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Sulfated polysaccharides with antioxidant and anticoagulant activity from the sea cucumber Holothuria fuscogliva

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Chinese Journal of Oceanology and Limnology 2017年第4期35卷 763-769页

作者：李荣锋于华华岳洋刘松邢荣娥陈晓琳李鹏程 Key Laboratory of Experimental Marine Biology Institute of OceanologyChinese Academy of Sciences University of Chinese Academy of Sciences

Sea cucumber is a traditional nutritional food and medicinal resource with many bioactive components in China. Holothuriafuscogliva is a big sea cucumber with a rich of bioactive polysaccharides. To investigate the bioactivities of the polysaccharides from sea cucumber H. fuscogliva, we prepared the sulfated polysaccharides （HfP） from sea cucumber H. fuscogliva using a protease hydrolysis method. Antioxidant activities of HfP were investigated, including hydroxyl radical scavenging activity and superoxide radical scavenging activity. And, the anticoagulant activities of HfP were studied, including the activated partial thromboplastin time （APTT）, prothrombin time （PT） and thrombin time （TT）. The average molecular weight was 1 867.1 Da, with a sulfate content of 20.7%. In addition, the molar ratio of monosaccharide composition of HfP was Man： Rha： Glc A： Glc： Gal： Xyl： Fuc=0.083 6： 0.437： 0.134： 0： 1.182： 0.748： 1. It had a strong antioxidant activity, the hydroxyl and superoxide radical scavenging activity ECs0 of HfP was 3.74 and 0.037 mg/mL, respectively. It also showed a good anticoagulant activity in our study. The APTT of HfP was much higher than that of heparin sodium, and the PT and TT of HfP was close to that ofheparin sodium at a low concentration. Therefore, HfP shows a good antioxidant and anticoagulant activity and it may become a potential candidate of the natural antioxidant and anticoagulant and will have a good application future in health product or medicine industry.

关键词： sulfated polysaccharides sea cucumber Holothuriafuscogliva antioxidant activity anticoagulant activity

In-vitro anticoagulant activity of fucoidan derivatives from brown seaweed Laminaria japonica

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Chinese Journal of Oceanology and Limnology 2011年第3期29卷 679-685页

作者：王晶张全斌张忠山侯赟张虹 Institute of Oceanology Chinese Academy of Sciences Graduate University of Chinese Academy of Sciences

Fucoidan, a group of sulfated heteropolysaccharides, was extracted from Laminaria japonica, an important economic alga species in China. The anticoagulant activity of fucoidan and its derivatives (including sulfated, phosphorylated, and aminated fucoidan) was examined using in-vitro anticoagulant systems. The correlation between chemical variations within the fucoidan group and anticoagulant activity was determined. The in-vitro anticoagulant properties of fucoidan and its derivatives were determined by measuring activated partial thromboplastin time (APTT), prothrombin time (PT), and thrombin time (TT). The results indicate anticoagulant activity in all samples using APTT and TT assays; however, only the fucoidan derivatives affected the PT assay. Thus, the fucoidan derivatives were able to inhibit both intrinsic and extrinsic blood coagulants. Fucoidan (FPS) and its derivatives presented better anticoagulant activity than low molecular weight fucoidan (DFPS) and its derivatives, suggesting that molecular weight and proper conformation are contributing factors for anticoagulant activity of polysaccharides. Amino groups have a positive charge and can thus change the charge density of fucoidan. Accordingly, among the tested samples, aminated fucoidan (NF) was the most active reflecting the importance of charge density for anticoagulant activity. Available data obtained using in-vitro models suggest that the sulfate content, sulfate/total-sugar ratio, molecular weight, and the substituted group of fucoidan are important factors for anticoagulant activity but that the influence of sulfate, phosphate and amino groups on anticoagulant activity was different.

关键词： fucoidan derivative Laminariajaponica anticoagulant activity

Preparation of low molecular weight Sargassum fusiforme polysaccharide and its anticoagulant activity

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Journal of Oceanology and Limnology 2018年第3期36卷 882-891页

作者： SUN Yuhao CHEN Xiaolin LIU Song YU Uuahua LI Rongfeng WANG Xueqin QIN Yukun LI Pengcheng Institute of Oceanology Chinese Academy of SciencesQingdao 266071China University of Chinese Academy of Sciences Beijing 100049China

Heparin has been used as an anticoagulant drug for many years, but it has significant side ef fects. In the search for good substitutes, low molecular weight(MW) polysaccharides from S argassum fusiforme have been examined and confi rmed to possess biological activities. Here, S. fusiforme polysaccharides(SFP) were extracted and subjected to a hydrogen peroxide(H_2O_2) oxidation method for the preparation of low-MW SFP(LSFP). The effects of temperature, pH, and H_2O_2 concentration on the degradation process were also examined. Several LSFP of 36, 9, 5.7, and 2.7 kDa were obtained under different conditions, and their anticoagulant activities studied in vitro. The results showed that SFP and LSFP prolonged activated partial thromboplastin(APTT), prothrombin(PT) and thrombin times(TT) significantly, indicating that these low MW polysaccharides possessed anticoagulant activity in the intrinsic, extrinsic, and common coagulation pathways. As these ef fects were related to the MW of the polysaccharides in APTT and TT but not in PT, the contents of the monosaccharide fucose and sulfate and the polysaccharide MW could have exerted combined ef fects. The details of this mechanism require further verifi cation.

关键词： anticoagulant activity Sargassum fusiforme low molecular weight degradation

Uncarialines A-E,new alkaloids from Uncaria rhynchophylla and their anticoagulant activity

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Natural Products and Bioprospecting 2023年第1期13卷 598-606页

作者： Ke-Pu Huang Li-Li Xu Sheng Li Yin-Ling Wei Lian Yang Xiao-Jiang Hao Hong-Ping He Yu Zhang School of Chinese Materia Medica Yunnan University of Chinese MedicineKunming 650500People’s Republic of China State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunming 650201People’s Republic of China

Uncarialines A-E(1-5),five undescribed monoterpene indole alkaloids,together with five known analogues were obtained from the stems of Uncaria *** 1-3 were unique 3,4-seco-tricyclic alkaloids with a 6/5/10 ring system,while 4 and 5 possessed a rare rearranged scaffold originated from corynantheine-type alkaloids with C-2/C-7 *** structures were characterized by a comprehensive analysis of MS,NMR,and *** effects on blood clotting times of human plasma were evaluated and alkaloid 5 had a slight prolongation effect on both thrombin time and activated partial thromboplastin time(p<0.001).

关键词： Uncaria rhynchophylla Monoterpene indole alkaloids Uncarialines A-E anticoagulant activity

Depolymerization of fucosylated chondroitin sulfate with a modified Fenton-system and anticoagulant activity of the resulting fragments

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Depolymerization of fucosylated chondroitin sulfate with a m...

Chemical Characteristics and anticoagulant Activities of Two Sulfated Polysaccharides from Enteromorpha linza (Chlorophyta)

中国食品科学技术学会第十三届年会

作者： Li Junhui Li Shan Zhi Zijian Yan Lufeng Liu Shanshan Ye Xingqian Ding Tian Robert J.Linhardt Chen Shiguo Zhejiang University Department of Food Science and NutritionZhejiang Key Laboratory for Agro-Food ProcessingFuli Institute of Food Science

Fucosylated chondroitin sulfate（fCS） from sea cucwnberlsostichopusbadionotus（fCS-Ib） with a chondroitin sulfate type E（CSE） backboneand 2,4-O-sulfofucose brancheshas shown excellent anticoagulant activityalthough show severe adverse *** represents aneffective methodtodiminishthis polysaccharide’s side *** present study reports a modified controlled Fenton system for degradation of fCS-Iband the anticoagulant activity of the resulting *** NMR analysis of the resulting fragments indicate thatno significant chemical changes in the backbone of fCSIband no loss of sulfo groups take place during *** in the molecular weight of fCS-Ibeshould result in a dramatic decrease inprolonging activated partial thromboplastin time and thrombin time.A decrease in the inhibition of thrombin by antithromin Ⅲ and heparin cofactor II and the slight decrease of the inhibition of factor X activity results in a significant increase of anti-FXa/anti-FIIa activity *** controlled free-radical depolymerization method enables preparation of GAG oligosaccharides suitable for investigation of clinical anticoagulant application.

关键词： sea cucumber fucosylated chondroitin sulfate free-radical depolymerization anticoagulant activity

来源： cnki会议评论

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Journal of Ocean University of China 2013年第1期12卷 175-182页

作者： QI Xiaohui MAO Wenjun CHEN Yin CHEN Yanli ZHAO Chunqi LI Na WANG Chunyan Key Laboratory of Marine Drugs Ministry of Education Institute of Marine Drug and Food Ocean University of China

Two sulfated polysaccharides, designated MP and SP, were extracted from the marine green alga Enteromorpha linza using hot water and then purified using ion-exchange and size-exclusion chromatography. The anticoagulant activities of MP and SP were examined by determination of their activated partial thromboplastin time （APTT）, thrombin time （TT） and prothrombin time （PT） using human plasma. Results showed that MP and SP were composed of abundant rhamnose with small amounts of xylose and glucuronic acid, whereas SP also contained a small amount of galactose. Approximate molecular weights of MP and SP were 535 and 502 kDa, respectively. As compared with SP, MP had higher contents of sulfate ester （19.0%） and uronic acid （14.9%）. The MP mainly consisted of （1→4）-linked rhamnose residues with partially sulfated groups at the C-3 position, and small amounts of （1→3, 4）-linked rhamnose, （1→2,4）-linked rhamnose, （1→4）-linked glucuronic acid and （1→4）-linked xylose residues. The SP contained abundant （1→4）-linked rhamnose with minor amounts of （1→3）-linked rhanmose, （1→3, 4）-linked rhamnose, （1→2, 4）-linked rhanmose, （1→4）4inked glucuronic acid, （1→4）-linked xylose, and （1→3）-linked galactose residues. The sulfate groups were mainly located at C-3 of （1→4）-linked rhamnose residues. Both MP and SP, in particular the former, effectively prolonged APTT and TT. This work demonstrates that MP and SP have unique structural characteristics distinct from those of other sulfated polysaccharides from Enteromorpha. The MP is a potential source of anticoagulant, and the difference in anticoagulant activities of the two sulfated polysaccharides is directly linked to the discrepancy of their chemical features.

关键词： Marine green alga Enteromorpha linza sulfated polysaccharide chemical characteristic anticoagulant activity

Neolignans and Norlignans from Insect Medicine Polyphaga plancyi and Their Biological Activities

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Natural Products and Bioprospecting 2021年第1期11卷 51-62页

作者： Hong-Jie Zhu Te Xu Yong-Ming Yan Zheng-Chao Tu Yong-Xian Cheng School of Pharmaceutical Sciences Shenzhen University Health Science CenterShenzhen 518060People’s Republic of China State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunming 650201People’s Republic of China International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Chinese Ministry of Education(MOE) College of PharmacyJinan UniversityGuangzhou 510632People’s Republic of China Drug Discovery Pipeline&Guangdong Provincial Key Laboratory of Biocomputing Guangzhou Institutes of Biomedicine and HealthGuangzhou 510530People’s Republic of China

Ten neolignans or norlignans(1-10)including eight new compounds were isolated from the whole bodies of Polyphaga plancyi *** structures were identified by spectroscopic *** 3,4,8,and 9 are racemates indicated by chiral HPLC *** separation followed by ECD calculations allowed to clarify the absolute configurations of all the *** the new compounds were evaluated for their biological properties toward extracellular matrix in rat renal proximal tubular cells,human cancer cells(K562,A549,and Huh7),EV71,ROCK2,JAK3,DDR1,and coagulation.

关键词： Polyphaga plancyi Insect medicine Lignans Renal protection anticoagulant activity

Design, Preparation and in vitro Bioactivity of Mono-PEGylated Recombinant Hirudin

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Chinese Journal of Chemical Engineering 2007年第6期15卷 775-780页

作者：候蓓蓓李世荣李晓晖修志龙 Department of Bioscience ＆ Biotechnology Dalian University of Technology Dalian 116024 China

Hirudin, the most potent inhibitor of thrombin found in nature, has a short half-life in serum, which sig-nificantly limits its clinical application as an anticoagulant. Recently, PEGylation has been commonly used as an effective method to prolong its half-life in serum. In contrast to the nonspecific pEGylation under basic conditions that targets lysine residues randomly, PEGylation sites under mildly acidic conditions preferably targets histidine residues, and there is only one histidine residue at 51 in r-hirudin; therefore, succinimidyl carbonyl methoxy poly-ethylene glycol （SC-mPEG, 20000） was attached to r-hirudin at mildly acidic pH to favor the formation of mono-PEGylated r-hirudin. The reaction mixture with high mono-PEGylated ratio was easily separated by a one-step ion-exchange chromatographic （IEC） procedure. Approximately 79.71% of the mono-PEGylated r-hirudin was PEGylated at His51, which showed that the acidic PEGylation operation prevented the PEGylation of active center （Lys47） of r-hirudin in pdnciple. *** with purity higher than. 95% was obtained as the pre-dominant product, and 34% of the anticoagulant activity was retained in vitro. The staining method for sodium dodecyl sulfate polyacrylamide gel electrophoresis （SDS-PAGE） was improved to obtain perfect electrophoretic pattern in less than 5min. More accurate molecular weight was deduced due to the use of PEGs as molecular weight standards.

关键词： r-hirudin histidine residues SC-rnPEG mono-PEGylation pH anticoagulant activity

Antimicrobial and anticoagulant activities of the spine of stingray Himantura imbricata

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Journal of Coastal Life Medicine 2014年第2期2卷 89-93页

作者： Kaliyamoorthy Kalidasan Velayudham Ravi Sunil Kumar Sahu Murugan Lakshmi Maheshwaran Kathiresan Kandasamy Centre of Advanced Study in Marine Biology Faculty of Marine SciencesAnnamalai UniversityParangipettai-608502Tamil NaduIndia

Objective:To study the spine structure of stingray Himantura imbricata(***)and to evaluate the anticoagulant properties of the spine extract obtained through various solvents extracts followed by antibacterial activity against human ***:Spines of *** were collected from Nagappattinam coast,Tamil Nadu,India and their spines were observed under the light *** grounded spines were subjected to extraction of metabolites using methanol,ethanol,chloroform and *** activity was evaluated by disc diffusion technique against 10 human ***,anticoagulant activity was also assessed by following United States Pharmacopeia ***:Light microscopic observation of spine revealed that the venom apparatus of the stingray *** consisted of two to three spines,glandular tissue and a *** spine extract showed potent antibacterial activity against all tested *** activity(14 mm)was found against Staphylococcus *** extract showed 91.50 USP units/mg of anticoagulant ***:Microscopic observations gave new insight about the spine structure of the *** spine extracts of *** showed potent activity against human pathogens revealed by the good zone of *** extracts conferred the most prominent antibacterial *** anticoagulant activity was also comparable with that of standard heparin.

关键词： Stingrays Himantura imbricata Spine Antimicrobial activity anticoagulant activity