Two new triterpenoids from Photinia serrulata

Two new triterpenoids, 2alpha,3beta,11alpha,13beta-tetrahydroxy-12-ketooleanan-28-oic acid(1) and 3beta-hydroxy-12-keto-9(11)-ursen-28,13beta-olide (2) were isolated from the leaves ofPhotinia serrulata. Their structures were identified by spectral methods. Compounds 1 and2 were assessed for cytotoxic activity against three human tumor cell lines (A-549, HCT-8,and BEL-7402), and they showed no cytotoxic effects at concentrations up to 5microg/mL.     

Two novel alkaloids from the stem of Saprosma hainanense and their cytotoxic activities in vitro

Two novel alkaloids, saprosmine A (1) and saprosmine B (2), were isolated from the stem of Saprosma hainanense MERR., along with five known alkaloids: marcanine A (3); cleistopholine (4); 4-methoxycarbonyl-5,10-benzogquinolinequinone (5); liriodenine (6); and quinoline (7). The chemical structures were established on the basis of extensive spectroscopic (IR, 1D-NMR, 2D-NMR, MS) data analysis and by comparison with spectroscopic data reported in the literature. Compounds 1 to 6 were evaluated for in vitro cytotoxic activities against the SPC-A-1 (human lung cancer), BEL-7402 (human hepatocellular carcinoma), SGC-7901 (human gastric cancer), and K-562 (human myelogenous leukaemia) cancer cell lines. Compounds 1 and 2 exhibited weak cytotoxic activities against K-562 cells. Compounds 3 and 5 showed cytotoxic activities against all four cancer cell lines.     

Evaluation on bioactivities of triterpenes from Bergenia emeiensis

Bergenia emeiensis is a traditional folk medicine in China. Most studies are focusing on the bioactivity of bergenin, neglecting other compounds. Therefore, in this present work, the antioxidant, antibacterial and anticancer abilities of triterpenes from B. emeiensis rhizomes (TBE) were comprehensively evaluated. The results showed that TBE could well scavenge DPPH with a lower EC50 of 0.29 mg/mL and could improve the cell viability of CHO cells against H₂O₂ induced cell death. Additionally, TBE also enhanced the resistance of C. elegans under thermal stress, exhibiting a strong antioxidant potential in vivo. Moreover, TBE showed a certain antibacterial ability on five kind strains such as Pseudomonas aeruginosa while TBE could not significantly inhibit the growth of plant pathogenic fungi. Furthermore, TBE possessed an excellent suppression ability on the proliferation of cancer cells especially Hela and Hep G2 cells with an IC50 of 41.79 μg/mL and 48.62 μg/mL at 48 h, respectively. After fractionally extracted with petroleum ether, ethyl acetate and ethanol, ethanol phase (EP) contained the most triterpenes, followed by ethyl acetate phase (EAP) and petroleum ether phase (PEP). Besides, EP and EAP exhibited a strong antioxidant capacity and also inhibited the proliferation of Hela and Hep G2 cells with the effect of pro-oxidation by inducing a high level of ROS and decreasing mitochondrial membrane potential, thus causing oxidative stress then inducing cell apoptosis. Therefore, these outcomes indicated the triterpenes from B. emeiensis possessed a strong antioxidant ability and an anticancer effect, thus making B. emeiensis become a promising potential alternative in pharmacological field.     

三唑类白杨素衍生物的设计、合成及其抗增殖活性研究

合成了2个系列的白杨素衍生物,采用噻唑蓝(MTT)法测试了所有化合物针对六种肿瘤细胞的体外抗增殖活性,包括MGC-803, BEL-7402, HepG2, HeLa, A549以及SGC-7901细胞.实验结果显示, 7-[1-(3-氟苯基)-1H-1,2,3-三唑-4-甲氧基]-白杨素(1c)与7-[1-(2-氯苯基)-1H-1,2,3-三唑-4-甲氧基]-白杨素(1g)针对MGC-803细胞的活性与先导化合物白杨素及阳性对照药5-氟尿嘧啶相比显著提高.因此,化合物1c与1g具有深入研究用以开发抗癌药物的潜能.     

Three new podocarpane-type diterpenoids from callus of Securinega suffruticosa

Three new podocarpane-type diterpenoids, 3beta,12-dihydroxy-13-methyl-6,8,11,13-podocarpatetraen (1), 3beta,12-dihydroxy-13-methyl-5,8,11,13-podocarpatetraen-7-one (2), and 1-(7-hydroxy-2,6-dimethyl-1-naphthyl)-4-methyl-3-pentanone (3) (20(10-->5)-abeo-4,5-seco-5(10),6,8,11,13-podocarpapentaen-3-one) were isolated from callus of Securinega suffruticosa. The structures were elucidated by spectroscopic methods. Compounds 1, 2, and 3 showed cytotoxic activity against five human cancer cell lines (A549, BEL 7402, BGC-823, HCT-8, A2780).     

Synthesis of novel heptaplatin derivatives and evaluation of their ability to inhibit proliferation of cancer cell lines

A series of novel heptaplatin derivatives were synthesized and evaluated for their ability to inhibit growth of two cancer cell lines: human colon carcinoma cell line HCT-8 and human hepatocarcinoma cell line Bel-7402. Majority of the synthesized compounds demonstrated superior activity against cancer cell lines compared to heptaplatin. Specifically, compounds 5a and 5b (5 µg/mL) had more pronounced efficacy against the HCT-8 cell line while 6b and 6c (0.5 µg/mL) had higher efficacy against Bel-7402 cell line.     

Three new phenolic glucosides from the roots of Rheum palmatum

A novel naphthalene glucoside, rheumone A (1), with an unprecedented skeleton containing a seven-membered lactone, and two new compounds, 1-O-phloroglucinyl-2-O-galloyl-6-O-cinnamoyl-β-D-glucoside (2) and chrysophanol 1-O-β-D-(6'-O-malonyl)glucoside (3), together with three known compounds (4-6) were isolated from the roots of Rheum palmatum. Their structures were elucidated mainly by spectroscopic analysis. These compounds were evaluated in vitro for their cytotoxicities towards human hepatocellular cancer cell lines Bel-7402 and Bel-7402/5Fu, and human gastric carcinoma cell line BGC-823. None of them showed cytotoxicity with IC(50) far beyond 50 μM.     

Constituents of Salvia microphylla

A new phenolic ester 2-( p-hydroxyphenyl)ethyl eicosaheptanoic acid ester (1) and a known one hexacosylferulate (2) were isolated from the acetone extract of Salvia microphylla. In addition, two sesquiterpenes beta-eudesmol (3) and 8alpha-hydroxy-beta-eudesmol (4), a diterpene carnosic acid 12-methyl ether (12-methoxycarnosic acid) (5), three triterpenes erithrodiol 3-acetate, oleanolic acid, lupeol and beta-sitosterol were obtained as known compounds from this plant extract. The structures of the isolated compounds were elucidated by spectroscopic methods, including one- and two- dimensional 1H- and 13C-NMR and MS spectroscopies. The selected compounds were tested for antimicrobial activity against standard bacterial strains, and only carnosic acid 12-methyl ether showed antimicrobial activity against S. aureus at 78 microg mL(-1).     

Cytotoxic and antimalarial prenylated xanthones from Cratoxylum cochinchinense

A new prenylated xanthone, 5-O-methylcelebixanthone (1), together with six known compounds; celebixanthone (2), 1,3,7-trihydroxy-2,4-di(3-methylbut-2-enyl)xanthone (3), cochinchinone A (4), alpha-mangostin (5), beta-mangostin (6) and cochinchinone C (7) were isolated from roots of Cratoxylum cochinchinense. Their structures were elucidated by spectroscopic methods. Compounds 2 and 4-7 showed cytotoxic activity against the human lung cancer cell line (NCI-H187) with IC(50) values ranging from 0.65 to 5.2 microg/ml. Compounds 1, 2, 6 and 7 also showed antimalarial activity against Plasmodium falciparum with IC(50) values of 3.2, 4.9, 7.2 and 2.6 microg/ml, respectively.     

乳香大环二萜类化学成分研究

采用硅胶柱层析,制备薄层层析等色谱方法,从乳香CO_2超临界提取物中分得7个大环二萜类化合物,经波谱方法鉴定为incensole acetate(1),incensole(2),incensole oxide acetate(3),isoincensole acetate(4),incensole oxide(5),isoincensoleoxide(6),isoincensolol(7),其中,化合物7为新化合物,化合物4为首次从该属植物中分离得到.采用四甲基偶氮唑蓝(MTT)法观察化合物对肿瘤细胞的抑制增殖作用.     

Racemic Norlignans as Diastereoisomers from Ferula sinkiangensis Resins with Antitumor and Wound-Healing Promotion Activities

Ferulasinkins A–D (1–4), four new norlignans, were isolated from the resins of Ferula sinkiangensis, a medicinal plant of the Apiaceae family. All of them were obtained as racemic mixtures, chiral HPLC was used to produce their (+)- and (−)-antipodes. The structures of these new compounds, including their absolute configurations, were elucidated by spectroscopic and computational methods. This isolation provides new insight into the chemical profiling of F. sinkiangensis resins beyond the well-investigated structure types such as sesquiterpene coumarins and disulfides. Compounds 2a and 3a were found to significantly inhibit the invasion and migration of triple-negative breast cancer (TNBC) cell lines via CCK-8 assay. On the other hand, the wound-healing assay also demonstrated that compounds 4a and 4b could promote the proliferation of human umbilical vein endothelial cells (HUVECs). Notably, the promoting effects of 4a and 4b were observed as more significant versus a positive control using basic fibroblast growth factor (bFGF).     

Bioactive extracts from Senecio samnitum Huet

The antimicrobial and cytotoxic activities of extracts from Senecio samnitum Huet are reported. Extracts from S. samnitum were able to inhibit the in vitro proliferation of four human tumor cell lines. The dichloromethane extract demonstrated effective cytotoxic activity with IC50 of 22.89 microg mL(-1) on the Caco-2 cell line and the EtOAc extract had IC50 value of 11.91 microg mL(-1) against the COR-L23 cell line. The n-hexane extract displayed the best antibacterial activity against Gram positive bacteria, particularly Staphylococcus aureus. The antifungal activity of all extracts was also seen, particularly against the dermatophytes Trichophyton tonsurans and Microsporum gypseum for the methanol and n-hexane extracts.     

Arenicolsterol A，来自海洋环节动物海蚯蚓中的一种新的细胞毒性烯醇式磺化甾醇

Marine organisms are the important source of the bioactive metabolites. A novel enolic sulfated sterol, arenicolsterol A, has been isolated from a marine annelid Arenicola cristata collected in the coast of Mainland of China.The structure was elucidated using all sorts of spectroscopic data including ESIMS, 1D and 2D NMR etc. The cytotoxic bioactivity of this sterol was evaluated by MTT assay. It could inhibit the growth of human cervix cancer cell line (Hela) and human non-small cell lung cancer cell line (NCI-h6) with IC50 of (3.1 0.6)μg/mL and (7.6 0.8)μg/mL.     

Anthraquinones, Cdc25B phosphatase inhibitors, isolated from the roots of Polygonum multiflorum Thunb

Three anthraquinones, Cdc25B phosphatase inhibitors, were isolated from the methanolic extract of the roots of Polygonum multiflorum Thunb. (Polygonaceae). Anthraquinones, physcion (1), emodin (2), and questin (3), inhibited the enzymatic activity of Cdc25B phosphatase with IC(50) values of 62.5, 30, and 34 microg mL(-1), respectively. Emodin (2) and questin (3) strongly inhibited the growth of human colon cancer cells, SW620 with GI(50) values of 6.1 and 0.9 microg mL(-1), respectively. Commercially available anthraquinones, chrysophanol (4), and rhein (5) also inhibited Cdc25B phosphatase with IC(50) values of 10.7 and 22.1 microg mL(-1), respectively.     

New cytotoxic steroid from Stachyurus imalaicus var. himalaicus

A phytochemical study of the ethanolic extract of Stachyurus imalaicus var. himalaicus was undertaken and as a result a new polyoxygenated steroid, named stachsterol ((20S)-20, 25-dihydroxy-4-cholesten-3-one, 1) and three known ecdysteroids, 20-hydroxyecdysone (2), 20-hydroxyecdysone-20, 22-monoacetonide (3) and polypodine B-20,22-monoacetonide (4), were isolated. Their structures were elucidated by spectroscopic methods, including UV, NMR, MS and HR-MS. The purified product 1 was found to have in vitro cytotoxic activity against human Hela cell lines with an IC50 value of 2.5 microg/mL. This is the first time that phytoecdysteroids have been found in the genus Stachyurus.     

Ceanothane- and lupane-type triterpenes with antiplasmodial and antimycobacterial activities from Ziziphus cambodiana

One new and eight known ceanothane- and lupane-type triterpenes were isolated from the root bark of Ziziphus cambodiana PIERRE (Rhamnaceae). Based on spectral analyses, the structure of the new compound was elucidated as 3-O-(4-hydroxy-3-methoxybenzoyl)ceanothic acid (3-O-vanillylceanothic acid) (1), while the known compounds were identified as lupeol (2), betulinaldehyde (3), betulinic acid (4), 2-O-E-p-coumaroyl alphitolic acid (5), alphitolic acid (6), zizyberanalic acid (7), zizyberenalic acid (8) and ceanothic acid (9). Compounds 1, 5 and 8 exhibited significant in vitro antiplasmodial activity against the parasite Plasmodium falciparum, with inhibitory concentration (IC50) values of 3.7, 0.9 and 3.0 microg/ml, respectively. Compounds 1 and 3-8 showed antimycobacterial activity against Mycobacterium tuberculosis with respective MIC values of 25, 25, 25, 12.5, 50, 50 and 100 microg/ml.     

聚乙烯胺类修饰萘酰亚胺衍生物的合成、DNA键合行为和活性研究

合成了二乙烯三胺、三乙烯四胺和四乙烯五胺等低分子量聚乙烯胺类修饰的萘酰亚胺衍生物.通过UV-Vis谱、荧光光谱、圆二色谱和热变性试验研究了合成化合物与小牛胸腺DNA的键合行为,同时通过四甲基偶氮唑蓝(MTT)染色法研究了化合物对Bel-7402(人肝癌细胞)、HL-60(白血病细胞)、A549(人肺癌细胞)和Hela(人宫颈癌细胞)等细胞株的体外抗肿瘤活性,化合物NI1对A549细胞显示良好的抑制活性,优于阳性对照顺铂.     

Antimicrobial activity of globulol isolated from the fruits of Eucalyptus globulus Labill

An antimicrobial sesquiterpene was separated by bioassay-guided isolation from the petroleum ether fraction of the ethanol crude extract of Eucalyptus globulus Labill (Myrtaceae) fruits, and was identified as globulol by physicochemical properties and spectroscopic analysis. Mycelial growth method revealed that the median effective inhibitory concentration (IC50) values of globulol on Alternaria solani, Fusarium oxysporum f.sp. niverum, F. graminearum, Rhizoctonia solani and Venturia pirina were 47.1 microg mL(-1), 114.3 microg mL(-1), 53.4 microg mL(-1), 56.9 microg mL(-1), 32.1 microg mL(-1) and 21.8 microg mL(-1), respectively. MTT-colorimetric assay revealed that IC50 values of globulol on Xanthomonas vesicatoria and Bacillus subtilis were 158.0 microg mL(-1) and 737.2 microg mL(-1), respectively. The results indicated that globulol could be a main antimicrobial compound in the ethanol crude extract of E. globulus fruits.     

Synthesis of novel 1,3,4-trisubstituted pyrazole derivatives and their evaluation as antitumor and antiangiogenic agents

Several 1,3,4-trisubstituted pyrazole derivatives were synthesized and screened for their cytotoxic effect in a primary 3 tumor cell line test at 10(-4) M drug concentration. Compounds 19 and 20 reduced the growth of one or more of these cell lines to less than 32% and escalated up to evaluation in the full panel of 60 human tumor cell lines at a minimum of 5 concentrations at 10 fold dilutions. Compound N'-(1-[1-[4-nitrophenyl]-3-phenyl-1H-pyrazol-4-yl]methylene)-2-chlorobenzohydrazide 19 proved to be the most active of these derivatives with full panel median growth inhibition (GI50), total growth concentration (TGI) and median lethal concentration (LC50) mean graph mid-point (MG-MID) of 3.79, 12.5 and 51.5 microM, respectively. In addition, compounds 19, 39, 40, 41, 43, 45, 47 were tested for their antiangiogenic properties by testing their ability to inhibit human umbilical vein endothelial cells (HUVECs) proliferation, cord formation and migration in response to chemoattractant. 3-Acetyl-2-(1-(4-nitrophenyl)-3-phenylpyrazol-4-yl)-5-(4-pyridyl)-1,3,4-oxadiazoline 39 showed significant antiangiogenic profile at non-cytotoxic doses, with HUVEC proliferation inhibition IC50 of 7.60 microM, chemotaxis IC50 of 0.86 microM and was superior to the reference celecoxib 2 in both tests. Furthermore, in contrary to the references TNP-470 and celecoxib, all the tested compounds interfered with the migratory function of HUVECs in response to vascular endothelium growth factor (VEGF) rather than the endothelial cells proliferation.     

D:C-friedooleanane-type triterpenoids from Lagenaria siceraria and their cytotoxic activity

Four new D:C-friedooleanane-type triterpenes, 3 beta-O-(E)-feruloyl-D:C-friedooleana-7,9(11)-dien-29-ol (1), 3 beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-ol (2), 3 beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid (3), and methyl 2 beta,3 beta-dihydroxy-D:C-friedoolean-8-en-29-oate (6), together with five known triterpenes with the same skeleton, 3-epikarounidiol (4), 3-oxo-D:C-friedoolena-7,9(11)-dien-29-oic acid (5), bryonolol (7), bryononic acid (8), and 20-epibryonolic acid (9), were isolated from the methanol extract of the stems of Lagenaria siceraria. The structures of those compounds were elucidated using spectroscopic methods. Compounds 3 and 9 showed significant cytotoxic activity against the SK-Hep 1 cell line with IC50 values of 4.8 and 2.1 microg/ml, respectively. Based on these initially promising results, the two D:C-friedooleanane triterpenes merit further study as potential anticancer agents.