烟曲霉GZWMJZ-152茶粕发酵代谢产物
|
摘要
在茶粕培养基摇床培养条件下,烟曲霉GZWMJZ-152将茶粕中的山茶苷A (1)和山茶苷B (2)代谢为山奈酚-3-O-芸香糖苷(3);在茶粕培养基静置发酵条件下,从发酵提取物中分离得到5个化合物,分别为山奈酚(4)、(-)Chaetominine (5)、trypacidin (6)、1,2-seco-trypacidin (7)、(-)-丁香脂素(8)。测试了8个化合物的α-葡萄糖苷酶抑制活性和DPPH自由基清除活性,其中化合物1–3,5–8具有较好的α-葡萄糖苷酶抑制活性,IC_(50)值在133.9–308.6μg/mL;化合物1,4,8具有较好的自由基清除活性,IC_(50)值在0.43–5.06μg/mL。
Aspergillus fumigatus GZWMJZ-152 can hydrolyze camelliaside A(1) and camelliaside B(2) into kaempferol 3-O-rutinoside(3) under the condition of shaking fermentation using Camellia seed cake medium.Five compounds, kaempferol(4),(-)chaetominine(5), trypacidin(6), 1,2-seco-trypacidin(7) and(-)-syringaresinol(8), were isolated under the condition of solid static fermentation on the same medium. The inhibitory effects of eight compounds on α-glycosidase and DPPH free radical scavenging activity were tested. Compounds 1–3, 5–8 exhibited α-glycosidase inhibitory activity with IC_(50) values ranging from 133.9 to 308.6μg/mL. Compounds 1, 4, 8 exhibited radical scavenging activity against DPPH with IC_(50) values ranging from 0.43 to 5.06μg/mL.
Aspergillus fumigatus GZWMJZ-152 can hydrolyze camelliaside A(1) and camelliaside B(2) into kaempferol 3-O-rutinoside(3) under the condition of shaking fermentation using Camellia seed cake medium.Five compounds, kaempferol(4),(-)chaetominine(5), trypacidin(6), 1,2-seco-trypacidin(7) and(-)-syringaresinol(8), were isolated under the condition of solid static fermentation on the same medium. The inhibitory effects of eight compounds on α-glycosidase and DPPH free radical scavenging activity were tested. Compounds 1–3, 5–8 exhibited α-glycosidase inhibitory activity with IC_(50) values ranging from 133.9 to 308.6μg/mL. Compounds 1, 4, 8 exhibited radical scavenging activity against DPPH with IC_(50) values ranging from 0.43 to 5.06μg/mL.
引文
Chen ZB,Hao JJ,Wang LP,Wang Y,Kong FD,Zhu WM,2016.Newα-glucosidase inhibitors from marine algae-derived Streptomyces sp.OUCMDZ-3434.Scientific Reports,6:20004
Chen YW,Miao CP,Wu SH,2012.Studies on transformed Panax notoginseng by Aspergillus terreus.Natural Product Research and Development,24(8):1014-1019(in Chinese)
Dai D,Zhong SM,Zheng J,2017.Optimization of ultrasonic wave-assisted extraction of polysaccharides from Camellia seed cake by response surface methodology.Food Research and Development,38(20):37-41(in Chinese)
Gao DF,Xu M,Zhao P,Zhang XY,Wang YF,Yang CR,Zhang YJ,2011.Kaempferol acetylated glycosides from the seed cake of Camellia oleifera.Food Chemistry,124(2):432-436
Ibrahim MF,Hussain FHS,Zanoni G,Vidari G,2016.The main constituents of Tulipa systola Stapf.roots and flowers:their antioxidant activities.Natural Product Research,31(17):2001-2007
Jiao RH,Xu S,Liu JY,Ge HM,Ding H,Xu C,Zhu HL,Tan RX,2006.Chaetominine,a cytotoxic alkaloid produced by endophytic Chaetomium sp.IFB-E015.Organic Letters,8(25):5709-5712
Jin C,Zhou J,Cui PW,Lin Y,Xu DH,Li SX,2016.Research progresses of Aspergillus transforming traditional Chinese medicinal materials.Journal of Hunan University of Chinese Medicine,36(6):81-92(in Chinese)
Li HZ,Zhang YQ,Liu Q,Sun CL,Li J,Yang P,Wang X,2016.Preparative separation of phenolic compounds from Chimonanthus praecox flowers by high-speed counter-current chromatography using a stepwise elution mode.Molecules,21(8):1016
Lu CH,Huang YJ,Shen YM,2005.Secondary metabolites of Aspergillus fumigatus var.fumigatus.Chinese Journal of Natural Medicines,3(5):269-271
Li JJ,2010.Screening of fungi for efficient degradation of cellulose in oil-tea-cake.Master Thesis,Anhui Agricultural University,Hefei.1-45(in Chinese)
Li XZ,Zhang S,Li WS,2012.α-Glucosidase inhibitory activity of Camellia cake polysaccharides in vitro.Journal of Hunan University(Natural Sciences),39(11):71-73(in Chinese)
Liang JF,Wang Y,Xiao YW,Chang J,Ji B,Zhu D,2017.Purification and characterization of geniposidehydrolyzingβ-glucosidase from endophytic Eupenicillium javanicum R57 harboring in Dongxiang wild rice.Mycosystema,36(11):1543-1555(in Chinese)
Malgesini B,Forte B,Borghi D,Quartieri F,Gennari C,Papeo G,2009.A straightforward total synthesis of(-)-chaetominine.Chemistry A European Journal,15(32):7922-7929
Park JS,Rho HS,Kim DH,Chang IS,2006.Enzymatic preparation of kaempferol from green tea seed and its antioxidant activity.Journal of Agricultural&Food Chemistry,54(8):2951-2956
Shen SA,Cheng HR,Li X,Li T,Yuan M,Zhou YH,Ding CB,2014.Effects of extraction methods on antioxidant activities of polysaccharides from camellia seed cake.European Food Research and Technology,238(6):1015-1021
Tian CX,2012.Studies on microbial detoxification of camellia oil waste.Master Thesis,Hunan Agricultural University,Changsha.1-49(in Chinese)
Xiao BK,Yang JY,Liu YR,Dong JX,Huang RQ,2015.Chemical constituents of Pittosporum illicioides.Chemistry of Natural Products,51(6):1126-1129
Xiao X,Liu JK,Fu SB,Sun DA,2011.Microbial transformation of diosgenin by filamentous fungus Cunninghamella echinulata.Journal of Asian Natural Products Research,13(3):270-275
Wang WL,Zhu TJ,Tao HW,Lu ZY,Fang YC,Gu QQ,Zhu WM,2007.Three novel structurally unique spirocyclic alkaloids from the halotolerant B-17 fungal strain of Aspergillus variecolor.Chemistry&Biodiversity,4(12):2913-2919
Wang YL,Li WF,Gui H,Chen XL,Cao HY,2017.Study on extraction procedure of tea saponin from seed cake of Camellia oleifera Abel.by using ultrasonic and cellulase.Journal of Anhui Agricultural Sciences,45(2):97-99(in Chinese)
Zhu JP,Luo F,Wang C,Zhong SM,Zheng XW,2016.Extracting tea saponin from oil-tea cake using water,alcohol extraction method.The Food Industry,37(1):107-109(in Chinese)
Zhou YL,Xu YC,Gong QY,Rao Q,Zuo MX,Zhu WM,Lin CH,Wang LP,2018.Antibacterial natural products from Guizhou cave-derived Aspergillus fumigatus GZWMJZ-152.Chinese Journal of Antibiotics,43(6):675-682(in Chinese)
Zong JF,Peng YR,Bao GH,Hou RY,Wan XC,2016.Two new oleanane-type saponins with anti-proliferative activity from Camellia oleifera Abel.seed cake.Molecules,21(2):188
Zhang CH,Chen YW,Zheng Y,Wu SH,Li SL,Li YY,Yang LY,2008.Study on the chemical components of transformation outcome of microbial transformation by Aspergil us niger.Natural Product Research and Development,20(4):585-588(in Chinese)
陈有为,苗翠苹,吴少华,2012.土生曲霉转化三七中药材的研究.天然产物研究与开发,24(8):1014-1019
戴丹,仲山民,郑剑,2017.响应面法优化超声波辅助提取油茶饼粕多糖.食品研究与开发,38(20):37-41
金灿,周晋,崔培梧,林艳,徐德宏,李顺祥,2016.曲霉转化中药材的研究进展.湖南中医药大学学报,36(6):81-92
李君君,2010.高效降解茶粕纤维素菌株的筛选.安徽农业大学硕士论文,合肥.1-45
李湘洲,张胜,李文生,2012.油茶饼粕多糖对体外α-葡萄糖苷酶的抑制作用.湖南大学学报(自然科学版),39(11):71-73
梁金凤,汪涯,肖依文,常军,季波,朱笃,2017.内生真菌Eupenicillium javanicum R57水解京尼平苷β-葡萄糖苷酶的分离纯化及其酶学性质.菌物学报,36(11):1543-1555
田璨熙,2012.茶粕微生物脱毒(皂素)研究.湖南农业大学硕士论文,长沙.1-49
王娅玲,李维峰,桂花,陈小龙,曹海燕,2017.超声辅助纤维素酶提取茶粕中茶皂苷的工艺研究.安徽农业科学,45(2):97-99
周彦伶,许言超,龚倩玉,饶青,左明星,朱伟明,林昌虎,王立平,2018.贵州洞穴真菌Aspergillus fumigatus GZWMJZ-152的抗菌活性产物.中国抗生素杂志,43(6):675-682
朱俊朋,罗凡,王超,仲山民,郑旭卫,2016.水提-醇萃法提取油茶饼粕中茶皂素.食品工业,37(1):107-109
张传会,陈有为,郑毅,吴少华,李绍兰,李冶滢,杨丽源,2008.黄山药的黑曲霉转化产物化学成分研究.天然产物研究与开发,20(4):585-588
Chen YW,Miao CP,Wu SH,2012.Studies on transformed Panax notoginseng by Aspergillus terreus.Natural Product Research and Development,24(8):1014-1019(in Chinese)
Dai D,Zhong SM,Zheng J,2017.Optimization of ultrasonic wave-assisted extraction of polysaccharides from Camellia seed cake by response surface methodology.Food Research and Development,38(20):37-41(in Chinese)
Gao DF,Xu M,Zhao P,Zhang XY,Wang YF,Yang CR,Zhang YJ,2011.Kaempferol acetylated glycosides from the seed cake of Camellia oleifera.Food Chemistry,124(2):432-436
Ibrahim MF,Hussain FHS,Zanoni G,Vidari G,2016.The main constituents of Tulipa systola Stapf.roots and flowers:their antioxidant activities.Natural Product Research,31(17):2001-2007
Jiao RH,Xu S,Liu JY,Ge HM,Ding H,Xu C,Zhu HL,Tan RX,2006.Chaetominine,a cytotoxic alkaloid produced by endophytic Chaetomium sp.IFB-E015.Organic Letters,8(25):5709-5712
Jin C,Zhou J,Cui PW,Lin Y,Xu DH,Li SX,2016.Research progresses of Aspergillus transforming traditional Chinese medicinal materials.Journal of Hunan University of Chinese Medicine,36(6):81-92(in Chinese)
Li HZ,Zhang YQ,Liu Q,Sun CL,Li J,Yang P,Wang X,2016.Preparative separation of phenolic compounds from Chimonanthus praecox flowers by high-speed counter-current chromatography using a stepwise elution mode.Molecules,21(8):1016
Lu CH,Huang YJ,Shen YM,2005.Secondary metabolites of Aspergillus fumigatus var.fumigatus.Chinese Journal of Natural Medicines,3(5):269-271
Li JJ,2010.Screening of fungi for efficient degradation of cellulose in oil-tea-cake.Master Thesis,Anhui Agricultural University,Hefei.1-45(in Chinese)
Li XZ,Zhang S,Li WS,2012.α-Glucosidase inhibitory activity of Camellia cake polysaccharides in vitro.Journal of Hunan University(Natural Sciences),39(11):71-73(in Chinese)
Liang JF,Wang Y,Xiao YW,Chang J,Ji B,Zhu D,2017.Purification and characterization of geniposidehydrolyzingβ-glucosidase from endophytic Eupenicillium javanicum R57 harboring in Dongxiang wild rice.Mycosystema,36(11):1543-1555(in Chinese)
Malgesini B,Forte B,Borghi D,Quartieri F,Gennari C,Papeo G,2009.A straightforward total synthesis of(-)-chaetominine.Chemistry A European Journal,15(32):7922-7929
Park JS,Rho HS,Kim DH,Chang IS,2006.Enzymatic preparation of kaempferol from green tea seed and its antioxidant activity.Journal of Agricultural&Food Chemistry,54(8):2951-2956
Shen SA,Cheng HR,Li X,Li T,Yuan M,Zhou YH,Ding CB,2014.Effects of extraction methods on antioxidant activities of polysaccharides from camellia seed cake.European Food Research and Technology,238(6):1015-1021
Tian CX,2012.Studies on microbial detoxification of camellia oil waste.Master Thesis,Hunan Agricultural University,Changsha.1-49(in Chinese)
Xiao BK,Yang JY,Liu YR,Dong JX,Huang RQ,2015.Chemical constituents of Pittosporum illicioides.Chemistry of Natural Products,51(6):1126-1129
Xiao X,Liu JK,Fu SB,Sun DA,2011.Microbial transformation of diosgenin by filamentous fungus Cunninghamella echinulata.Journal of Asian Natural Products Research,13(3):270-275
Wang WL,Zhu TJ,Tao HW,Lu ZY,Fang YC,Gu QQ,Zhu WM,2007.Three novel structurally unique spirocyclic alkaloids from the halotolerant B-17 fungal strain of Aspergillus variecolor.Chemistry&Biodiversity,4(12):2913-2919
Wang YL,Li WF,Gui H,Chen XL,Cao HY,2017.Study on extraction procedure of tea saponin from seed cake of Camellia oleifera Abel.by using ultrasonic and cellulase.Journal of Anhui Agricultural Sciences,45(2):97-99(in Chinese)
Zhu JP,Luo F,Wang C,Zhong SM,Zheng XW,2016.Extracting tea saponin from oil-tea cake using water,alcohol extraction method.The Food Industry,37(1):107-109(in Chinese)
Zhou YL,Xu YC,Gong QY,Rao Q,Zuo MX,Zhu WM,Lin CH,Wang LP,2018.Antibacterial natural products from Guizhou cave-derived Aspergillus fumigatus GZWMJZ-152.Chinese Journal of Antibiotics,43(6):675-682(in Chinese)
Zong JF,Peng YR,Bao GH,Hou RY,Wan XC,2016.Two new oleanane-type saponins with anti-proliferative activity from Camellia oleifera Abel.seed cake.Molecules,21(2):188
Zhang CH,Chen YW,Zheng Y,Wu SH,Li SL,Li YY,Yang LY,2008.Study on the chemical components of transformation outcome of microbial transformation by Aspergil us niger.Natural Product Research and Development,20(4):585-588(in Chinese)
陈有为,苗翠苹,吴少华,2012.土生曲霉转化三七中药材的研究.天然产物研究与开发,24(8):1014-1019
戴丹,仲山民,郑剑,2017.响应面法优化超声波辅助提取油茶饼粕多糖.食品研究与开发,38(20):37-41
金灿,周晋,崔培梧,林艳,徐德宏,李顺祥,2016.曲霉转化中药材的研究进展.湖南中医药大学学报,36(6):81-92
李君君,2010.高效降解茶粕纤维素菌株的筛选.安徽农业大学硕士论文,合肥.1-45
李湘洲,张胜,李文生,2012.油茶饼粕多糖对体外α-葡萄糖苷酶的抑制作用.湖南大学学报(自然科学版),39(11):71-73
梁金凤,汪涯,肖依文,常军,季波,朱笃,2017.内生真菌Eupenicillium javanicum R57水解京尼平苷β-葡萄糖苷酶的分离纯化及其酶学性质.菌物学报,36(11):1543-1555
田璨熙,2012.茶粕微生物脱毒(皂素)研究.湖南农业大学硕士论文,长沙.1-49
王娅玲,李维峰,桂花,陈小龙,曹海燕,2017.超声辅助纤维素酶提取茶粕中茶皂苷的工艺研究.安徽农业科学,45(2):97-99
周彦伶,许言超,龚倩玉,饶青,左明星,朱伟明,林昌虎,王立平,2018.贵州洞穴真菌Aspergillus fumigatus GZWMJZ-152的抗菌活性产物.中国抗生素杂志,43(6):675-682
朱俊朋,罗凡,王超,仲山民,郑旭卫,2016.水提-醇萃法提取油茶饼粕中茶皂素.食品工业,37(1):107-109
张传会,陈有为,郑毅,吴少华,李绍兰,李冶滢,杨丽源,2008.黄山药的黑曲霉转化产物化学成分研究.天然产物研究与开发,20(4):585-588