胶陀螺光敏毒性成分
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摘要
食用未经碱处理过的胶陀螺子实体,会出现嘴巴肿胀、暴露在日光下的皮肤灼痛等过敏症状,一直以来困扰着长白山当地居民对这一美食的需求。本文旨在找到胶陀螺Bulgaria inquinans中光敏活性成分。将胶陀螺子实体粉末用丙酮回流提取,浓缩得到浸膏,加吐温-80溶解后灌胃昆明种小鼠,进行光敏活性试验。把出现光敏反应的小鼠处死后,取下红肿的小鼠耳朵用甲醇索式提取得活性组分,进行薄层色谱层析和柱层析,得到一种活性单体化合物,经核磁共振和电子轰击质谱波谱综合解析鉴定该化合物为邻苯二甲酸二异丁酯(DiBP)。结果表明DiBP就是引起胶陀螺光敏中毒反应的活性成分,且经碱水降解后毒性降低。
The photosensitive toxic symptom caused by Bulgaria inquinans puzzled local residents of Changbai mountainous area all along. Eating the fungus without alkali treatment can cause swelling of mouth and burning pains of skin when exposure under sunlight. The study aimed at finding the photosensitive toxic components of B. inquinans. The active extract was obtained from B. inquinans fruiting bodies, using as dissolvent acetone. The extract was administrated to mice, and then the active component was further obtained from the methanolextract of mice's red swelling ears. The active compound was identified as diisobutyl phthalate(DiBP) by using 1 H-NMR and 13 C-NMR, and EI-MS spectroscopy. DiB P was proved to be the photosensitive toxic compound of B. inquinans causing photosensitivity of mice. DiBP can be degraded in alkaline water and the toxicity can be decreased.
The photosensitive toxic symptom caused by Bulgaria inquinans puzzled local residents of Changbai mountainous area all along. Eating the fungus without alkali treatment can cause swelling of mouth and burning pains of skin when exposure under sunlight. The study aimed at finding the photosensitive toxic components of B. inquinans. The active extract was obtained from B. inquinans fruiting bodies, using as dissolvent acetone. The extract was administrated to mice, and then the active component was further obtained from the methanolextract of mice's red swelling ears. The active compound was identified as diisobutyl phthalate(DiBP) by using 1 H-NMR and 13 C-NMR, and EI-MS spectroscopy. DiB P was proved to be the photosensitive toxic compound of B. inquinans causing photosensitivity of mice. DiBP can be degraded in alkaline water and the toxicity can be decreased.
引文
Bai L,Ma WC,Bao HY,2014.Study on photosensitive active groups of Bulgaria inquinans.Fungi Research,12(1):51-54(in Chinese)
Bi HT,Gao TT,Li ZH,Ji L,Yang W,Iteku BJ,Liu EX,Zhou YF,2013a.Structural elucidation and antioxidant activity of a water-soluble polysaccharide from the fruit bodies of Bulgaria inquinans Fries.Food Chemistry,138(2-3):1470-1475
Bi HT,Gao TT,Liu DB,Tai GH,Wei M,Zhou YF,2013b.Structures of(1→6)-β-d-glucans from Bulgaria inquinans Fries and their immunological activities.Carbohydrate Polymers,93(2):547-552
Bi HT,Han H,Li ZH,Ni WH,Chen Y,Zhu JJ,Gao TT,Hao M,Zhou YF,2011.A water-soluble polysaccharide from the fruit bodies of Bulgaria inquinans fries and its anti-malarial activity.Evidence-based Complementary and Alternative Medicine,2011(12):1-12
Bao HY,Li Y,Ding XK,Sun XB,2002.Studies on the photosensitive activity effect of Bulgaria inquinans.Acta Edulis Fungi,9:15-17(in Chinese)
Cui DB,Wang SQ,1997.Studies on chemical constituents of Bulgaria inguinans Fries.Chinese Journal of Chinese Materia Medica,22:485-486(in Chinese)
Edwards RL,Lockett HJ,1976.Constituents of the higher fungi.Part XVI.Bulgarhodin and bulgarein,novel benzofluoranthenequinones from the fungus Bulgaria inquinans Fries.Journal of the Chemical Society,Perkin Transactions 1,8(20):2149-2155
Feng HQ,Sun T,Jia DM,Mu JF,Zhang YM,2013.Study on chemical constituents and antimicrobial activity of extracts from fruit bodies of Bulgaria iuquiuaus Fr.Modern Agricultural Science and Technology,10:153-154
Jiang SS,Tsumuro T,Takubo M,Fujii Y,Kamei CK,2005.Antipruritic and antierythema effects of ascomycete Bulgaria inquinans extract in ICR mice.Biological&Pharmaceutical Bulletin,28(12):2197-2200
Kirk PM,Cannon PF,Minter DW,stalpers JA,2008.Dictionary of the Fungi.10th ed.CABI,Wallingford,UK.
Li N,Xu J,Li X,Zhang P,2013.Two new anthraquinone dimers from the fruit bodies of Bulgaria inquinans.Fitoterapia,84(3):85-88
Li X,Xu J,Meng DL,sha Y,2006.A new perylenequinone from the fruit bodies of Bulgaria inquinans.Journal of Asian Natural Products Research,8(8):743-736
Musso L,Dallavalle S,Merlini L,Bava A,Nasini G,Penco S,Giannini G,Giommarelli C,Cesare AD,Zuco V,Vesci L,Pisano C,Piaz FD,Tommasi ND,Zunino F,2010.Natural and semisynthetic azaphilones as a new scaffold for Hsp90 inhibitors.Bioorganic&Medicinal Chemistry,18(16):6031-6043
Ma WC,Yang SD,Bao HY,2010.Isolation and identification of several compounds from the fruiting bodies of Bulgaria inquinans.Edible Fungi of China,29(2):48-50(in Chinese)
Stadler M,Anke H,Dekermendjian K,Reiss R,sterner O,Witt R,1995.Novel bioactive azaphilones from fruit bodies and mycelial cultures of the ascomycete Bulgaria inquinans Fr.Natural Product Letters,7(1):7-14
Shen SP,You HH,Zhao Y,Li JQ,Zhu YQ,Guo Q,Li XX,Chen MQ,Yang X,2016.Effect of DIDP on allergic dermatitis of mice by oral exposure.Journal of Public Health and Preventive Medicine,27:1-5
Wang XB,2014.Research on chemical composition and photosensitive activity effect of Bulgaria inquinans Fr.Master Thesis,Jilin Agricultural University,Changchun.2-42(in Chinese)
Yang SD,2007.Studies on photosensitivity toxicity and Pharmacognosy of Bulgaria inguinans.Master Thesis,Jilin Agricultural University,Changchun.15-32(in Chinese)
Zhang P,Li X,Zhang YW,Li N,Meng DL,2007.Chemical constituents of organic acid part from Bulgaria inquinans.Journal of Shenyang Pharmaceutical University,24(8):482-484(in Chinese)
包海鹰,李玉,丁晓昆,孙晓波,2002.胶陀螺光敏毒性作用研究.食用菌学报,9(4):15-17
白璐,马伟才,包海鹰,2014.胶陀螺的光敏活性组分.菌物研究,12(1):51-54
崔东滨,王淑琴,1997.胶陀螺化学成分的研究.中国中药杂志,22(8):485-486
马伟才,杨树东,包海鹰,2010.胶陀螺子实体中几种化合物的分离鉴定.中国食用菌,29(2):48-50
王新斌,2014.胶陀螺的化学成分和光敏活性组分研究.吉林农业大学硕士论文,长春.2-42
杨树东,2007.胶陀螺光敏毒性及生药学的研究.吉林农业大学硕士论文,长春.15-32
张鹏,李铣,张玉伟,李宁,孟大利,2007.胶陀螺中有机酸类化学成分.沈阳药科大学学报,24(8):482-48
Bi HT,Gao TT,Li ZH,Ji L,Yang W,Iteku BJ,Liu EX,Zhou YF,2013a.Structural elucidation and antioxidant activity of a water-soluble polysaccharide from the fruit bodies of Bulgaria inquinans Fries.Food Chemistry,138(2-3):1470-1475
Bi HT,Gao TT,Liu DB,Tai GH,Wei M,Zhou YF,2013b.Structures of(1→6)-β-d-glucans from Bulgaria inquinans Fries and their immunological activities.Carbohydrate Polymers,93(2):547-552
Bi HT,Han H,Li ZH,Ni WH,Chen Y,Zhu JJ,Gao TT,Hao M,Zhou YF,2011.A water-soluble polysaccharide from the fruit bodies of Bulgaria inquinans fries and its anti-malarial activity.Evidence-based Complementary and Alternative Medicine,2011(12):1-12
Bao HY,Li Y,Ding XK,Sun XB,2002.Studies on the photosensitive activity effect of Bulgaria inquinans.Acta Edulis Fungi,9:15-17(in Chinese)
Cui DB,Wang SQ,1997.Studies on chemical constituents of Bulgaria inguinans Fries.Chinese Journal of Chinese Materia Medica,22:485-486(in Chinese)
Edwards RL,Lockett HJ,1976.Constituents of the higher fungi.Part XVI.Bulgarhodin and bulgarein,novel benzofluoranthenequinones from the fungus Bulgaria inquinans Fries.Journal of the Chemical Society,Perkin Transactions 1,8(20):2149-2155
Feng HQ,Sun T,Jia DM,Mu JF,Zhang YM,2013.Study on chemical constituents and antimicrobial activity of extracts from fruit bodies of Bulgaria iuquiuaus Fr.Modern Agricultural Science and Technology,10:153-154
Jiang SS,Tsumuro T,Takubo M,Fujii Y,Kamei CK,2005.Antipruritic and antierythema effects of ascomycete Bulgaria inquinans extract in ICR mice.Biological&Pharmaceutical Bulletin,28(12):2197-2200
Kirk PM,Cannon PF,Minter DW,stalpers JA,2008.Dictionary of the Fungi.10th ed.CABI,Wallingford,UK.
Li N,Xu J,Li X,Zhang P,2013.Two new anthraquinone dimers from the fruit bodies of Bulgaria inquinans.Fitoterapia,84(3):85-88
Li X,Xu J,Meng DL,sha Y,2006.A new perylenequinone from the fruit bodies of Bulgaria inquinans.Journal of Asian Natural Products Research,8(8):743-736
Musso L,Dallavalle S,Merlini L,Bava A,Nasini G,Penco S,Giannini G,Giommarelli C,Cesare AD,Zuco V,Vesci L,Pisano C,Piaz FD,Tommasi ND,Zunino F,2010.Natural and semisynthetic azaphilones as a new scaffold for Hsp90 inhibitors.Bioorganic&Medicinal Chemistry,18(16):6031-6043
Ma WC,Yang SD,Bao HY,2010.Isolation and identification of several compounds from the fruiting bodies of Bulgaria inquinans.Edible Fungi of China,29(2):48-50(in Chinese)
Stadler M,Anke H,Dekermendjian K,Reiss R,sterner O,Witt R,1995.Novel bioactive azaphilones from fruit bodies and mycelial cultures of the ascomycete Bulgaria inquinans Fr.Natural Product Letters,7(1):7-14
Shen SP,You HH,Zhao Y,Li JQ,Zhu YQ,Guo Q,Li XX,Chen MQ,Yang X,2016.Effect of DIDP on allergic dermatitis of mice by oral exposure.Journal of Public Health and Preventive Medicine,27:1-5
Wang XB,2014.Research on chemical composition and photosensitive activity effect of Bulgaria inquinans Fr.Master Thesis,Jilin Agricultural University,Changchun.2-42(in Chinese)
Yang SD,2007.Studies on photosensitivity toxicity and Pharmacognosy of Bulgaria inguinans.Master Thesis,Jilin Agricultural University,Changchun.15-32(in Chinese)
Zhang P,Li X,Zhang YW,Li N,Meng DL,2007.Chemical constituents of organic acid part from Bulgaria inquinans.Journal of Shenyang Pharmaceutical University,24(8):482-484(in Chinese)
包海鹰,李玉,丁晓昆,孙晓波,2002.胶陀螺光敏毒性作用研究.食用菌学报,9(4):15-17
白璐,马伟才,包海鹰,2014.胶陀螺的光敏活性组分.菌物研究,12(1):51-54
崔东滨,王淑琴,1997.胶陀螺化学成分的研究.中国中药杂志,22(8):485-486
马伟才,杨树东,包海鹰,2010.胶陀螺子实体中几种化合物的分离鉴定.中国食用菌,29(2):48-50
王新斌,2014.胶陀螺的化学成分和光敏活性组分研究.吉林农业大学硕士论文,长春.2-42
杨树东,2007.胶陀螺光敏毒性及生药学的研究.吉林农业大学硕士论文,长春.15-32
张鹏,李铣,张玉伟,李宁,孟大利,2007.胶陀螺中有机酸类化学成分.沈阳药科大学学报,24(8):482-48