Study On Lipid-soluble Ingredients And Their Bioactivities From Agarwood Originating From Gyrinops Salicifolia

Gyrinops salicifolia Ridl, an evergreen tree from Gyrinops genus in Thymelaeaceae family, is mainly distributed in East , Southeast Asia and Indonesian Islands . There are eight species in Gyrinops genus. Gyrinops salicifolia can produce agarwood as plants from Gyrinops genus. Many bioactive chemical constitutes studies on agarwood originating from plants from Aquilaria, (Aquilaria sinensis, Aquilaria malaccensis, Aquilaria crassna Pierre ex Lecomte) were reported.However, the report about bioactive chemical constitutes studies on agarwood originating from Gyrinops salicifolia is less in the domestic and overseas. In order to enrich the chemical constitutes of agarwood, find the bioactive compounds, and provide the scientific evidence for the development and utilization of agarwood resources,bioactive chemical constituents studies on agarwood originating from Gyrinops salicifolia were conducted.Thirty-nine compounds were isolated from the agarwood originating from Gyrinops salicifolia Ridl by column chromatography. Their structures were identified as :2-[2-(4-hydroxybenzene)ethyl]chromone (1), 7-hydroxy-2-(2-phenylethyl)chromone (2),8-chloro-6-hydroxy-2-(2-phenylethyl)chromone (3),6-hydroxy-7-methoxy-2-[2-(4-methoxybenzene)ethyl]chromone (4), 6,8-dihydroxy-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]chromone (5), 5-hydroxy-6-methox-2-(2-phenylethyl)-4H-1-benzopyran-4-one (6),7-hydroxy-6-methoxy-2-(2-phenylethyl)chromone (7), 6-methoxy-2-[2-(4-methoxyphenyl)ethyl]chromone (8), 6-hydroxy-7-methoxy-2-[2-(2-hydroxy-3-methoxybenzoyl)ethyl]chromone (9), (5S, 6S,7S,8R)-2-[2-(4-methoxyphenyl)ethyl]-5,6,7,8-tetrahydroxy-5,6,7,8-4-ketones (10), 5?,6?,7?,8?-(4-methoxy-2-phenylethyl)-5,6,7,8-tetrahydro-chromone (11),5?, 6/?, 7?-trihydroxy-8a-methoxy-2-(2-phenylethyl)-4-hydro-chromone (12), (5S,6R,7S)-5,6,7-trihydroxy-2-(3-hydroxy-4-methoxyphenethyl)-5,6,7,8-tetrahydro-4H-chromen-4-One (13),rel-(1aR,2R,3R,7bS)-1a,2,3,7b-tetrahydro-2,3-dihydroxy-5-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-7H-oxireno[f][1]benzopyran-7-one (14), rel-(1aR,2R,3R,7bS)-1a,2,3,7b-tetrahydro-2,3-dihydroxy-5-(2-phenylethyl)-7H-oxireno[f][1]benzopyran-7-one(15), 5-hydroxy-2- [2- (3-hydroxy-4-methoxybenzene) vinyl] chromone (16), 5,6:7,8-diepoxy-2-(2-phenylethyl)-5,6,7,8-tetrahydrochromone (17), (R)-6,7-dimethoxy-2-(2?hydroxy-2-phenylethyl)chromone (18), 6,7-dimethoxy-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]chromone (19), (3',6)-dihydroxy-4-methoxy-2-(2-phenyl)ethylchromone (20), 6-hydroxy-7-methoxy-2-[2-(3,4-hydroxyphenyl)ethyl]chromone (21), (5S,6S,7S,SR)-2-[2-(4-methoxyphenyl)ethyl]-5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone (22),Gyrinops salicifolia Ridl new polymerl A (23), Gyrinops salicifolia Ridl new polymer 1 B (24),2-(8,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalen-2-yl)propan-1-ol (25),1,5?dimethyl-3-(prop-1 -en-2-yl)decahydronaphthalen-l-ol (26), (1b,4ab,7b,8ab)-octahydro-7-[1-(hydroxymethyl)ethenyl]-1,8a-dimethylnaphthalen-4a(2H)-ol(1b,4ab,7b,8ab)-decahydro-4a-hydroxy-8,8a-dimethyl-a-methylidenenaphthalene-2-ethanol (27),rel-(2R 8S,8aR)-2-(1,2,3,5,6,7,8,8a-octahydro-8,8u-dimethyl-2-muphthyl)-prop2-en-1(28),(-)-rotundone (29), (+)-5-epi-aristolochene (30), eremophilanes-9-diene-11,12-diol (31),rel-3R,7R,9R,10S)-9,10-dimethyl-6-methylene-4-oxatricyclo[7.4.0.03'7] (32),1,5;8,12-diepoxy-guaia-12-one (33), 9?-hydroxy-selina-4,11-dien-14-al (34), Curcumol enol (35),(rel)-4?,5?,7?-eremophil-9-en-12,8?-olide (36), (2R)-d-cadin-4-ene-2,10-diol (37),?-sitosterol (38),Stigmasterol (39).Among the thirty-nine compounds, twenty-four compounds were 2-(2-phenylethyl)chromones (1 ? 24), thirteen compounds were sesquiterpenoids (25 ? 37), two compounds were steroids (38 ?39). Among them,compounds (9, 16,23 ?24) were new 2-(2-phenylethyl)chromone derivatives, compounds 25 ? 26 were new sesquiterpenes.Interestingly, six sesquiterpenoids had an aromatic odor and were considered to be the constituents of fragrant odour of agarwood.The cytotoxicities against K562, BEL-7402 and SGC-7901 were evaluated in vitro using the MTT method. The results indicated that compounds 3, 11, 14,19 and 31 showed moderate cytotoxicities; Compounds 12 , 18 and 21 showed weak cytotoxicities. The acetylcholinesterase (AChE) inhibitory activity was tested by Ellman's method. The results indicated that thirteen compounds including 10 ? 12?15?19?23 ?26 and 31 ?33 exhibited inhibitory activity. The antimicrobial activities against Staphylococcus aureus and Candid albicans were measured using paper disco diffusion method and the results indicated that only compound 6 showed weakantimicrobial activities.