Polyhydroxylated steroids from the Vietnamese starfish Luidia maculata.

Anti-proliferative activity of essential oil extracted from Thai medicinal plants on KB and P388 cell lines

The plant Aeschynomene fascicularis (Fabaceae) has been used in Mayan traditional medicine in the Yucatan peninsula. However, the compounds present in the plant responsible for its curative properties have not yet been investigated. Aeschynomene fascicularis root bark was extracted with 100% methanol to obtain a crude extract. The methanol extract was partitioned successively with solvents with increasing polarity to obtain the corresponding hexane (Hx), dichloromethane (DCM) and ethyl acetate fractions (EtOAc), as well as a residual water-alcoholic fraction. These fractions were tested for their cytotoxic activities using an MTT assay against Hep-2 cancer cell lines. The Hx fraction led to the isolation of spinochalcone C (1), spinochalcone A (2), isocordoin (3) and secundiflorol G (4). Their structures were identified based on spectroscopic evidence and chemical properties. All compounds were subjected to cytotoxicity and antiproliferative assays against a panel of seven cell lines, including one normal-type cell line. Spinochalcone A (2) exhibited cytotoxic activity against DU-145 cell line and antiproliferative activity against the KB cell line. Secundiflorol G (4) showed strong cytotoxic activity towards KB and Hep-2 cell lines. In addition, isocordoin (3) showed moderate activity on KB, Hep-2 and DU-145 cell lines. The active Compounds 2, 3 and 4 are potential therapeutic entities against cancer.

Background and Objectives:The perpetual search is on to find botanical complementary adjuncts to the conventional therapies used that is not only cost-effective but also reduces side effects associated with conventional synthetic drugs that are available in the market. The aim of this study was to assess the in vitro anticancer efficacy of hydroalcoholic fruit extract of cranberry against oral cancer KB cell line by Di-Methyl Thiazoldiphenyl Tetrazolium bromide assay (MTT) assay and its cytotoxicity on normal fibroblast cells.Materials and Methods:Vaccinium macrocarpon extract was prepared using a hydroethanolic solvent (water – 30%:ethanol – 70%) using the standardized maceration protocol. Standard KB and normal fibroblast (L929) cell lines were used. The minimum lethal effect of the extract was calculated using the MTT cytotoxicity assay.Results:The extract shows a satisfactory antiproliferative effect on the KB cell line and a higher cell viability percentage of the normal fibroblast cell line.Conclusion:V. macrocarpon can prove to be an adjunct to the existing anticancer drug therapy against oral cancer KB cell line.

Aim and Background: Oral squamous cell carcinoma (OSCC) is the 16th most common malignancy ranking worldwide. Among many types of cancer treatment, chemotherapy is the most common method. Major problems of treating OSCC with existing chemotherapeutic drugs are its adverse side effects and drug resistance. Anticancer properties present in fruits and vegetables might help to resolve these problems and prevent cancer. The purpose of the study is to assess the anticancer effect of watermelon and pumpkin seed extract on KB (OSCC) cell line. Materials and Methods: The KB cell line was grown in a minimal essential medium and maintained as monolayers in a culture plate. Citrullus lanatus (watermelon) and Cucurbita pepo (pumpkin) seed extracts from the fruit were extracted and subjected to Soxhlet extraction individually with organic solvent ethanol. 3-(4,5-Dimethylthiazol-2-yl)-2,5- Diphenyltetrazolium Bromide) (MTT) test was used to analyze the anticancer effect of the extracts on KB cell line. Results: The comparison between the average cell viability of pumpkin and watermelon seed extract showed a significant difference in cytotoxicity. The mean cell viability of pumpkin seed extract was 30.27%, while for the watermelon seed extract, it was higher at 42.70%, indicating that pumpkin seed extract was more cytotoxic than watermelon seed extract. Conclusion: Watermelon and pumpkin seeds have various properties such as anti-inflammatory, antioxidant, antibacterial, and anticancer effect. This study evaluated the anticancer property of pumpkin and watermelon seed extracts and indicated that as the concentration of the extract increases, the cell viability gradually decreases.

A new 3β-O-vanilloyl-taraxerol, microcisin (2.1) and eight known compounds (2.2-2.9) were isolated from the roots of M. tomentosa. Their structures were determined by spectroscopic analysis. All isolated compounds were evaluated for their cytotoxicity against KB and HeLa cell lines. Compounds 2.1, 2.3 and 2.5 showed moderate cytotoxicity against KB cell lines with IC50 values of 24.98, 28.06 and 22.57 µM, respectively. On the other hand, compound 2.3 showed moderate cytotoxicity against HeLa cells with an IC50 value of 29.38 µM. Three new xanthones, kaennacowanols A-C (3.1-3.3) together with nineteen known xanthones (3.4-3.22) were isolated from the roots of G. cowa. Their structures were determined by spectroscopic analysis. All isolated compounds were evaluated for their cytotoxicity against KB and HeLa cell lines. Compounds 3.17 and 3.22 showed good cytotoxicity against KB cell with IC50 values of 7.97 and 9.10 µM, respectively. On the other hand, compound 3.15 showed good cytotoxicity against HeLa cell with IC50 value of 9.34 µM. Three new pterocarpans, velucarpins A-C (4.1-4.3), three new isoflavanes, kaennavelutinols A-C (5.1-5.3) and a new isoflavone glycoside, kaennavelutinose (6.1) together with eleven known compounds including three known pterocarpans (4.4-4.6), two known isoflavanes (5.4-5.5) and six known isoflavones (6.2-6.7) were isolated from the roots of D. velutina. Their structures were determined by spectroscopic analysis. All isolated compounds were evaluated for their cytotoxicity against KB and HeLa cell lines. Compounds 4.3, 4.5, 5.3 and 5.5 showed good cytotoxicity against KB and HeLa cells with IC50 values of 8.22, 8.09, 8.29, 3.47 µM and 5.99, 8.69, 9.54, 5.17 µM, respectively.

Background:Recently, studies have concentrated on complementary medicine in treating a large number of diseases, including cancer. Unfortunately, many of these treatment methods do not provide a permanent solution, and even if they do, many do not have a scientific corroboration. A shift toward alternative medicine and natural methods is being preferred to reduce if not counter the toxic effects of the drugs that are used to treat such diseases. Studies have shown that amygdalin is a natural plant product to have an anticarcinogenic effect on many types of cancers. However, the effect of amygdalin on oral cancers has not been studied, and hence, the present study aimed to evaluate the anticarcinogenic effect of amygdalin extracted from apricots and almonds on human oral cancer cell lines.Materials and Methods:Oral cancer cell lines (KB cell line) were used in the present study. Ethanolic extracts of apricots and almonds were prepared using Soxhlet extraction method. The antiproliferative and cytotoxic activity on KB cell line was evaluated using 3-(4,5-dimethylthiazol-2-YL)-2,5-diphenyltetrazolium bromide assay.Results:Both the extracts exhibited cytotoxic and antiproliferative activity on KB cell lines. While almonds exhibited maximum efficacy at 50 μg/mL, apricots extract required 100 μg/mL concentrations.Conclusion:Ethanolic extracts of amygdalin from almonds and apricots were effective as an antiproliferative agent which caused apoptosis in oral cancer cell line.

Four new bibenzyls, bauhinols A-D (1-4), together with the two known bibenzyls 5 and 6, were isolated from the roots of Bauhinia saccocalyx, and their structures were elucidated by analyses of spectroscopic data. Bauhinol A (1) exhibits significant cytotoxicity towards NCI-H187 (small-cell lung cancer), BC (breast cancer), and KB (oral-cavity cancer) cell lines, with IC50 values of 2.7-4.5 microg/ml. Bauhinol B (2) is cytotoxic against NCI-H187 (IC50 = 1.1 microg/ml) and BC (IC50 = 9.7 microg/ml) cell lines, but inactive toward the KB cell line (at 20 microg/ml). Compound 2 also is mildly antifungal towards Candia albicans (IC50 = 28.9 microg/ml). Bibenzyl 6 is active against NCI-H187 (IC50 = 14.1 microg/ml) and BC (IC50 = 4.0 microg/ml) cells, but inactive (at 20 microg/ml) toward the KB cell line. Compounds 1, 2, and 6 show mild antimycobacterial activities, with MIC values of 25-50 microg/ml, but are inactive at 20 microg/ml against the K1 malarial parasite strain (Plasmodium falciparum). While bauhinol A (1) is inactive against cyclooxygenase 1 (COX-1) and cyclooxygenase 2 (COX-2), compounds 2 and 6 inhibit both COX-1 and COX-2, with IC50 values comparable to those of the standard drug, aspirin (Table 3).

Cannabigerol (1, CBG), methyl 4-[(2E)-3,7-dimethyl-2,6-octadienyl)oxy]-3-methoxybenzoate (2, DTM), 5-fluorouracil (3, FU) as a reference, and cannabidiol (4, CBD) were tested for their growth inhibitory effects against KB(ATCC NO, OCL 17) cell lines using two different assays, the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazoliumbromide (MTT) assay and the sulforhod-amine B protein (SRB) assay. These compounds showed inhibitory activity in vitro in the micromolar range against KB cell lines. In general, the antitumor activities of these compounds (1, 2, 3 and 4) were dose-dependent over the micromolar concentration range of 1 to 100 M. The comparison of IC50 values of these compounds in tumor cell lines showed that their susceptibility to these compounds decreases in the following order: DTM > CBD > 5-FU > CBG by MTT assay and DTM = CBD > 5-FU > CBG by SRB assay. CBG 1, DTM 2, 5-FU 3, and CBD 4 were tested for their cytotoxic effects on NIH 3T3 fibroblasts using two different assays, the MTT assay and SRB assay. These compounds exhibited potent cytotoxic activities in vitro in the micromolar range against NIH 3T3 fibroblasts. In general, the cytotoxic activities of these compounds (1, 2, 3 and 4) were dose-dependent over the micromolar concentration range of 1 to 100 M. The comparison of CD50 values of these compounds in NIH 3T3 fibroblasts shows that their susceptibility to these compounds in decreases the following order(:) CBD > 5-FU > DTM > CBG by MTT assay, CBD > 5-FU > CBG > DTM by SRB assay. These results suggest that DTM 2 has the most growth-inhibitory activity against KB cell lines.

A new flavonoid, macatanarin D (1), together with five known stilbenes (2-6), was isolated from fruit glandular trichomes of Macaranga tanarius. Their structures were elucidated on the basis of spectroscopic methods and through comparison with data reported in the literature. All isolated compounds were evaluated for their cytotoxic activities against KB and MCF-7 cell lines. Compounds 3, 4, and 5 showed the strongest activities against both cell lines with IC50 values in the range of 0.03–0.12 μM, and compound 2 only showed a significant cytotoxicity against KB cell line (IC50 = 0.26 μM) and a moderate cytotoxicity against MCF-7 (IC50 = 10.4 μM). Compounds 1 and 6 showed weak cytotoxic activities against KB cell line with IC50 values of 29.3 and 24.7 μM, respectively.

o-Aminophenol derivatives are of particular interest for their diverse biological activities and potential therapeutic applications. Such as, antioxidant, antibacterial, and cytotoxic activities. This study aimed to design and synthesize a series of novel o-aminophenol derivatives through an efficient multi-step process, characterize them using modern spectroscopic techniques, and evaluate their antimicrobial, antioxidant, and cytotoxic activities. A series of novel derivatives of o-aminophenol have been successfully synthesized with very high efficiency through a simple six-step process using readily available chemicals and straightforward reactions. The structures of all products were accurately determined using modern spectroscopic methods such as 1D and 2D NMR, as well as IR, MS spectroscopy, and X-ray methods. The antimicrobial activities of eight o-nitrophenol derivatives were assessed against Gram (-) and Gram (+) bacteria as well as fungi. In comparison, antioxidant activities were tested for two o-nitrophenol and 11 o-aminophenol derivatives using SC50 and EC50 assays. Cytotoxicity was evaluated on KB, HepG2, A549, and MCF7 cancer cell lines. Six synthesized compounds 5b, 5c, 5g, 6b, 6c, 6g exhibited unusual doublet signals in the H8 region of the 1H NMR spectrum, attributed to atropisomer formation. Eight o-nitrophenol derivatives demonstrated weak antimicrobial activity, with MIC values ranging from 100 to 200 μg/mL. Compound 5g showed activity against all tested bacterial and fungal strains. In antioxidant testing, eight o-aminophenol derivatives 6a, 6b, 6c, 6e, 6f, 6h, 6i, and 12b displayed excellent activity, with SC50 values between 18.95 and 34.26 μg/mL, approaching ascorbic acid's SC50 value of 12.60 μg/mL. Three derivatives 6d, 6g, and 12a showed superior antioxidant activity with EC50 values between 4.00 and 11.25 μg/mL, surpassing quercetin's standard of 9.8 μg/mL. Cytotoxicity assays revealed that oaminophenol derivatives 6b, 6c, 6f, 6i, and 12b exhibited moderate inhibitory effects on KB cell lines with IC50 values from 32 to 74.94 μg/mL. Compound 6i demonstrated moderate cytotoxic activity against HepG2, A549, and MCF7 cell lines, with IC50 values of 29.46, 71.29, and 80.02 μg/mL, respectively. Design, synthesis, antimicrobial activity, DPPH Radical Scavenging, Cytotoxic activity, Evaluation of H8 signal anomalies in certain compounds, and Single crystal X-ray diffraction analysis.

Phytochemical investigation of the CH2Cl2 extract from the roots of Garcinia schomburgkiana led to the isolation of two new depsidones, schomburgdepsidones A and B (GS1 and GS2), and one new xanthone, schomburgxanthone A (GS3), along with eight known compounds; oliveridepsidone A (GS4), oliveridepsidone D (GS5), 1,5-dihydroxyxanthone (GS6), nigrolineaxanthone E (GS7), 6-desoxyjacareubin (GS8), aucuparin (GS9), 3-hydroxy-5-methoxybiphenyl (GS10) and methyl-2,6-dihydroxy-4-methoxy-3(3'-methyl-2'-butenyl)-benzoate (GS11). The structures of the three new isolated compounds (GS1–GS3) were elucidated by using 1D- and 2D-NMR spectroscopy. The structures of the known compounds (GS4–GS11) were determined and confirmed by comparison of their 1H and 13C NMR spectroscopic data with previously published data. All 11 compounds were evaluated on the in vitro cytotoxicity against the KB, HeLa S-3, HT-29, MCF-7 and Hep G2 human cancer cell lines, and pancreatic lipase inhibitory activity. The tested compounds mostly showed moderate activities to inactive against the five human cancer cell lines, except for compound GS7 exhibited a good cytotoxicity against the KB, Hela S-3 and MCF-7 cell lines with IC50 values in the range of 3.17–6.07 μM. Compound GS3 showed a good cytotoxic activity against the KB cell line only, with an IC50 value of 8.14 μM. The result of the pancreatic lipase inhibitory activity of 11 compounds possessed moderately active of compounds GS1–GS3, GS7, GS8 and GS11 with IC50 values in the range of 23.71–80.78 μM, while the other tested compounds showed a weak activity (IC50 values >100 μM).

The phytochemical investigation of the CH2Cl2 crud extract from the roots of C. paniculatum Linn. afforded six known compounds, β-sitosterol (1.1), lupeol (1.2), oleanolic aldehyde acetate (1.3), the mixture of stigmasta-4,25-diene-3-one (1.4) and (22E)-stigmasta-4,22,25-trien-3-one (1.5) and (3β)-stigmasta-4,22,25-trien-3ol (1.6). All isolated compounds were tested for their cytotoxicity against KB and HeLa cell lines, oleanolic aldehyde acetate (1.3) showed significant cytotoxic activity against the KB cell line with IC50 value of 9.58 µg/mL. On the other hand, (3β)-stigmasta-4,22,25-trien-3ol (1.6) also exhibited moderate cytotoxic activity against the KB cell line with IC50 value of 13.14 µg/mL. To the best of our knowledge, this is the first report on chemical constituents and biological activity from this plant. The various chromatographic techniques of EtOAc and acetone crude extracts from the bark of W. trichostemon Miq. led to the isolation of a new tirucallane, trichostomonoate (2.1), along with eight known compounds, mangstenone F (2.2), desmethoxy kaunugin (2.3), grandifolinolenenone (2.4), cholest-4-en-6β-ol-3-one (2.5), sapelin E acetate (2.6), α-mangostin (2.7) 11α,20-dihydroxydammar-24-ene-3-one (2.8) and kaempferol (2.9). The new compound (2.1) displayed good potent cytotoxicity against only HeLa cells (IC50 3.8 µg/mL) in the in vitro tumor cell panel and showed moderate cytotoxicity against KB, COLO 205 and LLC cells (IC50 4.4, 5.3 and 5.5 µg/mL, respectively). The isolation and purification of the CH2Cl2, acetone and MeOH extracts from the tuber of B. superba Roxb. yielded the isolation of seven known compounds, β-sitosterol (1.1), 8-O-methylretusin (3.1), (6αR,11αR)-medicarpin (3.2), formononetin (3.3), 2,3-dihydroxypropyl hexacosanoate (3.4), ononin (3.5) and daidzein-7-O-glucoside (3.6). Compound 3.6 displayed moderate cytotoxicity against KB and HepG-2 (IC50 5.32 and 10.13 µg/mL, respectively). In addition, compounds 1.1, 3.1, 3.2, 3.5 and 3.6 were reported for the first time for this plant.

New depsidones and xanthone from the roots of Garcinia schomburgkiana

Context: Thai/Lanna medicinal plant recipes have been used for the treatment of several diseases including oral and cervical cancers.Objective: To investigate anti-proliferative activity on human cervical (HeLa) and oral (KB) cancer cell lines of medicinal plants selected from Thai/Lanna medicinal plant recipe database “MANOSROI III”.Materials and methods: Twenty-three methanolic plant crude extracts were tested for phytochemicals and anti-proliferative activity on HeLa and KB cell lines for 24 h by the sulforhodamine B (SRB) assay at the doses of 1 × 101–1 × 10−6 mg/ml. The nine extracts with the concentrations giving 50% growth inhibition (GI50) lower than 100 µg/ml were further semi-purified by liquid/liquid partition in order to evaluate and enhance the anti-proliferative potency.Results: All extracts contained steroids/triterpenoids, but not xanthones. The methanolic extracts of Gloriosa superba L. (Colchinaceae) root and Albizia chinensis (Osbeck) Merr. (Leguminosae–Mimosoideae) wood gave the highest anti-proliferative activity on HeLa and KB cell lines with the GI50 values of 0.91 (6.0- and 0.31-fold of cisplatin and doxorubicin) and 0.16 µg/ml (28.78- and 82.29-fold of cisplatin and doxorubicin), respectively. Hexane and methanol–water fractions of G. superba exhibited the highest anti-proliferative activity on HeLa and KB cell lines with the GI50 values of 0.15 (37- and 1.9-fold of cisplatin and doxorubicin) and 0.058 µg/ml (77.45- and 221.46-fold of cisplatin and doxorubicin), respectively.Discussion and conclusion: This study has demonstrated the potential of plants selected from MANOSROI III database especially G. superba and A. chinensis for further development as anti-oral and cervical cancer agents.

Cytotoxic arylbenzofuran and stilbene derivatives from the twigs of Artocarpus heterophyllus