The title compound, 16-epi-latrunculin B (3), has been isolated from the sponge Negombata magnifica collected from the Red Sea near Hurghada, Egypt. This new natural product was determined to be an epimer of latrunculin B (1), which was found in the same sponge collection. The structure of 3 was initially deduced from proton and carbon NMR chemical shift trends and proton-proton nuclear Overhauser effect experiments. The cytotoxicity (murine tumor and normal cell lines) and antiviral (HSV-1) properties of 3 and 1 were determined. A computational study applicable to this class of stereochemical problems was then investigated. Specifically, the complete set of vicinal and allylic coupling constants was calculated for each of the four diastereomers whose configurations differed at C(8) and C(16). These computed J's were then compared with the experimental J values (28 in number) determined for 1 and 3. This analysis resulted in the same assignment of relative configuration for compound 3 reached using the more classical methods. The validity of the method is established by the fact that the 28 computed coupling constants for (known) 1 and (newly determined) 3 varied from the experimental J values with an average of just 0.57 and 0.53 Hz, respectively. This strategy represents a general, powerful, and readily adoptable tool for determining the relative configuration of complex molecules.
Cytotoxicity-guided fractionation of the alcohol extract of the brown alga, Cystoseira myrica, afforded four new cytotoxic hydroazulene diterpenes, dictyone acetate (2), dictyol F monoacetate (4), isodictytriol monoacetate (6), and cystoseirol monoacetate (8), together with two known cytotoxic hydroazulene diterpenes, pachydictyol A (1) and dictyone (3). The constitution of each isolated compound has been determined on the basis of spectroscopic and chemical evidence.
Background:Higher plants are considered as a well-known source of the potent anticancer metabolites with diversity of chemical structures. For instance, taxol is an amazing diterpene alkaloid had been lunched since 1990.Objective:To isolate the major compounds from the fruit extract of Cucumis prophetarum, Cucurbitaceae, which are mainly responsible for the bioactivities as anticancer.Materials and Methods:Plant material was shady air dried, extracted with equal volume of chloroform/methanol, and fractionated with different adsorbents. The structures of obtained pure compounds were elucidated with different spectroscopic techniques employing 1D (1H and 13C) and 2D (COSY, HMQC and HMBC) NMR (Nuclear Magnetic Resonance Spectrometry) and ESI-MS (Eelectrospray Ionization Mass Spectrometry) spectroscopy. The pure isolates were tested towards human cancer cell lines, mouse embryonic fibroblast (NIH3T3) and virally transformed form (KA3IT).Results:Two cucurbitacins derivatives, dihydocucurbitacin B (1) and cucurbitacin B (2), had been obtained. Compounds 1 and 2 showed (showed potent inhibitory activities toward NIH3T3 and KA31T with IC50 0.2, 0.15, 2.5 and 2.0 μg/ml, respectively.Conclusion:The naturally cucurbitacin derivatives (dihydocucurbitacin B and cucurbitacin B) showed potent activities towards NIH3T3 and KA31T, could be considered as a lead of discovering a new anticancer natural drug.
Bioassay-guided fractionation of the extract of Jamaican marine sponge Plakortis sp. followed by preparative TLC and HPLC yielded several known methyl ester cyclic peroxides (1a, 2a, 3a, 4, 5), known plakortides (6,7), known bicyclic lactone (8) and new cyclic peroxide acids (1b, 2b, 3b). The chemical structures were elucidated by extensive interpretation of their spectroscopic data. These natural products showed remarkable in vitro cytotoxicity against several cancer cell lines.
This study revealed a differential cytotoxic activity of the petroleum ether extract (IC₅₀ =5 μg/mL) of the resinous exudates of Commiphora molmol against two mouse cell lines KA31T and NIH3T3 (untransformed and transformed mouse fibroblasts, respectively). Four new compounds (1-4) and five known compounds (5-9) were isolated from the petroleum ether extract. The identity of these new compounds was determined as γ-elemane lactone (1), 5-αH,8-βH-eudesma-1,3,7(11)-trien-8,12-olide (2), 2-hydroxy-11,12-dihydrofuranodiene (3), and 2-hydroxyfuranodiene (4). 1 and 2 displayed the highest cytotoxic activity against NIH3T3 cells. 7 and 9 exhibited moderate cytotoxic activity against KA31T cells. Compounds 3-6 showed weak cytotoxic activities against both cell lines. These results may explain the high efficacy of the petroleum ether fraction in several myrrh-derived pharmaceutical preparations.
Plant disease administration is difficult due to the nature of phytopathogens. Biological control is a safe method to avoid the problems related to fungal diseases affecting crop productivity and some human pathogenic bacteria. For that, the antimicrobial activity of the seaweed Sargassum muticum methanol and water extracts were investigated against human bacterial pathogens and fungal plant pathogens. By using 70 percent methanol, the seaweed powder was extracted, feeding additives assay, ultrastructure (TEM). Results revealed significant inhibition of S. muticum methanol extract against Salmonella typhi (25.66 mm), Escherichia coli (24.33 mm), Staphylococcus aureus (22.33 mm) and Bacillus subtilis. (19.66 mm), some fungal phytopathogens significantly inhibited Fusarium moniliforme (30.33mm), Pythium ultimum (26.33 mm), Aspergillus flavus (24.36mm), and Macrophomina phaseolina (22.66mm). Phytochemical investigation of S. muticum extract showed the presence of phenolic and flavonoid compounds. Results suggested that there is an appreciable level of antioxidant potential in S. muticum (79.86%) DPPH scavenging activity. Ultrastructural studies of Fusarium moniliforme hypha grown on a medium containing S. muticum extract at concentration 300mg/ml showed a thickening cell wall, disintegration of cytoplasm, large lipid bodies and vacuoles. In conclusion, our study revealed The antibacterial activity of S. muticum extract significantly against some Gram positive, Gram negative bacteria and antifungal activity against some phytopathogenic and some mycotoxin producer fungi. Flavonoids, phenolic play an important role as antioxidants and antimicrobial properties. Such study revealed that S. muticum methanol extract could be used as ecofriendly biocontrol for phytopathogenic fungi and feeding additives to protect livestock products.
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