Verbenachalcone, a novel dimeric dihydrochalcone with potentiating activity on nerve growth factor-action from Verbena littoralis.

A novel dimeric dihydrochalcone, verbenachalcone (1), was isolated from the aerial parts of Verbena littoralis. Its structure was elucidated, on the basis of spectral data interpretation, as 4,2',4',2' ",4' "-pentahydroxy-3' '-methoxy-3-O-4' '-tetrahydrobichalcone. This compound caused a significant enhancement of nerve growth factor-mediated neurite outgrowth from PC12D cells.     

Chemical studies on mexican plants used in traditional medicine, VI. Additional new 4-phenylcoumarins from Exostema caribaeum

Six additional 4-phenylcoumarins have been isolated from the MeOH extract of the bark of Exostema caribaeum. Their structures were determined by physical and chemical methods as 4'-5'-dihydroxy-7-methoxy-4-phenyl-5,2'-oxidocoumarin [1], 5,7,4'-trimethoxy-4-phenylcoumarin [2], 5,3'-dihydroxy-7,4'-dimethoxy-4-phenylcoumarin [3], 5-O-beta-D-galactopyranosyl-7,4'-dimethoxy-4-phenylcoumarin [6], 5-O-beta-D-glucopyranosyl-3',4'-dihydroxy-7-methoxy-4-phenylcoumarin+ ++ [7], and 5-O-(6"-acetyl)-beta-D-galactopyranosyl-3', 4'-dihydroxy-7-methoxy-4-phenylcoumarin [9]. The last four compounds are new natural products.     

Discovery of natural products from Curcuma longa that protect cells from beta-amyloid insult: a drug discovery effort against Alzheimer's disease

From Curcuma longa, two novel compounds, 4' '-(3' "-methoxy-4' "-hydroxyphenyl)-2' '-oxo-3' '-enebutanyl 3-(3'-methoxy-4'hydroxyphenyl)propenoate (calebin-A, 1) and 1,7-bis(4-hydroxy-3-methoxyphenyl)-1,4,6-heptatrien-3-one (2), and seven known compounds, 1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione (curcumin, 3), 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione (demethoxycurcumin, 4), 1,7-bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione (bisdemethoxycurcumin, 5), 1-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-6-heptene-3,5-dione (6), 1,7-bis(4-hydroxyphenyl)-1-heptene-3,5-dione (7), 1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one (8), and 1,5-bis(4-hydroxy-3-methoxyphenyl)-1,4-pentadien-3-one (9), were isolated following a bioassay-guided fractionation scheme utilizing an assay to detect protection of PC12 cells from beta-amyloid insult. Compounds 1, 3-5, and 7 were found to more effectively protect PC12 cells from betaA insult (ED(50) = 0.5-10 microg/mL) than Congo red (10) (ED(50) = 37-39 microg/mL).     

Antioxidant chalcone glycosides and flavanones from Maclura (Chlorophora) tinctoria

Four chalcone glycosides (1-4), including three new natural products, and three flavanones (5-7) were isolated from the methanol extract of stem bark of Maclura tinctoria. The new compounds have been characterized as 4'-O-beta-D-(2' '-p-coumaroyl)glucopyranosyl-4,2',3'-trihydroxychalcone (1), 4'-O-beta-D-(2' '-p-coumaroyl-6' '-acetyl)glucopyranosyl-4,2',3'-trihydroxychalcone (2), and 3'-(3-methyl-2-butenyl)-4'-O-beta-D-glucopyranosyl-4,2'-dihydroxychalcone (3); the known derivatives were elucidated as 4'-O-beta-D-(2' '-acetyl-6' '-cinnamoyl)glucopyranosyl-4,2',3'-trihydroxychalcone (4), eriodictyol 7-O-beta-D-glucopyranoside (5), naringenin (6), and naringenin 4'-O-beta-D-glucopyranoside (7). Their structures were determined by 1D and 2D NMR and ESIMS. The antioxidant activity of all the isolated compounds was determined by measuring free-radical-scavenging effects using two different assays, namely, the Trolox Equivalent Antioxidant Capacity (TEAC) assay and the coupled oxidation of beta-carotene and linoleic acid (autoxidation assay). The results showed that compound 3 was the most active in both antioxidant assays.     

乌桕叶化学成分研究

通过利用正相硅胶色谱、大孔吸附树脂柱色谱、葡聚糖凝胶LH-20色谱、制备薄层色谱和半制备HPLC等多种分离方法,运用现代波谱技术对所分离的化合物进行结构鉴定,从乌桕Sapium sebiferum叶中分离得到15个化合物,分别鉴定为(+)-(7R,7′R,7"S,7(')S,8S,8′S,8"S,8(')S)-4",4(')-dihydroxy-3,3′,3",3('),5,5′-hexamethoxy-7,9';7',9-diepoxy-4,8";4′,8(')-bisoxy-8,8′-dineo-lignan-7",7('),9",9(')-tetraol(1),1-(4′-hydroxy-3'-methoxyphenyl)-2-[4"-(3-hydroxy propyl)-2",6"-dimethoxyphenoxy]propane-1,3-dio1(2),苏式-2,3-二-(4-羟基-3-甲氧基苯)-3-甲氧基丙醇(3),threo-5-hydroxy-3,7-dimethoxyphenylpropane-8,9-diol(4),boropinol B(5),threo-8S-7-methoxysyringylglycerol(6),5-羟甲基糠醛(7),5-甲氧甲基-1H-吡咯-2-甲醛(8),槲皮素(9),山柰酚(10),没食子酸乙酯(11),松柏醛(12),香草醛(13),7-羟基-6-甲氧基香豆素(14),正二十七烷醇(15),除化合物9～ 11,14外,以上化合物均为首次从乌桕中分离得到.     

Mixed lignan-neolignans from Tarenna attenuata

Six new mixed lignan-neolignans and 20 known compounds were isolated from the whole plant of Tarenna attenuata. By analysis of physical and spectroscopic data, the structures of the new compounds were elucidated as (1R,5R,6R)-6-{4-O-[2-(1-(4-hydroxy-3-methoxyphenyl))glycerol]-3,5-dimethoxyphenyl}-3,7-dioxabicyclo[3.3.0]octan-2-one (1), 5' '-methoxyhedyotisol A (2), 4' '-O-(8-guaiacylglycerol)buddlenol A (3), 5' '-methoxy-4' '-O-(8-guaiacylglycerol)buddlenol A (4), 4,6-dimethoxy-5-hydroxy-3-hydroxymethyl-2-(3,4,5-trimethoxyphenyl)-2,3-dihydrobenzofuran (5), and 7-O-ethylguaiacylglycerol (6). Compounds 1, 5, 6, and 8 showed potent antioxidant activities against H2O2-induced impairment in PC12 cells, and compounds 1, 2, 5, and 7 scavenged DPPH radical strongly with IC50 values of 72, 87, 45, and 55 microM, respectively.     

Four new flavones and a new isoflavone from Iris bungei

Four new irisflavones A-D (1-4) and irilin D (5) have been isolated from the underground parts of Iris bungei along with known isoflavones, irilins A-B (6-7) and tlatancuayin (8). The structures of the new compounds were determined using NMR and mass spectroscopic methods and were found to be 2',5,7-trihydroxy-3,6-dimethoxyflavone (1), 2',5-dihydroxy-3,6,7-trimethoxyflavone (2), 2',5,6'-trihydroxy-3,6,7-trimethoxyflavone (3), 3,3',5-trihydroxy-2',7-dimethoxyflavone (4), and 3',4',5,7-tetrahydroxy-6-methoxyisoflavone (5). The structures of irisflavones 1, 3, and 4 were confirmed by single-crystal X-ray diffraction studies.     

A new antifungal metabolite from Penicillium expansum

A new antifungal compound, (3S)-4,6-dihydro-8-methoxy-3,5-dimethyl-6-oxo-3H-2-benzopyran (4), was isolated from Penicillium expansum. During the isolation procedure 4 was determined to be unstable and readily reacted with methanol, ethanol, and water, forming three new isochromans, (1S,3S)-6-hydroxy-1,8-dimethoxy-3,5-dimethylisochroman (1), 1-ethoxy-6-hydroxy-8-methoxy-3,5-dimethylisochroman (2), and 1,6-dihydroxy-8-methoxy-3,5-dimethylisochroman (3), respectively. (3S)-6-Hydroxy-8-methoxy-3,5-dimethylisochroman (5) was reisolated from P. expansum. In fungicide disk assays, compounds 1, 2, and 4 inhibited the mycelial growth of Lasiodiplodia theobromae at 100 microg/mL by 76%, 74%, and 69%, respectively.     

Wound healing activity of acylated iridoid glycosides from Scrophularia nodosa.

Three acylated iridoid glycosides (E)-6-O-(2", 4"-diacetyl-3" -O-p-methoxycinnamoyl)-alpha-L-rhamnopyranosyl catalpol (scopolioside A) (1), (E)-6-O-(2"-acetyl-3", 4"-di-O,O-p-methoxycinnamoyl)-alpha-L-rhamnopyranosyl catalpol (scrophuloside A(4)) (2) and (E)-6-O-(2",3"-diacetyl-4"-O-p-methoxycinnamoyl)-alpha-L-rhamnopyranosyl catalpol (scrovalentinoside) (3) have been isolated from the dried seed pods of Scrophularia nodosa by HPLC. Their structures were determined by 1D and 2D NMR, UV/Vis and mass spectroscopy and by comparison with published data. All three compounds were shown in vitro to stimulate the growth of human dermal fibroblasts. The effect was negatively dose-dependent for 2 and 3 for which fibroblast growth stimulation was highest at 0.78 microg/mL but was not significantly different from the control at 100 microg/mL. The presence of these compounds in the mature seed pods may explain the ethnobotanical use of this plant in Europe for healing wounds.     

Trypanocidal diarylheptanoids from Aframomum letestuianum

Three new diarylheptanoids, (4Z,6E)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-4,6-dien-3-one, letestuianin A (1), (4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-4,6-dien-3-one, letestuianin B (2), and 1,7-bis(4-hydroxyphenyl)heptan-3,5-dione, letestuianin C (3), as well as the known (4Z,6E)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hepta-4,6-dien-3-one (5) were isolated from Aframomum letestuianum. The known flavonoids 3-acetoxy-5,7,4'-trihydroxyflavanone, 3-acetoxy-7-methoxy-5,4'-dihydroxyflavanone, 7-methoxy-3,5,4'-trihydroxyflavone, and 3,3',4',5,7-pentahydroxyflavan were also obtained from this plant. Their structures were determined using a combination of 1D and 2D NMR techniques. The four diarylheptanoids were tested for growth inhibitory activity in vitro versus bloodstream forms of African trypanosomes. IC(50) values in the range of 1-3 microg/mL were found for compounds 3 and 5.     

阔苞菊的化学成分研究(Ⅱ)

目的在前期研究的基础上,进一步研究阔苞菊Plucheaindica的化学成分。方法利用各种柱色谱方法进行分离纯化,根据理化性质和波谱数据鉴定其结构。结果分离得到12个化合物,分别鉴定为multiflorenol(12)、8-羟基-1(10)-缬草烯-11-O-葡萄糖苷(13)、3′,4′,5,7-四羟基黄酮-3-O-β-D-葡萄糖苷(14)、4′,5,7-三羟基黄酮-3-O-β-D-葡萄糖苷(15)、3′,4′,5,7-四羟基黄酮-3-O-β-D-吡喃甘露糖苷(16)、(+)-表松脂醇(17)、松脂素(18)、党参苷Ⅱ(19)、4-烯丙基-2-甲氧基-6-羟基苯基葡萄糖苷(20)、咖啡酸(21)、3,4-二羟基-5-甲氧基苯甲醛(22)、5′-环-磷酸尿苷(23)。结论除化合物19外,其余化合物均为首次从该种植物中分离得到。     

Bromophenols from the red alga Rhodomela confervoides

Six new bromophenols, 3-bromo-4,5-bis(2,3-dibromo-4,5-dihydroxybenzyl)pyrocatechol (1), 2,2',3-tribromo-3',4,4',5-tetrahydroxy-6'-hydroxymethyldiphenylmethane (2), 2,2',3-tribromo-3',4,4',5-tetrahydroxy-6'-ethyloxymethyldiphenylmethane (3), (+/-)-2-methyl-3-(2,3-dibromo-4,5-dihydroxyphenyl)propylaldehyde (4), (+/-)-2-methyl-3-(2,3-dibromo-4,5-dihydroxyphenyl)propylaldehyde dimethyl acetal (5), and 3-bromo-4,5-dihydroxybenzoic acid methyl ester (6), together with eight known bromophenols, 3-bromo-4,5-dihydroxybenzaldehyde (7), 2,3-dibromo-4,5-dihydroxybenzyl alcohol (lanosol, 8), 2,3-dibromo-4,5-dihydroxybenzyl methyl ether (9), 2,3-dibromo-4,5-dihydroxybenzyl ethyl ether (10), 2,3-dibromo-4,5-dihydroxybenzylaldehyde (11), bis(2,3-dibromo-4,5-dihydroxybenzyl) ether (12), 3-bromo-4-(2,3-dibromo-4,5-dihydroxybenzyl)-5-methoxymethylpyrocatechol (13), and 2,2',3,3'-tetrabromo-4,4',5,5'-tetrahydroxydiphenyl methane (14), were isolated from the red alga Rhodomela confervoides. Their structures were elucidated by chemical and spectroscopic methods including IR, HRFABMS, and 1D and 2D NMR techniques.     

白花蛇舌草化学成分的研究

目的：对白花蛇舌草的化学成分进行研究。方法：采用聚酰胺,Sephadex LH-20,硅胶和HPLC等多种色谱方法进行分离,理化性质,光谱数据鉴定结构。结果：分离鉴定9个化合物：2,6-二羟基-1-甲氧基-3-甲基蒽醌(1),2-羟基-1-甲氧基-3-甲基蒽醌(2),2-羟基-3-甲基蒽醌(3),quercetin-3-O-［2-O-(6-O-E-sinapoyl)-β-D-glucopyranos-yl］-β-glucopyranoside(4),quercetin-3-O-［2-O-(6-O-E-feruloyl)-β-D-glucopyranosyl］-β-glucop-yranoside(5),kaempferol-3-O-［2-O-(6-O-E-feruloyl)-β-D-glucopyranosyl］-β-galactopyranoside(6),quercetin-3-O-(2-O-β-D-glucopyranosyl)-β-D-glucopyranoside(7),芦丁(8),槲皮素(9)。结论：化合物1和8为首次从该种植物中得到,其中化合物1为新化合物。     

Acylated flavone C-glycosides from Trollius ledebouri

Six new acylated flavone C-glycosides, 2'-O-(2'-methylbutyryl)isoswertisin (1), 3'-O-(2'"-methylbutyryl)isoswertisin (2), 2'-O-(2'"-methylbutyryl)vitexin (3), 2'-O-(2'"-methylbutyryl)orientin (4), 2'-O-(3'",4'"-dimethoxybenzoyl)vitexin (5), and 2'-O-(3'",4'"-dimethoxybenzoyl)orientin (6), and the known flavone C-glycoside, isoswertisin, were isolated from the flowers of Trollius ledebouri. The structures of 1-6 were elucidated by spectroscopic methods.     

光叶海桐根的化学成分(英文)

目的:对光叶海桐根的化学成分进行研究。方法:通过多种柱层析方法和制备高效液相对化合物进行分离纯化, 通过理化常数及波谱数据对其结构进行解析。结果:从光叶海桐根中分离得到 7 个化合物, 分别鉴定是 6α-羟基-京尼平苷(1), 10-O-咖啡酰基-脱乙酰基-交让木苷(2), (+)-南烛木树脂酚-3α-O-β-D-葡萄糖苷(3), (+)-南烛木树脂酚-3α-O-(6″-3,5-二甲氧基-4-羟基-苯甲酰基)-β-D-葡萄糖苷(4), (+)-南烛木树脂酚-3α-O-(6″-3-甲氧基-4-羟基-苯甲酰基)-β-D-葡萄糖苷(5), (-)-4-epi-南烛木树脂酚- 3α-O-β-D-葡萄糖苷(6)和(+)-丁香脂素-4,4'-O-双-β-D-葡萄糖苷(7)。结论:化合物 1-6 为该属首次分离, 化合物 7 为该种首次分离。     

New lignan glycosides with potent antiinflammatory effect, isolated from Justicia ciliata

Two new lignan glycosides, 4-O-[alpha-L-arabinopyranosyl-(1' "-->2' ')-beta-D-xylopyranosyl-(1' " '-->5' ')-beta-D-apiofuranosyl]diphyllin (1), named ciliatoside A (1), and 4-O-?[beta-D-apiofuranosyl-(1' " "-->3' ")-alpha-L-arabinopyranosyl-(1' "-->2' ')][beta-D-xylopyranosyl-(1' " '-->5' ')]-beta-D-apiofuranosyl?diphyllin (2), named ciliatoside B (2), were isolated from the whole plant of Justicia ciliata. The structures of 1 and 2 were determined by spectral and chemical methods. Compounds 1 and 2 strongly inhibited the accumulation of NO(2)(-) in lipopolysaccharide-stimulated RAW 264.7 cells in a concentration-dependent manner with IC(50) values of 27.1 +/- 1.6 and 29.4 +/- 1.4 microM, respectively.     

红花芒毛苣苔化学成分研究

目的:研究红花芒毛苣苔Aeschynanthus moningeriae的化学成分。方法:利用Diaion HP-20,Toyopearl HW-40,Sephadex LH-20,MCI-Gel CHP-20,RP18及硅胶等柱色谱法对红花芒毛苣苔中的化学成分进行分离纯化,根据理化性质和波谱技术鉴定化合物的结构。结果:从中分离鉴定了12个化合物,分别为5,7-二羟基-8-C-β-D-葡萄糖色酮碳苷(1),5-羟基-7,4’-二甲氧基黄酮(2),2,3,19,24-四羟基-12-烯-28-乌苏酸(3),2,3,19,24-四羟基-12-烯-28-乌苏酸-28-O-β-D-葡萄糖苷(4),5-羟基-6,4’-二甲氧基-7-[α-L-鼠李糖-1→6]-O-β-D-葡萄糖黄酮苷(5),5,7,3’,4’-四羟基-6-C-β-D-葡萄糖黄酮醇碳苷(6),5,7-二羟基-6-C-β-D-葡萄糖二氢黄酮碳苷(7);5,7,3’,4’-四羟基-6-C-β-D-葡萄糖二氢黄酮醇碳苷(8),胡萝卜苷(9),豆甾醇(10),β-谷甾醇(11),3-O-β-D-葡萄糖豆甾醇苷(12)。结论:化合物1为新化合物,其他化合物均为首次从该植物中分离得到。     

Isoflavone diglycosides from Glycosmis pentaphylla

Six new apiosyl-(1-->6)-glucosyl isoflavones (1-6) and four known ones were isolated from the stems of Glycosmis pentaphylla. The structures of the new glycosides are 3',7-dihydroxy-4',5,6-trimethoxyisoflavone 7-O-(5-O-trans-p-coumaroyl)-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (1), 2',7-dihydroxy-4',5',5,6-tetramethoxyisoflavone 7-O-(5-O-trans-p-coumaroyl)-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (2), 2',7-dihydroxy-4',5',5,6-tetramethoxyisoflavone 7-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (3), 7-hydroxy-4',8-dimethoxyisoflavone 7-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (4), 7-hydroxy-4',6-dimethoxyisoflavone 7-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (5), and 4',5-dihydroxy-3',7-dimethoxyisoflavone 4'-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (6). Their structures were established primarily by NMR experiments and chemical methods.     

Mono-, Bi-, and triphenanthrenes from the tubers of Cremastra appendiculata

Six newphenanthrene derivatives, including three monophenanthrenes (1-3), two biphenanthrenes (4 and 5), and a triphenanthrene (6), have been isolated from an ethanolic extract of the tubers of Cremastra appendiculata. Using spectroscopic methods, the structures of compounds 1-6 were determined as 1-hydroxy-4,7-dimethoxy-1-(2-oxopropyl)-1H-phenanthren-2-one (1), 1,7-dihydroxy-4-methoxy-1-(2-oxopropyl)-1H-phenanthren-2-one (2), 2-hydroxy-4,7-dimethoxyphenanthrene (3), 2,7,2'-trihydroxy-4,4',7'-trimethoxy-1,1'-biphenanthrene (4), 2,2'-dihydroxy-4,7,4',7'-tetramethoxy-1,1'-biphenanthrene (5), and 2,7,2',7',2' '-pentahydroxy-4,4',4' ',7' '-tetramethoxy-1,8,1',1' '-triphenanthrene (6), respectively. Compounds 1-6 and two known compounds, cirrhopetalanthin (7) and flavanthrinin (8), obtained previously from this plant, were evaluated against six human cancer cells and a normal cell line.     

Phytochemical investigation of Turnera diffusa

A phytochemical investigation of Turnera diffusa afforded 35 compounds, comprised of flavonoids, terpenoids, saccharides, phenolics, and cyanogenic derivatives, including five new compounds (1-5) and a new natural product (6). These compounds were characterized as luteolin 8-C-E-propenoic acid (1), luteolin 8-C-beta-[6-deoxy-2-O-(alpha-l-rhamnopyranosyl)-xylo-hexopyranos-3-uloside] (2), apigenin 7-O-(6' '-O-p-Z-coumaroyl-beta-d-glucopyranoside) (3), apigenin 7-O-(4' '-O-p-Z-coumaroylglucoside) (4), syringetin 3-O-[beta-d-glucopyranosyl-(1-->6)-beta-d-glucopyranoside] (5), and laricitin 3-O-[beta-d-glucopyranosyl-(1-->6)-beta-d-glucopyranoside] (6). Their structures were determined by spectroscopic and chemical methods.