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Synthesis of Indomethacin Conjugates with D-Glucosamine

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Chinese Chemical Letters 2005年第2期16卷 179-182页

作者： YiChunZHANG YingXiaLI HuaShiGUAN KeyLaboratoryofMarineDrugs MinistryofEducationMarineDrugandFoodInstituteOceanUniversityofChinaQingdao266003

Two series of indomethacin conjugates with D-glucosamine were prepared with theobjectives of reducing ulcerogenic potency, increasing the bioavailability of indomethacin andexerting the coordinative effects on osteoarthritis. The structures of the conjugates were identifiedby H NMR and C NMR. The ester conjugates inhibited edema as potent as indomethacin. 1 13

关键词： Indomethacin D-glucosamine NSAIDs glycoconjugates.

A New Furostanol Saponin from the Water-extract of Dioscorea nipponica Mak.,the Raw Material of the Traditional Chinese Herbal Medicine Wei Ao Xin

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Chinese Chemical Letters 2004年第10期15卷 1191-1194页

作者： ChengBinCUI ChiXU QianQunGU ShiDongCHU HaiHongJI GangJING marinedrugandfoodinstitute OceanUniversityofChinaQingdao266003 TOPSUNGroupCO. LTDXi＇an710075

O-a-D-Glucopyranosyl-furost-5(6),20(22)-dien-3a,26-diol 1, a new furostanol saponin, was isolated from the water-extract of Dioscorea nipponica Mak., the raw material of a traditional Chinese herbal medicine Wei Ao Xin. The structure of 1 was determined on the basis of its spectral data especially by NMR spectroscopy. The result provides the first example of naturally occurring furostanol saponins with a single saccharide chain at the C-26 position.

关键词： O-a-D-Glucopyranosyl-furost-5(6) 20(22)-dien-3a 26-diol furostanol saponin steroidal saponin structure NMR Dioscorea nipponica Dioscoreaceae.

Pterocarine, a New Diarylheptanoid from Pterocarya tonkinesis, its Cell Cycle Inhibition at G_0/G_1 Phase and Induction of Apoptosis in HCT-15 and K562 Cells

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Chinese Chemical Letters 2005年第2期16卷 215-218页

作者： HongBingLIU ChengBinCUI BingCAI QianQunGU DongYunZHANG QingChunZHAO HuaShiGUAN TianjinInstituteforBiomedicinalResearch（TIBiR） Tanjin300384 KeyLaboratoryofMarineDrugs MinistryofEducationChina marinedrugandfoodinstitute OceanUniversityofChinaQingdao266003／／BeijingInstituteofPharmacologyandToxicologyAMMSBeijing100850 KeyLaboratoryofMarineDrugs MinistryofEducationChina marinedrugandfoodinstitute OceanUniversityofChinaQingdao266003

Pterocarine (1), a new diarylheptanoidal compound, was isolated from Pterocaryatonkinesis (Franch.) Dode. together with a known diarylheptanoid, myricatomentogenin (2), througha bioassay-guided fractionation procedure. The structure of 1 was elucidated as (+)-3', 4''-epoxy-1-(4'-hydroxyphenyl)-7-(3''-hydroxyphenyl)-heptane-3-one by the spectroscopic *** (1) inhibited the proliferation of tsFT210, HCT-15 and K562 cells with the inhibitionrates of 20.2±2.4, 23.8±2.4 and 50.5±1.2% at 100 μg/mL, respectively. Flow cytometric analysisindicated that 1 could inhibit the cell cycle of tsFT210, HCT-15 and K562 cells at the G0/G1 phaseand could also induce apoptosis in HCT-15 (19%) and K562 (11%) cells.

关键词： Pterocarine diarylheptanoid phenolic compound structure cell cycle inhibitor apop-tosis inducer Pterocarya tonkinesis Juglandaceae.

Components of Stem Barks of Winchia calophylla A. DC. and Their Bronchodilator Activities

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Journal of Integrative Plant Biology 2005年第7期47卷 892-896页

作者： Wei-MingZHU Hong-PingHE Yue-MaoSHEN JunZHOU Xiao-JiangHAO StateKeyLaboratoryofPhytochemistryandPlantResourcesinWestChina KunmingInstituteofBotanytheChineseAcademyofSciencesKunming650204China KeyLaboratoryofMarineDrugs MinistryofEducationKeyLaboratoryofMarineDrugsofShandongProvinceMarineDrugandFoodInstituteOceanUniversityofChinaQingdao266003China

Abstract: The Dai medicinal plant Winchia calophylla A. DC. (Apocynaceae) has efficacy as an anti-cough and anti-asthmatic medication. In order to investigate its relative bioactive components, we studied the chemical constituents of this plant. Using repeated column chromatography, 28 compounds, including loganin, six phenolic compounds, 17 indole alkaloids, three pyridine alkaloids, and a quinoline alkaloid, were isolated from the stem barks of W. calophylla. Loganin, paeonol, N (4)-methyl akuammicine, and cantleyine exhibited a moderate relaxation effect on isolated smooth muscles of guinea-pig tracheal spirals and lung strips and may be the bioactive components responsible for the bronchodilation produced by W. calophylla.

关键词： alkaloid Apocynaceae bronchodilatation Winchia calophylla.

12α,13-Dihydroxyolean-3-oxo-28-oic acid, a New Triterpene,and the Known Oleanonic Acid as a New Cell Cycle Inhibitor from Schefflera venulosa

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Chinese Journal of Chemistry 2005年第3期23卷 242-244页

作者：刘睿顾谦群蔡冰刘红兵王磊管华诗 KeyLaboratoryofMarineDrugs MinistryofEducationMarineDrugandFoodInstituteOceanUniversityofChinaQingdaoShandong266003China TianjinInstituteforBiomedicinalResearch(TIBiR) Tianjin300384China

12±,13‐Dihydroxyolean‐3‐oxo‐28‐oic acid ( 1 ), a new pentacyclic triterpene, was isolated from Schefflera venulosa (Wight et Arn.) Harms through a bioassay‐guided fractionation procedure, together with the known oleanonic acid ( 2 ) as a new cell cycle inhibitor. Structures were established by spectroscopy. Compound 2 inhibited the proliferation of K562 cells with the IC 50 value of 0.13 µmol/mL by the SRB method and inhibited the cell cycle of tsFT210 cells at the G 0 /G 1 phase at the concentration higher than 10 µg/mL.

关键词： Schefflera venulosa triterpene 12α,13‐dihydroxyolean‐3‐oxo‐28‐oic acid oleanonic acid cell cycle inhibitor

Inhibitory effect of heparin-derived oligosaccharides on secretion of interleukin-4 and interleukin-5 from human peripheral blood T lymphocytes

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World Journal of Gastroenterology 2004年第23期10卷 3490-3494页

作者： Sheng-LiJi Hui-FeiCui FengShi Yan-QingChi Ji-ChaoCao Mei-YuGeng Hua-ShiGuan KeyLaboratoryofMarineDrugs MarineDrugandFoodInstituteOceanUniversityofChinaQingdao266003ShandongProvinceChina InstituteofBiochemicalandBiotechdrugs SchoolofPharmacyShandongUniversityJinan250012ShandongProvinceChina DepartmentofPharmacy ShandongProvincialHospitalJinan2500-21ShandongProvinceChina

AIM: To investigate the inhibitory effect of heparin-derived oligosaccharides (Oligs) on secretion of interleukin-4 (IL-4) and interleukin-5 (IL-5) from human peripheral blood T lymphocytes (PBTLs).METHODS: Oligs were prepared by three different heparin depolymerization methods and separated by gel filtration chromatography. PBTLs from ten adult patients with allergic eosinophilic gastroenteritis were treated with phytahematoagglutinin (PHA) and Oligs. The supernatants from the cell culture of PBTLs were harvested and subjected to the determination of IL-4 and IL-5 contents by ELISA ***: At the concentration of 5μg/mL, Oligs with different Mr had different effects on the secretion of IL-4 and IL-5. The tetrasaccharide with Mr of 1 142, produced by depolymerizing heparin with hydrogen peroxide, had the strongest inhibitory effect on the secretion of IL-4. It decreased the IL-4 content from 375.6±39.2 ng/L (PHA group) to 12.5±5.7 ng/L (P<0.01). The hexasaccharide with Mr of I 806, produced by depolymerizing heparin with βelimination method, had the strongest inhibitory effect on the secretion of IL-5. It decreased the IL-5 content from 289.2±33.4 ng/L (PHA group) to 22.0±5.2 ng/L (P<0.01).CONCLUSION: The inhibitory activity of Oligs on the secretion of IL-4 and IL-5 from human PBTLs closely depends on their molecular structure, and there may be an essential structure to act as an inhibitor. The most effective inhibitors of IL-4 and IL-5 secretion are tetrasaccharides and hexasaccharides, respectively.

关键词：抑制作用肝磷脂低聚糖分泌物白细胞间介素-4 白细胞间介素-5 外周血 T淋巴细胞 IL-4 多聚己糖

Effects of dermatan sulfate derivatives on platelet surface P-selectin expression and protein C activity in blood of inflammatory bowel disease patients

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World Journal of Gastroenterology 2004年第23期10卷 3485-3489页

作者： Sheng-LiJi Hai-YanDu Yan-QingChi Hui-FeiCui Ji-ChaoCao Mei-YuGeng Hua-ShiGuan KeyLaboratoryofMarineDrugs MarineDrugandFoodInstituteOceanUniversityofChinaQingdao266003ShandongProvinceChina InstituteofBiochemiCualniversity'Jinaannd25001B2 iotechshandoDngrUgsSchoolofPharmacyShandongUniversityJinan250012ShandongProvinceChina DepartmentofPharmacy ShandongProvincialHospitalJinan250021ShandongProvinceChina

AIM: To investigate the effect of derrnatan sulfate (DS) derivatives on platelet surface P-selectin expression and blood activated protein C (APC) activity in patients with inflammatory bowel disease (IBD), and to clarity the antiinflammatory mechanism of DS ***: Derrnatan sulfate (DS) was sulfated with chlorosulfonic acid to prepare polysulfated derrnatan sulfate (PSDS). The major disaccharides of DS and PSDS were determined by 1H nuclear magnetic resonance spectroscopy (^1H-NMR) and ^13NMR. Both DS and PSDS were depolymerized with hydrogen peroxide. The fragments were separated by gel filtration chromatography. The effects of DS derivatives on P-selectin expression were assayed by ELISA method,and blood APC activity was assayed by the synthetic chrornogenic substrate ***: The major disaccharides of DS and PSDS were IdoA-1→3-GalNAc-4-SO3 and IdoA-2SO3-1→3-GalNAc4, 6diSO3, respectively. Compared with the adenosine diphosphate stimulated group and IBD control group, DS and its derivatives all had significant inhibitory effects on P-selectin expression (P<0.01), but there was no difference between DS-derived oligosaccharides (DSOSs) and PSDS-derived oligosaccharides (PSDSOSs). The experiments on APC activity showed that DS and its derivatives all enhanced APC activity. The most active DSOS was the one with a relative molecular weight (Mr) of 4 825, which enhanced the APC activity from106.5±11.5% to 181.8±22.3% (P<0.01). With the decreaseof Mr, the activity of DSOSs decreased gradually. The effect of PSDS on APC activity enhancement was more significant than that of DS, and the APC activity was raised to 205.2±22.1% (P<0.01). All the PSDSOSs were more active than DSOSs on the basis of comparable Mr. With the decrease of Mr, the activity of PSDSOSs increased gradually, and the most active PSDSOS was PSDSOS3 with Mr of 2 749, which enhanced the APC activity to 331.2:1:27.8% (P<0.01), then the activity of PSDSOSs decreased ***:

关键词：硫酸皮肤素派生物血小板表面 P-选择蛋白基因表达蛋白质C 活动性炎性肠疾病 DS