猪苓与蜜环菌化学成分研究的相关分析进展Correlative analysis advance of chemical constituents of Polyporus umbellatus and Armillaria mellea
黄靖雯;赖长江生;袁媛;张敏;周骏辉;黄璐琦;
HUANG Jing-wen;LAI Chang-jiang-sheng;YUAN Yuan;ZHANG Min;ZHOU Jun-hui;HUANG Lu-qi;School of Traditional Chinese Medicine,Guangdong Pharmaceutical University;State Key Laboratory of Dao-di Herbs,National Resource Center for Chinese Materia Medica,China Academy of Chinese Medical Sciences;Hubei Mengyang Pharmaceutical Co.,Ltd;
摘要(Abstract):
共生的猪苓Polyporus umbellatus与蜜环菌Armillaria mellea均为药食兼用真菌,具有降血糖、调节免疫、抑制肿瘤等多种生物活性。猪苓菌核经菌丝体发育而来,其生长过程与共生蜜环菌有关;受其侵染,猪苓菌丝体可形成菌核。该文通过分析猪苓菌丝体、菌核和蜜环菌的化学成分,发现三者均含有甾体和含氮杂环等化合物,且猪苓菌核与蜜环菌中还含有三萜类次生代谢产物。猪苓菌核及其菌丝体的甾体种类存在显著差异,但部分成分存在一定的相关性。此外,猪苓菌核还特有长链脂肪酸、酰胺和苯酚等多种化合物,推测这些可能是因蜜环菌入侵而形成的多种次生代谢产物;而蜜环菌自身主要产生倍半萜、二萜等物质。猪苓与蜜环菌的化合物含量、种类与其共生繁殖密切相关,目前尚需对二者的共生机制进行深入研究,为提高二者产量及质量提供科学依据。
Medicinal Polyporus umbellatus is the dry sclerotia of P. umbellatus,with the effect of diuresis; Armillaria mellea is a parasitic fungus which can infect plants up to 300 genera,with sedative,anticonvulsant and some other biological activities. As the medicinal value of P. umbellatus and A. mellea is increasingly wide concerned,the market quantity demanded of them is gradually increased and the demand outstrips the supply. The symbiotic A. mellea and P. umbellatus are both the medicinal and edible fungi with diverse activities,including hypoglycemic action,improve immunity and antitumor and so on. The growth of the sclerotia forming from the mycelium of P. umbellatus is related to the infection of the symbiotic A. mellea and their secondary products. In this study,by comparing the chemical constituents of the mycelium and sclerotia of P. umbellatus and A. mellea,we found that they all produced steroids and nitrogen-containing heterocycles. The sclerotia of P. umbellatus and A. mellea also produced triterpenes secondary metabolites. In addition,the mycelium and infected sclerotia of P. umbellatus mainly produced different steroids,and the sclerotia produced some other special secondary metabolites,such as long-chain fatty acids,ceramides,phenol and so on. By analyzing above all kinds of differences,speculated that these may be caused by the infection of the symbiotic A. mellea which mainly produced sesquiterpenes,diterpenes and other secondary metabolites. The contents and types of compounds of P. umbellatus and A. mellea are closely related to their symbiosis and reproduction,therefore,many symbiosis mechanisms should be found by utilizing more molecular biology technology to elucidate this complex symbiotic infection and provide scientific basis for improving the yield and quality of P. umbellatus and A. mellea.
关键词(KeyWords):
蜜环菌;猪苓菌核;猪苓菌丝体;化学成分;共生;次生代谢
Armillaria mellea;sclerotia of Polyporus umbellatus;mycelium of Polyporus umbellatus;chemical constituents;symbiotic relationship;secondary metabolites
基金项目(Foundation): 科技基础性工作专项(2015FY111500);; 中央级公益性科研院所基本科研业务费专项资金项目(ZZ10-008)
作者(Author):
黄靖雯;赖长江生;袁媛;张敏;周骏辉;黄璐琦;
HUANG Jing-wen;LAI Chang-jiang-sheng;YUAN Yuan;ZHANG Min;ZHOU Jun-hui;HUANG Lu-qi;School of Traditional Chinese Medicine,Guangdong Pharmaceutical University;State Key Laboratory of Dao-di Herbs,National Resource Center for Chinese Materia Medica,China Academy of Chinese Medical Sciences;Hubei Mengyang Pharmaceutical Co.,Ltd;
Email:
DOI: 10.19540/j.cnki.cjcmm.20170512.009
参考文献(References):
- [1]中国药典.一部[S].2015:318.
- [2]侯敢,黄迪南,祝其锋.猪苓多糖对小鼠腹腔巨噬细胞一氧化氮生成的影响及其机理[J].中国老年学杂志,2000(4):233.
- [3]赵英永.中药猪苓的化学成分及其药理学研究[D].西安:西北大学,2010.
- [4]刘汉卿,郭勇全,肖萍,等.猪苓的研究与应用[J].广州化工,2010,38(10):40.
- [5]夏琴,周进,李敏,等.猪苓种植生产的研究进展[J].中药与临床,2015,6(2):119.
- [6]Ota Y,Intini M,Hattori T.Genetic characterization of heterothallic and nonheterothallic Armillaria melleasensu stricto[J].Mycol Res,2000,104(9):1046.
- [7]刘景圣,袁媛,田忠华.蜜环菌的活性成分研究及其在功能性食品中的应用[J].食品科学,2003,24(6):165.
- [8]杨淑云,林远崇,羿红,等.珍稀食药用菌——蜜环菌的开发与应用[J].生物学杂志,2007,24(3):52.
- [9]王汉臣.世界蜜环菌属系统学研究进展[J].重庆师范大学学报:自然科学版,2010,27(1):62.
- [10]赵俊,戴玉成,秦国夫,等.新的中国蜜环菌生物种[J].菌物学报,2008,27(2):156.
- [11]郭顺星,徐锦堂.蜜环菌侵染后猪苓菌核防御结构的发生及功能[J].真菌学报,1993(4):283.
- [12]Lee H S,Hwang I H,Kim J A,et al.Chem Inform abstract:isolation of protein tyrosine phosphatase 1B inhibitory constituents from the sclerotia of Polyporus umbellatus Fries[J].Chem Inform,2011,42(25):697.
- [13]Sun Y,Yasukawa K.New anti-inflammatory ergostane-type ecdysteroids from the sclerotium of Polyporus umbellatus[J].Bioorg Med Chem Lett,2008,18(11):3417.
- [14]Zhou W W,Lin W H,Guo S X.Two new polyporusterones isolated from the scleratia of Polyporus umbellatus[J].Chem Pharm Bull,2007,55(8):1148.
- [15]Ohta K,Yaoita Y,Matsuda N,et al.Sterol constituents from the sclerotium of Polyporus umbellatus Fries[J].Nat Med,1996,50:179.
- [16]Ohsawa T,Yukawa M,Takao C,et al.Studies on constituents of fruit body of Polyporus umbellatus and their cytotoxic activity[J].Chem Pharm Bull,1992,40(1):143.
- [17]Yosioka I,Yamamoto T.The constituents of chuling.2-hydroxytetracosanoic acid[J].Yakugaku Zasshi,1964,84(84):742.
- [18]Zhou W W,Guo S X.Studies on the chemical constituents of the sclerotia of Polyporus umbellatus[J].Acta Pharm Sin,2007,42:259.
- [19]Zheng S Z,Yang H P,Ma X M,et al.Two new polyporusterones from Polyporus umbellatus[J].Nat Prod Res,2004,18(5):403.
- [20]Guo W J,Xing Y M,Chen J,et al.Growth Promoting Effects of Water Extract of Armillaria mellea Rhizomorph on mycelia of Polyporus umbellatus[J].Cryptogamie Mycol,2015,32(2):171.
- [21]Zhao Y,Yang L,Wang M,et al.1β-hydroxylfriedelin,a new natural pentacylic triterpene from the sclerotia of Polyporus umbellatus[J].J Chem Res,2009,2009:699.
- [22]Zhou W W,Guo S X.Components of the sclerotia of Polyporus umbellatus[J].Chem Nat Compd,2009,45(1):124.
- [23]Zhao Y Y,Chao X,Zhang Y M,et al.Cytotoxic steroids from Polyporus umbellatus[J].Planta Med,2010,76(15):1755.
- [24]陈晓梅,周微微,王春兰,等.猪苓菌丝体的化学成分研究[J].中国现代中药,2014,16(3):187.
- [25]周微微.猪苓菌核及发酵菌丝体化学成分研究及质量分析[D].北京:北京协和医科大学,2008.
- [26]张嘉,杨延旗,淡海,等.蜜环菌的化学成分[J].西北植物学报,2002,22(4):952.
- [27]Naoharu W,Tadashi O,Masaharu T,et al.A novel N6-substituted acenosine isolated from Armillaria melleaas a cerebral-protecting compound[J].Planta Med,1990,56(1):48.
- [28]Guo W J,Guo S X,Yang J S,et al.Triterpenes and steroids from Armillaria mellea,Vahl.ex Fr[J].Biochem Syst Ecol,2007,35(11):790.
- [29]Guo W J,Guo S X.Triterpene from Armillaria mellea[J].Chem Nat Compd,2011,46(6):995.
- [30]William A A,John B M.Metabolites of the honey mushroom,Armillaria mellea[J].Can J Chem,1987,65(7):7.
- [31]Yang J S,Su Y L,Wang Y L,et al.Isolation and structure of two new sesquiterpenoid aromatic esters:armillarigin and armillarikin[J].Planta Med,1989,55(5):479.
- [32]Yang J S,Chen Y W,Feng X Z,et al.Isolation and structure elucidation of armillaricin1[J].Planta Med,1989,55(6):564.
- [33]Li Z,Wang Y,Jiang B,et al.Structure,cytotoxic activity and mechanism of protoilludane sesquiterpene aryl esters from the mycelium of Armillaria mellea[J].J Ethnopharmacol,2016,184:119.
- [34]杨峻山,苏亚伦,王玉兰,等.蜜环菌菌丝体化学成分的研究(Ⅴ)[J].药学学报,1990,25(1):24.
- [35]杨峻山,苏亚伦,王玉兰,等.蜜环菌菌丝体化学成分的研究(Ⅵ)[J].药学学报,1990,25(5):353.
- [36]杨峻山,苏亚伦,王玉兰,等.蜜环菌菌丝体化学成分的研究(Ⅶ)[J].药学学报,1991,26(2):117.
- [37]Yang J S,Su Y L,Wang Y L,et al.Two novel protoilludance norsesquiterpenoid esters,armillasin and armillatin,from Armillaria mellea[J].Planta Med,1991,57(5):478.
- [38]Dervilla M X D,Rhona M H,Donal C,et al.Sesquiterpene aryl esters from Armillaria mellea[J].Phytochemistry,1990,29(8):2569.
- [39]Dervilla M X D,Rhona M H.Armillane,a saturated sesquiterpene ester from Armillaria mellea[J].Phytochemistry,1990,29(1):179.
- [40]Dervilla M X D,Fumiko A,Donal J C,et al.Antibacterial sesquiterpene aryl esters from Armillaria mellea[J].J Nat Prod,1985,48(1):10.
- [41]杨峻山,丛浦珠.蜜环菌菌丝体中倍半萜醇芳香酸酯的质谱研究[J].化学学报,1988,46(11):1093.
- [42]Chen C,Kuo Y,Cheng J,et al.Three new sesquiterpene aryl esters from the mycelium of Armillaria mellea[J].Molecules,2015,20(6):9994.
- [43]Dervilla M X D,Paul F Q,Donal J C,et al.Two new sespuiterpene esters from Armillarim mellea[J].Phytochemistry,1987,26(11):3075.
- [44]Misiek M,Williams J,Schmich K,et al.Structure and cytotoxicity of arnamial and related fungal sesquiterpenearyl esters[J].J Nat Prod,2009,72(10):1888.
- [45]杨峻山,苏亚伦,于德全,等.原伊鲁焼型倍半萜醇芳香酸酯的碳谱研究[J].波谱学杂志,1992,9(4):381.
- [46]Dervilla M X D,Tenji K,Olive D,et al.Sesquiterpenearyl esters from Armillaria tabescens[J].Phytochemistry,1997,44(8):1473.
- [47]徐楠.蜜环菌的化学成分及生物活性研究[D].长春:吉林农业大学,2012.
- [48]林桂权.植物次生代谢产物及其在环境胁迫中的抵御作用[J].福建稻麦科技,2009,27(3):39.
- [49]邢晓科,郭顺星.伴生菌对猪苓几种酶活性的影响[J].中国中药杂志,2004,29(4):310.
- [50]程曦,郝怀庆,彭励.植物细胞壁中纤维素合成的研究进展[J].热带亚热带植物学报,2011,19(3):283.
- [51]张华,孙纪全,包玉英.丛枝菌根真菌影响植物次生代谢产物的研究进展[J].农业生物技术学报,2015,23(8):1093.
- [52]李静,周立刚,文成敬.真菌甾体化合物的研究进展[J].天然产物研究与开发,2008,20(1):165.
- [53]邓玉清,王纪,虞龙.微生物麦角甾醇的研究进展[J].微生物学杂志,2001,21(3):45.
- 蜜环菌
- 猪苓菌核
- 猪苓菌丝体
- 化学成分
- 共生
- 次生代谢
Armillaria mellea - sclerotia of Polyporus umbellatus
- mycelium of Polyporus umbellatus
- chemical constituents
- symbiotic relationship
- secondary metabolites
- 黄靖雯
- 赖长江生
- 袁媛
- 张敏
- 周骏辉
- 黄璐琦
HUANG Jing-wen- LAI Chang-jiang-sheng
- YUAN Yuan
- ZHANG Min
- ZHOU Jun-hui
- HUANG Lu-qi
- School of Traditional Chinese Medicine
- Guangdong Pharmaceutical University
- State Key Laboratory of Dao-di Herbs
- National Resource Center for Chinese Materia Medica
- China Academy of Chinese Medical Sciences
- Hubei Mengyang Pharmaceutical Co.
- Ltd
- 黄靖雯
- 赖长江生
- 袁媛
- 张敏
- 周骏辉
- 黄璐琦
HUANG Jing-wen- LAI Chang-jiang-sheng
- YUAN Yuan
- ZHANG Min
- ZHOU Jun-hui
- HUANG Lu-qi
- School of Traditional Chinese Medicine
- Guangdong Pharmaceutical University
- State Key Laboratory of Dao-di Herbs
- National Resource Center for Chinese Materia Medica
- China Academy of Chinese Medical Sciences
- Hubei Mengyang Pharmaceutical Co.
- Ltd