Studies On The Chemical Constituents And Biological Activities Of Fruits Of Ailanthus Altissima Swingle And Galium Verum L.

1．Ailanthus altissima Swingle (Simaroubaceae) is widespread in China. The fruits ofthis plant have traditionally been used for the treatment of antimalarial, antibacterial andgynecopathia.Forty-one compounds were separated from the fruits of A. altissima Swingle byusing chromatographic and recrystallized methods.On the basis of physico-chemical properties and spectroscopic analysis, theirstructures were identified as follows. Steroids: stigmastane-3,6-dione (1) , stigmastane-3β,6β-diol (2) , stigmast-4-ene-3,6-dione (3) , 6β-hydroxystigmast-4-en-3-one (4) ,6α-hydroxystigmast-4-en-3-one (5) , stigmast-4-ene-3β,6β-diol (6) , stigmast-4-ene-3β,6α-diol (7) , stigmast-4-en-3-one (8) ,β-sitosterol (9) , daucosterol (10) , 3β-hydroxy-stigmast-5-en-7-one (11) , stigmast-5-ene-3β,7α-diol (12) , stigmast-5-ene-3β,7α,20ξ-triol (13) , ergesta-4,6,8(14) ,22-tetraen-3-one (14) , 5α,8α-epidioxyergesta-6,22-dien-3β-ol (15) , 5α,8α-epidioxyergesta-6,9(11) ,22-trien-3β-ol (16) . Triterpenoids: 9,19-cyclolanost-23(Z)-ene-3β,25-diol (17) , cycloart-25-ene-3β, 24ξ-diol (18/19) , 2β,20(S)-dihydroxydammar-24-en-3-one (20) ,β-amyirn (21) , olean-9(11) ,12-dien-3β-ol (22) ,D-friedoolean-14-en-3-one (23) , ursolic acid (24) , 22-hydroxyhopan-3-one (25) ,11β,20-epoxy-1β,2α,12α-pentahydroxypicrasa-3,13(21) -dien-16-one (26) . Cerebrosides: 1-O-β-D-glucopyranosyl-(2S,3R,4E,9E)-2-(2'R-hydroxyhexadecenoylamino)-4,9-octa-decadiene-1,3-diol (27) . Flavonoids: kaempferol (32) , quercetin (33) , quercetin 3-O-β-D-glucopyranoside (34) , kaempferol 3,7-O-bis-α-L-rhamnopyranoside (35) , 3-O-α-L-arabinofuranosyl kaempferol 7-O-α-L-rhamnopyranoside (36) . Lignanoids: (+)-isolariciresinol (40) , (+)-isolariciresinol 9-O-β-D-glucopyranoside (41) . Phenolicacids: vanillin (37) , gallic acid (38) , 6,7-dihydroxycoumarin (39) . Others: n-tetra-triacontane (28) , L-evonymitol (29) , D-mannitol (30) , D-sorbitol (31) .Among them, compound 27 was a new compound; compound 2 was a new naturalproduct; compounds 1-8, 11-25, 28-31, 34-41 were firstly isolated from this genus;compounds 10, 26, 32, 33 were isolated from the fruits of Ailanthus altissima Swinglefor the first time.A review on the biosynthesis, pharmacological actions and spectral characters of 锘縬uassinoid type triterpenoids was given on the base of references and our study work.2．Galium verum L. (Rubiaceae) is an herbal medicine widely distributed in the China,which has good therapy effect on phlebophlogosis and hepatitis as a famous folkmedicine.鈽匱hirty-four compounds were separated from G. verum L. by using chromatographicand recrystallized methods.鈽匫n the basis of physico-chemical properties and spectroscopic analysis, theirstructures were identified as follows. Flavonoids: isorhamnetin (1) , isorhamnetin3-O-伪-L-rhamnopyranosyl (1-6) -å°¾-D-glucopyranoside (2) , diosmetin (3) , diosmetin7-O-å°¾-D-glucopyranoside (4) , diosmetin 7-O-å°¾-D-xylopyranosyl-(1-6) -å°¾-D-gluco-pyranoside(5) , diosmetin 7-O-伪-L-rhamnopyranosyl-( 1-2) -[å°¾-D-xylopyranosyl-( 1-6) ]-å°¾-D-glucopyranoside (6) , kaempferol (7) , quercetin (8) , 3,5,7,3',4',3",5",7",3"',4"'-decahydroxyl-[8-CH₂-8"]-biflavone (9) . Anthraquinones.è·¯2, 5-dihydroxy-1, 3-di-methoxy-anthraquinone (10) , 2-hydroxy-1, 3-dimethoxy-anthraquinone (11) , physcione(12) , 1,3-dihydroxy-2-methyl-anthraquinone (13) , 2,8-dihydroxy-1-methoxy-anthra-quinone (14) ,1-hydroxy-2-hydroxymethyl-3-methoxy-anthraquinone (15) . Lignanoids:(+)-pinoresinol 4,4'-O-bis-å°¾-D-glucopyranoside (16) , (+)-epipinoresinol (17) , (+)-medioresinol (18) . Iridoids: morindolide (19) , monotropein (20) , deacetyl-asperulo-sidic acid (21) , 6伪-hydroxygeniposide (22) , deacetyl-asperuloside (23) . Triterpenoids:ursolic acid (29) , rubifolic acid (30) , ursolic aldehyde (31) . Phenolic acids:scopoletin (24) , ferulic acid (25) , phthalic acid bis-(2-ethyl-hexyl) ester (26) , p-hydroxy-phenylpropionic acid (27) , trans-dotriacontyl-coumarate (28) . Others: n-dotriacontanol (32) ,å°¾-sitosterol (33) , daucosterol (34) .鈽匒mong them, compounds 6, 9 and 10 were new compounds; compounds 1, 2,11,14-19, 23, 25-32 were firstly isolated from this genus; compounds 12, 24 were isolatedfrom the Galium verum L. for the first time.鈽匬harmacological tests showed that the extract of fruits of Ailanthus altissimaSwingle had the effect on E. coli, S. aureus, P. aeruginosa and S. typhiuriun in vitro.The EtOAc extract exhibited the best result, which gave the effective activity againsttested bacterium. By the chromatographic isolation, the major compounds obtained from this part were flavonoids and lignanoids. The n-butanol extract from G. verum L.showed the potential activity against tested bacterium. By the chromatographic isolation,the major compounds obtained from this part were flavonoids. Minimal inhibitoryconcentrations (MIC) of effective components were measured using two-fold dilutionmethod.The anti-oxidative activity of twenty-nine compounds isolated from fruits of A.altissima Swingle (seven compounds) and G. verum L. (twenty-two compounds) wastested, and some of them showed effective antioxidations.By MTT methods, the in vitro cytotoxicity activities against cancer cell lines of theextract were assayed. The emulsive part between petroleum and water of G. verum L.showed moderate activity against human cancer cell line (SF188) with an IC₅₀ value of342μg/ml; the n-butanol part displayed potential activity with an IC₅₀ value of 424μg/ml against MCF-7 cell line.