Glucosylated caffeoylquinic acid derivatives from the flower buds of Lonicera japonica

Three new glucosylated caffeoylquinic acid isomers (1-3), along with six known compounds, have been isolated from an aqueous extract of the flower buds of Lonicera japonica. Structures of the new compounds were determined by spectroscopic and chemical methods as (-)-4-O-(4-O-β-d-glucopyranosylcaffeoyl)quinic acid (1), (-)-3-O-(4-O-β-d-glucopyranosylcaffeoyl)quinic acid (2), and (-)-5-O-(4-O-β-d-glucopyranosylcaffeoyl)quinic acid (3), respectively. In the preliminary in vitro assays, two known compounds methyl caffeate and 2'-O-methyladenosine showed inhibitory activity against Coxsackie virus B3 with IC50 values of 3.70 μmol/L and 6.41 μmol/L and SI values of 7.8 and 12.1, respectively.

Liposoluble constituents from Iodes cirrhosa and their neuroprotective and potassium channel-blocking activity / 中国中药杂志

<p><b>OBJECTIVE</b>To study the chemical constituents of Iodes cirrhosa and evaluate their bioactivity.</p><p><b>METHOD</b>The compounds were isolated and purified by various kinds of column chromatography methods and their structures were determined by spectroscopic data analysis. Neuroprotective assay against serum deprivation induced SH-SYSY-JNK3 cell apoptosis was evaluated by MTr method while potassium channel-blocking activity was assayed in both non-specific and specific K+ channel-regulator screening models.</p><p><b>RESULT</b>Twenty-one compounds were obtained from an EtOAc portion of an ethanolic extract of the root of I. cirrhosa. Their structures were elucidated as 1beta, 3beta-dihydroxyurs-9(11),12-diene(1), bauerenyl acetate(2),3beta-hydroxy-11-oxo-olean-12-enyl palmitate(3), 3beta-acetoxy-urs-12-ene-11-one(4), betulinic acid(5), stigmasta-5, 22-diene-3beta-ol(6), 7beta-hydroxystigmasterol(7), stigmasta-5, 22diene-3beta-ol3-O-beta-D-glucopyranoside(8),scopoletin(9),scopolin(10),clovamide(11),methyl 3,5-di-O-caffeoylquinate(12),3,5-dicaffeoylquinic acid(13),2,6-dimethoxy-1,4-benzoquinone(14), protocatechualdehyde(15), vanillin(16), protocatechuic acid(17), vanillic acid(18),caffeic acid(19),azelaic acid(20),and succinic acid(21). Compound 3,4,6,9,10,14,15,18 and 20 showed neuroprotective activities against serum deprivation induced SH-SYSY-JNK3 cell apoptosis at a concentration of 1.0 x 10(6) mol x L(1) with relative protection rates of 177%, 144%, 137%, 137%, 143%, 145%, 137%, 189%, 130%, respectivley. Compound 16 could increase DiBAC4(3) fluorescence response in both non-specific and specific K+ channel-regulator screening models at the concentration of 1.0 x 10(-5) mol x L(-1).</p><p><b>CONCLUSION</b>Compound 1 was a new compound and all compounds were isolated from this genus for the first time. Compounds 3,4,6,9,10,14,15,18 and 20 showed neuroprotective activities while 16 exhibited K+ channel-blocking activity.</p>

Constituents from a water-soluble portion of ethanolic extract of Iodes cirrhosa / 中国中药杂志

<p><b>OBJECTIVE</b>To investigate chemical constituents of Iodes cirrhosa.</p><p><b>METHOD</b>Constituents were isolated by using a combination of various chromatographic techniques including column chromatography over silica gel, Sephadex LH-20, and C-18, as well as reversed-phase HPLC. Structures of the isolates were identified by spectroscopic and chemical methods.</p><p><b>RESULT</b>Twenty-four compounds were obtained from a H2O-soluble portion of an ethanolic extract of the root of lodes cirrhosa Turcz. Structures of the isolates were identified as (-)-(7R,8S,7'E) -4,7,9,9'-tetrahydroxy-3,3'-dimethoxy-8,4'-oxyneolign-7'-ene-9'-O-beta-D-glucopyra-noside (1), (-)-(7S,8S,7'E)-4,7,9,9'-tetrahydroxy-3,3'-dimethoxy-8,4'-oxyneolign-7'-ene-9'-O-beta-D-glucopyranoside(2), (+)-(7S,8S)-syringylglycerol 8-O-beta-D-glucopyranoside (3), (+)-(7S, 8S)-guaiacylglycerol 8-O-P-D-glucopyranoside (4), (-)-(7S, 8S)-4,7,9, 9'-tetrahydroxy-3,3'-dimethoxy-8,4'-oxyneolignan-7-O-beta-D-glucopyranoside (5),(-)-alaschanisoside A (6), (-)-(2R)-1-O-beta-D-glucopyranosyl-2-(2-methoxy-4-[1-(E)-propen-3-ol] phenoxyl propane-3-ol(7), (-)-(2R)-1-O-beta-D-glucopyranosyl-2-{2,6-dimethoxy-4-[1-(E)-propen-3-ol] phenoxyl} propane-3-ol(8), (-)-liriodendrin(9), (-)-(7S, 8R)-guaiacylglycerol 9-O-beta-D-glucopyranoside(10), (-)-(7R, 8R)-guaiacylglycerol 9-O-beta-D-glucopyranoside(11),(-)-(7R,8R)-syringylglycerol 9-O-beta-D-glucopyranoside(12), (-)-(7R,8R)-guaiacylglycerol 7-O-beta-D-glucopyranoside(13), (-)-11,13-dihydrodeacylcynaropicrin 3-O-beta-D-glucopyranoside(14), (-)-sweroside (15), (-)-2-hydroxy-5-(2-hydroxyethyl) phenyl beta-D-glucopyranoside(16), (-)-(1'R)-1'-(3-hydroxy-4-methoxyphenyl) ethane-1',2'-diol-3-O-beta-D-glucopyranoside(17), (-)-tachioside(18), (-)-3,5-dimethoxy-4-hydroxyphenyl beta-D-glucopyranoside(19), (-)-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone-3-O-beta-D-glucopy ranoside(20), (-)-2-methoxy4-(1-propionyl) phenyl beta-D-glucopyranoside(21), (-)-4-propionyl-3, 5-dimethoxyphenyl beta-D-glucopyranoside(22), erigeside C(23), and scopoletin beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranoside(24).</p><p><b>CONCLUSION</b>Compounds 1-24 were obtained from the genus for the first time.</p>