兩株植物內(nèi)生真菌的代謝產(chǎn)物及其生物活性研究
發(fā)布時(shí)間:2018-04-25 04:39
本文選題:植物內(nèi)生真菌 + 異海松烷型二萜 ; 參考:《山東大學(xué)》2017年碩士論文
【摘要】:本文對(duì)一株苔蘚內(nèi)生真菌Botrysphaer laricina和一株腳骨脆內(nèi)生真菌Leptosphaeriasp.L1201的代謝產(chǎn)物進(jìn)行了系統(tǒng)研究。采用硅膠、SephadexLH-20凝膠、十八烷基鍵合硅膠柱色譜,以及半制備型高效液相色譜等技術(shù)分離得到了41個(gè)化合物,采用NMR,MS,IR,UV以及X-射線單晶衍射技術(shù)鑒定了其結(jié)構(gòu),其中包括新化合物11個(gè)。對(duì)部分化合物進(jìn)行了體外細(xì)胞毒活性、NO生成抑制活性和醌還原酶誘導(dǎo)活性的篩選,發(fā)現(xiàn)多個(gè)化合物具有較強(qiáng)的活性。對(duì)從暖地大葉蘚Rhodobryum umgiganteum正常組織中分離得到的內(nèi)生真菌Botrysphaerialaricina在察氏培養(yǎng)基中培養(yǎng)產(chǎn)生的次級(jí)代謝產(chǎn)物進(jìn)行了系統(tǒng)的研究,共分離獲得了 21個(gè)化合物,其中有7個(gè)新化合物,鑒定為5個(gè)異海松烷型二貼botrysphaerins A-E(1-5)和 2 個(gè)混源萜類化合物 tricycloalternarenes K 和 L(6和7)。此外還獲得了 14個(gè)已知化合物,包括3個(gè)二萜類化合物sphaeropsidinsA和 B(8 和 9)以及 aspergiloid B(10);2 個(gè)二倍半萜化合物 fusaproliferin(11)和(-)-terpestacin(12);3 個(gè)混源萜類化合物 tricycloalternarenes 3a,4b 和 1b(13-15);4 個(gè)甾體類化合物stigmasterol(16)、β-sitosterol(17)、(22E)-ergosta-6,9,22-tien-3β,5α,8α-triol(18)和(22E)-ergosta-4,6,8(14),22-tetraen-3-one(19),以及 2 個(gè)脂肪族化合物 hexadecanoic acid(20)和 l-O-pentadecanoyl-sn-glycerol(21)。對(duì)部分化合物進(jìn)行了體外細(xì)胞毒活性、NO生成抑制活性和醌還原酶誘導(dǎo)活性的篩選,發(fā)現(xiàn)化合物3對(duì)MDA-MB-231、A549、Hep G2和Hela等腫瘤細(xì)胞株具有中等的細(xì)胞毒活性,化合物1、3-7、11和13可顯著抑制NO的生成,化合物3、7和10-15具有很強(qiáng)的醌還原酶誘導(dǎo)活性。從腳骨脆Cosearia balansae Gagnep.的正常組織中分離得到了內(nèi)生真菌菌株Leptosphaeriasp.L1201,對(duì)其在察氏培養(yǎng)基中培養(yǎng)產(chǎn)生的次級(jí)代謝產(chǎn)物進(jìn)行了系統(tǒng)的研究,共分離得到了 20個(gè)化合物,其中包括4個(gè)新化合物,鑒定為2個(gè)氧雜蒽酮類化合物leptosphaerins H和I(22和23),1個(gè)芳香醚類化合物leptosphin A(24)和1個(gè)芳香化合物leptosphinB(25)。此外還得到了 16個(gè)已知化合物,包括1個(gè)triketide類化合物sphaeropsidone(26);13個(gè)芳香化合物2,5-dimethyl-7-hydroxychromone(27)、(R)-(-)-O-methylmellein(28)、6-hydroxymellein(29)、2,3-dihydro-5-hydroxy-1H-2-isoindol-1-one(30)、bis(2-ethylhepty1)phthalate(31)、bis(2-ethyldecyl).phthalate(32)、monomethylsulochrin(33)、alternariol(34)、n-butyl-2,4-dihydroxy-3,6-dimethylbenzoate(35)、orselinic acid(36)、vanillic acid(37)、4-hydroxybenzoic acid(38)、ethyl phenyl ether(39),以及 2 個(gè)脂肪族化合物(R)-2-ethylhexan-1-ol(40)和linoleic acid(41)。經(jīng)活性篩選發(fā)現(xiàn)化合物34對(duì)Hep G2和Hela腫瘤細(xì)胞株具有中等的細(xì)胞毒活性,化合物24、34和35具有顯著的NO生成抑制活性,化合物25和36具有較強(qiáng)的醌還原酶誘導(dǎo)活性。
[Abstract]:The metabolites of a moss endophytic fungus, Botrysphaer laricina, and a foot brittleness endophytic fungus, Leptosphaeriasp.L1201, were systematically studied in this paper. 41 compounds were isolated by silica gel Sephadex LH-20 gel, octadecyl bonded silica gel column chromatography and semi-synthetic high performance liquid chromatography. Their structures were identified by NMRM MS IR UV and X ray single crystal diffraction. These include 11 new compounds. Some of the compounds were screened for inhibition of no production and quinone reductase induction activity in vitro. It was found that many compounds had strong activity. The secondary metabolites of endophytic fungus Botrysphaerialaricina isolated from the normal tissue of Rhodobryum umgiganteum were systematically studied in Cha's medium. A total of 21 compounds were isolated, 7 of which were new compounds. It was identified as five isophoran type botrysphaerins A-EH1-5) and two mixed terpenoids, tricycloalternarenes K, LX 6 and 7 O. In addition, 14 known compounds were obtained. 鍖呮嫭3涓簩钀滅被鍖栧悎鐗﹕phaeropsidinsA鍜,
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