Antiproliferative activity of Citrus juices and HPLC evaluation of their flavonoid composition

The antiproliferative activity of fresh fruit juices extracted from Citrus sinensis (cv. Washington Navel and cv. Sanguinello), C. deliciosa cv. Avana, C. clementina cv. Nules, C. aurantium subsp. myrtifolia , was evaluated against K562 (human chronic myelogenous leukemia), HL-60 (human leukemia) and MCF-7 (human breast adenocarcinoma) cell lines. All the juices tested showed antiproliferative activity. Moreover, the pattern of the main flavanone compounds in the juices has been determined by HPLC analysis.     

Novel indole C-glycosides from Isatis indigotica and their potential cytotoxic activity

Two novel indole C-glycosides, which were the first reported alkaloids C-glycosides from Isatis indigotica, together with five known alkaloids were isolated. The novel alkaloids were elucidated to be indole-3-acetonitrile-4-methoxy-2-C-β-D-glucopyranoside (1) and N-methoxy-indole-3-acetonitrile-2-C-β-D-glucopyranoside (2) on the basis of spectroscopic analysis. 1 exhibited significant cytotoxic activities against human myeloid leukemia HL-60 and human liver cancer HepG2 cells with the IC₅₀ of 1.3 ± 0.1 and 2.1 ± 0.3 μM, respectively. 2 showed potential cytotoxic activities against HL-60 and human myeloid leukemia Mata cells with the IC₅₀ of 5.1 ± 0.4 and 12.1 ± 0.8 μM, respectively.     

Triterpenoids from Calophyllum inophyllum and their growth inhibitory effects on human leukemia HL-60 cells

A new friedelane-type triterpene (1), along with seven known triterpenoids, was isolated from the stems and leaves of Calophyllum inophyllum Linn. Their structures were established as 3β, 23-epoxy-friedelan-28-oic acid (1), friedelin (2), epifriedelanol (3), canophyllal (4), canophyllol (5), canophyllic acid (6), 3-oxo-friedelan-28-oic acid (7), and oleanolic acid (8) by spectroscopic methods (NMR, EI-MS). The growth inhibitory effects of these triterpenoids on human leukemia HL-60 cells were determined.     

Triterpenes and steroids from the roots of Scorzonera austriaca

A new D:B-friedoolean-type triterpene, 3β-acetoxyglutin-5(10)-en-6-oxo (1), together with seventeen known compounds (2-18) was isolated from the roots of Scorzonera austriaca. Their structures were elucidated mainly by NMR and HR-ESI-MS, as well as on comparison with the reported data. Cytotoxicities of compounds 2, 4, 6, 10-14 and 16 against selected cancer cells of human promyelocytic leukemia (HL-60) and human hepatoma (BEL-7404) were measured in vitro.     

Two new biphenanthrenes with cytotoxic activity from Bulbophyllum odoratissimum

Two new dimeric phenanthrenes, bulbophythrins A (1) and B (2), were isolated from Bulbophyllum odoratissimum. Their structures were elucidated by HR-ESI-MS, 1D and 2DNMR spectroscopy. They were evaluated in vitro for their inhibitory ability against the growth of human leukemia cell lines K562 and HL-60, human lung adenocarcinoma A549, human hepatoma BEL-7402 and human stomach cancer SGC-7901. Both compounds showed significant cytotoxicity against the tested cell lines. Compound 1 exhibited some selectivity against HL-60 and BEL-7402 with IC₅₀ values of 1.27 × 10^− 3 and 1.22 × 10^− 3 µmol/ml respectively, whereas 2 was most active against A549 with IC₅₀ value of 1.18 × 10^− 3 µmol/ml.     

Aromatic compounds from endophytic fungus Colletotrichum sp. L10 of Cephalotaxus hainanensis Li

Six aromatic compounds were isolated from the endophytic fungus Colletotrichum sp. of Cephalotaxus hainanensis Li [Cephalotaxus mannii Hook. f.]. Their structures were determined on the basis of chemical and spectroscopic methods. The compound 2 was the enantiomer of compound 1. The compound 4 was the epimeride of the compound 3. The compounds 1, 2, 4 and 5 were evaluated for cytostatic activity against HL-60 and PC-3 cells.     

Two new nortriterpenoid saponins from Salicornia bigelovii Torr. and their cytotoxic activity

Investigation of characteristic constituents of Salicornia bigelovii Torr. led to isolation of two new 30-nortriterpenoid glycosides, Bigelovii A (1), Bigelovii B (2), together with two known 30-nortriterpenoid glycosides 3-4 and three known oleanane-type triterpenoid glycosides 5-7. The structures of new compounds were elucidated by extensive 1D and 2D NMR, and MS spectroscopic analysis, and chemical evidences. All compounds were isolated for the first time from Chenopodiaceae. Thus compounds 1-4 were evaluated for their cytotoxicity and compouds 1, 3 showed moderate activity against four cell lines, HL-60 (promyelocytic leukemia), MCF-7 (breast carcinoma), HepG2 (liver carcinoma) and A549 (lung carcinoma), with IC(50) values of 6.18, 78.08, 13.64 and >100μM for 1; 31.87, >100, ~100, >100μM for 3, respectively.     

Two new cytotoxic triterpenoid saponins from the roots of Clematis argentilucida

Bioassay-guided fractionation of the n-BuOH extract of the roots of Clematis argentilucida led to the isolation of two new triterpenoid saponins along with a known one, cussonside B (3). By extensive spectral analysis and chemical evidences, the structures of the two new saponins were determined to be 3β-O-[β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl] hederagenin-11,13-dien-28-oic acid (1) and 3β-O-{β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl} oleanolic acid (2), respectively. Saponin 1 is the first example of triterpenoid saponins with two double bonds located at C-11 and C-13 in the aglycone from the genus Clematis. The two new saponins exhibited significant cytotoxicity against human leukemia HL-60 cell lines, human hepatocellular carcinoma Hep-G2 cell lines and human glioblastoma U251MG cell lines with a range of IC(50) values from 2.74 to 25.40μM, while 3 showed inactivity against all of the three cancer cell lines.     

黑荆树树皮原花色素生物活性的研究

对黑荆树树皮中原花色素的提取及生物活性进行了研究.实验分别以水、甲醇和乙醇作为提取溶剂,对黑荆树皮中原花色素的提取进行了探讨,通过测定其总抽出物含量和原花色素粗提物得率的影响,确定了适宜的提取条件,并重点对原花色素生理活性包括抗肿瘤和抗氧化活性进行了评价.利用MTT比色法对原花色素抗肿瘤活性进行了测定,利用清除DPPH自由基能力测定了其抗氧化能力.实验结果表明,黑荆树树皮是一种富含原花色素的植物资源.提取溶剂选择性试验结果表明,乙醇作为提取溶剂,不仅可以得到较高提取率的原花色素,而且所得原花色素粗提物具有较高的生理活性.黑荆树树皮原花色素适宜提取工艺条件为:溶剂浓度 70%,提取温度 60 ℃,液料比7∶1.体外癌细胞培养的抑制作用测试结果显示,黑荆树树皮提取得到的原花色素粗产品对人早幼粒白血病细胞HL-60有中效,分别对人低分化胃腺癌细胞BGC-823和人肝癌细胞BEL-7402有弱效.自由基清除能力测定结果显示黑荆树树皮中原花色素提取物有很强的抗氧化活性.     

Cytotoxicity and structure activity relationships of phytosterol from Phyllanthus emblica

Fourteen sterols (1–14), including two new sterols, trihydroxysitosterol (2) and 5α,6β,7α-7α-acetoxysitosterol (3), were isolated from the branches and leaves of Phyllanthus emblica L. The isolated compounds and a structurally related sterol 15 from Aphanamixis grandifolia were screened for cytotoxicity in two tumor cell lines (HL-60 and SMMC-7721) and a non-tumor cell line (HL-7702) using RSB assay. Within the series of phytosterol derivatives tested, compound 15 was the most active, displaying potent cytotoxicity against HL-60 with IC₅₀ of 5.10 μmol/L, and most of the active compounds showed selective cytotoxicity against tumor and non-tumor cell lines, especially compound 10 with a safety index of 4.42.     

Andirolides Q–V from the flower of andiroba (Carapa guianensis,Meliaceae)

Two new gedunins, an andirobin, two mexicanolides, and a phragmalin-type limonoid, named Andirolides Q (1), R (2), S (3), T (4), U (5), and V (6), were isolated from an oil of the flower of Carapa guianensis AUBLET (Meliaceae). Their structures have been elucidated on the basis of spectroscopic analyses using 1D and 2D NMR spectra and FABMS. Andirolide S (3) and Andirolide T (4) showed significant cytotoxic activity against the murine P388 leukemia cell line (IC₅₀ of 1.4 μM for 3; 1.8 μM for 4) and the human HL-60 leukemia cell line (IC₅₀ of 1.3 μM for 3 and 4).     

Isolation and identification of C-19 fatty acids with anti-tumor activity from the spores of Ganoderma lucidum (reishi mushroom)

We previously showed that ethanolic extracts of spores of Ganoderma lucidum inhibit tumor cell proliferation and induce apoptosis of HL-60 cells. The active constituents appeared to be long-chain fatty acids, particularly carbon-19 (C-19) fatty acids which have not been reported in spores of Ganoderma lucidum. In the present study, two of these C-19 fatty acids which are key compounds in the activities, were identified as their 2-naphthyl ester derivatives after esterification of a mixture of fatty acids obtained from the spores. The active compounds were determines as nonadecanoic acid and cis-9-nonadecenoic acid. The location of the double bond of cis-9-nonadecenoic acid was demonstrated by GC-MS analysis, based on the fragmentation pattern of the adduct prepared from the fatty acid and dimethyl disulfide.     

Cytotoxic activity of some Asarum plants

The cytotoxic activity against some tumor cell lines of 16 commonly used species of Asarum was evaluated in this study. All of these plants were widely used in Asian countries as traditional medicines or folk medicines. Their inhibitory activities against four tumor cell lines (HL-60, BGC-823, KB and Bel-7402) were compared. It was observed that 10 of the tested extracts (eight ethanol extracts and two water extracts) among 32 extracts of these plants showed cytotoxic activity. Those 95% ethanol extractions from A. caudigerellum, A. forbesii, A. inflatum and A. maximum exhibited the highest cytotoxic activity, and 95% ethanol extracts or water extracts of A. sieboldii var. seoulense, A. himalaicum, A. splendens and A. crispulatum showed selective activity against one or two cells among the tested tumor cells. This is the first report of Asarum plants possessing cytotoxic activity against tumor cell lines.     

红树属植物内生真菌多样性及其代谢产物研究进展

红树林是生长在热带和亚热带潮间带河口地带的耐盐植物群落,分布在南纬30°与北纬30°之间,具有盐胁迫、高矿物组成、强还原性、频繁的潮汐等特征,也使植物对营养、空间的竞争异常激烈,特殊生境使红树林植物内生真菌多样性丰富,必然会造成不同于其他生态系统的良好生物活性、独特化学结构的活性功能分子。红树属是红树林植物中分布较广泛的一个属,包括8个种,分别是红海榄、红树、红茄苳、美洲红树、Rhizophora harrisonii、R.racemosa、树冬红树和萨摩红树。迄今为止,从红树属分离出内生真菌类群已达23目41科64属,其中对拟盘多毛孢属、青霉属和毛霉属的内生真菌代谢产物研究的最为广泛;从红树属内生真菌中分离鉴定出195种天然产物,包括生物碱类、萜类化合物、香豆素类、色酮类化合物、醌类化合物、杂氧蒽醌类化合物、肽类、酚酸类化合物、内酯类等化合物,从红树属植物中发现许多结构新颖的次生代谢产物,从中国南海红树林红茄苳内生拟盘多毛孢真菌中发现一系列罕见的具有亲脂性取代基的新色酮类化合物pestalotiopsones A-F (107—112),从拟盘多毛孢属JCM2A4中发现2个具有柔性结构的补身烷型倍半萜-环青霉醛酸的新骨架化合物pestalotiopens A和B (83, 84)。此外,许多化合物显示出良好的抗肿瘤、抗菌和抗氧化等生物活性,如化合物pestalpolyol 1(119)具有很强的抑制作用,对小鼠淋巴瘤L5178Y细胞的半抑制浓度(half maximal inhibitory concentration,IC₅₀)值为4.10μmol·L^-1。从内生真菌毛霉QEN-189中分离到的吲哚生物碱rhizovarins A,B和F(46, 47, 50)对肺癌细胞A549抑制作用强,IC₅₀值分别为11.5、6.3和9.2μmol·L^-1,对白血病细胞HL-60有强抑制作用,IC₅₀值为9.6、5和7μmol·L^-1。     

Flavonoids with antiplasmodial and cytotoxic activities of Macaranga triloba

A new flavanone derivative, malaysianone A (1), four prenylated flavanones, 6-prenyl-3'-methoxyeriodictyol (2), nymphaeol B (3), nymphaeol C (4) and 6-farnesyl-3',4',5,7-tetrahydroxyflavanone (5), and two coumarins, 5,7-dihydroxycoumarin (6) and scopoletin (7), were isolated from the dichloromethane extract of the inflorescences of Macaranga triloba. The structures of these compounds were elucidated based on spectroscopic methods including nuclear magnetic resonance (NMR-1D and 2D), UV, IR and mass spectrometry. The cytotoxic activity of the compounds was tested against several cell lines, with 5 inhibiting very strongly the growth of HeLa and HL-60 cells (IC(50): 1.3 μg/ml and 3.3 μg/ml, respectively). Compound 5 also showed strong antiplasmodial activity (IC(50): 0.06 μM).     

Antioxidant neolignan and phenolic glucosides from the fruit of Euterpe oleracea

Three new glucosides, namely, (–)-7R8S-7′,8′-dihydroxy-dihydrodehydroconiferyl alcohol-9-O-β-d-glucopyranoside (1), (+)-7S8R-7′,8′-dihydroxy-dihydrodehydroconiferyl alcohol-9-O-β-d-glucopyranoside (2) and 4-hydroxy-2-methoxyphenyl 1-O-[6-(hydrogen 3-hydroxy-3-methylpentanedioate)]-β-d-glucopyranoside (3), along with 6 known compounds were isolated from the fruit of Euterpe oleracea Mart. Their structures were elucidated based on spectroscopic analyses including NMR, HR-ESI-MS and CD. All the isolated compounds demonstrated significant antioxidant activity and 2 displayed moderate cytotoxicity against HL-60 cells.     

Two new amide alkaloids with anti-leukaemia activities from Aconitum taipeicum

Two new amide alkaloids, named 3-isopropyl-tetrahydropyrrolo [1,2-a] pyrimidine-2,4(1H,3H)-dione (1) and 1-acetyl-2,3,6-triisopropyl-tetrahydropyrimidin-4(1H)-one (2), were isolated from the roots of Aconitum taipeicum. Their chemical structures were characterized on the basis of MS, 1D- and 2D NMR. The anti-leukaemia activities of the compounds were also tested. The results indicated that the compounds exhibited more significant cell growth inhibitory activities against HL-60 cells than adriamycin, with the IC₅₀ of 1.1 ± 0.03 μg/mL and 1.6 ± 0.07 μg/mL respectively. In addition, two compounds showed anti-tumor activities against K562 cells as well.     

Diterpenoids from Isodon sculponeatus

Phytochemical investigation of the aerial parts of Isodon sculponeatus afforded six new 7,20-epoxy-ent-kauranoids, sculponins U–Z (1–6), and 11 known diterpenoids (7–17). The structures of these new compounds were elucidated primarily by means of extensive spectroscopic analysis, and the absolute configuration of 1 was determined by single crystal X-ray diffraction. Compound 5 exhibited weak cytotoxic activity against HL-60, SMMC-7721, MCF-7, and SW-480 cell lines, and it also inhibited NO production in LPS-stimulated RAW264.7 cells, with IC₅₀ value of 13.8 μM.     

Apoptotic activities of ethanol extracts from some Apiaceae on human leukaemia cell lines

Apiaceae are a family of medicinal plants widely used in traditional medicine. The apoptotic activities of seven ethanol extracts from fruits of seven species of Apiaceae, Eryngium planum, Archangelica officinalis, Pastinaca sativa, Heracleum sibiricum, Carum carvi, Foeniculum vulgare, Levisticum officinale against ML-1--human acute myeloblastic leukaemia, J-45.01--human acute T cell leukaemia, EOL--human eosinophilic leukaemia, HL-60--human Caucasian promyelocytic leukaemia, 1301--human T cell leukaemia lymphoblast, C-8166--human T cell leukaemia, U-266B1--human myeloma, WICL--human Caucasian normal B cell, and H-9--human T cell, were investigated.     

Lignans from Schisandra hernyi with DNA cleaving activity and cytotoxic effect on leukemia and Hela cells in vitro

The lignans, gomisin G (1), schisantherin A (2), benzoylgomisin Q (3) and isoanwulignan (4) were isolated from the stems of Schisandra henryi. Compound 1 showed moderate DNA strand scission activity and significant cytotoxic effect on leukemia and Hela cells in vitro. Compound 1 represents a new type of DNA strand scission agent.