锦灯笼中酸浆苦素类化学成分的研究

目的 研究锦灯笼95％乙醇提取物的石油醚、氯仿、醋酸乙酯萃取部位中化学成分.方法 利用硅胶柱色谱、反相ODS柱色谱、制备液相色谱等方法进行分离、纯化,根据化合物的理化性质和光谱数据鉴定其结构.结果 分离得到了7个化合物,经结构鉴定分别为酸浆苦素A(1)、酸浆苦素D(2)、酸浆苦素L(3)、酸浆苦素O(4)、木犀草素(5)、木犀草素-7-O-β-D-葡萄糖苷(6)和胡萝卜苷(7).结论 共分离得到7个化合物,并对酸浆苦素类化合物1～4进行了较为详细的解析和更为全面的NMR归属.     

HPLC法同时测定锦灯笼果实中5种成分及等级鉴定

目的建立HPLC同时定量测定锦灯笼果实中木犀草苷、木犀草素、酸浆苦素A、酸浆苦素P和酸浆苦素O的方法并选择分级标准的测试成分。方法利用Agilent TC-18(4.6 mm×150 mm,5μm)色谱柱分离,乙腈-0.2%磷酸进行梯度洗脱,体积流量为1.0 mL/min,切换波长,0～24 min(350 nm),24～37 min(220 nm)。结果木犀草苷、木犀草素、酸浆苦素A、酸浆苦素P、酸浆苦素O分别在0.052～0.26μg/mL(r=0.999 5),0.04～0.2μg/mL(r=0.999 5),0.048～0.24μg/mL(r=0.999 6),0.04～0.2μg/mL(r=0.999 7),和0.36～1.8μg/mL(r=0.999 7)范围内线性关系良好,平均回收率大于98%。结论由于木犀草素、酸浆苦素P和O含有量过低,故以木犀草苷和酸浆苦素A为分级标准的测试成分是合理的。     

酸浆化学成分及酸浆苦素G的结构订正

目的:对吉林产酸浆的化学成分进行研究。方法:运用层析手段和波谱方法分离并鉴定了8个化合物。结果:对酸浆苦素G(physalin G,1)的结构进行了订正并对其核磁数据进行了正确归属,其余化合物分别为酸浆苦素A(physalin A,2),酸浆苦素B(physalin B,3),酸浆苦素D(physalin D,4),酸浆苦素P(physalin P,5),金圣草黄素(chrysoeriol,6),马尾藻甾醇(saringosterol,7),丁香酸(syringic acid,8)。结论:化合物1的6位构型订正为R,化合物6~8为首次从该属中分离得到。     

细皱香薷叶的化学成分研究

目的 研究细皱香薷Elsholtzia rugulosa叶的化学成分.方法 采用柱色谱法进行分离和纯化,通过波谱分析鉴定结构.结果 从乙醇提取物中分离得到了12个化合物,鉴定结构分别为洋芹索-7-O-β-D-葡萄糖苷(Ⅰ)、木犀草素-7-O-β-D-葡萄糖苷(Ⅱ)、刺槐素-7-O-β-D-葡萄糖苷(Ⅲ)、木犀草素-7-O-(6"-乙酰基)-β-D-葡萄糖苷(Ⅳ)、苯甲醇-β-D-葡萄糖苷(Ⅴ)、prunasin(Ⅵ)、β-谷甾醇(Ⅶ)、桦木酸(Ⅷ)、2α-羟基乌苏酸(Ⅸ)、2α-羟基齐墩果酸(Ⅹ)、洋芹素(Ⅺ)和木犀草素(Ⅻ).结论 化合物Ⅰ、Ⅲ、Ⅳ、Ⅸ和Ⅹ为首次从该种植物中分离得到.     

小酸浆中甾体类化学成分研究

目的研究小酸浆Physalis minima全草中甾体类化学成分。方法利用硅胶柱色谱、Sephadex LH-20凝胶柱色谱、中压ODS柱色谱及半制备高效液相色谱等方法分离纯化,根据理化常数和核磁共振谱、质谱等光谱数据鉴定化合物结构。结果从小酸浆全草的乙醇提取物中分离得到7个甾体类化学成分,其中酸浆苦素类化合物2个,分别鉴定为16,24-cyclo-13,14-secoergost-2-ene-18,26-dioicacid-14:17,14:27-diepoxy-5α,6β,13α,20α,22β,25β-hexahydroxy-1,15-dioxo-γ-lactone-δ-lactone(1)、酸浆苦素D(2);醉茄内酯类化合物5个,分别鉴定为physagulin L(3)、physagulin M(4)、physaminimin F(5)、physagulin K(6)、withagulatin A(7)。结论化合物1为新化合物,命名为25-羟基酸浆苦素D;化合物3、4、7为首次从该植物中分离得到。     

苦蘵的化学成分及其细胞毒活性研究

目的对酸浆属植物苦蘵Physalis angulata的全草进行化学成分及肿瘤细胞毒活性研究。方法运用硅胶、Sephadex LH-20凝胶等柱色谱和HPLC等方法,并结合液质联用分析技术,采用活性跟踪的方法从苦蘵全草中分离细胞毒活性成分。根据理化常数测定和各种谱学(1D和2D NMR、MS)数据分析等鉴定化合物结构,MTT法测定化合物的细胞毒活性。结果从苦蘵全草的95%乙醇水提取物中共分离得到12个化合物,分别鉴定为酸浆苦素A(1)、酸浆苦素B(2)、酸浆苦素C(3)、酸浆苦素D(4)、酸浆苦素F(5)、酸浆苦素H(6)、酸浆苦素I(7)、5α-乙氧基-6β-羟基-5,6-二氢酸浆苦素B(8)、酸浆苦素O(9)、β-谷甾醇(10)、2-羧基苯胺羰酸甲酯(11)、2-(乙酰胺基)-苯甲酸(12)。结论化合物11为新天然产物,化合物1~3、9为首次从苦蘵中分得,化合物1~9为酸浆苦素类(physalins)甾体化合物。细胞毒活性实验结果显示,化合物1~9对肺癌细胞株A549均具有较强的增殖抑制活性,其中以2、3、6、8的抑制活性最为显著,其IC50值为1.9~20.2μmol/L。     

蒌蒿叶的黄酮类成分研究

目的 为阐明蒌蒿的有效成分,对其叶进行了系统的化学成分研究.方法 乙醇提取、石油醚脱脂,大孔树脂、硅胶柱色谱分离.结果 分离得到12个黄酮类化合物,经光谱方法 分别鉴定为雷杜辛黄酮醇(retusine,Ⅰ)、阿亚黄素(ayanin,Ⅱ)、木犀草素-4',7-二甲醚(4',7-dimethylluteolin,Ⅲ)、柯伊利素(chrysoerid,Ⅳ)、芹菜素(apigenin,Ⅴ)、木犀草素(luteolin,Ⅵ)、3',4',5,7-四羟基二氢黄酮(3',4',5,7-tetrahydroxyflavanone,Ⅶ)、山柰素(kaempferol,Ⅷ)、槲皮素(quercetin,Ⅸ)、芹菜素-7-O-β-D-葡萄糖苷(apigenin-7-O-β-D-glucoside,Ⅹ)、木犀草素-7-O-β-D-葡萄糖苷(luteolin-7-O-β-D-glucoside,Ⅺ)、芦丁(rutin,Ⅻ).结论 其中化合物Ⅰ、Ⅱ、Ⅵ～Ⅹ为首次从该植物中分离得到.Fe2 半胱氨酸诱发肝微粒体脂质过氧化方法 测定单体化合物的抗氧化活性强度为Ⅸ(64.73%)＞Ⅵ(64.18%)＞Ⅶ(63.75%)＞Ⅷ(60.18%)＞Ⅺ(59.03%)＞Ⅻ(47.09%).初步分析黄酮化合物的抗氧化活性的构效关系如下:分子中的酚羟基的数目和可以形成氢键的酚羟基数目与分子的抗氧化活性正相关.     

毛酸浆宿萼的化学成分研究

目的研究毛酸浆Physalis pubescensL.干燥宿萼的化学成分。方法利用硅胶柱色谱法、Sephadex LH-20凝胶柱色谱法、中压柱色谱及半制备高效液相色谱等方法分离纯化;通过核磁共振谱、质谱等光谱数据鉴定化合物结构。结果 分离得到10个化合物,分别鉴定为β-谷甾醇(1)、7,3′,4′-三甲基槲皮素(2)、5,4′-二羟基-3,7-二甲氧基黄酮(3)、山柰酚(4)、3-甲氧基-4-羟基苯甲酸(5)、2-羟甲基-5-羟基-γ-吡喃酮(6)、槲皮素(7)、商陆素(8)、木犀草素(9)、胡萝卜苷(10)。结论化合物2~6为首次从酸浆属植物中分离得到。     

锦灯笼化学成分的研究(Ⅱ)

前文[1]曾报道从通化产茄科植物锦灯笼Physalis alkekengi L.var.francheti(Mast.)Makino中分离鉴定了4种化合物即酸浆苦素A,B,R及豆甾醇,我们又对前文的氯仿萃取部分及正丁醇部分进行硅胶柱层析,分离得到了3个化合物,分别鉴定为酸浆苦素L(Ⅰ)、M(Ⅱ)及阿魏酸(Ⅲ).其中阿魏酸为首次从该植物中分得.     

蒙药小白蒿化学成分的研究

目的 研究小白蒿Artemisia frigida氯仿和醋酸乙酯提取物中的化学成分.方法 采用硅胶和LH-20柱色谱法进行分离,运用各种波谱法和标准品对照法鉴定分离得到的化合物.结果 鉴定了13个化合物,分别为槲皮素(Ⅰ)、木犀草素(Ⅱ)、5,7,3'-三羟基-4'-甲氧基黄酮(Ⅲ)、5,7,3'-三羟基-6,4'-二甲氧基黄酮(Ⅳ)、5,3'-二羟基-6,7,4'-三甲氧基黄酮(Ⅴ)、5,3'-二羟基-3,6,7,4'-四甲氧基黄酮(Ⅵ)、对甲基苯酚(Ⅶ)、7-羟基香豆素(Ⅷ)、7-甲氧基香豆素(Ⅸ)、咖啡酸(Ⅹ)、β-谷甾醇(Ⅺ)、6,7-二羟基香豆素(Ⅻ)、7-羟基-5,6-二甲氧基香豆素(Ⅻ).结论 所有化合物均为首次从该植物中分得.     

Steroids and flavonoids from Physalis alkekengi var. franchetii and their inhibitory effects on nitric oxide production

Four new steroidal compounds possessing a rare 13,14-seco-16,24-cycloergostane skeleton, physalin Y ( 1), physalin Z ( 2), physalin I ( 6), and physalin II ( 7), were isolated from the 80% EtOH extract of calyces from Physalis alkekengi var. franchetii together with 11 known steroids ( 3- 5 and 8- 15) and eight flavonoids ( 16- 23). The structures of the new compounds were elucidated primarily on the basis of 1D and 2D NMR and mass spectroscopic studies. The relative configuration of the 3-OH group of 3, 4, and 5 was also established or re-established. The inhibitory effects of compounds 1- 23 on nitric oxide production in lipopolysaccaride-activated macrophages were evaluated.     

Isolation, structures, and structure - cytotoxic activity relationships of withanolides and physalins from Physalis angulata

Phytochemical investigation of Physalis angulata was initiated following primary biological screening. Fractionation of CHCl3 and n-BuOH solubles of the MeOH extract from the whole plant was guided by in vitro cytotoxic activity assay using cultured HONE-1 and NUGC cells and led to the isolation of seven new withanolides, withangulatins B-H (1-7), and a new minor physalin, physalin W (8), along with 14 known compounds, including physaprun A, withaphysanolide, dihydrowithanolide E, physanolide A, withaphysalin A, and physalins B, D, F, G, I, J, T, U, and V. New compounds (1-8) were fully characterized by a combination of spectroscopic methods (1D and 2D NMR and MS) and the relative stereochemical assignments based on NOESY correlations and analysis of coupling constants. Biological evaluation of these compounds against a panel of human cancer cell lines showed broad cytotoxic activity. Withangulatin B (1) and physalins D (10) and F (11) displayed potent cytotoxic activity against a panel of human cancer cell lines with EC50 values ranging from 0.2 to 1.6 microg/mL. Structure-activity relationship analysis indicated that withanolides and physalins with 4beta-hydroxy-2-en-1-one and 5beta,6beta-epoxy moieties are potential cytotoxic agents.     

百两金根的化学成分研究

目的 百两金为传统苗药,其化学成分的有关研究报道较少,本研究目的在于研究百两金的化学成分。方法 将百两金干燥根体积分数70%乙醇提取物利用硅胶、重结晶、ODS及制备/半制备HPLC进行分离纯化,根据理化性质及波谱数据对所得化合物结构进行鉴定。结果 从百两金根中得到了20个化合物。分别为岩白菜素 (1)、甲基岩白菜素 (2)、11-O-没食子酰岩白菜素 (3)、 syringin (4)、(+)-syringaresinol-O-β-D-glucopyranoside (5)、(-)-(7R,8S,7′R,8′S)-4,9,4′,9′-tetrahydroxy-3,3′-dimethoxy-7,7′-epoxylignan-9-O-β-D-xylopyranoside (6)、saracoside (7)、isolariciresinol-4-O-β-D-glucopyranoside (8)、(7S,8R)-urolignoside (9)、staphylionoside D (10)、蚱蜢酮 (11)、l-borneol 6-O-β-D-aiosyl-β-D-glucoside (12)、(+)-angelicoidenol 2-O-β-D-glucopyranoside (13)、牡荆素-2″-O-鼠李糖苷 (14)、根皮苷 (15)、phenethyl alcohol β-D-(2′-O-β-D-glucopyranosyl)glucopyranoside (16)、phenylethyl-β-D-glucopyranoside (17)、菖蒲碱C (18)、己内酰胺 (19)、蔗糖 (20)。结论 其中化合物5~19为首次从紫金牛科植物中分离得到,化合物4为首次从紫金牛属植物中分离得到,化合物2和3为首次从该植物中分离得到。其中化合物6是自国内学者2013年从岭南杜鹃分离得到以来第二次被分离得到。     

Antimycobacterial physalins from Physalis angulata L. (Solanaceae)

Crude extracts and fractions from aerial parts of Physalis angulata have been bioassayed for antimycobacterial activity. Fraction A1-29-12 containing physalins B, F and D exhibited a minimum inhibitory concentration value (MIC) against Mycobacterium tuberculosis H(37)Rv strain of 32 microg/mL. Purified physalin B and physalin D were also tested showing MIC values against Mycobacterium tuberculosis H(37)Rv strain of > 128 microg/mL and 32 microg/mL respectively, suggesting that physalin D plays a relevant role in the antimycobacterial activity displayed. Structural elucidation of both physalins D and B was based on detailed (13)C and (1)H NMR spectral analysis with the aid of 2D-correlation spectroscopy ((1)H-(1)H, COSY, HSQC and HMBC). The assignment of the (13)C chemical shift for physalin D is reported here for the first time.     

皮孔葱臭木化学成分的研究

目的对皮孔葱臭木Dysoxylum lenticellatum茎干的化学成分及其细胞毒活性进行研究。方法利用正相硅胶、RP-18柱色谱、葡聚糖凝胶Sephadex LH-20等手段进行分离纯化,根据波谱数据鉴定化合物的结构,采用MTT法进行细胞毒活性测定。结果分离鉴定了12个化合物,分别为β-谷甾醇(1)、豆甾醇(2)、3-oxo-24,25,26,27-tetranortirucall-7-ene-23(21)-lactone(3)、3α-hydroxy-24,25,26,27-tetranortirucall-7-ene-23(21)-lactone(4)、laxiracemosin H(5)、laxiracemosin B(6)、24,25-epoxy-tirucall-7-ene-3,23-dione(7)、丁酰鲸鱼醇(8)、齐墩果酸(9)、蒲公英赛酮(10)、蒲公英赛醇(11)和8-hydroxy-6-methoxy-3-pentylisocoumarin(12)。结论 12个化合物均为首次从该种植物中分离得到,化合物8、10～12为首次从该属植物中分离得到,化合物5、6是甘遂烷型生物碱,化合物3具有明显体外肿瘤细胞生长抑制活性。     

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??OBJECTIVE To investigate the chemical components of the root of Actinidia chinensis. METHODS The compounds were separated and purified by column chromatography and their structures were elucidated by spectroscopic methods. RESULTS Ten compounds were obtained from the aqueous extracts of the root of Actinidia chinensis. The structures were determined as chlorogenic acid(1), crptochlorogenic acid(2), neochlorogenic acid(3), 3-O-coumaroylquinic acid(4), caffeic acid(5), trans-p-hydroxycinnamic acid(6), esculin(7), scopoletin(8), scopolin(9), and isofraxoside(10). CONCLUSION Compounds 1-4, 6, and 8-10 are obtained from genus Actinidia for the first time and compund 5 is isolated from this plant for the first time.
     

土茯苓内生芒果球座菌的次级代谢产物及其抗肿瘤活性研究

目的研究土茯苓内生芒果球座菌Guignardia mangiferae的次级代谢产物及其抗肿瘤活性。方法采用硅胶柱、反相硅胶柱、凝胶柱和制备薄层色谱等色谱技术进行分离纯化,通过现代波谱技术进行结构鉴定;以神经胶质瘤细胞SF-268、乳腺癌细胞MCF-7、大细胞肺癌细胞NCI-H460为供试细胞株,采用SRB法对化合物进行体外抗肿瘤活性研究。结果从土茯苓内生芒果球座菌的100 L液体发酵提取物中分离得到12个化合物,经波谱数据分析鉴定其中10个化合物,分别为15-hydroxyl tricycloalternarene 5b(1)、guignardiaene D(2)、guignardiaene C(3)、guignardone A(4)、guignardone B(5)、3-(4-甲苯氧基)-丙酸(6)、2,4-壬二醇(7)、麦角甾酮(8)、酪醇(9)、对羟基苯甲醛(10)。杂合萜类化合物1～5对SF-268细胞具有选择性的抑制作用,化合物6、7对MCF-7细胞具有选择性的抑制作用。结论化合物6～10均为首次从该属真菌中得到,其中化合物6、7为新的天然产物。     

Physalin A induces apoptosis via p53-Noxa-mediated ROS generation,and autophagy plays a protective role against apoptosis through p38-NF-κB survival pathway in A375-S2 cells

Ethnopharmacological relevance

Physalin A is a bioactive withanolide isolated from natural plant Physalis alkekengi L. var. franchetii (Mast.) Makino, a traditional Chinese herbal medicine named Jindenglong which has long been used for the treatment of cough, sore throat, hepatitis, eczema, dysuria and tumors in China.

Aim of the study

Based on the previous study that physalin A induced cytotoxic effect in human melanoma A375-S2 cells, this study was designed to further illustrate the molecular mechanisms underlying.

Materials and methods

Cell viability was evaluated in A375-S2 cells by MTT assay, and the mechanisms involved in physalin A-induced A375-S2 cell death were investigated by phase contrast microscopy and fluorescence microscopy, siRNA transfection, flow cytometry and western blot analysis.

Results

We demonstrated that physalin A decreased the proportion of viable A375-S2 cells in a time- and dose-dependent manner, and exposure of A375-S2 cells to physalin A led to both apoptosis and autophagy. Moreover, physalin A-induced apoptosis was triggered by activation of p53-Noxa pathway and intracellular reactive oxygen species (ROS) generation. The administration of ROS scavengers NAC and GSH resulted in the complete inhibition of physalin A-induced ROS generation and apoptosis. Application of p53 inhibitor PFT-α or transfection with Noxa-siRNA could also lead to the same results. Autophagy, demonstrated by the punctuate distribution of monodansylcadaverine staining, as well as the change of LC3-II/LC3-I proportion and Beclin 1 activation, played a protective role against apoptosis via up-regulation of the p38-NF-κB survival pathway in A375-S2 cells. Additionally, inhibition of autophagy by the specific autophagic inhibitor 3MA or blocking the p38-NF-κB pathway with p38 inhibitor SB203580 or NF-κB inhibitor PDTC obviously promoted physalin A-induced apoptosis.

Conclusions

Physalin A induced apoptotic cell death via p53-Noxa-mediated ROS generation, and autophagy played a protective role against apoptosis through up-regulating the p38-NF-κB survival pathway in A375-S2 cells. These results stated the possibility that physalin A would be a potential agent for the treatment of melanoma in the future.     

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??OBJECTIVE To study the chemical constituents and their proliferation activity on rat osteoblasts of Semen Sojae Praeparatum. METHODS The compounds were isolated by chromatography on silica gel column,MCI and sephadex LH-20 column. Their structures were elucidated by spectral analysis. The proliferation test was performed by using rat osteoblasts with MTT assays in vitro. RESULTS Twelve compounds were obtained and identified as daidzin(1), daidzein(2),genistein(3), genistin(4), glycitein(5), glycitin(6),apigenin(7), ??-sitosterol(8), stigmasterol(9), campesterol(10), syringaldehyde(11), syringic acid(12), respectively. CONCLUSION Compounds 5-11 are isolated from Semen Sojae Praeparatum for the first time. The five isoflavones show proliferation activity on rat osteoblasts, and aglycones proved to show better activity than glycosides.
     

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??OBJECTIVE To study the generality of the structure-activity relationships(SARs)of 3-deoxylation and 6-deoxylation of the sugar moiety in SGLT2 inhibitors. METHODS Based on the earlier study, 3-deoxycanagliflozin(compound 5), 6-deoxyipragliflozin(compound 6), 6-deoxyempagliflozin(compound 7)and 3-deoxyempagliflozin(compound 8)were synthesized and evaluated by in vitro hSGLT2 and hSGLT1 inhibitory assay. RESULTS The deoxylated SGLT2 inhibitors were synthesized from their corresponding aryl halides 9a-9c and 3-/6-deoxylated perbenzylated gluconolactones 11a-11b.In vitro hSGLT2 and hSGLT1 inhibitory assay showed that compounds 5 and 8 almost lost SGLT2 inhibitory activity, while compounds 6 and 7 exhibited similar activities to their corresponding parent compounds. CONCLUSION It seems a general rule that 6-deoxylation of the sugar moiety in SGLT2 inhibitors has no effect on the SGLT2 inhibitory activity, whereas the effect of 3-deoxylation on SGLT2 inhibitory activity depends on the structures of the specific SGLT2 inhibitors, which does not show a universal rule.