Elucidation of flavonoids from potent Iranian Scutellaria species against Influenza A (H1N1) virus.

Objectives: Influenza A virus (IAV) is a contagious illness. Different species of Scutellaria genus are used as a traditional remedy to reduce influenza symptoms. This study aimed to investigate the anti-influenza capacity of several species of Iranian Scutellaria and identify active compounds of the most potent species for the first time. Materials and Methods: Some Iranian species of Scutellaria were collected from different regions of Iran, including S. pinnatifida with mucida, viridis, and alpina subspecies; S. tournefortii; S. tomentosa; S. persica. They were fractionated to chloroform and methanol. The total phenols and flavonoids of samples were examined by the folin-ciocalteau and aluminum-flavonoid complex methods, respectively. The 50% cytotoxic concentrations (CC50) on MDCK cells and non-cytotoxic concentrations (NCTC) were determined by MTT assay. The percentage of cell protection against IAV and their effect on virus titer were investigated in pre-, post-, and co-penetration treatment groups. Phytochemicals of the most effective species were isolated by various chromatographic methods and identified by different spectroscopic methods. Results: Methanol fraction of S. pinnatifida subsp. viridis demonstrated the highest amounts of flavonoid content and best activity against influenza A virus in all combination treatments, which reduced the virus titer by 5 logs with no cytotoxicity. Kaempferol-3-O-glucoside, quercetin-3-O-glucoside, apigenin-4'-methoxy-7-O-glucoside, luteolin, and luteolin-7-O-glucoside were purified and identified from this species. Conclusion: Scutellaria pinnatifida subsp. viridis can be introduced as a source of flavonoids with acceptable anti-influenza activity. S. tomentosa also showed potent antiviral effects and is a candidate for elucidation in further studies.

Trigonella teheranica: a valuable source of phytochemicals with antibacterial, antioxidant and cytotoxic properties.

Trigonella genus is a member of Fabaceae family, which is used as medicinal plant. The aim of this study was investigation of phytochemicals and some biological activities of Trigonella teheranica for the first time. The essential oils (EOs) of different parts (leaves, fruits and roots) were obtained and analyzed by GC-MS. Also, their chloroform and methanol extracts were prepared, too. The antimicrobial effects, antioxidant activities and cytotoxic effects against cancer (MDA-MB-231, MRC5 and HT-29) cell lines were investigated. N-hexadecanoic acid was the major compound of leaves and fruits EOs, and hexanal was abundant component of roots EO. The extracts showed stronger antibacterial effects than volatile oils against Gram-positive bacteria such as Staphylococcus aureus and Bacillus subtilis. All methanol extracts showed strong antioxidant effects, while the volatile oils, especially of leaves was the most effective in cytotoxic assay. Also, three derivatives of coumaric acid were isolated and identified from T. teheranica.

Potential antiviral effects of some native Iranian medicinal plants extracts and fractions against influenza A virus.

BACKGROUND: Influenza A virus (IAV) infection is a continual threat to the health of animals and humans globally. Consumption of the conventional drugs has shown several side effects and drug resistance. This study was aimed to screen some Iranian medicinal plants extracts and their fractions against influenza A virus. METHODS: Glycyrrhiza glabra (rhizome), Myrtus commonis (leaves), Melissa officinalis (leaves), Hypericum perforatum (aerial parts), Tilia platyphyllos (flower), Salix alba (bark), and Camellia sinensis (green and fermented leaves) were extracted with 80% methanol and fractionated with chloroform and methanol, respectively. The cytotoxicity of the compounds were determined by MTT colorimetric assay on MDCK cells. The effective concentrations (EC50) of the compounds were calculated from the MTT results compared to the negative control with no significant effects on cell viability. The effects of EC50 of the compounds on viral surface glycoproteins and viral titer were tested by HI and HA virological assays, respectively and compared with oseltamivir and amantadine. Preliminary phytochemical analysis were done for promising anti-IAV extracts and fractions. RESULTS: The most effective samples against IAV titer (P ≤ 0.05) were crude extracts of G. glabra, M. officinalis and S. alba; methanol fractions of M. communis and M. officinalis; and chloroform fractions of M. communis and C. sinensis (fermented) mostly in co- and pre-penetration combined treatments. The potential extracts and fractions were rich in flavonoids, tannins, steroids and triterpenoids. CONCLUSION: The outcomes confirmed a scientific basis for anti-influenza A virus capacity of the extracts and fractions from the selected plants for the first time, and correlated their effects with their phytochemical constituents. It is worth focusing on elucidating pure compounds and identifying their mechanism(s) of action.

The Effect of Garlic Tablets on the Endometriosis-Related Pains: A Randomized Placebo-Controlled Clinical Trial.

Endometriosis is a common chronic inflammatory disease. Garlic contains components that have antiproliferative, anti-inflammatory, and antioxidative effects. The current study aimed to evaluate the effectiveness of garlic on endometriosis symptoms. This was a randomized placebo-controlled triple-blind clinical trial. A convenience sample of 60 women was randomly allocated into two groups. The intervention group received usual care supplemented with 400 mg garlic tablets, and the placebo group received identical placebo tablets. A four-part Visual Analogue Scale (VAS) was used to measure the severity of pains. The pains were measured on four occasions (before the intervention and on one-, two-, and three-month follow-ups). Data were analyzed using the t-test, chi-square, repeated measures ANOVA, and ANCOVA by SPSS 16. The overall severity of pain reduced from 6.51 ± 0.86 to 1.83 ± 1.25 in the intervention group (p < 0.05). It increased from 6.41 ± 1.12 to 6.65 ± 1.37 in the control group (p = 0.02). The repeated measures ANOVA showed that there is a significant difference in the change of pain scores between intervention and control groups (p < 0.001, np2 = 0.572). Garlic extract can reduce pelvic and back pain, dysmenorrhea, and dyspareunia which are important symptoms of endometriosis.

Possible potential of Astrodaucus genus in development of anticancer drugs.

OBJECTIVE: Many pharmaceutical factories have dramatically improved the quality of herbal remedies in cancer treatment. The results of somestudies have shown anticancer effect of Astrodaucus genus. Therefore, the aim of this article was to review the chemical ingredients and biological effects of Astrodaucus genus especially A. persicus from the family Apiaceae (Umbelliferae). MATERIALS AND METHODS: Online databases ScienceDirect, PubMed, Scopus, and Google Scholar were searched using the keywords Astrodaucus, Apiaceae, Biologic, Phytochemistry, and Benzodioxole to retrieve studies published between 1970 and 2020. RESULTS: The Astrodaucus genus has two species, Astrodaucus persicus (Boiss.) Drude and Astrodaucus orientalis (L.) Drude. In this genus, 5 new biologically active phytochemicals with benzodioxole structure were introduced and their biological effects were assessed. CONCLUSION: Since many of the most commonly used anticancer drugs such as etoposide, teniposide, podophyllotoxin and sanguinarine have benzodioxole structureand according to the results of biological tests, it seems that more researchwith these perspectives should be done on this genus.

Cuminum cyminum fruits as source of luteolin- 7-O-glucoside, potent cytotoxic flavonoid against breast cancer cell lines.

Cuminum cyminum is famous for its spicy fruits used for culinary and therapeutic properties worldwide. Brine shrimp test was performed for detecting cytotoxic fractions and subfractions. Ethyl acetate (EA) and hexane (HE) fractions demonstrated LC50 of 52.40 and 60.77 µg/ml against Artemia salina while other fractions showed no toxicity (LC50> 500 µg/ml). Bioguided elucidation of EA and HE fractions were carried out and cytotoxicity of pure compounds were investigated against breast cancer cell lines (MCF-7 and MDA-MB-231) and normal cell line (NIH/3T3) by MTT assay. Four flavone structures as luteolin, apigenin, luteolin-7-O-glucoside and apigenin-7-O-glucoside from EA and cuminoid A from HE were purified and identified. Luteolin-7-O-glucoside demonstrated potent anticancer activities against MCF-7 cell line (IC50 of 3.98 µg/ml) with selectivity index of 8.0. In conclusion, flavonoids especially luteolin-7-O-glucoside play a significant role in cytotoxic effect of C. cyminum fruits and can be introduced as candidate for chemopreventive and chemotherapeutic drugs.

Strong insecticidal potential of methanol extract of Ferulago trifida fruits against Anopheles stephensi as malaria vector.

Many researchers have focused on controlling pest insects and vectors by natural products because of their low environmental pollution. The present study was conducted to evaluate the antioxidant and larvicidal activities of chloroform and methanol extracts of the leaves, fruits, roots, and isolated coumarin compounds (prantschimgin, oxypeucedanin, and 6-hydroxymethylherniarin) of Ferulago trifida from the Apiaceae family against Anopheles stephensi as one of the main malaria vectors. For insecticidal evaluation, A. stephensi larvae were exposed to different concentrations of the extracts and pure compounds (0.625-1280 ppm) according to the WHO protocol. The mortality percentages were measured 24 h after treatment and lethal concentration values were calculated. In addition, radical scavenging activities of the mentioned extracts and compounds were measured by the DPPH method. The methanol extract of fruits showed potent insecticidal properties with LC50 and LC90 values of 2.94 and 18.12 ppm, respectively. The chloroform extracts of the fruits and leaves were the second and third extracts with larvicidal effects. Among pure compounds, only oxypeucedanin showed moderate toxicity against A. stephensi with LC50 and LC90 values of 116.54 and 346.41 ppm, respectively. The antioxidant activities of the methanol extracts of leaves and fruits were stronger than other extracts with IC50 values of 155.83 and 159.32 ppm, respectively. In conclusion, the methanol extract of F. trifida fruits can be used as a potent bio-insecticide in green control programs of mosquitoes, especially A. stephensi.

Antimalarial and cytotoxic activities of roots and fruits fractions of Astrodaucus persicus extract.

OBJECTIVES: Astrodaucus persicus (Apiaceae) is one of the two species of this genus which grows in different parts of Iran. Roots of this plant were rich in benzodioxoles and used as food additive or salad in Iran and near countries. The aim of present study was evaluation of antimalarial and cytotoxic effects of different fractions of A. persicus fruits and roots extracts. MATERIALS AND METHODS: Ripe fruits and roots of A. persicus were extracted and fractionated by hexane, chloroform, ethyl acetate and methanol, separately. Antimalarial activities of fractions were performed based on Plasmodium berghei suppressive test in mice model and percentage of parasitemia and suppression were determined for each sample. Cytotoxicity of fruits and roots fractions were investigated against human breast adenocarcinoma (MCF-7), colorectal carcinoma (SW480) and normal (L929) cell lines by MTT assay and IC50 of them were measured. RESULTS: Hexane fraction of roots extract (RHE) and ethyl acetate fraction of fruits extract (FEA) of A. persicus demonstrated highest parasite inhibition (73.3 and 72.3%, respectively at 500 mg/kg/day) which were significantly different from negative control group (P<0.05). In addition, RHE showed potent anticancer activities against MCF-7 (IC50 of 0.01 µg/ml), SW480 (IC50 of 0.36 µg/ml) and L929 (IC50 of 0.70 µg/ml) cell lines. CONCLUSION: According to the results, RHE and FEA fractions of A. persicus could be introduced as excellent choice for antimalarial drug discovery. In addition, cytotoxic activity of RHE was noticeable.

Astrodaucus persicus as a new source of bioinsectisides against malaria vector, Anopheles stephensi.

OBJECTIVE: To determine the larvicidal activities of petroleum ether, chloroform, ethyl acetate and methanol fractions of roots and fruits extracts of Astrodaucus persicus from Apiaceae family against malaria vector, Anopheles stephensi (An. stephensi). METHODS: Twenty five third instar larvae of An. stephensi were exposed to various concentrations (10-160 g/L) of fractions and were assayed according to World Health Organization protocol. The larval mortality was calculated after 24 h treatment. RESULTS: Among tested fractions, the highest larvicidal efficacy was observed from ethyl acetate fraction of fruits extract with 50% and 90% mortality values (LC50 and LC90) of 34.49 g/L and 108.61 g/L, respectively. Chloroform fraction of fruits extract was the second larvicidal sample with LC50 of 45.11 g/L and LC90 of 139.36 g/L. Petroleum ether fractions of fruits and roots and methanol fraction of fruits showed moderate toxicity against An. stephensi. CONCLUSIONS: Astrodaucus persicus is a potential source of valuable and natural larvicidal compounds against malaria vector, An. stephensi and can be used in mosquitoes control programs as an alternative to synthetic insecticides.

Securigenin glycosides as hypoglycemic principles of Securigera securidaca seeds.

Seeds of Securigera securidaca (Fabaceae) are used in Iranian folk medicine as an antidiabetic treatment. In this study, the antihyperglycemic activity of chloroform and methanol fractions (CF and MF) from S. securidaca seed extract was investigated and their bioactive constituents were identified. The antidiabetic effects of fractions were assessed by streptozocin-induced diabetic Naval Medical Research Institute mice. The hypoglycemic activity of MF at 100 mg/kg and CF at 400 mg/kg was comparable with glibenclamide (3 mg/kg). MF at 400 mg/kg and CF at 600 mg/kg showed equal hypoglycemic responses to 12.5 IU/kg insulin (P > 0.05). Three cardiac glycosides were isolated as active constituents responsible for the hypoglycemic activity. Securigenin-3- O -ß-glucopyranosyl-(1 â†’ 4)-ß-xylopyranoside (1) was a major compound in seeds. Securigenin-3- O -inositol-(1 â†’ 3)-ß-glucopyranosyl-(1 â†’ 4)-ß-xylopyranoside (2) and securigenin-3- O -α-rhamnopyranosyl-(1 â†’ 4)-α-glucopyranoside (3) were found as new natural products. When 1-3 were tested at 10 mg/kg there was a significant reduction of blood glucose levels in diabetic mice, comparable to that of 3 mg/kg glibenclamide (P > 0.05). The hypoglycemic effect was due to an increase in insulin secretion; the insulin levels in the diabetic mice significantly improved and were comparable with those in healthy animals (P > 0.05). Compounds responsible for the hypoglycemic properties of S. securidaca seeds were identified as cardiac glycosides and were found to act via an increase of insulin levels in a diabetic mouse model.

New Benzodioxole Compounds from the Root Extract of Astrodaucus persicus.

There are many efforts for identification of natural compounds from dietary or medicinal plants. Young roots and aerial parts of A. persicus have been used as food additive or salad vegetable in some parts of Iran. In this study, different fractions of the root extract of A. persicus were subjected for isolation and purification of secondary metabolites. The methanol extract of the roots was fractionated with hexane (HE), chloroform (CL), ethyl acetate (EA) and methanol (ME). Five novel compounds were isolated from HE, CL and EA using different chromatographic techniques and were identified by 1H-NMR, 13C-NMR, 2D-NMR and MS spectroscopic methods. Elucidated compounds with benzodioxole structure were characterized for the first time as 5-((propanoyl methyl)amino)-4,7-dimethoxybenzo[d][1,3]dioxole (1), 5-(3-ethyloxiran-2-yloxy)-4,7-dimethoxybenzo[d][1,3]dioxole (2), 4,7-dimethoxy-5-(propanonyl) benzo[d][1,3]dioxole (3), 4-ethoxybenzo[d][1,3]dioxol-6-carbaldehyde (4), and 4-(O-ß-D-glucopyranosyl)-6-(3-propanyloxiran-2-yloxy)benzo[d][1,3]dioxole (5).

The Comparison of vaginal cream of mixing yogurt, honey and clotrimazole on symptoms of vaginal candidiasis.

BACKGROUND: Vulvovaginal candidiasis is known as one of the most common fungal infection among women of reproductive age and considered as an important public health problem. In recent years, due to resistance to common antifungal medication, the use of traditional medicine of anti-fungal and herbal treatment increased. Therefore the objective of this study was to determine the effects of vaginal cream, mixture of yogurt and honey and comparing it with clotrimazole vaginal cream on symptoms of Vulvovaginal candidiasis in patients. METHODS: In this randomized, triple blind clinical trial of 70 non-pregnant women infected with Candidal vulvovaginitis were placed in two groups of Vaginal cream mixed of yogurt and honey recipients (N=35) and clotrimazole vaginal cream (N=35). Both groups were treated for 7 days. At the beginning of study, Clinical and laboratory signs and symptoms were registered 7 and 14 days after treatment by questionnaire, observation form and secretions culture results. Data by chi-square test, t test, McNemar tests were analyzed by SPSS version 21. Significance level of 0.05 was considered. RESULTS: The result of present study reveals the significant differences in symptom improvement of ' yogurt and honey, than clotrimazole group (P<0.05) and also Positive results of the first cultures (one week after treatment) in "yogurt and honey" and clotrimazole (20% versus 8.6%) and second time cultivation (14 days after treatment) (17/1% versus 8.6%) were similar and there was no significant differences between the two groups. (P>0.05) CONCLUSION: This study indicated that he therapeutic effects of vaginal cream, yogurt and honey is not only similar with clotrimazole vaginal cream but more effective in relieving some symptoms of vaginal candidiasis. Therefore, the use of this product can be suggested as an herbal remedy for candida infection treatment.