Extraction, Purification And Identification Of Organic Small Molecules Of Jellyfish Stomopholus Meleagris

Jellyfish (Stomopholus meleagris), one of edible giant jellyfish species, is widely distributed from the Yellow sea, Bohai Sea, to the Eastern Sea of China. Jellyfish has been consumed in China for more than one thousand years and proved to be of good nutrient and medicinal values by classics of Chinese traditional medicine and modern scientific research. Large quantities of jellyfish is harvested between summer and autumn when the ambient temperature is high. Jellyfish has high water content and is apt to suffer from autolysis afer harvest. So far, jellyfish is mainly processed according to traditional procedures of low yield as a lot of biologically ative constituents were lost during processing which leads to low utilization ratio of the resource and environmental pollution. Thus more and more conerns have been attracted to the efficient comprehensive exploitation of jellyfish. Researchers have reported some macromolecules, such as venom, collagen, peptide, polysaccharide and glycoprotein, and their biological activities from jellyfish while low molecular weight organic components, among which compounds of new structures and unique activities are possibly to be be found, were rarely investigated.For the first time, systemic extaction, separation, purification and structure elucidation were carried out on the low molecular weight natural products of jellyfish (Stomopholus meleagris). Methanol extracts of fresh jellyfish was partitioned successively with petroleum ether, ethyl acetate, and n-butanol. Then silica gel chromatography,flash RP18 silica gel chromatography, Sephadex LH-20 gel filtration and PTLC were performed for the isolation and purification of the compounds, and TLC,¹H NMR,¹³C NMR, DEPT, HMQC, HMBC, 1H1H COSY, NOESY, GC-MS, ESI MS, and chemical derivatization analyses as well as data comparison with reported literatures were applied for the structure elucidation. Thirty-five compounds, of which 22were identified, were isolated and purified from jellyfish (Stomopholus meleagris), and other 43compounds were identified according to the results of GC-MS analysis of all the purified and partially purified compounds. Generally, 65 compounds were identified from jellyfish, among which there were 1 new compound, 3 new natural products while 64 in all were identified fom this species for the first time.The 64compounds are as follows:Compounds identified by NMR:cholesta-8α-methoxyl-22-en-3β, 6β-diol(1), cholesta-5-methoxyl-3, 6-diol(2), cholesterol(3), ergosterol(4), dibatyl phthalate(5), cholesta-5-en-3-hydroxy-7-one(6), eicosanol, 2, 3-dihydroxypropyl ether(7), carboceric acid, 2, 3-dihydroxypropyl ester(8), hexadecanol, 2, 3-dihydroxypropyl ether(9), pentacosanol, 2, 3-dihydroxypropyl ether(10), cholesta-5-en-3,7β-diol (11), choleta-5-en-3β,7α-diol (12), cholesta-6-methoxyl-3, 5-diol(13), 1α-butoxy, 2-desoxyribose(14), thymine(15), 2'-O-methyluridine(16), uracil(17), 2'-deoxythymidine(18), 2'-deoxyuridine(19), uridine(20), glycerol(21), phenyl- alanine(22) ,Compounds identified by GC-MS: cholesta-4-en-3-one(23), 24-nor-22, 23-methylenecholest-5-en-3β-ol TMS ether(24), cholestanol(25), stigmasterol(26), sitosterol(27), stigmasta-5, 24(28)-dien-3β-ol(28) cholesta-4-en-3-one(29), ergosta-5, 24-dien-3β-ol(30), ergosta-5-en-3β-ol(31), ergosta-5, 22-dien-3β-ol(32) , 26, 27-dinorergosta-5, 22-dien-3β-ol(33), 27-norergosta-5, 22-dien-3β-ol(34), ergostanol(35), 20-methyl-pregn-20-en-3β-ol(36), cholesta-7-en-3-one(37), cholesta-3, 5-diene-7-one(38), cholesta-3, 5-diene, 3-hydroxy- pregn-5en-20-one(39), cholesta-3, 6-dione(40), 5α, 6α-epoxy-cholestan-3β-ol(41), 26-nor- cholesten-5- en-3β-ol-25-one(42), cholest- 8(14)-en-3-one(43) ,cholesta-5,24-dien-3-ol(44),tetradecanoic acid,2-hydroxy-1- [hydroxymethyl]ethyl ester(45), Octadecanoic acid,2-hydroxy-1- [hydroxymethyl]ethyl ester(46), hexadecanoic acid, 2, 3-bis {[trimethylsilyl]oxy}propyl ester(47), [Z]-9-octadecanoic acid, 2-hydroxy- 1-[hydroxymethyl]ethyl ester(48), [Z]-9-octadecanoic acid, 2, 3-dihydroxypropyl ester(49), 1, 2, 3 , 5-tetrakis-o- [trimethylsilyl] -arabinofuranose(50), [E]-11-hexadecenal(51), squalene(52), tetradecanal(53), [Z]-10-pentadecen-1-ol(54), [Z]-9-hexadecen-1-ol(55), [E]-9-octadecen-1-ol(56), [Z]-13-octadecenal(57), cis-11-hexadecenal(58), [Z]-14-Tricosenyl formate (59), oleyl alchohol(60), otadecenamide(61), hexadecanamide(62), dodecanamide(63), [Z]-13-docosenamide(64), [Z]-9-dtadecenamide(65).The results showed jellyfish Stomopholus meleagris contains sterols, nucleosides, glycerylethers, glycerylesters, long-chain aliphatic alcohols, and long-chain amides. After structure searching on SciFinder cholesta-8-methoxyl-22-en-3, 6-diol was found to be a new compound, cholesta-5-methoxyl-3, 6-diol, 1α-butoxy, 2-desoxyribose and 1β-butoxy, 2-desoxyribose were found to be new natural products. For the first time sterols with methoxyl, seldom reported from marine animals, were found in our research and 3 of them were identified.Our research supplied useful fundamental chemical data of micromolecular compositon of jellyfish Stomopholus meleagris, which may contribute to further study of biologically active functional factors and exploitation of jellyfish (Stomopholus meleagris) .