, , OHa bFrom Sargassum ilicifolium dH Assignment determined by comparison with our data from Sargassum ilicifolium. Original assignment in parentheses Chemical shift determined from the HSQC spectrumalcohol . Djerassi and coworkers synthesized both C epimers of stigmasta,dienbol and proved that the sample of Ikekawa was a mixture of both isomers . Isolations from living organisms were reported from the marine sponge Haliclona spfrom the perennial herbaceous plant Saxifraga montana H. and other folks. In , stigmasta,dienbol was isolated in the PubMed ID:https://www.ncbi.nlm.nih.gov/pubmed/22922283 Chinese brown alga Sargassum thunbergii by the group of Guo . The present report describes t
he very first isolation of stigmasta,dienbol from the brown alga S. ilicifolium. In an antimicrobial agar diffusion test, the crude 
extract of S. ilicifolium was identified to become very active against the Gramnegative bacteria Shigella boydii and Klebsiella oxytoca, the Grampositive bacteria Streptococcus pneumoniae and Staphylococcus aureus, as well as the yeasts Candida membranaefaciens, Trichosporon mucoides, and Cryptococcus neoformans (Table). Important activity was also observed against the Gramnegative bacterium Enterobacter cloacae and the Grampositive bacterium Bacillus cereus. No activity was found against the Gramnegative bacteria Pseudomonas aeruginosa, Escherichia coli, Salmonella enteridis, and also the yeast Candida albicans Sargassum incisifolium The brown alga Sargassum incisifolium was extracted with ethyl acetate. The ethyl [D-Ala2]leucine-enkephalin acetate extract was adsorbed onsilica gel and subjected to flash chromatography with diethyl ether and after that methanol. Purification on the diethyl ether fraction by column chromatography afforded fucosterol . The methanol fraction was subjected to normalphase column chromatography to give two fractions. Fraction afforded a mixture of inseparable monogalactosyldiacylglycerols bearing fatty acid side chains with only few olefinic groups based on the intensity of vinylic signals within the H NMR spectrum. Fraction was further purified by reversedphase HPLC applying THF O (::) as mobile phase to afford OpalmitoylOstearidonoylObDgalactopyranosylglycerol (Fig.) as an amorphous gum. The M NH peak at mz . and the M NH Na H peak at m z . within the ESImass spectrum of in mixture using the number and intensity of H and C NMR signals led for the molecular formula CHO. In accordance with ESI mass spectrometry minor amounts of various other monogalactosyldiacylglycerols bearing fatty acids using a reduced 
degree of unsaturation are present inside the mixture. This corresponds to findings of Marcolongo et al. who investigated the monogalactosyldiacylglycerol fraction isolated in the thermophilic bluegreen alga Phormidium sp. ETS and identified palmitic acid and stearidonic acid as principal acyl elements during their fatty acid analysis by GC . The IR spectrum of exhibited absorption bands corresponding to ML281 biological activity hydroxyl (cm) and carboxylic ester Table Position , , aM. P. Rahelivao et al. C NMR spectroscopic data of From Sargassum ilicifolium dC (MHz, CDCl) (C)Assignment depending on comparison with our information from Sargassum ilicifolium. Original assignment in parentheses(cm) groups. The D and D NMR spectra of displayed signals for any carbon chain bearing 4 methyleneinterrupted double bonds, a saturated carbon chain, a sugar moiety, a glycerol unit, and two carbonyl groups. The sugar residue could be identified as bDgalactose by comparison in the C NMR shifts with those of many sugars listed in Ref. along with the standard prot., , OHa bFrom Sargassum ilicifolium dH Assignment based on comparison with our data from Sargassum ilicifolium. Original assignment in parentheses Chemical shift determined in the HSQC spectrumalcohol . Djerassi and coworkers synthesized each C epimers of stigmasta,dienbol and proved that the sample of Ikekawa was a mixture of both isomers . Isolations from living organisms were reported in the marine sponge Haliclona spfrom the perennial herbaceous plant Saxifraga montana H. and others. In , stigmasta,dienbol was isolated from the PubMed ID:https://www.ncbi.nlm.nih.gov/pubmed/22922283 Chinese brown alga Sargassum thunbergii by the group of Guo . The present report describes t
he very first isolation of stigmasta,dienbol from the brown alga S. ilicifolium. In an antimicrobial agar diffusion test, the crude extract of S. ilicifolium was located to be very active against the Gramnegative bacteria Shigella boydii and Klebsiella oxytoca, the Grampositive bacteria Streptococcus pneumoniae and Staphylococcus aureus, and the yeasts Candida membranaefaciens, Trichosporon mucoides, and Cryptococcus neoformans (Table). Significant activity was also observed against the Gramnegative bacterium Enterobacter cloacae along with the Grampositive bacterium Bacillus cereus. No activity was identified against the Gramnegative bacteria Pseudomonas aeruginosa, Escherichia coli, Salmonella enteridis, plus the yeast Candida albicans Sargassum incisifolium The brown alga Sargassum incisifolium was extracted with ethyl acetate. The ethyl acetate extract was adsorbed onsilica gel and subjected to flash chromatography with diethyl ether and after that methanol. Purification with the diethyl ether fraction by column chromatography afforded fucosterol . The methanol fraction was subjected to normalphase column chromatography to offer two fractions. Fraction afforded a mixture of inseparable monogalactosyldiacylglycerols bearing fatty acid side chains with only few olefinic groups according to the intensity of vinylic signals in the H NMR spectrum. Fraction was additional purified by reversedphase HPLC making use of THF O (::) as mobile phase to afford OpalmitoylOstearidonoylObDgalactopyranosylglycerol (Fig.) as an amorphous gum. The M NH peak at mz . along with the M NH Na H peak at m z . within the ESImass spectrum of in combination together with the quantity and intensity of H and C NMR signals led towards the molecular formula CHO. As outlined by ESI mass spectrometry minor amounts of several other monogalactosyldiacylglycerols bearing fatty acids with a lower degree of unsaturation are present inside the mixture. This corresponds to findings of Marcolongo et al. who investigated the monogalactosyldiacylglycerol fraction isolated from the thermophilic bluegreen alga Phormidium sp. ETS and identified palmitic acid and stearidonic acid as major acyl elements during their fatty acid analysis by GC . The IR spectrum of exhibited absorption bands corresponding to hydroxyl (cm) and carboxylic ester Table Position , , aM. P. Rahelivao et al. C NMR spectroscopic information of From Sargassum ilicifolium dC (MHz, CDCl) (C)Assignment based on comparison with our data from Sargassum ilicifolium. Original assignment in parentheses(cm) groups. The D and D NMR spectra of displayed signals for a carbon chain bearing 4 methyleneinterrupted double bonds, a saturated carbon chain, a sugar moiety, a glycerol unit, and two carbonyl groups. The sugar residue may very well be identified as bDgalactose by comparison in the C NMR shifts with these of various sugars listed in Ref. plus the common prot.