五种共生菌化学成分与生物活性研究
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摘要
本文对两种苦楝内生真菌、两种丹参内生细菌和一种华山松大小蠹共生真菌的化学成分进行了提取分离、结构鉴定以及生物活性研究。利用多种色谱技术(正相和反相硅胶、PTLC和Sephadex LH-20等)以及多种波谱分析方法(1H-NMR、13C-NMR、1H-1H COSY、HSQC、HMBC、NOESY和MS等)分离鉴定了82个化合物的结构,包括2个新化合物和1个新天然产物。此外,本文采用杂色云芝Coriolus versicolor对丹皮酚进行了生物转化的研究。主要研究结果如下：
1.从苦楝内生真菌烟曲霉LN-4的固体发酵产物中共分离并鉴定了39个化合物：fumitremorgin C (1-1),cyclotryprostatin A (1-2), cyclotryprostatin B (1-3), verruculogen TR-2(1-4),12β-hydroxy-verruculogen TR-2(1-5),12β-hydroxy-13a-methoxyverruculogen TR-2(1-6), fumitremorgin B (1-7), verruculogen (1-8), tryprostatin A (1-9), cyclo-L-tryptophyl-L-proline (1-10), terezine D (1-11), fumiquinazolines F (1-12), fumiquinazolines G (1-13), fumiquinazolines D (1-14), fumiquinazolines A (1-15),3-hydroxyfumiquinazolines A (1-16),6-methoxylspirotryprostatins B (1-17), spiro[5H,10H-dipyrrolo[1,2-a:1',2'-d]pyrazine-2(3H),2'-[2H]-indole]-3',5,10(1'H)-trione(1-18), pseurotin A (1-19), pseurotin A1(1-20), tryptoquivaline O (1-21), fumigaclavine B (1-22), bisdethiobis(methylthio)gliotoxin (1-23),环(脯氨酸-甘氨酸)(1-24),环(脯氨酸-丙氨酸)(1-25),环(D-脯氨酸-L-丙氨酸)(1-26),环(脯氨酸-丝氨酸)(1-27),环(丝氨酸-4-OH-脯氨酸)(1-28),环(亮氨酸-4-OH-脯氨酸)(1-29),环(丙氨酸-4-OH-脯氨酸)(1-30),环(苯丙氨酸-4-OH-D-脯氨酸)(1-31),环(苯丙氨酸-甘氨酸)(1-32),环(脯氨酸-4-OH-脯氨酸)(1-33),环(丙氨酸-甘氨酸)(1-34),尿嘧啶(1-35),4,8-dihydroxy-l-tetralone (1-36),trans-(3RS,4RS)-3,4-Dihydro-3,4,8-trihydroxynaph thalen-1(2H)-one (1-37), cis-(3RS,4SR)-3,4-Dihydro-3,4,8-trihydroxy-naphthalen-1(2H)-one(1-38)和helvolic acid (1-39)。其中化合物1-6为新的吲哚类生物碱；化合物1-16为新天然产物。活性测试结果显示：有16个化合物对8种植物病原菌具有不同程度的抑制作用,其中1-6、1-7、1-8和1-39活性最强,与阳性对照多菌灵和恶霉灵的活性相当；有18个化合物具有较强的海虾致死活性,其中1-7和1-8活性最强,LC50分别为13.6和15.8μtg/ml；有9个化合物对3龄粘虫有拒食活性,其中1-7、1-8和1-15活性最强,拒食率分别为50.0%、55.0%和45.0%。
2.从苦楝内生真菌Fusarium sp.LN-11的固体发酵产物中共分离和鉴定了11个化合物：环(脯氨酸-甘氨酸)(2-1),环(脯氨酸-丙氨酸)(2-2),环(D-脯氨酸-L-丙氨酸)(2-3),环(丙氨酸-4-OH-脯氨酸)(2-4),环(丙氨酸-甘氨酸)(2-5),环(苯丙氨酸-甘氨酸)(2-6),对甲氧基苯乙酸(2-7),亚油酸(2-8),三油酸甘油酯(2-9),cerevisterol (2-10)和过氧化麦角甾醇(2-11)。活性测试结果显示,在100μg/ml浓度下,化合物2-4对丰年虾的校正死亡率为72.8%。
3.筛选了丹参中分离得到的8株内生细菌的抗氧化、抗细菌和抗植物病原菌活性。结果显示Pseudomonas brassicacearum subsp. Neoaurantiaca (B1)和Bacillus aryabhattai(B5)有较强的抗氧化和抗植物病原菌活性。
4.从丹参内生细菌Pseudomonas brassicacearum subsp. Neoaurantiaca的液体发酵物中分离并鉴定了12个化合物：Neoaurpeptide (3-1),环(甘氨酸-丙氨酸)(3-2),环(丙氨酸-丙氨酸)(3-3),环(脯氨酸-甘氨酸)(3-4),环(脯氨酸-丝氨酸)(3-5),环(丙氨酸-4-OH-脯氨酸)(3-6),环(缬氨酸-脯氨酸)(3-7),环(甘氨酸-酪氨酸)(3-8),环(丙氨酸-酪氨酸)(3-9),环(酪氨酸-4-OH-脯氨酸)(3-10),3-甲基海因(3-11)和2-哌啶酮(3-12)。其中化合物3-1为新化合物。活性测试结果显示,化合物3-1、3-6、3-8、3-9和3-10有中等强度的海虾致死活性,LC50值分别为68.2、46.1、71.0、71.0和79.5μg/ml；有7个化合物对测试的3种丹参病原菌有不同程度的抑制作用,其中3-5的活性最强,MIC值为25-50μg/ml。
5.从丹参内生细菌Bacillus aryabhattai的液体发酵物中分离并鉴定了6个化合物：环(脯氨酸-甘氨酸)(4-1),环(丙氨酸-4-OH-脯氨酸)(4-2),环(亮氨酸-4-OH-脯氨酸)(4-3),环(丙氨酸-甘氨酸)(4-4),尿嘧啶(4-5)和尿素(4-6)。活性测试结果显示,化合物4-2有中等强度的海虾致死活性,LC50值为46.1μg/ml；化合物4-2和4-3对测试的3种丹参病原菌具有中等强度的抑制作用,MIC值为50-100μg/ml。
6.从华山松大小蠹共生真菌秦岭细粘束孢的液体发酵产物中分离并鉴定了14个化合物：6-methoxymethyleugenin (5-1),6-hydroxymethyleugenin (5-2),3-methoxy-6,8-dihydroxy-3-methyl-3,4-dihydroisocoumarin (5-3),对羟基苯乙醇(5-4), maculosin (5-5), scytalone (5-6),对甲氧基苯乙酸(5-7),丁二酸(5-8),过氧化麦角甾醇(5-9),22E,24R-5α,6α-epoxyergosta-8(14),22-diene-3β,7α-diol (5-10),单油酸甘油酯(5-11),cerevisterol (5-12), ergosterol peroxide3-O-β-D-glucopyranoside (5-13)和22E,24R-ergosta-7,22-diene-3β,5α,6β,9α-tetraol (5-14)。活性测试结果显示,化合物5-1、5-5和5-12对华山松切根苗有较强的致死活性,第五天时,3个化合物的处理组的死亡率都达到95%以上；同时可以降低2年生华山松幼苗的叶绿素含量。
7.采用杂色云芝Coriolus versicolor转化了丹皮酚,得到两个转化产物2,4-二羟基苯乙酮(6-2)和2,5-二羟基-4-甲氧基苯乙酮(6-3)。活性测试结果显示,化合物6-3的抗氧化和抗菌活性强于底物丹皮酚。
The chemical constituents and their bioactivities of two endophytic fungi isolated from Melia azedarach, two endophytic bacteria of Salvia miltiorrhiza Bunge and one symbiotic fungus associated with D. armandi on host P. armandi were studied.82compounds were obtained from the cultures of the microbial materials. The structures were elucidated based on spectral data(1H-NMR、13C-NMR、1H-1H COSY、HMQC、HMBC、NOESY and MS). We also report the biotransformation of paeonol by the white-rot Basidiomycete Coriolus versicolor. The results are concluded as follows:
1. Two new alkaloids,12β-hydroxy-13α-methoxy verruculogen TR-2(1-6),3-hydroxyfumiquinazoline A (1-16) and37known compounds:fumitremorgin C (1-1), cyclotryprostatin A (1-2), cyclotryprostatin B (1-3), verruculogen TR-2(1-4),12β-hydroxy-verruculogen TR-2(1-5), fumitremorgin B (1-7), verruculogen (1-8), tryprostatin A (1-9), cyclo-L-tryptophyl-L-proline (1-10), terezine D (1-11), fumiquinazolines F (1-12), fumiquinazolines G (1-13), fumiquinazolines D (1-14), fumiquinazolines A (1-15),3-hydroxyfumiquinazolines A (1-16),6-methoxylspirotryprostatins B (1-17), spiro[5H,10H-dipyrrolo[1,2-a:1',2'-d]pyrazine-2(3H),2'-[2H]-indole]-3',5,10(1'H)-trione (1-18), pseurotin A (1-19), pseurotin A1(1-20), tryptoquivaline O (1-21), fumigaclavine B (1-22), bisdethiobis(methylthio)gliotoxin (1-23), cyclo-(Pro-Gly)(1-24), cyclo-(Pro-Ala)(1-25), cyclo-(D-Pro-L-Ala)(1-26), cyclo-(Pro-Ser)(1-27), cyclo-(Ser-trans-4-OH-Pro)(1-28), cyclo-(Leu-4-OH-Pro)(1-29), cyclo-(Ala-trans-4-OH-Pro)(1-30), cyclo-(cis-OH-D-Pro-L-Phe)(1-31), cyclo-(Gly-Phe)(1-32), cyclo-(Pro-trans-4-OH-Pro)(1-33), cyclo-(Gly-Ala)(1-34), uracil (1-35),4,8-dihydroxy-l-tetralone (1-36), trans-(3RS,4RS)-3,4-Dihydro-3,4,8-trihydroxynaphthalen-1(2H)-one (1-37), cis-(3RS,4SR)-3,4-Dihydro-3,4,8-trihydroxy-naphthalen-1(2H)-one (1-38) and helvolic acid (1-39) were isolated from the fermentation broth of Aspergillus fumigatus LN-4, an endophytic fungus isolated from the stem bark of Melia azedarach.
These isolated compounds were evaluated for in vitro antifungal activities against phytopathogenic fungi, toxicity to brine shrimps, and antifeedant activities against armyworm larvae(Mythimna separata Walker). Among them, sixteen compounds showed potent activities against8phytopathogenic fungi, and four of them,1-6,1-7,1-8and1-39, exhibited antifungal activities with MIC values of6.25-50μg/ml, which were comparable to two positive controls carbendazim and hymexazol. In addition, of eighteen that exerted moderate lethality activity toward brine shrimps, both compounds1-7and1-8showed significant toxicities with their corresponding median lethal concentration (LC50) values of13.6and15.8μg/ml. Furthermore, among nine metabolites that were found to possess antifeedant activity against armyworm larvae, both compounds1-7,1-8and1-15gave best activity with the antifeedant index (AFI)50.0%,55.0%and45%, respectively.
2. Eleven known compounds:cyclo-(Pro-Gly)(2-1), cyclo-(Pro-Ala)(2-2), cyclo-(D-Pro-L-Ala)(2-3), cycl-(Ala-4-OH-Pro)(2-4), cyclo-(Ala-Gly)(2-5), cyclo-(Phe-Gly)(2-6),4-methoxyphenylacetic acid (2-7), linoleic acid (2-8), trielaidin (2-9), cerevisterol (2-10) and ergosterol peroxide (2-11) were isolated from the organic extract of fermentation broths of Fusarium sp. LN-11, an endophytic fungus isolated from the leaves of Melia azedarach. Compound2-4was shown to be moderate active toward brine shrimp larvae at a concentration of100μg/ml with mortality rate of72.8%.
3. The antioxidant, antibacterial and antifungal activities by the DPPH method, the micro-broth dilution method and the Poison Food Technique of eight endophytic bacterial stains, which isolated from the roots of Salvia miltiorrhiza Bunge, were tested in vitro. The results showed that Pseudomonas brassicacearum subsp. Neoaurantiaca (B1) and Bacillus aryabhattai (B5) had more effective at antioxidant, antibacterial and antifungal activities than other endophtic bacteria.
4. A novel alkaloid Neoaurpeptide (3-1) and11known compounds:cyclo-(Gly-L-Ala)(3-2), cyclo-(L-Ala-L-Ala)(3-3), cyclo-(L-Pro-Gly)(3-4), cyclo-(L-Pro-L-Ser)(3-5), cyclo-(L-Ala-trans-4-hydroxy-L-Pro)(3-6), cyclo-(L-Val-L-Pro)(3-7), cyclo-(Gly-L-Tyr)(3-8), cyclo-(L-Ala-L-Tyr)(3-9), cyclo-(L-Tyr-trans-4-hydroxy-L-Pro)(3-10),3-methyl hydantoin (3-11) and2-piperidinone (3-12) were isolated from the culture of Pseudomonas brassicacearum subsp. Neoaurantiaca, an endophytic bacterium found inside the tissue of Salvia miltiorrhiza Bunge. Compounds3-1,3-6,3-8,3-9and3-10exerted moderate lethality activity toward brine shrimps, and were found to show significant activities with LC50values of68.2,46.1,71.0,71.0and79.5μg/ml, respectively. In addition, seven compounds showed potent activities against3phytopathogenic fungi which can cause Danshen root rot disease, and3-5showed remarkable antifungal activity with MIC values ranging from25to50μg/ml.
5. Six known compounds:cyclo-(Pro-Gly)(4-1), cyclo-(Ala-4-OH-Pro)(4-2), cyclo-(Leu-4-OH-Pro)(4-3), cyclo-(Ala-Gly)(4-4), uracil (4-5) and urea (4-6) were isolated from the fermentation broth of Bacillus aryabhattai, an endophytic bacterium found inside the tissue of Salvia miltiorrhiza Bunge. Compound4-2exerted moderate lethality activity toward brine shrimps, and was found to show significant activities with LC50values of46.1μg/ml. Compounds4-2and4-3showed potent activities against3phytopathogenic fungi which can cause Danshen root rot disease, exhibited antifungal activities with MIC values of50-100μg/ml,
6. Three toxins,6-methoxymethyleugenin (5-1), maculosin (5-5) and cerevisterol (5-12), together with11other compounds:6-hydroxymethyleugenin (5-2),3-methoxy-6,8-dihydroxy-3-methyl-3,4-dihydroisocoumarin (5-3),4-hydroxyphenylethanol (5-4), scytalone (5-6),4-methoxyphenylacetic acid (5-7), succinic acid (5-8), ergosterol peroxide (5-9),22E,24R-5α,6α-epoxyergosta-8(14),22-diene-3β,7α-diol (5-10), glycerol-1-monooleate (5-11), ergosterol peroxide3-O-β-D-glucopyranoside (5-13) and22E,24R-ergosta-7,22-diene-3β,5α,6β,9α-tetraol (5-14) have been isolated from the ethyl acetate extracts of the cultures of Leptographium qinlingensis, an ophiostomatoid fungal pathogen associated with a forest pest Dendroctonus armandi, which causes enormous deaths of its host trees Pinus armandi. Phytotoxic test showed that, after5days, the treated groups were almost completely wilted, and their lethal rates are above95%for these three compounds. Similarly, three toxins can reduced chlorophyll content of two-year-old field seedlings.
7. Biotransformation of substrate paeonol was investigated with the white-rot basi diomycete Coriolus versicolor. Two biotransformed products,2,4-dihydroxyacetophenone (6-2) and2,5-dihydroxy-4-methoxyacetophenone (6-3), were isolated and identified by spectral methods. Compound6-3showed higher antioxidant, antibacterial, antifungal a ctivities than substrate paeonol.
1.从苦楝内生真菌烟曲霉LN-4的固体发酵产物中共分离并鉴定了39个化合物：fumitremorgin C (1-1),cyclotryprostatin A (1-2), cyclotryprostatin B (1-3), verruculogen TR-2(1-4),12β-hydroxy-verruculogen TR-2(1-5),12β-hydroxy-13a-methoxyverruculogen TR-2(1-6), fumitremorgin B (1-7), verruculogen (1-8), tryprostatin A (1-9), cyclo-L-tryptophyl-L-proline (1-10), terezine D (1-11), fumiquinazolines F (1-12), fumiquinazolines G (1-13), fumiquinazolines D (1-14), fumiquinazolines A (1-15),3-hydroxyfumiquinazolines A (1-16),6-methoxylspirotryprostatins B (1-17), spiro[5H,10H-dipyrrolo[1,2-a:1',2'-d]pyrazine-2(3H),2'-[2H]-indole]-3',5,10(1'H)-trione(1-18), pseurotin A (1-19), pseurotin A1(1-20), tryptoquivaline O (1-21), fumigaclavine B (1-22), bisdethiobis(methylthio)gliotoxin (1-23),环(脯氨酸-甘氨酸)(1-24),环(脯氨酸-丙氨酸)(1-25),环(D-脯氨酸-L-丙氨酸)(1-26),环(脯氨酸-丝氨酸)(1-27),环(丝氨酸-4-OH-脯氨酸)(1-28),环(亮氨酸-4-OH-脯氨酸)(1-29),环(丙氨酸-4-OH-脯氨酸)(1-30),环(苯丙氨酸-4-OH-D-脯氨酸)(1-31),环(苯丙氨酸-甘氨酸)(1-32),环(脯氨酸-4-OH-脯氨酸)(1-33),环(丙氨酸-甘氨酸)(1-34),尿嘧啶(1-35),4,8-dihydroxy-l-tetralone (1-36),trans-(3RS,4RS)-3,4-Dihydro-3,4,8-trihydroxynaph thalen-1(2H)-one (1-37), cis-(3RS,4SR)-3,4-Dihydro-3,4,8-trihydroxy-naphthalen-1(2H)-one(1-38)和helvolic acid (1-39)。其中化合物1-6为新的吲哚类生物碱；化合物1-16为新天然产物。活性测试结果显示：有16个化合物对8种植物病原菌具有不同程度的抑制作用,其中1-6、1-7、1-8和1-39活性最强,与阳性对照多菌灵和恶霉灵的活性相当；有18个化合物具有较强的海虾致死活性,其中1-7和1-8活性最强,LC50分别为13.6和15.8μtg/ml；有9个化合物对3龄粘虫有拒食活性,其中1-7、1-8和1-15活性最强,拒食率分别为50.0%、55.0%和45.0%。
2.从苦楝内生真菌Fusarium sp.LN-11的固体发酵产物中共分离和鉴定了11个化合物：环(脯氨酸-甘氨酸)(2-1),环(脯氨酸-丙氨酸)(2-2),环(D-脯氨酸-L-丙氨酸)(2-3),环(丙氨酸-4-OH-脯氨酸)(2-4),环(丙氨酸-甘氨酸)(2-5),环(苯丙氨酸-甘氨酸)(2-6),对甲氧基苯乙酸(2-7),亚油酸(2-8),三油酸甘油酯(2-9),cerevisterol (2-10)和过氧化麦角甾醇(2-11)。活性测试结果显示,在100μg/ml浓度下,化合物2-4对丰年虾的校正死亡率为72.8%。
3.筛选了丹参中分离得到的8株内生细菌的抗氧化、抗细菌和抗植物病原菌活性。结果显示Pseudomonas brassicacearum subsp. Neoaurantiaca (B1)和Bacillus aryabhattai(B5)有较强的抗氧化和抗植物病原菌活性。
4.从丹参内生细菌Pseudomonas brassicacearum subsp. Neoaurantiaca的液体发酵物中分离并鉴定了12个化合物：Neoaurpeptide (3-1),环(甘氨酸-丙氨酸)(3-2),环(丙氨酸-丙氨酸)(3-3),环(脯氨酸-甘氨酸)(3-4),环(脯氨酸-丝氨酸)(3-5),环(丙氨酸-4-OH-脯氨酸)(3-6),环(缬氨酸-脯氨酸)(3-7),环(甘氨酸-酪氨酸)(3-8),环(丙氨酸-酪氨酸)(3-9),环(酪氨酸-4-OH-脯氨酸)(3-10),3-甲基海因(3-11)和2-哌啶酮(3-12)。其中化合物3-1为新化合物。活性测试结果显示,化合物3-1、3-6、3-8、3-9和3-10有中等强度的海虾致死活性,LC50值分别为68.2、46.1、71.0、71.0和79.5μg/ml；有7个化合物对测试的3种丹参病原菌有不同程度的抑制作用,其中3-5的活性最强,MIC值为25-50μg/ml。
5.从丹参内生细菌Bacillus aryabhattai的液体发酵物中分离并鉴定了6个化合物：环(脯氨酸-甘氨酸)(4-1),环(丙氨酸-4-OH-脯氨酸)(4-2),环(亮氨酸-4-OH-脯氨酸)(4-3),环(丙氨酸-甘氨酸)(4-4),尿嘧啶(4-5)和尿素(4-6)。活性测试结果显示,化合物4-2有中等强度的海虾致死活性,LC50值为46.1μg/ml；化合物4-2和4-3对测试的3种丹参病原菌具有中等强度的抑制作用,MIC值为50-100μg/ml。
6.从华山松大小蠹共生真菌秦岭细粘束孢的液体发酵产物中分离并鉴定了14个化合物：6-methoxymethyleugenin (5-1),6-hydroxymethyleugenin (5-2),3-methoxy-6,8-dihydroxy-3-methyl-3,4-dihydroisocoumarin (5-3),对羟基苯乙醇(5-4), maculosin (5-5), scytalone (5-6),对甲氧基苯乙酸(5-7),丁二酸(5-8),过氧化麦角甾醇(5-9),22E,24R-5α,6α-epoxyergosta-8(14),22-diene-3β,7α-diol (5-10),单油酸甘油酯(5-11),cerevisterol (5-12), ergosterol peroxide3-O-β-D-glucopyranoside (5-13)和22E,24R-ergosta-7,22-diene-3β,5α,6β,9α-tetraol (5-14)。活性测试结果显示,化合物5-1、5-5和5-12对华山松切根苗有较强的致死活性,第五天时,3个化合物的处理组的死亡率都达到95%以上；同时可以降低2年生华山松幼苗的叶绿素含量。
7.采用杂色云芝Coriolus versicolor转化了丹皮酚,得到两个转化产物2,4-二羟基苯乙酮(6-2)和2,5-二羟基-4-甲氧基苯乙酮(6-3)。活性测试结果显示,化合物6-3的抗氧化和抗菌活性强于底物丹皮酚。
The chemical constituents and their bioactivities of two endophytic fungi isolated from Melia azedarach, two endophytic bacteria of Salvia miltiorrhiza Bunge and one symbiotic fungus associated with D. armandi on host P. armandi were studied.82compounds were obtained from the cultures of the microbial materials. The structures were elucidated based on spectral data(1H-NMR、13C-NMR、1H-1H COSY、HMQC、HMBC、NOESY and MS). We also report the biotransformation of paeonol by the white-rot Basidiomycete Coriolus versicolor. The results are concluded as follows:
1. Two new alkaloids,12β-hydroxy-13α-methoxy verruculogen TR-2(1-6),3-hydroxyfumiquinazoline A (1-16) and37known compounds:fumitremorgin C (1-1), cyclotryprostatin A (1-2), cyclotryprostatin B (1-3), verruculogen TR-2(1-4),12β-hydroxy-verruculogen TR-2(1-5), fumitremorgin B (1-7), verruculogen (1-8), tryprostatin A (1-9), cyclo-L-tryptophyl-L-proline (1-10), terezine D (1-11), fumiquinazolines F (1-12), fumiquinazolines G (1-13), fumiquinazolines D (1-14), fumiquinazolines A (1-15),3-hydroxyfumiquinazolines A (1-16),6-methoxylspirotryprostatins B (1-17), spiro[5H,10H-dipyrrolo[1,2-a:1',2'-d]pyrazine-2(3H),2'-[2H]-indole]-3',5,10(1'H)-trione (1-18), pseurotin A (1-19), pseurotin A1(1-20), tryptoquivaline O (1-21), fumigaclavine B (1-22), bisdethiobis(methylthio)gliotoxin (1-23), cyclo-(Pro-Gly)(1-24), cyclo-(Pro-Ala)(1-25), cyclo-(D-Pro-L-Ala)(1-26), cyclo-(Pro-Ser)(1-27), cyclo-(Ser-trans-4-OH-Pro)(1-28), cyclo-(Leu-4-OH-Pro)(1-29), cyclo-(Ala-trans-4-OH-Pro)(1-30), cyclo-(cis-OH-D-Pro-L-Phe)(1-31), cyclo-(Gly-Phe)(1-32), cyclo-(Pro-trans-4-OH-Pro)(1-33), cyclo-(Gly-Ala)(1-34), uracil (1-35),4,8-dihydroxy-l-tetralone (1-36), trans-(3RS,4RS)-3,4-Dihydro-3,4,8-trihydroxynaphthalen-1(2H)-one (1-37), cis-(3RS,4SR)-3,4-Dihydro-3,4,8-trihydroxy-naphthalen-1(2H)-one (1-38) and helvolic acid (1-39) were isolated from the fermentation broth of Aspergillus fumigatus LN-4, an endophytic fungus isolated from the stem bark of Melia azedarach.
These isolated compounds were evaluated for in vitro antifungal activities against phytopathogenic fungi, toxicity to brine shrimps, and antifeedant activities against armyworm larvae(Mythimna separata Walker). Among them, sixteen compounds showed potent activities against8phytopathogenic fungi, and four of them,1-6,1-7,1-8and1-39, exhibited antifungal activities with MIC values of6.25-50μg/ml, which were comparable to two positive controls carbendazim and hymexazol. In addition, of eighteen that exerted moderate lethality activity toward brine shrimps, both compounds1-7and1-8showed significant toxicities with their corresponding median lethal concentration (LC50) values of13.6and15.8μg/ml. Furthermore, among nine metabolites that were found to possess antifeedant activity against armyworm larvae, both compounds1-7,1-8and1-15gave best activity with the antifeedant index (AFI)50.0%,55.0%and45%, respectively.
2. Eleven known compounds:cyclo-(Pro-Gly)(2-1), cyclo-(Pro-Ala)(2-2), cyclo-(D-Pro-L-Ala)(2-3), cycl-(Ala-4-OH-Pro)(2-4), cyclo-(Ala-Gly)(2-5), cyclo-(Phe-Gly)(2-6),4-methoxyphenylacetic acid (2-7), linoleic acid (2-8), trielaidin (2-9), cerevisterol (2-10) and ergosterol peroxide (2-11) were isolated from the organic extract of fermentation broths of Fusarium sp. LN-11, an endophytic fungus isolated from the leaves of Melia azedarach. Compound2-4was shown to be moderate active toward brine shrimp larvae at a concentration of100μg/ml with mortality rate of72.8%.
3. The antioxidant, antibacterial and antifungal activities by the DPPH method, the micro-broth dilution method and the Poison Food Technique of eight endophytic bacterial stains, which isolated from the roots of Salvia miltiorrhiza Bunge, were tested in vitro. The results showed that Pseudomonas brassicacearum subsp. Neoaurantiaca (B1) and Bacillus aryabhattai (B5) had more effective at antioxidant, antibacterial and antifungal activities than other endophtic bacteria.
4. A novel alkaloid Neoaurpeptide (3-1) and11known compounds:cyclo-(Gly-L-Ala)(3-2), cyclo-(L-Ala-L-Ala)(3-3), cyclo-(L-Pro-Gly)(3-4), cyclo-(L-Pro-L-Ser)(3-5), cyclo-(L-Ala-trans-4-hydroxy-L-Pro)(3-6), cyclo-(L-Val-L-Pro)(3-7), cyclo-(Gly-L-Tyr)(3-8), cyclo-(L-Ala-L-Tyr)(3-9), cyclo-(L-Tyr-trans-4-hydroxy-L-Pro)(3-10),3-methyl hydantoin (3-11) and2-piperidinone (3-12) were isolated from the culture of Pseudomonas brassicacearum subsp. Neoaurantiaca, an endophytic bacterium found inside the tissue of Salvia miltiorrhiza Bunge. Compounds3-1,3-6,3-8,3-9and3-10exerted moderate lethality activity toward brine shrimps, and were found to show significant activities with LC50values of68.2,46.1,71.0,71.0and79.5μg/ml, respectively. In addition, seven compounds showed potent activities against3phytopathogenic fungi which can cause Danshen root rot disease, and3-5showed remarkable antifungal activity with MIC values ranging from25to50μg/ml.
5. Six known compounds:cyclo-(Pro-Gly)(4-1), cyclo-(Ala-4-OH-Pro)(4-2), cyclo-(Leu-4-OH-Pro)(4-3), cyclo-(Ala-Gly)(4-4), uracil (4-5) and urea (4-6) were isolated from the fermentation broth of Bacillus aryabhattai, an endophytic bacterium found inside the tissue of Salvia miltiorrhiza Bunge. Compound4-2exerted moderate lethality activity toward brine shrimps, and was found to show significant activities with LC50values of46.1μg/ml. Compounds4-2and4-3showed potent activities against3phytopathogenic fungi which can cause Danshen root rot disease, exhibited antifungal activities with MIC values of50-100μg/ml,
6. Three toxins,6-methoxymethyleugenin (5-1), maculosin (5-5) and cerevisterol (5-12), together with11other compounds:6-hydroxymethyleugenin (5-2),3-methoxy-6,8-dihydroxy-3-methyl-3,4-dihydroisocoumarin (5-3),4-hydroxyphenylethanol (5-4), scytalone (5-6),4-methoxyphenylacetic acid (5-7), succinic acid (5-8), ergosterol peroxide (5-9),22E,24R-5α,6α-epoxyergosta-8(14),22-diene-3β,7α-diol (5-10), glycerol-1-monooleate (5-11), ergosterol peroxide3-O-β-D-glucopyranoside (5-13) and22E,24R-ergosta-7,22-diene-3β,5α,6β,9α-tetraol (5-14) have been isolated from the ethyl acetate extracts of the cultures of Leptographium qinlingensis, an ophiostomatoid fungal pathogen associated with a forest pest Dendroctonus armandi, which causes enormous deaths of its host trees Pinus armandi. Phytotoxic test showed that, after5days, the treated groups were almost completely wilted, and their lethal rates are above95%for these three compounds. Similarly, three toxins can reduced chlorophyll content of two-year-old field seedlings.
7. Biotransformation of substrate paeonol was investigated with the white-rot basi diomycete Coriolus versicolor. Two biotransformed products,2,4-dihydroxyacetophenone (6-2) and2,5-dihydroxy-4-methoxyacetophenone (6-3), were isolated and identified by spectral methods. Compound6-3showed higher antioxidant, antibacterial, antifungal a ctivities than substrate paeonol.
引文
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