群体感应抑制活性导向分离腐皮镰刀菌中代谢产物
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摘要
本实验采用群体感应抑制(quorum sensing inhibitory, QSI)活性导向法,对分离自山东威海近海底泥的真菌WH7-2开展代谢产物研究。综合菌落形态和转录间隔区(Internal Transcribed Spacer, ITS)全序列分析,菌株WH7-2鉴定为腐皮镰刀菌Fusariumsolani。综合运用多种色谱方法,从该真菌大米发酵产物的活性部位中分离得到11个化合物。分别鉴定为(2E, 5E)-3, 5, 7-三甲基-2, 5-辛二烯酸(1)、不饱和脂肪酸酯混合物(2—4)、镰红菌素-3-甲醚(5)、脱水镰红菌素(6)、(22E)-5α, 8α-过氧化麦角甾-6, 22-二烯-3β-醇(7)、(22E)-5α, 8α-过氧化麦角甾-6, 9 (11), 22-三烯-3β-醇(8)、3β-羟基-胆甾-5-烯-7-酮(9)、6β-羟基-胆甾-4-烯-3-酮(10)和(22E)-胆甾-5, 22-二烯-3β-醇(11)。其中不饱和脂肪酸酯混合物(2—4)具有QSI活性,其他化合物无QSI活性。除5和6外,其他化合物均为首次从腐皮镰刀菌F. solani中发现。
In this study, we investigated the metabolites from coastal mud-derived fungus WH7-2 by using the quorum sensing inhibitory(QSI) activity-oriented approach. The strain WH7-2 was identified as F. solani by analyzing its morphological characteristics and internal transcribed spacer(ITS) sequence. Chemical investigation of the rice fermentation product led to the isolation of 11 compounds. Their structures were elucidated as(2 E, 5 E)-3, 5, 7-trimethyl-2, 5-octadienoic acid(1), mixtures of unsaturated fatty acid ester(2, 3 and 4), 3-methyl ether fusarubin(5), Anhydrofusarubin(6),(22 E)-5α, 8α-epidioxy-ergosta-6,22-diene-3β-ol(7),(22 E)-5α, 8α-epidioxy-ergosta-6, 9(11), 22-triene-3β-ol(8), 3β-hydroxycholest-5-en-7-one(9),6β-hydroxy-cholest-4-en-3-one(10), and(22 E)-cholest-5, 22-dien-3β-ol(11). All compounds were evaluated for their QSI activities, and only the mixtures of unsaturated fatty acid ester(2-4) exhibited QSI activity. All the compounds except 5 and 6 were first reported from F. solani.
In this study, we investigated the metabolites from coastal mud-derived fungus WH7-2 by using the quorum sensing inhibitory(QSI) activity-oriented approach. The strain WH7-2 was identified as F. solani by analyzing its morphological characteristics and internal transcribed spacer(ITS) sequence. Chemical investigation of the rice fermentation product led to the isolation of 11 compounds. Their structures were elucidated as(2 E, 5 E)-3, 5, 7-trimethyl-2, 5-octadienoic acid(1), mixtures of unsaturated fatty acid ester(2, 3 and 4), 3-methyl ether fusarubin(5), Anhydrofusarubin(6),(22 E)-5α, 8α-epidioxy-ergosta-6,22-diene-3β-ol(7),(22 E)-5α, 8α-epidioxy-ergosta-6, 9(11), 22-triene-3β-ol(8), 3β-hydroxycholest-5-en-7-one(9),6β-hydroxy-cholest-4-en-3-one(10), and(22 E)-cholest-5, 22-dien-3β-ol(11). All compounds were evaluated for their QSI activities, and only the mixtures of unsaturated fatty acid ester(2-4) exhibited QSI activity. All the compounds except 5 and 6 were first reported from F. solani.
引文
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MAHAPATRA S,BANERJEE D,2012.Structural elucidation and bioactivity of a novel exopolysaccharide from endophytic Fusarium solani SD5[J].Carbohydrate Polymers,90(1):683-689.
MARTINELLI D,GROSSMANN Q,SéQUIN U,et al,2004.Effects of natural and chemically synthesized furanones on quorum sensing in Chromobacterium violaceum[J].BMCMicrobiology,4:25.
SHIONO Y,ARIEFTA N R,ANWAR C,et al,2016.New metabolites produced by Fusarium solani T-13 isolated from a dead branch[J].Phytochemistry Letters,17:232-237.
SONG H H,LEE H S,LEE C,2011.A new cytotoxic cyclic pentadepsipeptide,neo-N-methylsansalvamide produced by Fusarium solani KCCM90040,isolated from potato[J].Food Chemistry,126(2):472-478.
TADPETCH K,CHUKONG C,JEANMARD L,et al,2015.Cytotoxic naphthoquinone and a new succinate ester from the soil fungus Fusarium solani PSU-RSPG227[J].Phytochemistry Letters,11:106-110.
TATUM J H,BAKER R A,BERRY R E,1985.Three further naphthoquinones produced by Fusarium solani[J].Phytochemistry,24(12):3019-3021.
TATUM J H,BAKER R A,BERRY R E,1987.Naphthoquinones and derivatives from Fusarium[J].Phytochemistry,26(3):795-798.
TRISUWAN K,RUKACHAISIRIKUL V,BORWORNWIRIYAPANK,et al,2013.Pyrone derivatives from the soil fungus Fusarium solani PSU-RSPG37[J].Phytochemistry Letters,6:495-497.
WHITELEY M,DIGGLE S P,GREENBERG E P,2017.Progress in and promise of bacterial quorum sensing research[J].Nature,551(7680):313-320.
刘彩霞,李平林,唐旭利,等,2012.中国南海聚裂丛柳珊瑚化学成分研究[J].中国海洋药物,31(5):5-10.LIU CAIXIA,LI PINGLIN,TANG XULI,et al,2012.Studies on chemical constituents of the South China Sea gorgonian Rumphella aggregata[J].Chinese Journal of Marine Drugs,31(5):5-10(in Chinese with English abstract).
刘梨萍,于瑞同,袁瑾,等,2014.莲叶桐树枝的化学成分[J].青岛科技大学学报(自然科学版),35(2):162-166.LIULIPING,YU RUITONG,YUAN JIN,et al,2014.Study on the chemical constituents of the branch of Hernandia ovigera L.[J].Journal of Qingdao University of Science and Technology(Natural Science Edition),35(2):162-166(in Chinese with English abstract).
钱西勇,张兴旺,唐旭利,等,2016.中国南海扁小尖柳珊瑚Muricella sibogae化学成分研究[J].中国海洋药物,35(1):65-68.QIAN XIYONG,ZHANG XINGWANG,TANG XULI,et al,2016.Study on chemical constituents of gorgonian Muricella sibogae[J].Chinese Journal of Marine Drugs,35(1):65-68(in Chinese with English abstract).
宋双,薛艳钰,陆勇军,等,2015.南海红树林内生真菌Fusarium solani 387#次级代谢产物研究[J].中山大学学报(自然科学版),54(5):67-71.SONG SHUANG,XUEYANYU,LU YONGJUN,et al,2015.The secondary metabolites of the mangrove endophytic fungus Fusarium solani 387#[J].Acta Scientiarum Naturalium Universitatis Sunyatseni,54(5):67-71(in Chinese with English abstract).
吴荣翠,张红,李平林,等,2013.中国南海花刺柳珊瑚化学成分研究[J].中国海洋药物,32(4):23-28.WU RONGCUI,ZHANG HONG,LI PINGLIN,et al,2013.Studies on chemical constituents of Echinogorgia flora[J].Chinese Journal of Marine Drugs,32(4):23-28(in Chinese with English abstract).
郁步竹,宋成芝,杜芝芝,等,2009.滑桃树内生真菌Fusarium sp.1RGa-1b中萘醌类代谢产物及其抗菌活性研究[J].天然产物研究与开发,21(4):574-576.YU BUZHU,SONGCHENGZHI,DU ZHIZHI,et al,2009.Naphthaquinones from Fusarium sp.1RGa-1b,an endophytic fungus associated with Trewia nudiflora(euphorbiaceae)[J].Natural Product Research and Development,21(4):574-576(in Chinese with English abstract).
MAHAPATRA S,BANERJEE D,2012.Structural elucidation and bioactivity of a novel exopolysaccharide from endophytic Fusarium solani SD5[J].Carbohydrate Polymers,90(1):683-689.
MARTINELLI D,GROSSMANN Q,SéQUIN U,et al,2004.Effects of natural and chemically synthesized furanones on quorum sensing in Chromobacterium violaceum[J].BMCMicrobiology,4:25.
SHIONO Y,ARIEFTA N R,ANWAR C,et al,2016.New metabolites produced by Fusarium solani T-13 isolated from a dead branch[J].Phytochemistry Letters,17:232-237.
SONG H H,LEE H S,LEE C,2011.A new cytotoxic cyclic pentadepsipeptide,neo-N-methylsansalvamide produced by Fusarium solani KCCM90040,isolated from potato[J].Food Chemistry,126(2):472-478.
TADPETCH K,CHUKONG C,JEANMARD L,et al,2015.Cytotoxic naphthoquinone and a new succinate ester from the soil fungus Fusarium solani PSU-RSPG227[J].Phytochemistry Letters,11:106-110.
TATUM J H,BAKER R A,BERRY R E,1985.Three further naphthoquinones produced by Fusarium solani[J].Phytochemistry,24(12):3019-3021.
TATUM J H,BAKER R A,BERRY R E,1987.Naphthoquinones and derivatives from Fusarium[J].Phytochemistry,26(3):795-798.
TRISUWAN K,RUKACHAISIRIKUL V,BORWORNWIRIYAPANK,et al,2013.Pyrone derivatives from the soil fungus Fusarium solani PSU-RSPG37[J].Phytochemistry Letters,6:495-497.
WHITELEY M,DIGGLE S P,GREENBERG E P,2017.Progress in and promise of bacterial quorum sensing research[J].Nature,551(7680):313-320.