石果衣菌藻次级代谢产物的初步研究
|
摘要
荒漠地衣石果衣Endocarpon pusillum中未能检测出任何次级代谢产物,然而,其共生菌基因组中却含有14个PKS基因和2个NRPS基因。通过激活培养后从中分离出3个次级代谢产物,4,6,9-三羟基-7-甲基-1H,3H-萘并[1,8-cd]吡喃-1,3-二酮(lamellicolic anhydride)、石果衣菌素A(endocarpin A)及石果衣菌素B(endocarpin B),后二者为新结构化合物。从其共生藻柯氏复球藻Diplosphaera chodatii中分离出3个脱镁叶绿素类化合物,即脱镁叶绿素甲酯酸b(phaeophorbide b)、13-表-脱镁叶绿素甲酯酸a(13-epi-phaeophorbide a)及脱镁叶绿素甲酯酸a(phaeophorbide a)。其中脱镁叶绿素甲酯酸b具有中等的清除DPPH活性。
In the desert lichen Endocarpon pusillum can not be detected any secondary metabolite.But,its mycobiont genome contains fourteen PKS genes and two NRPS genes.Through the activation of culture in vermiculite medium,three secondary metabolites have been obtained from the mycobiont,including a new isoindolin-1-one compound(endocarpin A),a new naphthoquinone(endocarpin B) and lamellicolic anhydride.Other three demagnesium chlorophyll compounds were isolated from its phycobiont Diplosphaera chodatii.They are phaeophorbide b,13-epi-phaeophorbide a and phaeophorbide a.Phaeophorbide b owned medium antioxidant activity based on the ability to scavenge DPPH free radicals in vitro.
In the desert lichen Endocarpon pusillum can not be detected any secondary metabolite.But,its mycobiont genome contains fourteen PKS genes and two NRPS genes.Through the activation of culture in vermiculite medium,three secondary metabolites have been obtained from the mycobiont,including a new isoindolin-1-one compound(endocarpin A),a new naphthoquinone(endocarpin B) and lamellicolic anhydride.Other three demagnesium chlorophyll compounds were isolated from its phycobiont Diplosphaera chodatii.They are phaeophorbide b,13-epi-phaeophorbide a and phaeophorbide a.Phaeophorbide b owned medium antioxidant activity based on the ability to scavenge DPPH free radicals in vitro.
引文
Chee CF,Lee HB,Ong HC,Ho AS,2005.Photocytotoxic pheophorbide-related compounds from Aglaonema simplex.Chemistry&Biodiversity,2(12):1648-1655
Cheng HH,Wang HK,Ito J,Bastow KF,Tachibana Y,Nakanishi Y,Xu Z,Luo TY,Lee KH,2001.Cytotoxic pheophorbide-related compounds from Clerodendrum calamitosum and C.cyrtophyllum.Journal of Natural Products,64(7):915-919
Choomuenwai V,Beattie KD,Healy PC,Andrews KT,Fechner N,Davis RA,2015.Entonalactams A-C:isoindolinone derivatives from an Australian rainforest fungus belonging to the genus Entonaema.Phytochemistry,117:10-16
Duan H,Takaishi Y,Momota H,Ohmoto Y,Taki T,2002.Immunosuppressive constituents from Saussurea medusa.Phytochemistry,59(1):85-90
Elsebai MF,Kehraus S,Lindequist U,Sasse F,Shaaban S,Gutschow M,Josten M,Sahl HG,Konig GM,2011.Antimicrobial phenalenone derivatives from the marine-derived fungus Coniothyrium cereale.Organic&Biomolecular Chemistry,9(3):802-808
Elshobary ME,Osman ME,Abo-Shady AM,Komatsu E,Perreault H,Sorensen J,Piercey-Normore MD,2016.Algal carbohydrates affect polyketide synthesis of the lichen-forming fungus Cladonia rangiferina.Mycologia,108(4):646-56
Hargus JA,Fronczek FR,V icente MG,Smith KM,2007.Mono-(L)-aspartylchlorin-e6.Photochemistry and Photobiology,83(5):1006-1015
Li EW,Jiang LH,Guo LD,Zhang H,Che YS,2008.Pestalachlorides A-C,antifungal metabolites from the plant endophytic fungus Pestalotiopsis adusta.Bioorganic&Medicinal Chemistry,16(17):7894-7899
L?sgen S,Schl?rke O,Meindl K,Herbst-Irmer R,Zeeck A,2007.Structure and biosynthesis of chaetocyclinones,new polyketides produced by an endosymbiotic fungus.European Journal of Organic Chemistry,2007:2191-2196
Ma K,Han JJ,Bao L,Wei T,Liu H,2014.Two sarcoviolins with antioxidative and alpha-glucosidase inhibitory activity from the edible mushroom Sarcodon leucopus collected in T ibet.Journal of Natural Products,77(4):942-947
Michael WR,Walter AS,1980.Synthesis of covalently linked dimeric derivatives of chlorophyll a,pyrochlorophyll a,chlorophyll b,and bacteriochlorophyll a.Journal of Organic Chemistry,45(10):1969-1974
Nash TH III,Ryan BD,Gries C,Bungartz F,2002.Lichen flora of the Greater Sonoran Desert Region.Vol.1.Lichens Unlimited,Arizona State University,Arizona.1-531
Nash TH III,Gries C,Bungartz F,2007.Lichen Flora of the Greater Sonoran Desert Region.Vol.3.Lichens Unlimited,Arizona State University,Arizona.1-567
Okai Y,Higashi OK,1997.Potent anti-inflammatory activity of pheophytin a derived from edible green alga,Enteromorpha prolifera(Su Jiao-nori).International Journal of Immunopharmacology,19(6):355
Shan R,Stadler M,Anke H,Sterner O,1997.Naphthalenone and phthalide metabolites from Lachnum papyraceum.Journal of Natural Products,60(8):804-805
Shen L,Zhao SD,Zhu HJ,2011.Absolute configuration determination for natural products(I)-absolute configureation determination for ketone,lactone and alcohol by comparing computed optical rotations and 13CNMR with the experimental results.Chemical Journal of Chinese Universities,32(11):2568-2573(in Chinese)
Shrestha G,Clair LL,2013.Lichens:a promising source of antibiotic and anticancer drugs.Phytochemistry Reviews,12(1):229-244
Song FH,Liu XR,Guo H,Ren B,Chen CX,Piggott AM,Yu K,Gao H,Wang Q,Liu M,Liu XT,Dai HQ,Zhang LX,Capon RJ,2012.Brevianamides with antitubercular potential from a marine-derived isolate of Aspergillus versicolor.Organic Letters,14(18):4770-4773
Tang MK,Zhang DM,Xuan NHB,Tsui KW,Waye MY,Kong SK,2009.Photodynamic therapy inhibits p-glycoprotein mediated multi-drug resistance via JNK activation in human hepatocellular carcinoma using the photosensitizer pheophorbide a.Molecular Cancer,8(1):56
Wang BT,Qi QY,Ma K,Pei YF,Han JJ,Xu W,Li EW,Liu HW,2014.Depside alpha-glucosidase inhibitors from a culture of the mushroom Stereum hirsutum.Planta Medica,80(11):918-924
Wang JH,2016.A new lichen species of Sarcogyne and preliminary study of its fungal secondary metabolites.Master Thesis,Institute of Microbiology,Chinese Academy of Sciences,Beijing.1-51(in Chinese)
Wang JH,Wei JC,Li EW,2016.A preliminary study of the isoprenylated chromones from lichenized fungus Sarcogyne parviascifera.Mycosystema,36(4):492-502(in Chinese)
Wang YY,Liu B,Zhang XY,Zhou QM,Zhang T,Li H,Yu YF,Zhang XL,Hao XY,Wang M,Wang L,Wei JC,2014.Genome characteristics reveal the impact of lichenization on lichen-forming fungus Endocarpon pusillum Hedwig(Verrucariales,Ascomycota).BMCGenomics,15:34-52
Wei JC,2018.An enumeration of lichenized and lichenicolous fungi in China.China Forestry Publishing House,Beijing.1-586(in press)
Zhang T,2011.A preliminary research on the biology of vegetative reproduction and resistance of desert lichen symbionts.Ph D Desertation,Institute of Microbiology,Chinese Academy of Sciences,Beijing.50-51(in Chinese)
沈岚,赵声定,朱华结,2011.天然产物的绝对构型研究(Ⅰ)--通过比较旋光和碳谱的实验值与计算值确定酮类、内酯类和醇类化合物的绝对构型.高等学校化学学报,32(11):2568-2573
王娇红,2016.网盘衣属地衣新种及其真菌次级代谢产物的初步研究.中国科学院微生物研究所硕士论文,北京.51
王娇红,李二伟,魏江春,2016.小囊网盘衣真菌新色原酮类次级代谢产物初步研究.菌物学报,36(4):492-502
张涛,2011.荒漠地衣共生菌藻营养繁殖及其抗旱生物学初步研究.中国科学院微生物研究所博士论文,北京.50-51
Cheng HH,Wang HK,Ito J,Bastow KF,Tachibana Y,Nakanishi Y,Xu Z,Luo TY,Lee KH,2001.Cytotoxic pheophorbide-related compounds from Clerodendrum calamitosum and C.cyrtophyllum.Journal of Natural Products,64(7):915-919
Choomuenwai V,Beattie KD,Healy PC,Andrews KT,Fechner N,Davis RA,2015.Entonalactams A-C:isoindolinone derivatives from an Australian rainforest fungus belonging to the genus Entonaema.Phytochemistry,117:10-16
Duan H,Takaishi Y,Momota H,Ohmoto Y,Taki T,2002.Immunosuppressive constituents from Saussurea medusa.Phytochemistry,59(1):85-90
Elsebai MF,Kehraus S,Lindequist U,Sasse F,Shaaban S,Gutschow M,Josten M,Sahl HG,Konig GM,2011.Antimicrobial phenalenone derivatives from the marine-derived fungus Coniothyrium cereale.Organic&Biomolecular Chemistry,9(3):802-808
Elshobary ME,Osman ME,Abo-Shady AM,Komatsu E,Perreault H,Sorensen J,Piercey-Normore MD,2016.Algal carbohydrates affect polyketide synthesis of the lichen-forming fungus Cladonia rangiferina.Mycologia,108(4):646-56
Hargus JA,Fronczek FR,V icente MG,Smith KM,2007.Mono-(L)-aspartylchlorin-e6.Photochemistry and Photobiology,83(5):1006-1015
Li EW,Jiang LH,Guo LD,Zhang H,Che YS,2008.Pestalachlorides A-C,antifungal metabolites from the plant endophytic fungus Pestalotiopsis adusta.Bioorganic&Medicinal Chemistry,16(17):7894-7899
L?sgen S,Schl?rke O,Meindl K,Herbst-Irmer R,Zeeck A,2007.Structure and biosynthesis of chaetocyclinones,new polyketides produced by an endosymbiotic fungus.European Journal of Organic Chemistry,2007:2191-2196
Ma K,Han JJ,Bao L,Wei T,Liu H,2014.Two sarcoviolins with antioxidative and alpha-glucosidase inhibitory activity from the edible mushroom Sarcodon leucopus collected in T ibet.Journal of Natural Products,77(4):942-947
Michael WR,Walter AS,1980.Synthesis of covalently linked dimeric derivatives of chlorophyll a,pyrochlorophyll a,chlorophyll b,and bacteriochlorophyll a.Journal of Organic Chemistry,45(10):1969-1974
Nash TH III,Ryan BD,Gries C,Bungartz F,2002.Lichen flora of the Greater Sonoran Desert Region.Vol.1.Lichens Unlimited,Arizona State University,Arizona.1-531
Nash TH III,Gries C,Bungartz F,2007.Lichen Flora of the Greater Sonoran Desert Region.Vol.3.Lichens Unlimited,Arizona State University,Arizona.1-567
Okai Y,Higashi OK,1997.Potent anti-inflammatory activity of pheophytin a derived from edible green alga,Enteromorpha prolifera(Su Jiao-nori).International Journal of Immunopharmacology,19(6):355
Shan R,Stadler M,Anke H,Sterner O,1997.Naphthalenone and phthalide metabolites from Lachnum papyraceum.Journal of Natural Products,60(8):804-805
Shen L,Zhao SD,Zhu HJ,2011.Absolute configuration determination for natural products(I)-absolute configureation determination for ketone,lactone and alcohol by comparing computed optical rotations and 13CNMR with the experimental results.Chemical Journal of Chinese Universities,32(11):2568-2573(in Chinese)
Shrestha G,Clair LL,2013.Lichens:a promising source of antibiotic and anticancer drugs.Phytochemistry Reviews,12(1):229-244
Song FH,Liu XR,Guo H,Ren B,Chen CX,Piggott AM,Yu K,Gao H,Wang Q,Liu M,Liu XT,Dai HQ,Zhang LX,Capon RJ,2012.Brevianamides with antitubercular potential from a marine-derived isolate of Aspergillus versicolor.Organic Letters,14(18):4770-4773
Tang MK,Zhang DM,Xuan NHB,Tsui KW,Waye MY,Kong SK,2009.Photodynamic therapy inhibits p-glycoprotein mediated multi-drug resistance via JNK activation in human hepatocellular carcinoma using the photosensitizer pheophorbide a.Molecular Cancer,8(1):56
Wang BT,Qi QY,Ma K,Pei YF,Han JJ,Xu W,Li EW,Liu HW,2014.Depside alpha-glucosidase inhibitors from a culture of the mushroom Stereum hirsutum.Planta Medica,80(11):918-924
Wang JH,2016.A new lichen species of Sarcogyne and preliminary study of its fungal secondary metabolites.Master Thesis,Institute of Microbiology,Chinese Academy of Sciences,Beijing.1-51(in Chinese)
Wang JH,Wei JC,Li EW,2016.A preliminary study of the isoprenylated chromones from lichenized fungus Sarcogyne parviascifera.Mycosystema,36(4):492-502(in Chinese)
Wang YY,Liu B,Zhang XY,Zhou QM,Zhang T,Li H,Yu YF,Zhang XL,Hao XY,Wang M,Wang L,Wei JC,2014.Genome characteristics reveal the impact of lichenization on lichen-forming fungus Endocarpon pusillum Hedwig(Verrucariales,Ascomycota).BMCGenomics,15:34-52
Wei JC,2018.An enumeration of lichenized and lichenicolous fungi in China.China Forestry Publishing House,Beijing.1-586(in press)
Zhang T,2011.A preliminary research on the biology of vegetative reproduction and resistance of desert lichen symbionts.Ph D Desertation,Institute of Microbiology,Chinese Academy of Sciences,Beijing.50-51(in Chinese)
沈岚,赵声定,朱华结,2011.天然产物的绝对构型研究(Ⅰ)--通过比较旋光和碳谱的实验值与计算值确定酮类、内酯类和醇类化合物的绝对构型.高等学校化学学报,32(11):2568-2573
王娇红,2016.网盘衣属地衣新种及其真菌次级代谢产物的初步研究.中国科学院微生物研究所硕士论文,北京.51
王娇红,李二伟,魏江春,2016.小囊网盘衣真菌新色原酮类次级代谢产物初步研究.菌物学报,36(4):492-502
张涛,2011.荒漠地衣共生菌藻营养繁殖及其抗旱生物学初步研究.中国科学院微生物研究所博士论文,北京.50-51