红树属植物内生真菌多样性及其代谢产物研究进展
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  • 英文篇名:Advances in Endophytic Fungi Diversity and Secondary Metabolites in Rhizophora Plants
  • 作者:周婧 ; 杨琦 ; 李钢 ; 徐静
  • 英文作者:Zhou Jing;Yang Qi;Li Gang;Xu Jing;Key Laboratory of Tropical Biological Resources of Ministry of Education Institute of Tropical Agriculture and Forestry,Hainan University;Key Laboratory of Advanced Materials of Tropical Island Resources of Ministry of Education College of Materials and Chemical Engineering, Hainan University;
  • 关键词:红树属 ; 次生代谢产物 ; 生物活性 ; 天然产物 ; 微生物
  • 英文关键词:Rhizophora;;secondary metabolites;;bioactivity;;natural product;;miroorganism
  • 中文刊名:林业科学
  • 英文刊名:Scientia Silvae Sinicae
  • 机构:海南大学热带农林学院热带生物资源教育部重点实验室;海南大学材料与化工学院热带岛屿资源先进材料教育部重点实验室;
  • 出版日期:2019-01-15
  • 出版单位:林业科学
  • 年:2019
  • 期:01
  • 基金:国家自然科学基金项目(81660584);; 海南省重点研发计划项目(ZDYF2017099);; 海南大学科研团队培育专项(hdkytg201705)
  • 语种:中文;
  • 页:92-105
  • 页数:14
  • CN:11-1908/S
  • ISSN:1001-7488
  • 分类号:S718.4
摘要
红树林是生长在热带和亚热带潮间带河口地带的耐盐植物群落,分布在南纬30°与北纬30°之间,具有盐胁迫、高矿物组成、强还原性、频繁的潮汐等特征,也使植物对营养、空间的竞争异常激烈,特殊生境使红树林植物内生真菌多样性丰富,必然会造成不同于其他生态系统的良好生物活性、独特化学结构的活性功能分子。红树属是红树林植物中分布较广泛的一个属,包括8个种,分别是红海榄、红树、红茄苳、美洲红树、Rhizophora harrisonii、R.racemosa、树冬红树和萨摩红树。迄今为止,从红树属分离出内生真菌类群已达23目41科64属,其中对拟盘多毛孢属、青霉属和毛霉属的内生真菌代谢产物研究的最为广泛;从红树属内生真菌中分离鉴定出195种天然产物,包括生物碱类、萜类化合物、香豆素类、色酮类化合物、醌类化合物、杂氧蒽醌类化合物、肽类、酚酸类化合物、内酯类等化合物,从红树属植物中发现许多结构新颖的次生代谢产物,从中国南海红树林红茄苳内生拟盘多毛孢真菌中发现一系列罕见的具有亲脂性取代基的新色酮类化合物pestalotiopsones A-F (107—112),从拟盘多毛孢属JCM2A4中发现2个具有柔性结构的补身烷型倍半萜-环青霉醛酸的新骨架化合物pestalotiopens A和B (83, 84)。此外,许多化合物显示出良好的抗肿瘤、抗菌和抗氧化等生物活性,如化合物pestalpolyol 1(119)具有很强的抑制作用,对小鼠淋巴瘤L5178Y细胞的半抑制浓度(half maximal inhibitory concentration,IC_(50))值为4.10μmol·L~(-1)。从内生真菌毛霉QEN-189中分离到的吲哚生物碱rhizovarins A,B和F(46, 47, 50)对肺癌细胞A549抑制作用强,IC_(50)值分别为11.5、6.3和9.2μmol·L~(-1),对白血病细胞HL-60有强抑制作用,IC_(50)值为9.6、5和7μmol·L~(-1)。
        Mangroves are composed of a large group of salt-tolerant plant communities growing in tropical and subtropical intertidal estuarine zones, which are distributed approximately in the area between 30° N and 30° S latitude. Rhizophora genus is a kind of mangroves,and all woody plants located in tropical and subtropical intertidal coastal regions, and comprises of 8 species, including R. stylosa, R. apiculata, R. mucronata, R. mangle, R. harrisonii, R. racemosa, R. annamalayana and R. samoensis. Those plants have the characteristics of salt stress, high mineral composition, strong reducibility and frequent tides, which make plants extremely competitive for nutrition and space. The special growth environment entriches the diversity of endophytic fungi in Rhizophora, and it is bound to produce active molecules with biological activity and unique chemical structure different from other ecosystems. So far, the endophytic fungi isolated from Rhizophora genera are reported with 23 orders, 41 families and 64 genera. Amongst, Pestalotiopsis, Penicillium and Mucor have been widely studied. Meanwhile, 195 secondary metabolites have been identified from the Rhizophora endophytic fungi, including alkaloids, terpenoids, coumarins, ketones, quinones, anthraquinones, peptides, phenolic acids, lactones and other compounds. Some secondary metabolites with unusual structures are identified in Rhizophora endophytic fungi. Novel hybrid sesquiterpene-cyclopaldic acid metabolites with unusual carbon skeletons, pestalotiopens A and B(83, 84), pestalotiopsones A-F(107-112)are obtained from the endophytic fungus Pestalotiopsis sp. JCM2A4 is isolated from the leaves of the Chinese mangrove, R. mucronata. Most of them show antitumor, antibacterial, antioxidant activities. Some compounds have significant bioactivities, as exemplified by pestalpolyol 1(119), a novel polyketone derivative isolated from P. clavispora. Compound 119 has a strong inhibitory effect on mouse lymphoma cell line L5178 Y with an IC_(50) value of 4.10 μmol·L~(-1). The indole diterpene alkaloids, rhizovrin A, B and F(46, 47, 50), isolated from endophytic fungi Mucor irregularis QEN-189, have strong inhibitory effects on lung cancer cells A549, with IC_(50) values of 11.5, 6.3 and 9.2 μmol·L~(-1), respectively, as well as inhibitory effects on leukemia myeloid cells HL-60, with IC_(50) values of 9.6, 5.0 and 7.0 μmol·L~(-1), respectively.
引文
高剑. 2013. 红树内生真菌多样性及其生态分布. 湛江: 广东海洋大学硕士学位论文.(Gao J. 2013. Diversity and ecological distribution of endophytic fungi associated with mangroves. Zhanjiang:MS thesis of Guangdong Ocean University. [in Chinese])
    林文翰. 2005. 红树附生微生物的化学成分研究. “863”计划资源环境技术领域办公室.DT新材料.厦门:第三届海洋高技术论坛, 41-47.(Lin W H. 2005. Studies on the chemical constituents of epiphytic microorganisms of Mangrove. “863” Program Office in the Field of Resources, Environment and Technology. DT New Material. Xiamen: The 3th High Tech Marine Forum, 41-47. [in Chinese])
    徐静. 2015. 红树林微生物天然产物化学研究. 北京:科学出版社.(Xu J. 2015. Natural Products of Mangrove-Derived Microbes. Beijing: Science Press. [in Chinese])
    中国科学院中国植物志编辑委员会. 2004. 中国植物志.第52卷.第2册.北京:科学出版社, 127-130.(Editorial Committee of Flora of Chinese Academy of Sciences. 2004. Flora of China. Vol.52(2).Beijing: Science Press, 127-130.[in Chinese])
    邹运. 2015. 两种地衣中内生真菌物种多样性的比较研究. 济南: 山东师范大学硕士学位论文.(Zou Y. 2015. Comparative study of species diversity of endolichenic fungi in two kinds of lichens. Jinan:MS thesis of Shandong Normal University. [in Chinese])
    Agrios. 2005. Plant Pathology. 5th ed. Elsevier Academic Press, London.
    An C Y, Li X M, Li C S,et al. 2013. Aniquinazolines A-D, four new quinazolinone alkaloids from marine-derived endophytic fungus Aspergillus nidulans. Marine Drugs, 11(7):2682-2694.
    Ananda K, Sridhar K R. 2002. Diversity of endophytic fungi in the roots of mangrove species on the west coast of India. Canadian Journal of Microbiology, 48(10):871-878.
    Arfi Y, Buée M, Marchand C,et al. 2011. Multiple markers pyrosequencing reveals highly diverse and host-specific fungal communities on the mangrove trees Avicennia marina and Rhizophora stylosa. FEMS Microbiol Ecol, 79: 433-444.
    Beau J, Mahid N, Burda W N,et al. 2012.Epigenetic tailoring for the production of anti-infective cytosporones from the marine fungus Leucostoma persoonii. Marine Drugs, 10(4):762-774.
    Brady S F, Wagenaar M M, Singh M P,et al.2000.The cytosporones, new octaketide antibiotics isolated from an endophytic fungus. Organic Letters, 32:4043-4046.
    Buatong J, Phongpaichit S, Rukachaisirikul V, et al. 2011.Antimicrobial activity of crude extracts from mangrove fungal endophytes. World Journal of Microbiology & Biotechnology, 27:3005-3008.
    Burmeister H R, Bennett G A, Vesonder R F,et al. 1974. Antibiotic produced by Fusarium equiseti NRRL 5537. Antimicrobial Agents & Chemotherapy, 5(6):634-639.
    Chen J, Qiu X, Wang R,et al. 2009. Inhibition of human gastric carcinoma cell growth in vitro and in vivo by cladosporol isolated from the paclitaxel-producing strain Alternaria alternata var. monosporus. Biological & Pharmaceutical Bulletin, 32(12):2072-2074.
    Cohen S D. 2006. Host selectivity and genetic variation of Discula umbrinella, isolates from two oak species: Analyses of intergenic spacer region sequences of ribosomal DNA. Microbial Ecology, 52(3):463-469.
    Ding B, Wang Z, Huang X,et al. 2016. Bioactive α-pyrone meroterpenoids from mangrove endophytic fungus Penicillium sp. Natural Product Research,30(24): 2805-2812.
    Elavarasi A, Rathna G S, Kalaiselvam M. 2012. Taxol producing mangrove endophytic fungi Fusarium oxysporum, from Rhizophora annamalayana. Asian Pacific Journal of Tropical Biomedicine, 2(2):S1081-S1085.
    Fan Y, Yi W, Liu P,et al. 2013. Indole-diterpenoids with anti-H1N1 activity from the aciduric Fungus Penicillium camemberti OUCMDZ-1492. Journal of Natural Products, 76(7):1328-1336.
    Fl D S S, Rom?odumaresq A S, Lacava P T,et al. 2013.Species diversity of culturable endophytic fungi from Brazilian mangrove forests. Current Genetics, 59(3):153-166.
    Gao S S, Li X M, Williams K,et al. 2016. Rhizovarins A-F, indole-diterpenes from the mangrove-derived endophytic fungus Mucor irregularis QEN-189. Journal of Natural Products, 79(8):2066-2074.
    Godoy M D, de Lacerda L D. 2015. Mangroves response to climate change: A review of recent findings on mangrove extension and distribution. Anais Da Academia Brasileira De Ciências, 87(2):651-667.
    Gopal B, Chauhan M. 2006.Biodiversity and its conservation in the Sundarban Mangrove Ecosystem. Aquatic Sciences, 68(3):338-354.
    Harrison J W, Scrowston R M, Lythgoe B. 1996.Taxine. Part IV. The constiuents of taxine-I. J Chem Soc, 95:641-655.
    Hemberger Y, Xu J, Wray V,et al. 2013. Pestalotiopens A and B: Stereochemically challenging flexible sesquiterpene-cyclopaldic acid hybrids from Pestalotiopsis sp. Chemistry-A European Journal, 19(46):15556-15564.
    Hemphill C F P, Daletos G, Liu Z,et al. 2016. Polyketides from the Mangrove-derived fungal endophyte Pestalotiopsis clavispora. Tetrahedron Letters, 57(19):2078-2083.
    Huang M, Li J, Liu L,et al. 2016. Phomopsichin A-D; four new chromone derivatives from mangrove endophytic fungus Phomopsis sp. 33#. Marine Drugs, 14(11):215-220.
    Jalgaonwala R E, Mohite B V, Mahajan R T. 2011. A review: Natural products from plant associated endophytic fungi. Journal of Microbiology and Biotechnology Research, 1(2):21-32.
    Klaiklay S, Rukachaisirikul V, Phongpaichit S, et al. 2012a. Anthraquinone derivatives from the mangrove-derived fungus Phomopsis sp. PSU-MA214. Phytochemistry Letters, 5(4):738-742.
    Klaiklay S, Rukachaisirikul V, Phongpaichit S, et al. 2013. Flavodonfuran: a new difuranylmethane derivative from the mangrove endophytic fungus Flavodon flavus PSU-MA201. Natural Product Research, 27(19):1722-1726.
    Klaiklay S, Rukachaisirikul V, Tadpetch K, et al. 2012b. Chlorinated chromone and diphenyl ether derivatives from the mangrove-derived fungus Pestalotiopsis sp. PSU-MA69. Tetrahedron, 68(10):2299-2305.
    Koch E W, Barbier E B, Silliman B R,et al. 2009. Non-linearity in ecosystem services: temporal and spatial variability in coastal protection. Frontiers in Ecology & the Environment, 7(1):29-37.
    Kumaresan V, Suryanarayanan T S. 2002. Endophyte assemblages in young, mature and senescent leaves of Rhizophora apiculata: evidence for the role of endophytes in mangrove litter degradation. Fungal Diversity, 9(2):81-91.
    Liu A R, Wu X P, Xu T. 2007.Research advances in endophytic fungi of mangrove. Chin J App Ecol, 13: 366-378.
    Liu T, Li Z L, Wang Y,et al. 2011. A new alkaloid from the marine-derived fungus Hypocrea virens. Natural Product Research, 25(17):1596-1599.
    Moricca S, Ragazzi A. 2008. Fungal endophytes in Mediterranean oak forests: a lesson from Discula quercina. Phytopathology, 98(4):380-386.
    Osorio J A, Wingfield M J, Roux J. 2014. A review of factors associated with decline and death of mangroves, with particular reference to fungal pathogens. South African Journal of Botany, 103:295-301.
    Peng X, Wang Y, Sun K,et al. 2011.Cerebrosides and 2-pyridone alkaloids from the halotolerant fungus Penicillium chrysogenum grown in a hypersaline medium. Journal of Natural Products, 74(5):1298-1302.
    Piapukiew J, Whalley A J S, Sihanonth P. 2010. Endophytic fungi from mangrove plant species of Thailand: their antimicrobial and anticancer potentials. Botanica Marina, 53(6):555-564.
    Rukachaisirikul V, Rodglin A, Phongpaichit S,et al. 2012b. α-pyrone and seiricuprolide derivatives from the mangrove-derived fungi Pestalotiopsis spp. PSU-MA92 and PSU-MA119. Phytochemistry Letters, 5(1):13-17.
    Rukachaisirikul V, Rodglin A, Sukpondma Y,et al. 2012a. Phthalide and Isocoumarin derivatives produced by an Acremonium sp. isolated from a mangrove Rhizophora apiculata. Journal of Natural Products, 75(5):853-858.
    Rukachaisirikul V, Sommart U, Phongpaichit S,et al. 2008. Metabolites from the endophytic fungus Phomopsis sp. PSU-D15. Phytochemistry, 69: 783-787.
    Schmit J P, Shearer C A. 2003. A checklist of mangrove-associated fungi, their geographical distribution and known host plants. Mycotaxon,85(1):423-477.
    Shiono Y, Sasaki T, Shibuya F,et al. 2013. Isolation of a phomoxanthone A derivative, a new metabolite of tetrahydroxanthone, from a Phomopsis sp. isolated from the mangrove, Rhizhopora mucronata. Natural Product Communications, 8(12):1735.
    Sun H, Gao S S, Li X M,et al. 2013. Chemical constituents of marine mangrove-derived endophytic fungus Alternaria tenuissima EN-192. Chinese Journal of Oceanology and Limnology, 31(2):464-470.
    Suryanarayanan T S, Kumaresan V, Johnson J A. 1998. Foliar fungal endophytes from two species of the mangrove Rhizophora. Canadian Journal of Microbiology, 44(10):1003-1006.
    Suryanarayanan T S, Senthilarasu G, Muruganandam V. 2001. Endophytic fungi from Cuscuta reflexa and its host plants. Fungal Diversity, 4:117-123.
    Tarman K, Safitri D, Setyaningsih I. 2014. Endophytic fungi isolated from Rhizophora mucronata and their antibacterial activity. Squalen Bulletin of Marine & Fisheries Postharvest & Biotechnology, 8(2):69-76.
    Ukoima H N, Ikata M. 2013. Mycoparasitism on some fungal isolates of Rhizophora racemosa Linn. American Journal of Scientific Research, 84:139-144.
    Verma V C, Gond S K, Kumar A,et al. 2007.The endophytic mycoflora of bark, leaf, and stem tissues of Azadirachta indica A. Juss (Neem) from Varanasi (India). Microbial Ecology, 54(1):119-125.
    Wanderley Costa I P, Maia L C, Cavalcanti M A. 2012. Diversity of leaf endophytic fungi in mangrove plants of Northeast Brazil.Brazilian Journal of Microbiology,43(3):1165-1173.
    Wang J, Lu W, Min C,et al. 2011. The endophytic fungus AGR12 in the stem of Rhizophora stylosa Griff and its antibacterial metabolites. Chinese Journal of Antibiotics, 36(2):102-106.
    Wang Y, Zhu H, Tam N F Y. 2014. Polyphenols, tannins and antioxidant activities of eight true mangrove plant species in South China. Plant and Soil, 374(1):549-563.
    Wani M C, Taylor H L, Wall M E,et al. 1971.Plant antitumor agents.VI.The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J Chem Soc, 93(9): 2325-2327.
    Wheeler M H, Stipanovic R D, Puckhaber L S. 1999. Phytotoxicity of equisetin and epi-equisetin isolated from Fusarium equiseti and F. pallidoroseum. Mycological Research, 103(8):967-973.
    Wier A M, Tattar T A, Klekowski E J. 2000. Disease of red mangrove (Rhizophora mangle) in Southwest Puerto Rico caused by Cytospora rhizophorae. Biotropica, 32(2):299-306.
    Xing X, Guo S. 2011. Fungal endophyte communities in four Rhizophoraceae mangrove species on the south coast of China. Ecological Research, 26(2):403-409.
    Xu F, Tao W, Cheng L,et al. 2006. Strain improvement and optimization of the media of taxol-producing fungus Fusarium maire. Biochemical Engineering Journal, 31(1):67-73.
    Xu J, Aly A H, Wray V,et al. 2009b.Polyketide derivatives of endophytic fungus Pestalotiopsis sp. isolated from the Chinese mangrove plant Rhizophora mucronata. Journal of Natural Products, 72(4):662-665.
    Xu J, Ebada S S, Proksch P. 2010.Pestalotiopsis, a highly creative genus: chemistry and bioactivity of secondary metabolites. Fungal Diversity, 44: 15-31.
    Xu J, Kjer J, Sendker J,et al. 2009a. Cytosporones, coumarins, and an alkaloid from the endophytic fungus Pestalotiopsis sp. isolated from the Chinese mangrove plant Rhizophora mucronata. Bioorganic & Medicinal Chemistry, 17(20):7362-7367.
    Xu J, Kjer J, Sendker J,et al. 2011a. Chromones from the endophytic fungus Pestalotiopsis sp. isolated from the Chinese mangrove plant Rhizophora mucronata. Tetrahedron Letters, 52: 21-25.
    Xu J, Lin Q, Wang B,et al. 2011b.Pestalotiopamide E, a new amide from the endophytic fungus Pestalotiopsis sp. Journal of Asian Natural Products Research,13: 373-376.
    Zang L Y, Wei W, Guo Y, et al. 1992. Sesquiterpenoids from the mangrove-derived endophytic fungus Diaporthe sp. Journal of Natural Products, 75(10):1744-1749.
    Zhang P, Li X, Wang B G. 2016. Secondary metabolites from the marine algal-derived endophytic fungi: Chemical diversity and biological activity. Planta Medica, 82(9/10):832-842.
    Zhang W, Becker D, Cheng Q.2006. A mini-review of recent W.O. patents (2004-2005) of novel anti-fungal compounds in the field of anti-infective drug targets. Recent Patents on Anti-Infective Drug Discovery, 1(2):225-230.
    Zheng C J, Huang G L, Xu Y,et al. 2016. A new benzopyrans derivatives from a mangrove-derived fungus Penicillium citrinum from the South China Sea. Natural Product Research, 30(7):821-827.

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