Phenolic derivatives from Ruprechtia polystachya and their inhibitory activities on the glucose-6-phosphatase system

Two new compounds, 5-methyl-2-(2-methylbutanoyl)phloroglucinol 1-O-(6-O-β-D-apiofuranosyl)-β-D-glucopyranoside (1) and trans-2,3-dihydrokaempferol 3-O-(4-O-sulfo)-α-L-arabinopyranoside (2), together with 14 known flavonoids, trans-dihydrokaempferol 3-O-α-L-arabinopyranoside (3), trans-taxifolin 3-O-α-L-arabinofuranoside (4), quercetin 3-O-α-L-rhamnopyranoside (5), quercetin 3'-O-α-L-arabinofuranoside (6), catechin 3-O-α-L-rhamnopyranoside (7), trans-taxifolin 3-O-α-L-arabinopyranoside (8), cis-dihydrokaempferol 3-O-α-L-arabinopyranoside (9), catechin (10), myricetin 3-O-α-L-rhamnopyranoside (11), quercetin 3-O-α-L-arabinopyranoside (12), quercetin 3-O-α-L-arabinofuranoside (13), quercetin 3-O-(3″-galloyl)-α-L-rhamnopyranoside (14), quercetin 3-O-(2″-galloyl)-α-L-rhamnopyranoside (15), and epicatechin 3-O-gallate (16), were isolated from the leaves of Ruprechtia polystachya Griseb. (Polygonaceae). Their structures were established on the basis of extensive 1D- and 2D-NMR experiments as well as MS analyses. All compounds, except 1, showed inhibition of the enzyme glucose-6-phosphatase in intact microsomes.     

古蔺雪胆中的新三萜皂苷

从采自四川汉源县的古蔺雪胆(Hemsleya penxianensis var.gulinensiks)中分到9个三萜皂苷化合物,通过化学反应和光谱方法鉴定了它们的结构。其中7个为已知化合物,分别为齐墩果酸-28-O-β-D-比喃葡萄糖苷(1),3-O-β-D-吡喃葡萄糖醛基齐墩果酸苷(3),3-O-β-D-吡喃葡萄糖醛基—齐墩果酸—28-O-α-L-吡喃阿拉伯糖苷(4),3-O-β-D-吡喃葡萄糖醛基—齐墩果酸—28-O-β-D-吡喃葡萄糖苷(5),3-O-α-L-阿拉伯糖基—(1→3)—β—D-吡喃葡萄糖醛基—齐墩果酸—28—O—β—D—吡喃葡萄糖苷(6),3—O—(6′—丁酯)—β-D-吡喃葡萄糖醛基—齐墩果酸—28-O-α-L-阿拉伯糖苷(7),3-O-(6′-丁酯)—β—D吡喃葡萄糖醛基—齐墩果酸—28-O-β-D-吡喃葡萄糖苷(8)。两个新化合物,即雪胆皂苷A(2)和雪胆皂苷B(9)。     

半卧狗娃花中的黄酮类化合物

从半卧狗娃花(Heteropappus semiprost Griers)全草的乙醇提取物中分离并鉴定了7个黄酮类化合物,通过波谱分析及化学方法鉴定其结构为:3′,4′,5,7-四羟基黄酮(1),3′-甲氧基槲皮素(2),槲皮素-3-O-α-L-吡喃鼠李糖甙(3),槲皮素-3-O-β-D-吡喃半乳糖甙(4),异鼠李亭-3-O-β-D-吡喃半乳糖甙(5),槲皮素-3-O-α-L-吡喃鼠李糖(1→6)-β-D-吡喃葡萄糖甙(6),异鼠李亭-3-O-α-L-吡喃鼠李糖(1→6)-β-D-吡喃葡萄糖甙(7),其中化合物1~5为首次从本属植物中分离得到。     

Discovery of Four New Compounds from Macropanax membranifolius and Their Cytotoxic Activity

A phytochemical investigation of the methanolic extract of the Macropanax membranifolius C.B. Shang leaves led to the isolation of three new flavans, (2R,3R)-4′-O-methylcatechin 5-O-β-D-glucopyranoside ( 1 ), (2S,3S)-4′-O-methylcatechin 5-O-β-D-glucopyranoside ( 2 ), (2S,3R)-4′-O-methylcatechin 5-O-β-D-glucopyranoside ( 3 ), one new triterpene glycoside 3-O-β-D-xylopyranosyl-(1→6)-[β-D-xylopyranosyl-(1→2)]-β-D-glucopyranosyl-oleanolic acid 28-O-β-D-glucopyranoside ( 4 ), together with nine known compounds ( 5 - 13 ). Their chemical structures were elucidated based on HR-ESI-MS, NMR spectroscopic data. The absolute configurations of compounds 1 – 3 were established by electronic circular dichroism (ECD) spectra. At concentration of 20 μM, compounds 1 – 13 showed the percentages of dead cell in the range of 2.14 % to 33.61 % against KB, HepG2, HL60, P388, HT29, and MCF7 cancerous cell lines by SRB assay.     

碎米花杜鹃根的化学成分研究

采用硅胶柱色谱、Sephadex LH-20柱色谱等手段从碎米花杜鹃Rhododendron spiciferum根中分离得到15个化合物,根据化合物的理化性质和光谱数据分别鉴定为(-)-南烛木树脂酚(1)、(+)-环合橄榄树脂素(2)、(-)-南烛木树脂酚-9-O-β-D-葡萄吡喃糖苷(3)、(-)-南烛木树脂酚-9-O-β-D-木吡喃糖苷(4)、3,5,7-三羟基色原酮-3-O-α-L-鼠李吡喃糖苷(5)、3,5,7-三羟基色原酮-3-O-α-L-阿拉伯吡喃糖苷(6)、柚皮素(7)、圣草酚(8)、紫杉叶素(9)、儿茶素(10)、紫杉叶素-3-O-α-L-阿拉伯吡喃糖苷(11)、黄杞苷(12)、紫杉叶素-3-O-α-L-阿拉伯呋喃糖苷(13)、蒲公英赛醇(14)、蒲公英赛醇乙酸酯(15)。其中化合物1~6、8、9、13~15为首次从该植物中分得。     

New Isopropyl Chromone and Flavanone Glucoside Compounds from the Leaves of Syzygium cerasiforme (Blume) Merr. & L.M.Perry and Their Inhibition of Nitric Oxide Production

A new isopropyl chromone ( 1 ) and a new flavanone glucoside ( 2 ) together with eleven known compounds ( 3–13 ) were isolated from the leaves of Syzygium cerasiforme (Blume) Merr. & L.M.Perry. Their structures were elucidated as 5,7-dihydroxy-2-isopropyl-6,8-dimethyl-4H-chromen-4-one ( 1 ), 5,7-dihydroxyflavanone 7-O-β-D-(6′′-O-galloylglucopyranoside) ( 2 ), strobopinin ( 3 ), demethoxymatteucinol ( 4 ), pinocembrin-7-O-β-D-glucopyranoside ( 5 ), (2S)-hydroxynaringenin-7-O-β-D-glucopyranoside ( 6 ), afzelin ( 7 ), quercetin ( 8 ), kaplanin ( 9 ), endoperoxide G3 ( 10 ), grasshopper ( 11 ), vomifoliol ( 12 ), litseagermacrane ( 13 ) by the analysis of HR-ESI-MS, NMR, and CD spectral data. Compounds 1 , 2 , 5 , 6 and 10 inhibited NO production on LPS-activated RAW264.7 cells with IC₅₀ values of 12.28±1.15, 8.52±1.62, 7.68±0.87, 9.67±0.57, and 6.69±0.34 μM, respectively, while the IC₅₀ values of the other compounds ranging from 33.38±0.78 to 86.51±2.98 μM, compared to that of the positive control, N^G-monomethyl-L-arginine acetate (L-NMMA) with an IC₅₀ value of 32.50±1.00 μM.     

桂火绳中化学成分的研究

从梧桐科火绳属桂火绳中提取分离到22个化合物,经结构鉴定为:羽扇豆醇(1),白桦脂酸(2),齐墩果酸(3),丁香脂素(4),(+)-异落叶松树脂醇(5),东莨菪内酯(6),对羟基肉桂酸(7),二十七碳酸单甘油酯(8),2-十八烯酸单甘油酯(9),sitoindosideⅡ(10),儿茶素(11),表儿茶素(12),表儿茶素3-O-β-D-吡喃木糖甙(13),山奈酚3-O-β-D-吡喃葡萄糖甙(14),5,7,4'-三羟基异黄酮(15),4'-O-methylgallocatechin(16),反式-二氢槲皮素-3-O-α-阿拉伯糖甙(17),顺式-二氢槲皮素-3-O-α-阿拉伯糖甙(18),反式-二氢槲皮素-3-O-β-吡喃葡萄糖甙(19),3,5,7,3',5'-五羟基-4'-甲氧基异黄酮(20),山奈酚-3-O-β-D-吡喃葡萄糖(6→1)-α-L-吡喃鼠李糖甙(21),以及槲皮素3-O-β-D-吡喃葡萄糖(6→1)-β-D-吡喃葡萄糖甙(22),这些化学成分首次从该属植物中分离出来。     

Two new anti-plasmodial flavonoid glycosides from Duranta repens

The CHCl₃-soluble fraction of the whole plant of Duranta repens showed anti-plasmodial activity against the chloroquine-sensitive (D6) and chloroquine-resistant (W2) strains of Plasmodium falciparum, with IC₅₀ values of 8.5?±?0.9 and 10.2?±?1.5?μg/mL, respectively. From this fraction, two new flavonoid glycosides, 7-O-α-d-glucopyranosyl-3,4′-dihydroxy-3′-(4-hydroxy-3-methylbutyl)-5,6-dimethoxyflavone (1) and 7-O-α-d-glucopyranosyl(6′′′-p-hydroxcinnamoyl)-3,4′-dihydroxy-3′-(4-hydroxy-3-methylbutyl)-5,6-dimethoxyflavone (2), along with five known flavonoids, 3,7,4′-trihydroxy-3′-(4-hydroxy-3-methylbutyl)-5,6-dimethoxyflavone (3), 3,7-dihydroxy-3′-(4-hydroxy-3-methylbutyl)-5,6,4′-trimethoxyflavone (4), 5,7-dihydroxy-3′-(2-hydroxy-3-methyl-3-butenyl)-3,6,4′-trimethoxyflavone (5), 3,7-dihydroxy-3′-(2-hydroxy-3-methyl-3-buten-yl)-5,6,4′-trimethoxyflavone (6), and 7-O-α-d-glucopyranosyl-3,5-dihydroxy-3′-(4′′-acetoxy-3′′-methylbutyl)-6,4′-dimethoxyflavone (7), have been isolated as anti-plasmodial principles. Their structures were deduced by spectroscopic analysis including 1D and 2D NMR techniques. The compounds (1–7) showed potent anti-plasmodial activities against D6 and W2 strains of Plasmodium falciparum, with IC₅₀ values in the range of 5.2–13.5?μM and 5.9–13.1?μM, respectively.     

New Triterpenoid Glycosides from Hemsleya penxianensis var. gulinensis

Two new triterpenoid saponins were isolated from the rools of Hemsleya penxianensis var. gulinensis together with seven known saponins oleanolic acid 28-O-β-D-glucopyranoside (1), oleanolic acid 3-O-β-D-glucuropyranoside(3), 3-O-β-D-glucuropyranosyl-oleanolic acid-28-O-α-L-arabinopyranoside(4).     

Study on Chemical Components from Derris taiwaniana and Their Lung Epithelial Cell Protect Effects

The ethanol extract of roots of Derris taiwaniana gave two undescribed compounds, 3,3′-dimethoxy-5′-hydroxystilbene-4-O-β-apiofuranosyl-(1→6)-β-D-glucopyranoside ( 1 ) and 4′,5-dihydroxy-3′-methoxyisoflavone-7-O-β-apiofuranosyl-(1→6)-β-D-glucopyranoside ( 2 ), along with thirty known components. Among them, compounds 14 , 16 – 17 , 23 , 26 – 32 were isolated from this genus for the first time. Their structures were established based on physico-chemical properties and spectroscopic data, the lung epithelial cell protective effects were evaluated using NNK-induced MLE-12 cells. Among them, 2α,3α-epoxy-5,7,3′,4′-tetrahydroxyflavan-(4β-8-catechin) ( 30 ) showed the best significant protective effect, speculated to be the key component of D. taiwaniana that plays a protective role in lung epithelial cells.     

Six New Constituents from the Fruit of Hypericum patulum and Their Anti-Inflammatory Activity

Four new xanthone glucosides, 3-hydroxy-2-methoxyxanthone-4-O-β-D-glucopyranoside ( 1 ), 4,8-dihydroxy-2-methoxyxanthone-3-O-β-D-glucopyranoside ( 2 ), 2-methoxyxanthone-5-O-β-D-glucopyranoside ( 3 ), 4-hydroxy-2-methoxyxanthone-3-O-β-D-glucopyranoside ( 4 ), a new phenolic acid, 4,4′-dihydroxy-3,3′-imino-di-benzoic acid monomethyl ester ( 5 ), and a new isoquinoline, methyl 6-hydroxy-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylate ( 6 ) were isolated from the fruit of Hypericum patulum. The structural elucidation of the isolated compounds was primarily based on HR-ESI-MS, UV, IR, 1D and 2D NMR. All compounds were evaluated for their inhibitory effect against LPS-induced NO production in RAW 264.7 cells. Compound 2 , 3 exhibited moderate inhibitory activity against NO production.     

天山棱子芹化学成分的研究

从天山棱子芹中首次分离得到15个已知化合物,通过NMR、MS及IR等波谱数据,分别鉴定为6,7-二羟基香豆素(1),( )-marmesin(2),marmesinin(3),5,7,4'-三羟基黄酮(4),莰非醇3-O-α-L-吡喃鼠李糖甙(5),藤黄菌素3'-O-β-D-吡喃葡萄糖甙(6),(R)-6-hydroxy-3-(2-hydroxypropan-2-yl)-6-methylcyclohex-2-enone(7),4-羟基苯甲酸(8),3-甲氧基4羟基苯甲酸(9),3-甲氧基-4,5-亚甲二氧基苯甲酸(10),丁香酸甲酯(11),丁香酸甲酯4-O-β-D-吡喃葡萄糖甙(12),姜油酮4’-O-β-D-吡喃葡萄糖甙(13),2-(4-羟基苯基)-乙醇(14)和正二十八醇(15)。其中化合物7为一新的天然产物。     

菝葜中三个新的二氢山萘酚酰化糖苷(英文)

从菝葜根茎中共分离得到3个新的二氢黄酮醇酰化糖苷(1～3)和1个已知的二氢黄酮醇苷(4),分别被鉴定为:(2R,3R)-二氢山萘酚3-氧-(6″-氧-乙酰基)-β-D-葡萄糖苷(1),(2R,3R)-二氢山萘酚3-氧-(2″-氧-乙酰基)-β-D-葡萄糖苷(2),(2R,3R)-二氢山萘酚3-氧-(3″-氧-乙酰基)-β-D-葡萄糖苷(3)及(2R,3R)-二氢山萘酚3-氧-β-D-葡萄糖苷(4)。其结构通过MS,1D NMR和2D NMR等光谱分析和化学方法确定。研究结果表明,二氢黄酮醇的酰化糖苷可能是菝葜属的特征成分。     

Two new guaiane sesquiterpenes from Datura metel L. with anti-inflammatory activity

Chemical investigation of an acidic methanol extract of the whole plants of Datura metel resulted in the isolation of two new guainane sesquiterpenes, 1β,5α,7β-guaiane-4β,10α,11-triol (1) and 1α,5α,7α-11-guaiene-2α,3β,4α,10α,13-pentaol (2), along with eight known compounds: pterodontriol B (3), disciferitriol (4), scopolamine (5), kaempferol 3-O-β-d-glucosyl(1 → 2)-β-d-galactoside 7-O-β-d-glucoside (6), kaempferol 3-O-β-glucopyranosyl(1 → 2)-β-glucopyranoside-7-O-α-rhamnopyranoside (7), pinoresinol 4′′-O-β-d-glucopyranoside (8), (7R,8S,7′S,8′R)-4,9,4′,7′-tetrahydroxy-3,3′-dimethoxy-7,9′-epoxy-lignan-4-O-β-d-glucopyranoside (9), and (7S,8R,7′S,8′S)-4,9,4′,7′-tetrahydroxy-3,3′-dimethoxy-7,9′-epoxylignan-4-O-β-d-glucopyranoside (10). Their structures were elucidated by extensive spectroscopic methods, including 1D and 2D NMR and MS spectra. Compounds 2-4 and 6-10 were shown to have modest anti-inflammatory effects through inhibition of NO production in LPS-stimulated BV cells.     

Molecular complexes of ivy and licorice saponins with sildenafil citrate (Viagra) and their biological activity

The molecular complexation of triterpene glycosides α-hederin (hederagenin 3-O-α-L-rhamnopyranosyl-(l → 2)-O-α-L-arabinopyranoside), hederasaponin C (hederagenin 3-O-α-L-rhamnopyranosyl-(l → 2)-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(l → 4)-O-β-D-glucopyranosyl-(l → 6)-O-β-D-glucopyranoside), and glycyram (monoammonium glycyrrhizinate) with sildenafil citrate was investigated for the first time using electrospray ionization mass spectroscopy. The glycosides form a complex in a 1: 1 molar ratio. The influence of the complex on Avena sativa seeds germination and its ichthyotoxicity against Poecilia reticulata were studied.     

New Phenylpropanoid Glycosides from Illicium majus and Their Radical Scavenging Activities

Chemical investigation of the ethanol extract of the branch and leaves of Illicium majus resulted in the isolation of four new phenylpropanoid glycosides ( 1 – 4 ) and one new phenolic glycoside ( 9 ), along with 13 known ones. Spectroscopic techniques were used to elucidate the structures of the new isolates such as 3-[(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]propyl β-D-glucopyranoside ( 1 ), [(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-3-yl]methyl 2-O-α-L-rhamnopyranosyl-β-D-glucopyranoside ( 2 ), [(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-3-yl]methyl 2-O-α-L-rhamnopyranosyl-β-D-xylopyranoside ( 3 ), 3-[(2R,3S)-3-({[2-O-(4-O-acetyl-α-L-rhamnopyranosyl)-β-D-xylopyranosyl]oxy}methyl)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]propyl acetate ( 4 ), and 4-(2-hydroxyethyl)phenyl 3-O-β-D-glucopyranosyl-β-D-glucopyranoside ( 9 ). Free radical scavenging activities of the isolates were elucidated through the DPPH assay method. The most active compounds, 1-O-caffeoyl-β-D-glucopyranose ( 17 ) and soulieana acid 1 ( 18 ), exhibited moderate radical scavenging activities (IC₅₀=37.7±4.4 μM and IC₅₀=97.2±3.4 μM, respectively). The antibacterial activities of the isolates against Staphylococcus aureus and Escherichia coli were also assessed, and no activity was shown at the measured concentration (<32 μg/mL).     

Conversion of Cellobiose into Lactose

Benzyl 2, 3, 6-tri-O-acetyl-4-O-(2,3-di-O-acetyl-4,6-di-O-methylsulfonyl-β-d-glucopyranosyl)-β-d-glucopyranoside (VI) was prepared from α-cellobiose octaacetate. Displacement of the sulfonyl esters of VI with acyloxy-groups in N, N-dimethyl formamide in the presence of sodium benzoate gave 4-O-β-d-galactopyranosyl-d-glucopyranose derivative (lactose derivative). Elimination of blocking groups of the derivative yielded lactose hydrate (IX), though the overall yield of lactose from cellobiose octaacetate was less than 2%.     

虎眼万年青属植物Ornithogalum thyrsoide 的甾体皂苷及黄酮类化学成分

运用硅胶、Sephadex LH-20、ODS柱层析及半制备高效液相色谱技术对一引种虎眼万年青属植物Ornithogalum thyrsoides的化学成分进行研究,从其乙醇提取物的乙酸乙酯部分分离得到7个化合物.通过MS、NMR等波谱技术确定其结构分别为(23S,24S,25S)-23,24-dihydroxyruscogenin- 1-O-α-L-rhamnopyranosyl(1 →2)-α-L-arabinopyranoside(1),(24S,25S)-3β,24-dihydroxyspirost-5 -en- 1β-yl O-α -L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside(2),β-胡萝卜苷(3)β-谷甾醇(4),山奈酚-4′-O-β-D-吡喃葡萄糖苷(5),千层纸素A(6)和汉黄芩素(7).其中,化合物1、5～7为首次从该属植物中分离得到.体外药理活性结果显示这7个化合物对HCT-8、Bel-7402、BGC-823、A549及A2780实体瘤细胞株无明显细胞毒活性.     

Triterpene saponins from Cyclamen hederifolium

Five triterpene saponins never reported before, hederifoliosides A-E, and four known triterpene saponins were isolated from the tubers of Cyclamen hederifolium. The structures of hederifoliosides A-E were determined as 3β,16α-dihydroxy-13β,28-epoxyolean-30-oic acid 3-O-{[β-D-glucopyranosyl-(1 → 2)-O]-β-D-xylopyranosyl-(1 → 2)-O-β-D-glucopyranosyl-(1 → 4)-O-α-L-arabinopyranoside}, 3β,16α-dihydroxy-13β,28-epoxyolean-30-oic acid 3-O-{[β-D-glucopyranosyl-(1 → 2)-O]-β-D-xylopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-O-α-L-arabinopyranoside}, 3β,16α-dihydroxy-13β,28-epoxyolean-30-al 3-O-{[β-D-glucopyranosyl-(1 → 2)-O]-β-D-xylopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-[β-D-glucopyranosyl-(1 → 6)]-O-β-D-glucopyranosyl-(1 → 4)-O-α-L-arabinopyranoside}, 30-O-β-D-glucopyranosyl-(1 → 2)-O-β-D-glucopyranosyl-3β,16α,30-trihydroxyolean-12-en-28-al 3-O-{[β-D-glucopyranosyl-(1 → 2)-O]-β-D-xylopyranosyl-(1 → 2)-O-β-D-glucopyranosyl-(1 → 4)-O-α-L-arabinopyranoside}, 30-O-β-D-glucopyranosyl-(1 → 2)-O-β-D-glucopyranosyl-3β,16α,28,30-tetrahydroxyolean-12-en 3-O-{[β-D-glucopyranosyl-(1 → 2)-O]-β-D-xylopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-O-α-L-arabinopyranoside}, by a combination of one- and two-dimensional NMR techniques, and mass spectrometry. The cytotoxic activity of the isolated compounds was evaluated against a small panel of cancer cell lines including Hela, H-446, HT-29, and U937. None of the tested compounds, in a range of concentrations between 1 and 50 μM, caused a significant reduction of the cell number.     

Glycosylation of trans-Resveratrol by Plant-Cultured Cells

Plant-cultured cells of Catharanthus roseus converted trans-resveratrol into its 3-O-β-D-glucopyranoside, 4'-O-β-D-glucopyranoside, 3-O-(6-O-β-D-xylopyranosyl)-β-D-glucopyranoside, and 3-O-(6-O-α-L-arabinopyranosyl)-β-D-glucopyranoside. The 3-O-(6-O-β-D-xylopyranosyl)-β-D-glucopyranoside and 3-O-(6-O-α-L-arabinopyranosyl)-β-D-glucopyranoside compounds of trans-resveratrol are both new. Incubation of plant-cultured cells of Ipomoea batatas and Strophanthus gratus with trans-resveratrol gave trans-resveratrol 3-O-β-D-glucopyranoside and trans-resveratrol 4'-O-β-D-glucopyranoside.