食用菌中萜类物质及其生物活性研究进展
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摘要
近年来,自然资源因其在开发新的生物活性物质方面的巨大潜力而备受关注。食用菌分布广泛,营养物质丰富,具有抗炎、抗肿瘤、抑菌等多种药理作用。萜类物质来源广泛,种类繁多,是天然物质中最多的一类,大量研究表明食用菌中的萜类化合物具有多种生物活性,在医药行业具有重要的开发利用价值。本文主要对食用菌中萜类物质的抗炎、抗肿瘤、抗氧化及抑菌等生物活性进行综述,并对食用菌的开发利用进行展望。
In recent years,natural resources have attracted much attention for their great potential in exploiting new bioactive substances.Edible mushroom was widely distributed,rich in nutrients,and has many pharmacological effects such as anti-inflammatory,anti-tumor,antibacterial and so on.The terpenoids have a wide range of sources and a wide variety of species.They are the most abundant natural materials.A large number of studies have shown that terpenoids in edible mushroom have a variety of biological activities and have important development and utilization value in the pharmaceutical industry.In this paper,the anti-inflammatory,anti-tumor,anti-oxidation and antibacterial bioactivities of terpenoids in edible mushroom were reviewed,and the development and utilization of edible mushroom were prospected.
In recent years,natural resources have attracted much attention for their great potential in exploiting new bioactive substances.Edible mushroom was widely distributed,rich in nutrients,and has many pharmacological effects such as anti-inflammatory,anti-tumor,antibacterial and so on.The terpenoids have a wide range of sources and a wide variety of species.They are the most abundant natural materials.A large number of studies have shown that terpenoids in edible mushroom have a variety of biological activities and have important development and utilization value in the pharmaceutical industry.In this paper,the anti-inflammatory,anti-tumor,anti-oxidation and antibacterial bioactivities of terpenoids in edible mushroom were reviewed,and the development and utilization of edible mushroom were prospected.
引文
[1]张金霞,陈强,黄晨阳,等.食用菌产业发展历史、现状与趋势[J].菌物学报,2015,34(4):524-540.
[2]王慧杰.食用菌的药用保健价值[J].食用菌,2001,23(3):41-42.
[3]孙丽超,李淑英,王凤忠,等.萜类化合物的合成生物学研究进展[J].生物技术通报,2017,33(1):64-75.
[4]Taofiq O,Martins A,Barreiro M F,et al.Anti-inflammatory potential of mushroom extracts and isolated metabolites[J].Trends in Food Science&Technology,2016,50:193-210.
[5]蒉霄云,何晋浙,王静,等.微波提取灵芝中三萜类化合物的研究[J].中国食品学报,2010,10(2):89-96.
[6]Bergendorff O,Sterner O.The sesquiterpenes of Lactarius deliciosus,and Lactarius deterrimus[J].Phytochemistry,1988,27(1):97-100.
[7]Xu Z,Yan S,Bi K,et al.Isolation and identification of a new anti-inflammatory cyathane diterpenoid from the medicinal fungus Cyathus hookeri Berk.[J].Fitoterapia,2013,86(1):159-162.
[8]Fang L Z,Shao H J,Yang W Q,et al.Two new azulene pigments from the fruiting bodies of the basidiomycete Lactarius hatsudake[J].Helvetica Chimica Acta,2010,89(7):1463-1466.
[9]Pyysalo H,Seppa E L,Widen K G.Application of gas chromatography to the analysis of sesquiterpene lactones from Lactarius(Russulaceae)mushrooms[J].Journal of Chromatography A,1980,190(2):466-470.
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[11]贾红岩,王亚涛,张芝华,等.高效液相色谱法测定不同产地及品种灵芝三萜类成分的含量[J].微生物学通报,2017,44(1):238-244.
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[29]Ma K,Bao L,Han J,et al.New benzoate derivatives and hirsutane type sesquiterpenoids with antimicrobial activity and cytotoxicity from the solid-state fermented rice by the medicinal mushroom Stereum hirsutum[J].Food Chemistry,2014,143:239-245.
[30]杜建.中药抗肿瘤机制研究进展[J].康复学报,2009,19(4):1-5.
[31]Ou Y,Li Y,Qian X,et al.Guanacastane-type diterpenoids from Coprinus radians[J].Phytochemistry,2012,78:190-196.
[32]罗都强,梁舒鹃,师耀龙,等.具有抗肿瘤活性的乳菇菌素及其制备方法和应用[P].河北:CN101475458,2009-07-08.
[33]Tsai W C,Rao Y K,Lin S S,et al.Methylantcinate A induces tumor specific growth inhibition in oral cancer cells via Baxmediated mitochondrial apoptotic pathway[J].Bioorganic&Medicinal Chemistry Letters,2010,20(20):6145-6148.
[34]Chiang PC,Lin SC,Pan SL,et al.Antroquinonol displays anticancer potential against human hepatocellular carcinoma cells:a crucial role of AMPK and m TOR pathways[J].Biochemical Pharmacology,2010,79(2):162-171.
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[36]Yoshikawa K,Tori K,Arihara S,et al.A new eudesmane sesquiterpene from the fruit body of Lactarius laeticolorus[J].Natural Medicines,2001,55(2):87-89.
[37]王涛.灵芝三萜的提纯及其对前列腺癌细胞生长的影响[D].广州:南方医科大学,2016.
[38]王华.杏鲍菇中三萜类化合物的抗氧化、抗肿瘤活性的研究[D].天津:天津大学,2012.
[39]Boonsong S,Klaypradit W,Wilaipun P.Antioxidant activities of extracts from five edible mushrooms using different extractants[J].Agriculture&Natural Resources,2016,50(2):89-97.
[40]Puttaraju N G,Venkateshaiah S U,Dharmesh S M,et al.Antioxidant activity of indigenous edible mushrooms.[J].Journal of Agricultural&Food Chemistry,2006,54(26):9764-9772.
[41]肖星凝,袁娅,廖霞,等.食用菌抗氧化活性成分及其抗氧化作用机制研究进展[J].食品与机械,2016,32(11):207-211.
[42]程水明,桂元,沈思,等.茯苓皮三萜类物质抗氧化活性研究[J].食品科学,2011,32(9):27-30.
[43]Wang Y,Bao L,Yang X,et al.Bioactive sesquiterpenoids from the solid culture of the edible mushroom Flammulina velutipes growing on cooked rice[J].Food Chemistry,2012,132(3):1346-1353.
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[45]刘晓珍,聂少平,李文娟,等.黑灵芝中性提取物三萜含量测定及抗氧化作用研究[J].南昌大学学报(工科版),2011,33(4):332-337.
[46]沈思,李孚杰,梅光明,等.茯苓皮三萜类物质含量的测定及其抑菌活性的研究[J].食品科学,2009,30(1):97-100.
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[2]王慧杰.食用菌的药用保健价值[J].食用菌,2001,23(3):41-42.
[3]孙丽超,李淑英,王凤忠,等.萜类化合物的合成生物学研究进展[J].生物技术通报,2017,33(1):64-75.
[4]Taofiq O,Martins A,Barreiro M F,et al.Anti-inflammatory potential of mushroom extracts and isolated metabolites[J].Trends in Food Science&Technology,2016,50:193-210.
[5]蒉霄云,何晋浙,王静,等.微波提取灵芝中三萜类化合物的研究[J].中国食品学报,2010,10(2):89-96.
[6]Bergendorff O,Sterner O.The sesquiterpenes of Lactarius deliciosus,and Lactarius deterrimus[J].Phytochemistry,1988,27(1):97-100.
[7]Xu Z,Yan S,Bi K,et al.Isolation and identification of a new anti-inflammatory cyathane diterpenoid from the medicinal fungus Cyathus hookeri Berk.[J].Fitoterapia,2013,86(1):159-162.
[8]Fang L Z,Shao H J,Yang W Q,et al.Two new azulene pigments from the fruiting bodies of the basidiomycete Lactarius hatsudake[J].Helvetica Chimica Acta,2010,89(7):1463-1466.
[9]Pyysalo H,Seppa E L,Widen K G.Application of gas chromatography to the analysis of sesquiterpene lactones from Lactarius(Russulaceae)mushrooms[J].Journal of Chromatography A,1980,190(2):466-470.
[10]王伟,尚德静,温磊.灵芝发酵菌丝三萜类化合物含量的测定[J].中国食用菌,2006,25(1):30-32.
[11]贾红岩,王亚涛,张芝华,等.高效液相色谱法测定不同产地及品种灵芝三萜类成分的含量[J].微生物学通报,2017,44(1):238-244.
[12]Daniewski W M,Kroszczya Ski W,Wawrzua A,et al.Constituents of higher fungi.Part XVI.Identification of Lactarius species by HPLC using sesquiterpene monohydroxylactone contents as characteristic chemotaxonomic features[J].Journal of Liquid Chromatography,1984,7(14):2915-2920.
[13]Gao J J,Min B S,Ahn E M,et al.New triterpene aldehydes,lucialdehydes A-C,from Ganoderma lucidum and their cytotoxicity against murine and human tumor cells[J].Cheminform,2002,33(48):837-840.
[14]Fang L Z,Shao H J,Yang W Q,et al.Two new azulene pigments from the fruiting bodies of the basidiomycete Lactarius hatsudake[J].Helvetica Chimica Acta,2007,89(7):1463-1466.
[15]Liu C,Yang N,Song Y,et al.Ganoderic acid C1 isolated from the anti-asthma formula,ASHMITMsuppresses TNF-αproduction by mouse macrophages and peripheral blood mononuclear cells from asthma patients[J].International Immunopharmacology,2015,27(2):224-231.
[16]Lee Y H,Lee N H,Bhattarai G,et al.Anti-inflammatory effect of pachymic acid promotes odontoblastic differentiation via HO-1 in dental pulp cells[J].Oral Diseases,2013,19(2):193-199.
[17]Saba E,Son Y,Jeon B R,et al.Acetyl eburicoic acid from Laetiporus sulphureus var.miniatus suppresses inflammation in murine macrophage RAW 264.7 cells[J].Mycobiology,2015,43(2):131-136.
[18]Kamo T,Asanoma M,Hisao shibata A,et al.Antiinflammatory lanostane-type triterpene acids from Piptoporus betulinus[J].Journal of Natural Products,2003,66(8):1104-1106.
[19]Choi S,Nguyen V T,Tae N,et al.Anti-inflammatory and heme oxygenase-1 inducing activities of lanostane triterpenes isolated from mushroom Ganoderma lucidum,in RAW264.7 cells[J].Toxicology&Applied Pharmacology,2014,280(3):434-442.
[20]Dudhgaonkar S,Thyagarajan A,Sliva D.Suppression of the inflammatory response by triterpenes isolated from the mushroom Ganoderma lucidum[J].International Immunopharmacology,2009,9(11):1272-1280.
[21]Akihisa T,Nakamura Y,Tagata M,et al.Anti-inflammatory and anti-tumor-promoting effects of triterpene acids and sterols from the fungus Ganoderma lucidum[J].Chemistry&Biodiversity,2007,4(2):224-231.
[22]Cai T G,Cai Y.Triterpenes from the fungus Poria cocos and their inhibitory activity on nitric oxide production in mouse macrophages via blockade of activating protein-1 pathway[J].Chemistry&Biodiversity,2011,8(11):2135-2143.
[23]Deng J S,Huang S S,Lin T H,et al.Analgesic and antiinflammatory bioactivities of eburicoic acid and dehydroeburicoic acid isolated from Antrodia camphorata on the inflammatory mediator expression in mice[J].Journal of Agricultural&Food Chemistry,2013,61(21):5064-5071.
[24]Han J J,Chen Y H,Bao L,et al.Anti-inflammatory and cytotoxic cyathane diterpenoids from the medicinal fungus Cyathus africanus[J].Fitoterapia,2013,84(3):22-31.
[25]Kamo T,Imura Y,Hagio T,et al.Anti-inflammatory cyathane diterpenoids from Sarcodon scabrosus[J].Bioscience,Biotechnology,and Biochemistry,2004,68(6):1362-1365.
[26]Maria C M,Pagiotti R,Campagna V,et al.Glaucopine C,a new diterpene from the fruiting bodies of Sarcodon glaucopus[J].Natural Product Research,2006,20(10):917-921.
[27]Wang S,Bao L,Zhao F,et al.Isolation,identification,and bioactivity of monoterpenoids and sesquiterpenoids from the mycelia of edible mushroom Pleurotus cornucopiae[J].Journal of Agricultural&Food Chemistry,2013,61(21):5122-5129.
[28]Wang S,Bao L,Han J,et al.Pleurospiroketals A-E,perhydrobenzannulated 5,5-spiroketal sesquiterpenes from the edible mushroom Pleurotus cornucopiae[J].Journal of natural products,2013,76(1):45-50.
[29]Ma K,Bao L,Han J,et al.New benzoate derivatives and hirsutane type sesquiterpenoids with antimicrobial activity and cytotoxicity from the solid-state fermented rice by the medicinal mushroom Stereum hirsutum[J].Food Chemistry,2014,143:239-245.
[30]杜建.中药抗肿瘤机制研究进展[J].康复学报,2009,19(4):1-5.
[31]Ou Y,Li Y,Qian X,et al.Guanacastane-type diterpenoids from Coprinus radians[J].Phytochemistry,2012,78:190-196.
[32]罗都强,梁舒鹃,师耀龙,等.具有抗肿瘤活性的乳菇菌素及其制备方法和应用[P].河北:CN101475458,2009-07-08.
[33]Tsai W C,Rao Y K,Lin S S,et al.Methylantcinate A induces tumor specific growth inhibition in oral cancer cells via Baxmediated mitochondrial apoptotic pathway[J].Bioorganic&Medicinal Chemistry Letters,2010,20(20):6145-6148.
[34]Chiang PC,Lin SC,Pan SL,et al.Antroquinonol displays anticancer potential against human hepatocellular carcinoma cells:a crucial role of AMPK and m TOR pathways[J].Biochemical Pharmacology,2010,79(2):162-171.
[35]Kim KH,Noh HJ,Choi SU,et al.Lactarane sesquiterpenoids from Lactarius subvellereus and their cytotoxicity[J].Bioorganic&Medicinal Chemistry Letters,2010,20(18):5385-5388.
[36]Yoshikawa K,Tori K,Arihara S,et al.A new eudesmane sesquiterpene from the fruit body of Lactarius laeticolorus[J].Natural Medicines,2001,55(2):87-89.
[37]王涛.灵芝三萜的提纯及其对前列腺癌细胞生长的影响[D].广州:南方医科大学,2016.
[38]王华.杏鲍菇中三萜类化合物的抗氧化、抗肿瘤活性的研究[D].天津:天津大学,2012.
[39]Boonsong S,Klaypradit W,Wilaipun P.Antioxidant activities of extracts from five edible mushrooms using different extractants[J].Agriculture&Natural Resources,2016,50(2):89-97.
[40]Puttaraju N G,Venkateshaiah S U,Dharmesh S M,et al.Antioxidant activity of indigenous edible mushrooms.[J].Journal of Agricultural&Food Chemistry,2006,54(26):9764-9772.
[41]肖星凝,袁娅,廖霞,等.食用菌抗氧化活性成分及其抗氧化作用机制研究进展[J].食品与机械,2016,32(11):207-211.
[42]程水明,桂元,沈思,等.茯苓皮三萜类物质抗氧化活性研究[J].食品科学,2011,32(9):27-30.
[43]Wang Y,Bao L,Yang X,et al.Bioactive sesquiterpenoids from the solid culture of the edible mushroom Flammulina velutipes growing on cooked rice[J].Food Chemistry,2012,132(3):1346-1353.
[44]Yoo N H,Kim J P,Yun B S,et al.Hirsutenols D,E and F,new sesquiterpenes from the culture broth of Stereum hirsutum[J].The Journal of Antibiotics,2006,59(2):110.
[45]刘晓珍,聂少平,李文娟,等.黑灵芝中性提取物三萜含量测定及抗氧化作用研究[J].南昌大学学报(工科版),2011,33(4):332-337.
[46]沈思,李孚杰,梅光明,等.茯苓皮三萜类物质含量的测定及其抑菌活性的研究[J].食品科学,2009,30(1):97-100.
[47]Kawagishi H,Masui A,Tokuyama S,et al.Erinacines J and Kfrom the mycelia of Hericium erinaceum[J].Cheminform,2007,38(2):8463-8466.
[48]Ishikawa N K,Fukushi Y,Yamaji k,et al.Antimicrobial cuparene-type sesquiterpenes,enokipodins C and D,from a mycelial culture of Flammulina velutipes[J].Journal of Natural Products,2001,64(7):932-934.
[49]Luo D Q,Wang F,Bian X Y,et al.Rufuslactone,a new antifungal sesquiterpene from the fruiting bodies of the basidiomycete Lactarius rufus[J].Journal of Antibiotics,2006,37(2):456-459.
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