, sulfur), 2-acetylpyrrole (nutty, walnut, bread) were identified as the key odorants in the cooked meat of farmed obscure puffer based on posterior intensity and time-intensity methods.     

滨蒿的化学成分

目的进一步研究菊科植物滨蒿(Artemisia scoparia)中的化学成分。方法采用硅胶柱色谱法、中低压柱色谱法、ODS柱色谱法、Sephadex LH 20柱色谱法以及高效液色谱法进行分离和纯化,并依据理化性质和波谱解析鉴定其化学结构。结果从植物滨蒿地上部分的体积分数为60%乙醇提取物(420 g)中分得6个化合物,分别鉴定为3羟基二十二酸2(5乙酰基2,3二氢苯并呋喃2基)丙酯(1)、2′(3′甲氧基3甲基丁烯基)对甲氧基乙酰苯(2)、5,8二甲氧基6,7亚甲二氧基香豆素(3)、8甲氧基6,7亚甲二氧基香豆素(4)、6去甲氧基茵陈色原酮(5)、2,4二羟基6甲氧基乙酰苯(6)。结论化合物1~6均为首次从该植物中得到,其中化合物1、2为新化合物。     

柚皮中的化学成分

从芸香科植物柚Citrusgrandis的果皮中分离得到了 5个化合物 .经光谱数据的分析 ,分别鉴定为木栓酮 (1)、5 羟甲基糠醛 (2 )、柠檬苦素 (3)、闹米林 (4 )及胡萝卜苷 (5 ) .其中 1和 2为首次从该种植物中分离得到的已知成分     

Isoform selective inhibition and inactivation of human cytochrome P450s by methylenedioxyphenyl compounds

1. A series of methylenedioxyphenyl compounds were evaluated for their inhibitory and inactivation effects on nine human cytochrome P450 (CYP) activities using microsomes from human B-lymphoblast cells expressing specific human CYP isoforms. 2. Methylenedioxyphenyl compounds which possess a bulky structure such as 1,4-benzothiazine showed substantial inhibition of S-warfarin 7-hydroxylation catalysed by CYP2C9, S-mephenytoin 4'-hydroxylation by CYP2C19, bufuralol 1'-hydroxylation by CYP2D6, and testosterone 6beta-hydroxylation by CYP3A4. Regarding ethoxyresorufin O-deethylation catalysed by CYP1A1 and benzyloxyresorufin O-dealkylation by CYP2B6, the subtle change of a substitution of the 1,4-benzothiazine structure affected the inhibition selectivity. Ethoxyresorufin O-deethylation by CYP1A2, coumarin 7-hydroxylation by CYP2A6, and chlorzoxazone 6-hydroxylation by CYP2E1 were not inhibited by almost any of the methylenedioxyphenyl compounds. The inhibitory effects of methylenedioxyphenyl compounds that possess a short chain amino group on the human CYP isoforms were not significant. 3. The methylenedioxyphenyl compounds inactivated CYP1A1 (k(inact) = 0.034 min(-1) and K(i) = 0.81 microM), CYP2C9 (k(inact) = 0.041 and 0.042 min(-1) and K(i) = 0.56 and 0.15 microM), CYP2D6 (k(inact) = 0.044-0.339 min(-1) and K(i) = 0.21-19.88 microM), and CYP3A4 (k(inact) = 0.076-0.251 min(-1) and K(i) = 0.25-0.69 microM). These results suggested that the methylenedioxyphenyl compounds investigated in this study would be potent mechanism-based inactivators of these human CYP isoforms. In contrast, CYP2B6 and CYP2C19 were not inactivated. 4. The present study suggested that the selectivity of inhibition or inactivation of human CYP isoforms by methylenedioxyphenyl compounds may vary according to the structure of the side chain.     

知母脂溶性化学成分的分离与鉴定

目的研究知母的化学成分。方法利用各种色谱法进行分离,根据理化性质和波谱分析鉴定化合物结构。结果从知母的体积分数为70%的乙醇提取物中分离得到6个已知成分,分别鉴定为十七烷酸-1-甘油酯(2,3-dihydroxypropyl heptadecoate,1)、大黄酚(chrysophanol,2)、大黄素(emodin,3)、构树宁B(broussonin B,4)、单甲基-顺-扁柏树脂酚[monomethyl-Z-(-)hinokiresinol,5]、顺-扁柏树脂酚[Z-(-)hinokiresinol,6]。结论化合物1-4为首次从该属植物中分离得到。     

Iridoids from the roots of Valeriana jatamansi

Two new iridoids, jatamanvaltrates N (1) and O (2), together with four known compounds (3-6), were isolated from the roots of Valeriana jatamansi. Their structures and relative configurations were elucidated by spectroscopic methods (IR, ESI-MS, HR-ESI-MS, 1D, and 2D NMR) and by comparison of their NMR spectral data with those of related compounds. All the isolated compounds were evaluated for their neuroprotective effects, and only compound 1 showed weak neuroprotective activities.     

A convenient synthesis by microwave heating and pharmacological evaluation of novel benzoyltriazole and saccharine derivatives as 5-HT(1A) receptor ligands.

A series of novel 1,2,3-4-benzoyltriazole and saccharine derivatives were designed and synthesized by microwave heating. They were evaluated on a battery of receptors, including serotonin 5-HT(1A,) 5-HT(2A) and 5-HT(2C), and the most interesting compounds were further evaluated on dopaminergic D(1), D(2) and adrenergic alpha(1), alpha(2) receptors. Conventional and microwave heating of the reactions were compared. Synthesis by microwave heating gave the desired compounds in better yields than those obtained by conventional heating. The overall times for the syntheses were considerably reduced. All compounds displayed moderate affinity for 5-HT(1A) receptor. The most interesting compound 33 showed a high affinity (K(i)=93 nM) which was combined with no affinity on the other receptors considered.     

红厚壳茎叶的化学成分

目的研究红厚壳(Calophyllum inophyllumL.)茎叶的化学成分。方法用硅胶、SephadexLH-20柱色谱等方法进行分离纯化,根据理化性质及光谱数据确定化合物的结构。结果分离得到10个化合物,分别鉴定为蒲公英甾醇(taraxasterol,1)、豆甾醇(stigmasterol,2)c、lovane-2β,9-αdi-ol(3)、12-methoxyinophyllum D(4)、calophyllic acid和isocalophyllic acid(5)i、nophyllum D(6)、calo-phyllolide(7)、莽草酸(shikimic acid,8)、没食子酸(gallic acid,9)、原儿茶酸(protocatechuic acid,10)。结论化合物1和3为首次从该属植物中分离得到,化合物8为首次从该植物中分离得到。     

黄腊果果皮化学成分的分离与鉴定

目的研究黄腊果果皮的化学成分。方法采用反复硅胶柱色谱法、Sephadex LH-20柱色谱法、重结晶和HPLC等方法进行分离纯化,并通过NMR技术鉴定其化学结构。结果从黄腊果中分离得到8个化合物,分别鉴定为:3-羟基-2-甲基-4-吡喃酮(3-hydroxy-2-methyl-4-pyrone,1)、芥子醛(sinapaldehyde,2)、2-甲基-4-吡喃酮-3-O-β-D-吡喃葡萄糖苷(2-methyl-4-pyrone-3-O-β-D-glucopyr-anoside,3)、3,5-二甲氧基-4-羟基苯甲酸-7-O-β-D-葡萄糖苷(3,5-dimethoxyl-4-hydroxybenzoic acid-7-O-β-D-glucopyranoside,4)、胡萝卜苷(daucosterol,5)、β-谷甾醇(sitosterol,6)、3-O-α-L-吡喃鼠李糖-(1→2)-α-L-吡喃阿拉伯糖-30-降甲基齐墩果-12,20(29)-二烯-28-羧酸(3-O-α-Lrhamnopyrano-syl-(1→2)-α-L-arabinopyranosyl-30-norolean-12,20(29)-dien-28-oic acid,7)、3-O-β-D-吡喃葡萄糖-(1→3)-α-L-吡喃鼠李糖-(1→2)-α-L-吡喃阿拉伯糖-30-降甲基齐墩果-12,20(29)-二烯-28-羧酸(3-O-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-D-glucopyranosyl-(1→3)-α-L-arabi-nopyranosyl-30-norolean-12,20(29)-dien-28-oic acid,8)。结论化合物1-4为首次从木通科植物中分离得到,化合物6-8为首次从黄腊果中分离得到。     

Chemical constituents from the stem bark of Trewia nudiflora L. and their antioxidant activities

Three new compounds, namely, (+)-dihydrodehydrodiconiferyl alcohol 4- O- beta-(6'- O-galloyl)-glucopyranoside ( 1), 4,4'- O-dimethylellagic acid 3-(2'- O-acetyl)- alpha-rhamnopyranoside ( 2), and ethyl O- beta-(6'-galloyl)-glucopyranoside ( 3), together with eleven known ones, were isolated from the stem bark of Trewia nudiflora. Their structures were elucidated by means of 1D, 2 D NMR and HR-MS analyses. The antioxidant activities of these compounds were evaluated with the DPPH radical-scavenging assay. Compound 1 showed significant antioxidant activity. In addition, compounds 1, 2 and 3 rescued the H (2)O (2)-induced PC12 cell death at 0.4 microM in the MTT assay.     

Three new polyphenols from the rhizomes of Arachniodes exilis

Three new polyphenols, araspidin BB (1), arachniodesin A (2) and arachniodesin B (3), together with two known compounds, epicatechin (4) and procyanidin B-2 (5), were isolated from the rhizomes of Arachniodes exilis. The structures of three new compounds were elucidated as 5-methyl-methylene-bis-phlorobutyrophenone (1), 4beta-ethoxycarbonylmethylepicatechin (2) and epicatechin-(4beta --> 8)-4beta-ethoxycarbonylmethylepicatechin (3), on the basis of their spectral analysis and by comparing them with the related model compounds. Compounds 4 and 5 were obtained from the title plant for the first time.     

元宝草的化学成分研究

目的：对元宝草的化学成分进行研究。方法：利用硅胶、聚酰胺、Sephadex LH-20和大孔树脂柱层析对化合物进行分离，并利用光谱技术和理化性质进行结构鉴定。结果：从元宝草乙醇提取液的二氯甲烷萃取物中分离得到5个化合物，鉴定为二十八烷醇（octacosanol，化合物1）、三十烷酸（triacontanoic acid，化合物2）、豆甾醇（stigmasterol，化合物3）、苯甲酸（benzoic acid，化合物4）和1-羟基-7-甲氧基咕吨酮（1-hydroxy-7-methoxy-xanthone，化合物5）；从乙酸乙酯萃取物中分离得到3个化合物，鉴定为没食子酸（3，4，5-trihydroxy-benzoic acid，化合物6）、槲皮素（quercetin，化合物7）和1，3，6，7-四羟基咕吨酮（1，3，6，7-tetrahydroxy-xanthone，化合物8）。结论：除化合物7以外，其余7个化合物均为首次从元宝草中分离得到。     

海洋来源真菌草酸青霉(Penicillium oxalicum)次级代谢产物的分离与鉴定

目的研究海洋来源真菌草酸青霉(Penicillium oxalicum)的次级代谢产物。方法采用重结晶、硅胶柱色谱、Sephadex LH-20柱色谱、开放ODS柱色谱等方法进行分离纯化;根据理化性质及光谱数据确定化合物的结构。结果分离得到10个化合物,分别鉴定为N-acetyl-hydrazinobenzoic acid(1)、N-[2-cis-(4-hydroxyphenyl)ethenyl]formamide(2)、p-hydroxyphenylacetamide(3)、penipanoid A(4)、penipanoid C(5)、2-(4-hydroxybenzyl)quinazolin-4(3H)-one(6)、oxaline(7)、meleagrin(8)、(3R,4R)-3,4,8-trihydroxy-3,4-dihydro-1(2H)-naphthalenone(9)和(3R,4R)-3,4,6,8-tetrahydroxy-3,4-dihydro-1(2H)-naphthalenone(10)。结论化合物1为新天然产物,化合物9、10为首次从青霉属真菌中分离得到。     

Chemical constituents of the aerial parts of Glycyrrhiza uralensis and their inhibitory activities against PTP1B and α-glucosidase

In the present study, a total of 11 compounds were isolated from the aerial parts of Glycyrrhiza uralensis, including two new compounds, glycyuralin Q (1) and glycyuralin R (2), and nine known compounds, including licoriphenone (3), orobol (4), trifoliol (5), 7,2′,4′-trihydroxy-5-methoxy-3-arylcoumarin (6), 11-hydroxy-9(Z),12(Z)-octadecadienoic acid (7), 11-hydroxy-9(E),12(E)-octadecadienoic acid (8), licoricone (9), glycyrin (10), and 2′-hydroxyformononetin (11). Structures of the new compounds were identified by 1D, 2D NMR and HR-MS data analyses. Compounds 1, 2 and 10 showed potent inhibitory activities against PTP1B, with IC₅₀ values of 1.43, 4.71 and 3.79 μM, respectively. Compounds 2, 4 and 10 inhibited α-glucosidase with IC₅₀ values of 13.61, 11.13 and 17.48 μM, respectively.     

Eremophilane sesquiterpenes from Cacalia ainsliaeflora

Chemical investigation of Cacalia ainsliaeflora afforded four new eremophilane sesquiterpenes (1 - 3, 5) and a known sesquiterpene (4), which were identified as 3 beta-angeloyloxy-8 alpha-hydroxy-6 beta-methoxyeremophil-7(11),9(10)-dien-8,12-olide (1), 3 beta-angeloyloxy-6 beta,8 alpha-dihydroxyeremophil-7(11),9(10)-dien-8,12-olide (2), 3 beta-angeloyloxy-8 alpha-hydroxy-6 beta-ethoxyeremophil-7(11),9(10)-dien-8,12-olide (3), 3 beta-angeloyloxy-8-oxo-eremphila-6,9-dien-12-oic acid (4), and 3,8-oxo-eremophila-6,9-dien-12-oic acid (5) respectively. These compounds were assayed against Escherichia coli, Staphylococcus aureus and Bacillus subtilis, and compounds 1, 2, 4 and 5 showed weak antibacterial activity. The structures of the compounds were established by 1D and 2D NMR experiments.     

Two new compounds from Senecio cannabifolius

Chemical investigation of the water extracts from the Senecio cannabifolius Less. led us to find two new compounds (1 and 2), along with 12 known compounds (3-14). The two new compounds were determined as (E, 4R)-4-hydroxy-4,5,5-trimethyl-3-(3-oxobut-1-enyl)cyclohex-2-enone (1) and (E)-4-((1S, 3R, 4R)-1-hydroxy-4,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl)but-1-en-3-o-ne (2), respectively. The structures of other compounds were elucidated by extensive analysis of spectral data and in comparison with the literature values. Compounds 1 and 2 were evaluated for inhibitory activity against lipopolysaccharide-induced NO production in RAW 264.7 macrophages, and compound 1 showed potent inhibitory activity with IC(50) value of 30.65?μM.     

真菌Penicillium sp. DT-F27次级代谢产物及其活性研究

摘要：目的 一株海洋来源真菌Penicillium sp. DT-F27次级代谢产物及其抗肿瘤活性的研究。方法 采用硅胶柱色谱、反相高效液相制备色谱等方法,对该真菌发酵产物的乙酸乙酯提取物进行分离纯化;采用波普解析方法对化合物的结构进行鉴定;采用MTT法测定化合物对人前列腺癌PC-3细胞的抗肿瘤作用。结果 从真菌Penicillium sp. DT-F27的发酵物中分离得到15个化合物,分别为麦角甾醇（1）,dehydrocyclopeptine（2）,3-O-methylviridicatin（3）,verrucofortine（4）,cyclopenin（5）,cyclo(dehydroala-L-Leu)（6）,cyclopenol（7）,4-hydroxy-2-methoxy acetanilide（8）,trans-(3RS,4RS)-3,4-dihydro-3,4,8-trihydroxynaphthalen-1(2H)-one（9）,cyclo(D-Pro-D-Val)（10）,brevianamide F（11）,cyclo(L-Pro-L-Val)（12）,anacine（13）,cyclo(L-Orn-L-Tyr-L-Orn-L-Ala)（14）,cyclo(L-Pro-L-Tyr)（15）。结论 从真菌Penicillium sp. DT-F27的次级代谢产物中分离15化合物,其中麦角甾醇（1）和3-O-methylviridicatin（3）具有较强的抗肿瘤活性,抑制率分别为45.6%和34.8%。