Isolation and lipoxygenase-inhibition studies of phenolic constituents from Ehretia obtusifolia

The phenolic compounds methyl 2-O-feruloyl-1a-O-vanillactate (1), caffeic anhydride (2), and trans 4-hydroxycyclohexyl-2-O-p-coumaroyl beta-D-glucopyranoside (3) have been isolated from the AcOEt-soluble fraction of Ehretia obtusifolia, along with methyl rosmarinate (4) and rosmarinic acid (5), which are reported for the first time from this species. Their structures were determined by means of 1D- and 2D-NMR techniques. Compounds 1-5 inhibited lipoxygenase in a concentration-dependent manner, with Ki values ranging from 0.85-57.6 microM. Compounds 1, 2, 4, and 5 showed noncompetitive inhibition, whereas 3 was found to be an uncompetitive inhibitor of lipoxygenase.     

湖北旋覆花化学成分及抗结核活性研究

为进一步研究湖北旋覆花花序中的化学成分及抗结核活性。实验采用硅胶柱色谱、反相硅胶柱色谱以及制备型高相液相等方法进行了成分系统研究,肉汤二倍稀释法测定化合物的体外抗结核分支杆菌活性。从其花序中分离得到10个化合物。应用波谱学方法分别鉴定为:7,8-epoxy-9-(isobutyryloxy)thymolisobutyrate(1)、10-(2-methylbutyloxy)-8,9-epoxythymolisobutyrate(2)、stigmasterol(3)、ayapin(4)、ergolide(5)、5,10-epi-2,3-dihydroaromatin(6)、xanthalongin(7)、bigelovin(8)、carpesiolin(9)、aromaticin(10)。化合物1、2、5、6、8～10均为首次从该植物中分离得到。其中化合物5～10均为倍半萜类化合物。化合物5、6、8～10对结核分枝杆菌细胞株具有较好的抑制活性,最小抑制浓度MIC值分别为10.00、30.00、5.00、3.15、3.15μM,9和10的活性效果显著。     

大火草根部的化学成分

大火草（Ａｎｅｍｏｎｅ　ｔｏｍｅｎｔｏｓａａ（Ｍａｘｉｍ．）Ｐｅｉ）根状茎提取物的乙酸乙酯部分对粘虫（ＬｅｕｃａｎｉａｓｅｐａｒａｔａＷａｌｋｅｒ）有较好的非选择性拒食活性。从该部分分离得到１１个化合物,通过ＮＭＲ、ＭＳ等波谱分析确定它们的结构分别为４,５-二甲氧基-７-甲基香豆素（１）、４-甲氧基-５-甲基-６,７-二氧亚甲基香豆素（２）、４,７-二甲氧基-５-甲基香豆素（３）、齐墩果酸（４）、齐墩果酮酸（５）、齐墩果酸-３-Ｏ-β-Ｄ-吡喃木糖甙（６）、β-谷甾醇（７）、豆甾醇（８）、胡萝卜甙（９）、豆甾醇-３-Ｏ-β-Ｄ-吡喃葡萄糖甙（１０）和过氧化麦角甾醇（１１）。这些化学成分均为首次从该植物中分离得到,其中１和２为新化合物。     

Synthesis and in vitro pharmacology at AMPA and kainate preferring glutamate receptors of 4-heteroarylmethylidene glutamate analogues

2-Amino-3-[3-hydroxy-5-(2-thiazolyl)-4-isoxazolyl]propionic acid (1) is a potent AMPA receptor agonist with moderate affinity for native kainic acid (KA) receptors, whereas (S)-E-4-(2,2-dimethylpropylidene)glutamic acid (3) show high affinity for the GluR5 subtype of KA receptors and much lower affinity for the GluR2 subtype of AMPA receptors. As an attempt to develop new pharmacological tools for studies of GluR5 receptors, (S)-E-4-(2-thiazolylmethylene)glutamic acid (4a) was designed as a structural hybrid between 1 and 3. 4a was shown to be a potent GluR5 agonist and a high affinity ligand and to indiscriminately bind to the AMPA receptor subtypes GluR1-4 with lower affinities. Compounds 4b-h, in which the 2-thiazolyl substituent of 4a was replaced by other heterocyclic rings, which have previously been incorporated as 5-substituents in AMPA analogues, as exemplified by 1 were also synthesized. Compounds 4b-h were either inactive (4e,f) or weaker than 4a as affinity ligands for GluR1-4 and GluR5 with relative potencies comparable with those of the corresponding AMPA analogues as AMPA receptor agonists. Compounds 4a-h may be useful tools for the progressing pharmacophore mapping of the GluR5 agonist binding site.     

南山茶果皮化学成分的研究

反复采用硅胶柱色谱法、Sephadex LH-20柱色谱法、ODS柱色谱法、反复重结晶等方法对南山茶果皮的化学成分进行分离纯化,并通过理化常数测定和波谱分析等方法进行结构鉴定。从南山茶果皮中分离并得到了10个化合物,分别鉴定为槲皮素(1)、山奈酚(2)、原儿茶酸(3)、山柰酚-3-O-β-D-葡萄糖基-(6→1)-2′′′,4′′′-O-二乙酰基-α-L-鼠李糖基-(3→1)-2′′′′,3′′′′,4′′′′-O-三乙酰基-α-L-鼠李糖苷(4)、山柰酚-3-O-β-D-葡萄糖基-(6→1)-4′′′-O-乙酰基-α-L-鼠李糖基-(3→1)-3′′′′-O-乙酰基-α-L-鼠李糖苷(5)、3-甲氧基鞣花酸(6)、鞣花酸(7)、羽扇豆烷醇(8)、β-谷甾醇(9)和胡萝卜苷(10)。化合物2、6、7均为首次从南山茶中分离得到,其中化合物6、7为首次从山茶属植物中分离得到。     

壮丽含笑中的倍半萜成分及其化学分类学意义

壮丽含笑 (ＭｉｃｈｅｌｉａｌａｃｅｉＷ Ｗ Ｓｍｉｔｈ)为木兰科含笑属植物 ,常绿乔木 ,分布于我国云南西南部 ,生于海拔 15 0 0ｍ的林中。枝粗壮 ,花梗具佛焰苞状苞片约 5枚 ,心皮狭卵圆形具 3～ 4ｍｍ的花柱等特征 ,形态分类学上认为该种是含笑属中较原始而特殊的种类 (刘玉壶等 ,1996)。通过初步药理筛选实验 ,表明其嫩枝的脂溶性提取物在浓度为 1 5 μｇ/ｍＬ时对两种人肿瘤细胞株ＨＣＴ - 8及ＳＩＨａ的抑制率分别为5 7 0 %及 2 1 3% ,对ＧＬＣ - 82细胞株的抑制率尤其明显 ,为 84 6% ;对ＣｏｎＡ刺激的小鼠脾淋巴细胞增殖反应在浓…     

New bisabolane sesquiterpenes and coumarin from Leontopodium longifolium

From the roots of Leontopotium longifolium, three new bisabolane sesquiterpenes, rel-(1S,4R,5S,6R)-4,5-diacetoxy-6-[(R)-1,5-dimethylhexa-3,5-dienyl]-3-methylcyclohex-2-enyl (Z)-2-methylbut-2-enoate (1), rel-(1S,4R,5S,6R)-4,5-diacetoxy-6-[(R)-5-hydroxy-1,5-dimethylhex-3-enyl]-3-methylcyclohex-2-enyl (Z)-2-methylbut-2-enoate (2), rel-(1R,2S,4R,5S)-4-acetoxy-2-[(R)-5-hydroxy-1,5-dimethylhex-3-enyl]-5-methylcyclohexyl (Z)-2-methylbut-2-enoate (3), and a new coumarin, 2,3-dihydro-5-hydroxy-2-(1-methylethenyl)-7H-pyrano[2,3-g][1,4]benzodioxin-7-one (4) together with nine known compounds have been isolated. The structures of these compounds were established by spectroscopic methods. Compounds 1 and 2 exhibited moderate cytotoxic activities against human promyelocytic leukemia (HL-60) cells.     

Natural PTP1B inhibitors from Broussonetia papyrifera

Two new compounds, 8-(1,1-dimethylallyl)-5'-(3-methylbut-2-enyl)-3',4',5,7-tetrahydroxyflanvonol (1), 3'-(3-methylbut-2-enyl)-3',4',7-trihydroxyflavane (2) and three known compounds 3,3',4',5,7-pentahydroxyflavone (3), uralenol (4), broussochalcone A (5) were isolated from the roots of Broussonetia papyrifera, and their structures determined by spectroscopic methods. Compounds 1, 3, 4 and 5 significantly show the inhibitory activities against the PTP1B enzyme.     

New bis-catechols 5-lipoxygenase inhibitors

Three polyhydroxy-2-phenylnaphthalenes (1-3) and the oxy analogue of tetrahydroxypavinan (4) were prepared and evaluated for their antioxidant properties (inhibition of diphenylpycrylhydrazyl radical (DPPH), reduction of iron (III) ion) and inhibition of 5-lipoxygenase (5-LO) activity. Their three-dimensional structures were established on the basis of spectroscopic data and semiempirical calculations. Compounds 1 and 2 were found as potent 5-LO inhibitors as nordihydroguaiaretic acid (NDGA), whereas 4 is 2.5 times less potent than NDGA. The reliability of the 3-D structures with the 5-LO inhibition properties is discussed. Their antioxidant properties show that tested compounds are expected to act as redox inhibitors.     

观光木酚性成分研究

从观光木(Tsoongiodendron odorum Chun)茎枝的80％乙醇提取物中分离得到11个酚性化合物,经波谱鉴定为:对羟基苯甲醛(1)、香草醛(2)、1,3,5-三甲氧基苯(3),丁香醛(4)、香草酸(5)、苏式-2,3-二-(4-羟基-3-甲氧基苯)-3-甲氧基丙醇(6)、赤式-2,3-二-(4-羟基-3-甲氧基苯)-3-甲氧基丙醇(7)、丁香酸(8)、3-羟基-1-(4-羟基-3,5-二甲氧基苯)-1-丙酮(9)、对羟基苯乙醇(10)和C-veratroylglycol( 11).其中,化合物1～4和6～ 11为首次从该植物中分离得到.     

Further study on anti-inflammatory oxygenated steroids from the octocoral Dendronephthya griffini

Five new steroids, namely griffinisterones F-I (1-4) and griffinipregnone (5) have been isolated from the octocoral Dendronephthya griffini. The structures of these compounds were elucidated by extensive spectroscopic analysis. Compounds 1-3 were found to significantly inhibit the accumulation of the pro-inflammatory iNOS protein of the LPS-stimulated RAW264.7 macrophage cells at 10 microM. At the same concentrations 2 also could significantly inhibit the accumulation of the pro-inflammatory COX-2 protein.     

Alkaloids from Heimia salicifolia

Two alkaloids, 9β,2′-dihydroxy-4′′,5′′-dimethoxy-lythran-12-one or 9β-hydroxyvertine (1) and (2S,4S,10R)-4-(3-hydroxy-4-methoxyphenyl)-quinolizidin-2-acetate (2), as well as seven known alkaloids, lythrine (3), dehydrodecodine (4), lythridine (5), vertine (6), heimidine (7), lyfoline (8) and epi-lyfoline (9), were isolated from Heimia salicifolia. The structures of these compounds were elucidated by extensive spectroscopic techniques. Furthermore, the structures of 2, 3, and 6 were confirmed by X-ray crystallography, including absolute configuration determination of 2 and 6. Compounds 6 and 9 showed moderate antimalarial activity.     

Fasciculols H and I, two lanostane derivatives from Chinese mushroom Naematoloma fasciculare

Two new highly oxygenated fasciculol-type lanostane derivatives, fasciculols H and I (1 and 2, resp.), together with five known compounds, 3-7, were isolated from the fruiting bodies of the Chinese toxic mushroom Naematoloma fasciculare. Their structures were elucidated on the basis of spectroscopic analyses including 2D-NMR (HMBC, HSQC, NOESY, (1)H,(1)H-COSY). Compounds 5-7 were identified for the first time in this mushroom. Compounds 1, 3, 4, and 5 were evaluated for inhibitory activity against human glioma cell line U87 and nuclear factor-κB.     

Two New Phenolic Glycosides from Viburnum cylindricum ( Caprifoliaceae)

从水红木( Viburnum cylindricum ) 植物中分离出2 个新化合物, 1- phloroglucinyl- ( 6-methybutyryl )-B-D- glucopyranoside命名为cylindrin A ( 1) , 1- [ 4- ( 3- hydroxy-l propyl ) ]- pyrocatechol- ( 6-methybutyryl )-B-D- glucopyranoside, 命名为cylindrin B ( 2) , 以及7 个已知化合物tachioside ( 3) , syingic acid-4-B-D- glucopyran oside ( 4) , 1-B-D-glucopyranosyloxy-3-methoxy-5- hydroxybenzene ( 5 ) , 4- hydroxy- 3-methoxypheno-l 1-O-B-D- glucoside ( 6 ) , 4-hydroxy- 2, 6- dimethoxypheno-
l 1-O-B-D- glucoside ( 7) , phlorogluc ino-l 1-O-B-D-glucoside ( 8 ) , 1-B-D- glucosyloxy-2- ( 3-methoxy- 4- hydroxyphenyl) propane- 1, 3- diol ( 9) . 它们的结构经波谱方法得到鉴定。3~ 9 为首次从该种植物中分离得到。     

水红木中两个新的酚苷成分

从水红木（Viburnum cylindricum）植物中分离出2个新化合物,1-phlomglucinyl-（6-methybutyryl）-β-D-glucopyranoside命名为cylindrin A（1）,1-[4-（3-hydroxyl-propyl）]-pyrocatechol-（6-methybutyryl）-β-D—glucopyranoside,命名为cylindrin B（2）。以及7个已知化合物tachioside（3）,syingic acid-4-β-D-glucopyran oside（4）,1-β-D—glucopyanosyloxy-3-methoxy-5-hydroxybenzene（5）,4-hydroxy-3-methoxyphenol-1-O-β-D-glucoside（6）,4-hydroxy-2,6-dimethoxyphen-1-O-β-D-glucoside（7）,phlorogluc inol-1-O-β-D-glucoside（8）,1-β-D-glucosyloxy-2-（3-nrethoxy-4-hydroxyphenyl）propane-1,3-diol（9）．它们的结构经波谱方法得到鉴定。3—9为首次从该种植物中分离得到。     

Three new arylbenzofurans from Lavandula angustifolia and their bioactivities

Three new arylbenzofurans, 2-(7-methoxy-2-(4-methoxyphenyl)-3-methylbenzofuran-5-yl)ethanol (1), 4-(5-(2-hydroxyethyl)-7-methoxy-3-methylbenzofuran-2-yl)phenol (2), and 2-(6-methoxy-2-(4- methoxyphenyl)-3-methylbenzofuran-5-yl)ethanol (3), together with three known ones (4–6) were isolated from the whole plant of Lavandula angustifolia. Their structures were determined by means of HRESIMS and extensive 1D and 2D NMR spectroscopic studies. Compounds 1–3 and 5 were tested for their anti-tobacoo mosaic virus (TMV) activities, and Compounds 1–6 were tested for their cytotoxicity activities. In our assay, Compounds 1–3 showed high anti-TMV activity with inhibition rate of 38.2, 35.2, and 34.0%, which superior to positive control Ningnanmycin. Compounds 1–6 also showed weak inhibitory activities against some tested human tumor cell lines with IC50 values in the range of 2.2–8.2 μM.     

Rubralactone, rubralides A, B and C, and rubramin produced by Penicillium rubrum

Rubralactone (1), rubralides A, B and C (2-4), rubramin (5), and 2-formyl-3,5-dihydroxy-4-methylbenzoic acid (6), were isolated from Penicillium rubrum, and their structures established by spectroscopic methods including 2D NMR. The effects on plant growth of 1-6 were examined using the lettuce seedling bioassay. Compound 1 promoted root growth. Compounds 2, 3 and 5 inhibited the growth of lettuce seedlings, but 4 and 6 did not have any inhibitory effect on their growth.     

Homoisoflavonoids from Ophiopogon japonicus Ker-Gawler

From the ethyl acetate extract of the tuberous roots of Ophiopogon japonicus (Liliaceae) eight known and five new homoisoflavonoidal compounds were isolated. The new compounds are 5,7-dihydroxy-8-methoxy-6-methyl-3-(2'-hydroxy-4'-methoxybenzyl)chroman-4-one (1), 7-hydroxy-5,8-dimethoxy-6-methyl-3-(2'-hydroxy-4'-methoxybenzyl)chroman-4-one (2), 5,7-dihydroxy-6,8-dimethyl-3-(4'-hydroxy-3'-methoxybenzyl)chroman-4-one (3), 2,5,7-trihydroxy-6,8-dimethyl-3-(3',4'-methylenedioxybenzyl)chroman-4-one (4) and 2,5,7-trihydroxy-6,8-dimethyl-3-(4'-methoxybenzyl)chroman-4-one (5). Their structures have been elucidated by mass and NMR spectroscopy. Compounds 4 and 5 are the first isolated homoisoflavonoids with a hemiacetal function at position 2.     

Studies on the Chemical Constituents of the Leaves of WTBX]Pseudotaxus chienii (Cheng) Cheng

Fourteen compounds were isolated from the leaves of Pseudotaxus chienii (Cheng) Cheng which is uniquely indigenous to China, and their structures were identified mainly by spectrum analyses. Among them, 13 known compounds were determined as: 2-guaiacylpropane-1, 3-diol (1), vanillic acid (2), 3-methoxy-4-hydroxy cinnamic acid (3). 3. 5-dimethoxy-phenol (4), taxicatin (5), 5-oxymaltol (6), quercetin-3-rhamnoside (7), (±)-catechin (8), ecdysterone (9), β-sitosterol (10), D-glucose (11), (±)-10-nonacosanol (12) and octacosanoic acid (13). All these compounds butβ-sitosterol were isolated from this plant for the first time. Compounds 1 and 6 have never been reported in plant kingdom. Another compound was tentatively established as a new compound, named pseudotaxlactone (14).     

Fumiquinones A and B, nematicidal quinones produced by Aspergillus fumigatus

New nematicides named fumiquinones A (1) and B (2), together with spinulosin (3), LL-S490beta (4), and pseurotin A (5), were isolated from Aspergillus fumigatus and their structures were established by spectroscopic methods including 2D-NMR. Compound 1 showed effective nematicidal activities against Bursaphelenchus xylophilus and Pratylenchus penetrans without inhibiting plant growth except for lettuce seedlings. Compound 2 showed effective nematicidal activity against B. xylophilus, but had no inhibitory activity against P. penetrans. Compounds 3-5 showed effective nematicidal activities against B. xylophilus without any plant growth inhibition. Compounds 1-5 had no nematicidal activity against Caenorhabditis elegans. This is the first report of the nematicidal activities of compounds 3-5.