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Химия природных соединений
Редакция журнала 'Химия природных соединений'
Химия природных соединений

Редакция журнала 'Химия природных соединений'

0023-1150

Химия природных соединений/Journal Химия природных соединений
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    CHEMICAL COMPOSITION OF ESSENTIAL OILS FROM Hedyosmum orientate

    Luu D.Ngoc AnhTruong B.VuonBui V.Huong
    3页
    查看更多>>摘要:The plants of the Chloranthaceae family constitute a systematic group belonging to the angiosperm with four genera and about 75 species of herbs,shrubs,and small trees,including Ascarina,Chloranthns,Hedyosmum,and Sarcandra,and have a pantropical distribution[1,2].The genus Hedyosmum is the largest of the four genera of Chloranthaceae,It includes 44 extant species.While all other species are restricted to the New World,the only Hedyosmum orientate is distributed in Southeast Asia [3].The species Hedyosmum orientale Merr.& Chun is known as"Mat hung,"which means"honey flavor."It has a narrow distribution range,and in Vietnam it has only been recorded in Kon Plong District,Kon Tum Province [4,5].The chemical constituents of several of this species growing in China,such as sesquiterpenoids,were also isolated from the aerial parts,including hedyosumins A-E,hedyosmum F,10R-hydroxy-1,5RH-guaia-3,7(11)-dien-8R,12-olide,9R-hydroxyasterolide,spathulenol,13-hydroxy-8,9-dehydroshizukanolide,and aromadendrane-4β,10β-diol [6,7].Herein we describe the volatile compounds from the leaves,stems,roots,and fruits of Hedyosmum orientale Merr.& Chun,in Vietnam.

    METABOLITES FROM Ерiсhlоё bromicola OBTAINED BY CO-CULTURE WITH Pestalotiopsis microspore AS INHIBITORS OF CdC25A PHOSPHATASES,PLANT PATHOGENS,AND GRASSES

    Qiu-Yan SongFang-Shu ChengMeng Sun
    2页
    查看更多>>摘要:The interest in natural products from Epichloe endophytes diminishes year by year due to the difficulties involved in working with complex separation process and the continual rediscovery of the same bioactive chemical structures.With the goal of isolation of new bioactive alkaloids from Epichloe bromicola produced by induction of unexpressed pathways,a co-cultivation of E.bromicola with Pestalotiopsis microspore was performed.A follow-up study of the mixed fermentation of E.bromicola and P.microspore led to the isolation of 15 natural products,and their inhibitory effects against Cdc25A phosphatase,plant pathogens,and grasses were tested for the first time.A specimen of E bromicola(NI_201216)was deposited at the College of Pastoral Agriculture Science and Technology,Lanzhou University [1].microspore was purchased from China Forestry Culture Collection Center,For pure strain cultures,a 5 mm agar plug of a fungal preculture was inoculated in the center of a 100 mL Erlenmeyer flasks containing 40 mL of potato dextrose media.The contents of the Erlenmeyer flask were incubated at 25 ℃ on a rotary shaker at 140 rpm.The seed liquid of E.bromicola was inoculated in sterilized rice,and the sterilized rice fermentation in 1000 mL Erlenmeyer flasks(containing 100 g rice)was kept for 10 days at 25 ℃,Then the seed liquid of P.microspore was inoculated in the previous Erlenmeyer flasks,which was kept for 30 days at 25℃,The mixed rice culture was extracted with EtOAc four times to yield 12 g extract.The crude extract was then subjected to macroporous resin(D101)and eluted with H2O-EtOH(1:0-0:1 gradient system)to give five fractions labeled Frs.A-E.Fraction В was isolated by RP-18(Н2О-МеОН,1:0-0:1)and silica gel(CHCl3-MeOH,1:0-0:1)column chromatography to give compounds 1(20.0 mg),2(20.0 mg),3(12 mg),and 15(20.0 mg).Fraction С was purified by column chromatography on RP-18(H2O-MeOH,1:0-0:1)and silica gel(СНСl3-ЕtOАс,1:0:1)column chromatography to afford compounds 4(15.3 mg),5(12.6 mg),6(9.7 mg),7(5.1 mg),and 10(5.4 mg).Fraction D was subjected to Sephadex LH-20(CHCl3-MeOH,1:1)and silica gel(petroleum ether-acetone,1:0-0:1)column chromatography to produce compounds 8(1.8 mg),9(4.3 mg),11(2.5 mg),12(3.3 mg),13(2.5 mg),and 14(455.1 mg).

    STEROIDS AND TERPENOIDS FROM THE BARK OF Phyllanthus acidus

    Siow-Ping ТаnEric Nyak-Yong ТаnQian-Yu Lim
    2页
    查看更多>>摘要:Phyllanthus acidus(L.)Skeels is a member of Phyllanthaceae that originated from Madagascar and was transplanted to the Caribbean in 1793 when William Bligh brought the plant from Timor to Jamaica [1].It is commonly grown now in farms of Malaysia and Indonesia.It is a highly valued medicinal plant.It has been used by the local people to treat bronchial catarrh [2],skin rashes [3],and as emetic and purgative agents [1,4,5].It has also been reported to have antioxidant [6,7],antimicrobial [8,9],antidiabetic [10],anti-inflammatory [11],and hepatoprotective activities [6,11].As part of our ongoing investigation of bioactive compounds from plant species [12,13],we now investigate the natural compounds of P.acidus.The extraction of the bark of P.acidus afforded three steroids,7-oxo-β-sitosterol(1),β-sitostenone(2),and p-sitosterol(3);and four terpenoids,17p-hydroxy-norlup-20(29)-en-3-one(4),glochidon(5),phyllanthol(6),and squalene(7).Their structures were characterized by extensive spectroscopic methods such as IR,UV,NMR,and MS.All these compounds were isolated for the first time from P.acidus,except for compound 6 [14].

    CHEMICAL CONSTITUENTS OF THE ENDOPHYTIC FUNGUS Bipolaris maydis DERIVЕВ FROM THE Kandelia candel

    Thi-Minh-Dinh TranThanh-Nha TranThuc-Huy Duong
    2页
    查看更多>>摘要:Endophytic fungi derived from higher plants produce various bioactive metabolites [1].Such compounds have novel scaffolds and display interesting biological and pharmaceutical properties [2].The genus Bipolaris is associated with a number of plant pathogens [3].Recently,many cultures of Bipolaris fungi,i.e.,B.oryzae,B.eleusines,and B.sorokiniana,have been chemically studied [4-7].Dozens of compounds were reported,including diterpenes,sesterterpenes,and triterpenes.Most of the compounds possess unique chemical skeletons and display strong cytotoxicity toward cancer cell lines antifungal,enzyme inhibitory,and antilipid peroxidation activities.Bipolaris maydis was isolated from the mangrove plant Kandelia candel,popularly distributed in the South of Vietnam.Little is known on the chemistry of this fungus.In this paper,the isolation of seven compounds isolated from cultures of the titled fungus is described.Chemical structures of compounds were determined using NMR and MS spectroscopy as well as comparison with the data described in the literature.Seven compounds were elucidated as(R)-3-ethyl-6,7-dihydroxyphthalide(1),4-hydroxybenzoic acid(2),ergosta-4,6,8(14),22-tetraen-3-one(3),ergosterol peroxide(4),cerevi sterol(5),ergosterol(6),and emodin(7).To the best of our knowledge,all isolates(1-7)were isolated from this species for the first time.Compound 1 shared the same planar structure with(5)-3-ethyl-6,7-dihydroxyphthalide [8] but had positive specific rotation with [α]_D~(20)+110°(c 0.1,chloroform).Thus,this compound was elucidated to be a new compound whose absolute configuration was defined as(3R),Compound 1 showed moderate a-glucosidase inhibitory activity with IC_(50)77.9 ± 0.82)LiM(acarbose,positive control 83.7 ± 1.59 μM).

    CHEMICAL CONSTITUENTS OF Stachyurus chinensis

    Junwei SunChouqiang LiZheng Ma
    2页
    查看更多>>摘要:As a specific family merely spread in East Asia,Stachyuraceae contains only genus Stachyurus Sieb.et Zucc.,which is comprised of 16 species and 8 varieties.Among them,11 species and 7 varieties are distributed in China [1].The stalk pith of Stachyurus chinensis Franch.and Stachyurus himalaicus Hook.f.& Thomson ex Benth.is a well-known traditional Chinese medicine named Stachyuri Medulla Helwingiae Medulla,which possesses heat-clearing,diuretic,and milk secretion effects [2].Chemical investigations of S.himalaicus have revealed that it consists of graminone A,pinoresinol,oleanolic acid,daucosterol,P-sitosterol,gallic acid,ethyl gallate,butanedioic acid,tricontanoic acid,methyl tricontanoate,hexacosane,nonacosane,and triacontanol [3,4].However,to the best of our knowledge,such research has not been reported for S.chinensis until now.

    CHEMICAL CONSTITUENTS OF Cordyceps neovolkiana DL0004

    Chi-Dung NguyenThi-My-Ninh PhamThi-Bich-Hang Ha
    2页
    查看更多>>摘要:The genus Cordyceps is widely distributed in South Asia,Europe,and North America.In vitro and in vivo studies of this genus have validated its medicinal properties [1].The phytochemical investigation of this genus have resulted in over 200 bioactive metabolites having various scaffolds such as saccharides,polysaccharides,cylopeptides,sterols,polyketide,terpenoids,and alkaloids [1,2].The two most studied members of this genus,С sinensis and С militaris,are valuable traditional Chinese medicines and have been used in the treatment of liver and renal dysfunction and heart and lung diseases [3-7].Recently,other Cordyceps species have gained much chemical and biological attention [3,8-12].Cordyceps neovolkiana is widely distributed in the South of Vietnam.Phytochemical data of this species are scarce.In this paper,the isolation of 12 compounds from cultures of the titled fungus is described.The chemical structures of the compounds were determined using NMR and MS spectroscopy as well as comparison with data described in the literature.Isolates were elucidated as ergosta-4,6,8(14),22-tetraen-3-one(1),ergosterol peroxide(2),cerevisterol(3),melithasterol В(4),brassicasterol(5),ergosterol(6),ergosterol 3-O-β-D-glucopyranoside(7),1-dehydroxycordypyridone(8),thymine(9),nicotinamide(10),uridine(11),and 5-methylhaematommic acid(12).To the best of our knowledge,all the isolated compounds(1-12)were isolated from this species for the first time.The cytotoxicity of the isolates against K562 cell line was evaluated.Compound 1 showed potent activity with IC50 5.24 ± 0.38 |ig/mL(doxorubicin,positive control 4.87 ± 0.47 μg/mL).Compounds 2,4,and 6 showed moderate activity with IC_(50)45.05 ± 1.26,46.01 ± 3.54,and 34.03 ± 0.32 μg/mL,respectively,while the others showed no activity.

    СИНТЕЗ И ЦИТОТОКСИЧЕСКАЯ АКТИВНОСТЬ ГИДРАЗОНОВ 5а-ПРЕГНАНОЛОНА

    Н.Ш,НадараиаН.Н.БарбакадзеZu-Liang HeLi Yang...
    2页
    查看更多>>摘要:Стероидные гидразоны проявляют широкий спектр биологической активности,в том числе и цитотоксическую [1-3],В ряду 20-гидразонов 5а-прегнанолона найдены вещества,обладающие анаболической,антиовулящинной,противотуберкулезной,противопаразитарной и фунгицидной активностью [4-6].В продолжение работ по изучению [7,8] взаимосвязи структура-активность из 5а-прегнан-ЗР-ол-20-она(1)синтезировали новые 2-6 и известные 7,8 [4,5] гидразоны.Кетон 1 получили каталитическим гидрированием 5а-прегн-16-ен-Зβ-oл-20-она(9)по методике [9].Соединения 2-8 синтезировали взаимодействием стероида 1 с гидразинами и гидразидами(п-нитрофенил-и 2,4-динитрофенилгидразин,гидразиды м-бромбензойной,никотиновой,салициловой,изоникотиновой кислот и тиосемикарбазид)в метиловом или этиловом спирте в присутствии уксусной или соляной кислоты.

    ALKALOIDS FROM THE TWIGS OF Catharanthus roseus

    Zu-Liang HeLi Yang
    2页
    查看更多>>摘要:Catharanthus roseus(L.)G.Don {Apocynaceae)is a famous plant used to treat numerous diseases,including diabetes,malaria,and cancer [1].The plant is rich in indole alkaloids.Among them,vinblastine and vincristine are typical compounds that have been used extensively for the clinical treatment of human cancers,such as testicular carcinoma,acute leukemia,rhabdomyosarcoma,and breast cancer [2-4],In order to find further bioactive alkaloids,we studied С roseus collected from Yunnan of China and isolated 19 alkaloids and an amide.The air-dried twigs of C.roseus(24.7 kg)were powdered and extracted with acetone(five times,each 40 L)at room temperature.After evaporation of the solvent,the acetone extract was acidified to pH 1-2 with 3% aq.tartaric acid and then partitioned with EtOAc.The acidic aqueous phase was basified to pH 10 with NH4OH and then extracted with CHCI3 to yield crude alkaloids(138 g),which was subjected to column chromatography(CC)over silica gel eluting with gradient CHCl3-MeOH(1:0→0:1)to yield four fractions(Frs.1-4).Fraction 1(43 g)was separated by silica gel CC with gradient petroleum ether-acetone(50:0→2:1)to give two subfractions.Subfraction la(13 g)was further isolated on Sephadex LH-20 CC(CHCI3:MeOH3:2)and then purified on a silica gel column with petroleum ether-EtOAc-diethylamine(20:1:1)to afford 2(5.1 mg),8(128.5 mg),9(6.0 mg),and 20(5.7 mg).Subfraction lb(21 g)was further separated on a RP-18 column eluting with 70% aq.MeOH,and Sephadex LH-20 CC(CHCl3-MeOH,3:2)and then purified on silica gel column with CHCl3-MeOH(50:1)to produce 1(9.9 mg),3(8.3 mg),10(10.5 mg),11(15.8 mg),12(20.1 mg),and 13(19.6 mg).Fraction 3(30 g)was separated by silica gel CC with gradient petroleum ether-acetone(50:0→2:1)to give three subfi-actions.Subfraction 3a(9.6 g)was separated by Sephadex LH-20 CC(CHClg-MeOH,3:2)and on a silica gel column with petroleum ether-EtOAc-diethylamine(10:1:1)and then purified on a silica gel column with СНС1з-МеОН(20:1)to obtain 4(25.6 mg),5(5.2 mg),6(10.1 mg),7(6.4 mg),and 14(24.0 mg).Subfraction 3b(1.2 g)was purified by Sephadex LH-20 CC(MeOH 100%)and then on a silica gel column with CHCl3-MeOH(15:1)to give 15(9.2 mg)and 16(8.5 mg).Subfi-action 3c(6 g)was isolated by Sephadex LH-20 CC(СНС1з-МеОН,3:2)and then on a silica gel column with CHCl3-acetone(8:1)to furnish 15(8.7 mg),16(7.4 mg),17(6.2 mg),18(10.5 mg),19(9.9 mg).

    CHAETOGLOBOSINS IN ENDOPHYTIC Chaetomium sp.FROM Astragalus membranaceus

    Hongchi ZhangRui LiuFeng Zhou
    3页
    查看更多>>摘要:Chaetoglobosins,are well-known mycotoxins biosynthesized by a hybrid polyketide synthase nonribosomal peptide synthetase.Chaetoglobosins possess an indolyl group in place of the phenyl group present in cytochalasans,namely 10-(indol-3-yl)-[13] cytochalasans [1].They are a family of macrocyclic polyketide alkaloids belonging to the general group of cytochalasans and,because of its wide range of biological properties,has drawn great interest as cytotoxic,antifungal,phytotoxic,and nematicidal compounds [2].In the course of our search for biologically active metabolites from endophytic fungi of Chinese medicinal plants,a subculture of an isolate of Chaetomium sp.,obtained from roots of Astragalus membranaceus was cultivated on potato dextrose agar(PDA)media.The methanol extract of the culture showed significant antimicrobial activity.This prompted us to carry out secondary metabolite studies on this fungus,which resulted in the isolation of six chaetoglobosins.

    ОЧИСТКА И ИДЕНТИФИКАЦИЯ БАКТЕРИОЦИНА ИЗ Lactobacillus plantarum

    И.Т.ЯкубовX.Л.СахибназароваV.Urlacher
    2页
    查看更多>>摘要:Бактериоцины-пептиды,секретируемые бактериями и проявляющие антибактериальную активность против других штаммов того же вида или родственных видов [1,2].Бактериоцины,продуцируемые штаммами Lactobacillus plantarum,получили название плантарицины [3] и являются низкомолекулярными(М<10 кДа),катионными и термостабильными пептидами.В наших ранних исследованиях с поверхности листьев лекарственного растения мальва приземистая(Malva pusilla),произрастающего в Узбекистане,был выделен бактериоцин-синтезирующий штамм Lactobacillus plantarum Mal.Таксономическая принадлежность нового штамма была определена по генотипическим и фенотипическим признакам [4,5].