The chemical constituents of endophytic fungus Nigrospora chinensis of Gannan navel orange

References

• Akihisa T, Wijeratne EMK, Tokuda H, Enjo F, Toriumi M, Kimura Y, Koike K, Nikaido T, Tezuka Y, Nishino H. 2002. Eupha-7,9(11),24-trien-3β-ol (“antiquol C”) and other triterpenes from Euphorbia antiquorum latex and their inhibitory effects on epstein-barr virus activation. J Nat Prod. 65(2):158–162.
   PubMed Web of Science ®Google Scholar
• Appel HH. 1948. Estudio químico de la corteza del árbol Drimys winteri Forst [Chemical study of the bark of the Drimys winteri Forst tree]. Scientia. 15:31–32.
   Google Scholar
• Aricu AN, Kuchkova KI, Secara-Cushnir ES, Barba AN, Ungur ND, Vornicu N. 2020. Synthesis and antimicrobial activity of new drimane and homodrimane sesquiterpenoids with oxadiazole and thiadiazole fragments. Chem Nat Compd. 56(4):656–662.
   Web of Science ®Google Scholar
• Asakawa Y, Ludwiczuk A, Harinantenaina L, Toyota M, Nishiki M, Bardon A, Nii K. 2012. Distribution of drimane sesquiterpenoids and tocopherols in liverworts, ferns and higher plants: polygonaceae, canellaceae and winteraceae species. Nat Prod Commun. 7(6):685–692.
   PubMed Web of Science ®Google Scholar
• Beckmann L, Tretbar US, Kitte R, Tretbar M. 2022. Anticancer activity of natural and semi-synthetic drimane and coloratane sesquiterpenoids. Molecules. 27(8):2501.
   PubMed Web of Science ®Google Scholar
• Bermejo A, Llosa MJ, Cano A. 2011. Analysis of bioactive compounds in seven citrus cultivars. Food Sci Technol Int. 17(1):55–62.
   PubMed Web of Science ®Google Scholar
• Bezerra JDP, Crous PW, Aiello D, Gullino ML, Polizzi G, Guarnaccia V. 2021. Genetic diversity and pathogenicity of Botryosphaeriaceae species associated with symptomatic citrus plants in Europe. Plants. 10(3):492.
   Google Scholar
• Cai DJ, Rui YK. 2013. Determination of trace elements and rare earth elements in Gannan navel orange fruit by ICP-MS. Asian J Chem. 25(1):579–580.
   Google Scholar
• Chau CF, Huang YL, Lin CY. 2004. Investigation of the cholesterol-lowering action of insoluble fibre derived from the peel of Citrus sinensis L. cv. Liucheng. Food Chem. 87(3):361–366.
   Web of Science ®Google Scholar
• Chen XL, Sun MC, Chong SL, Si JP, Wu LS. 2021. Transcriptomic and metabolomic approaches deepen our knowledge of plant-endophyte interactions. Front Plant Sci. 12:700200.
   PubMed Web of Science ®Google Scholar
• Cheng BP, Huang YH, Peng AT, Ling JF, Song XB, Chen X. 2014. First report of leaf and fruit spot of Citrus reticulata Blanco cv. Nian Ju caused by Colletotrichum truncatum in China. Plant Dis. 98(3):422.
   PubMed Web of Science ®Google Scholar
• Cortes M, Delgado V, Saitz C, Armstrong V. 2011. Drimenol: a versatile synthon for compounds with trans-drimane skeleton. Nat Prod Commun. 6(4):477–490.
   PubMed Web of Science ®Google Scholar
• Echeverri F, Luis JG, Torres F, Quintones W, Alzate F, Cardona G, Archbold R, Roldan J, Lahlou E-H. 1997. Daniol, a new drimane sesquiterpene from polygonum punctatum leaves. Nat Prod Lett. 10(4):295–301.
   Web of Science ®Google Scholar
• Eldahshan OA, Halim AF. 2016. Comparison of the composition and antimicrobial activities of the essential oils of green branches and leaves of Egyptian navel orange (citrus sinensis (L.) osbeck var. malesy. Chem Biodivers. 13(6):681–685.
   PubMed Web of Science ®Google Scholar
• Faeth SH. 2002. Are endophytic fungi defensive plant mutualists? Oikos. 98(1):25–36.
   Web of Science ®Google Scholar
• Gottig N, Garavaglia BS, Garofalo CG, Orellano EG, Ottado J, Ausubel FM. 2009. A filamentous hemagglutinin-like protein of Xanthomonas axonopodis pv. citri, the phytopathogen responsible for citrus canker, is involved in bacterial virulence. PLoS One. 4(2):e4358.
   PubMed Web of Science ®Google Scholar
• Guo QY, Liu K, Deng WH, Zhong BL, Yang WX, Chun J. 2018. Chemical composition and antimicrobial activity of Gannan navel orange (Citrus sinensis Osbeck cv. Newhall) peel essential oils. Food Sci Nutr. 6(6):1431–1437.
   PubMed Web of Science ®Google Scholar
• Hu MY, Zhang L, Ruan Z, Han PH, Yu YJ. 2021. The regulatory effects of citrus peel powder on liver metabolites and gut flora in mice with non-alcoholic fatty liver disease (NAFLD). Foods. 10(12):3022.
   PubMed Web of Science ®Google Scholar
• Hu Y, Tao LJ, Tan H, Zhang M, Shimizu K, Zhang F, Zhang CF. 2017. An active drimane-type lactone from Polygonum jucundum attenuates lipopolysaccharide-induced acute lung injury in mice through TLR4-MAPKs signaling pathway. Inflammation. 40(4):1204–1213.
   PubMed Web of Science ®Google Scholar
• Huang DY, Nong XH, Zhang YQ, Xu W, Sun LY, Zhang T, Chen GY, Han CR. 2022. Two new 2,5-diketopiperazine derivatives from mangrove-derived endophytic fungus Nigrospora camelliae-sinensis S30. Nat Prod Res. 36(14):3651–3656.
   PubMed Web of Science ®Google Scholar
• Huang Y, Valiante V. 2022. Chemical diversity and biosynthesis of drimane-type sesquiterpenes in the fungal kingdom. ChemBioChem. 23(17):e202200173.
   PubMed Web of Science ®Google Scholar
• Jansen BJM, Groot A. 1991. The occurrence and biological activity of drimane sesquiterpenoids. Nat Prod Rep. 8(3):309–318.
   PubMed Web of Science ®Google Scholar
• Kawaguchi K, Kikuchi S, Hasunuma R, Maruyama H, Ryll R, Kumazawa Y. 2004. Suppression of infection-induced endotoxin shock in mice by a citrus flavanone naringin. Planta Med. 70(1):17–22.
   PubMed Web of Science ®Google Scholar
• Kuang C, Jing SX, Liu Y, Luo SH, Li SH. 2016. Drimane sesquiterpenoids and isochromone derivative from the endophytic fungus Pestalotiopsis sp. M-23. Nat Prod Bioprospect. 6(3):155–160.
   PubMedGoogle Scholar
• Lacerda ÍCDS, Polonio JC, Golias HC. 2022. Endophytic fungi as a source of antiviral compounds - a review. Chem Biodivers. 19(6):e202100971.
   PubMed Web of Science ®Google Scholar
• Li FZ, Renata H. 2021. A chiral-pool-based strategy to access trans-syn-fused drimane meroterpenoids: chemoenzymatic total syntheses of polysin, N-acetyl-polyveoline and the chrodrimanins. J Am Chem Soc. 143(43):18280–18286.
   PubMed Web of Science ®Google Scholar
• Li JY, Wang N. 2011. The wxacO gene of Xanthomonas citri ssp. citri encodes a protein with a role in lipopolysaccharide biosynthesis, biofilm formation, stress tolerance and virulence. Mol Plant Pathol. 12(4):381–396.
   PubMed Web of Science ®Google Scholar
• Li Y, Zuo YM, Feng J. 2018. Mechanisms of the ameliorative effect of naringenin on the diabetic cardiomyopathy: research progress. J Int Pharm Res. 45(10):743–747.
   Google Scholar
• Li YH, Liang L, Xu CH, Yang TM, Wang YX. 2021. UPLC-Q-TOF/MS-based untargeted metabolomics for discrimination of navel oranges from different geographical origins of China. LWT - Food Sci Technol. 137(4):110382.
   Google Scholar
• Liu SS, Jiang JX, Huang R, Wang YT, Jiang BG, Zheng KX, Wu SH. 2019. A new antiviral 14-nordrimane sesquiterpenoid from an endophytic fungus Phoma sp. Phytochem Lett. 29:75–78.
   Web of Science ®Google Scholar
• Liu YD, Sun XD, Zhou JM, Zhang HL, Yang C. 2010. Linear and nonlinear multivariate regressions for determination sugar content of intact Gannan navel orange by vis-NIR diffuse reflectance spectroscopy. Math Comput Model. 51(11–12):1438–1443.
   Web of Science ®Google Scholar
• Ma MZ, Ge HJ, Yi WW, Wu B, Zhang ZZ. 2020. Bioactive drimane sesquiterpenoids and isocoumarins from the marine-derived fungus Penicillium minioluteum ZZ1657. Tetrahedron Lett. 61(7):151504.
   Web of Science ®Google Scholar
• Metwaly AM, Kadry HA, El-Hela AA, Mohammad AEI, Ma GY, Cutler SJ, Ross SA. 2014. Nigrosphaerin A a new isochromene derivative from the endophytic fungus Nigrospora sphaerica. Phytochem Lett. 7:1–5.
   PubMed Web of Science ®Google Scholar
• NBSPRC. 2019. National Bureau of Statistics of the People’s Republic of China.
   Google Scholar
• Raghavan S, Gurunathan J. 2021. Citrus species - a golden treasure box of metabolites that is beneficial against disorders. J Herb Med. 28(7):100438.
   Google Scholar
• Sadeghi F, Samsampour D, Seyahooei MA, Bagheri A, Soltani J. 2019. Diversity and spatiotemporal distribution of fungal endophytes associated with Citrus reticulata cv. Siyahoo. Curr Microbiol. 76(3):279–289.
   PubMed Web of Science ®Google Scholar
• Schulz B, Boyle C, Draeger S, Römmert AK, Krohn K. 2002. Endophytic fungi: a source of novel biologically active secondary metabolites. Mycol Res. 106(9):996–1004.
   Web of Science ®Google Scholar
• Shi H, Fang LC, Tan CH, Shi LL, Zhang WB, Li CC, Luo TP, Yang Z. 2011. Total syntheses of drimane-type sesquiterpenoids enabled by a gold-catalyzed tandem reaction. J Am Chem Soc. 133(38):14944–14947.
   PubMed Web of Science ®Google Scholar
• Shirane N, Takenaka H, Ueda K, Hashimoto Y, Katoh K, Ishii H. 1996. Sterol analysis of DMI-resistant and sensitive strains of Venturia inaequalis. Phytochemistry. 41(5):1301–1308.
   Web of Science ®Google Scholar
• Tao ZZ, Yi L, Lu ZJ, Li FZ, Lai XH, Zhong BL, Chen CX. 2011. Investigation and research on the infection rate of Citrus tristeza virus for major production regions of Gannan navel oranges. Chin Sci Bull. 27(16):297–300.
   Google Scholar
• Tripoli E, Guardia ML, Giammanco S, Majo DD, Giammanco M. 2007. Citrus flavonoids: molecular structure, biological activity and nutritional properties: a review. Food Chem. 104(2):466–479.
   Web of Science ®Google Scholar
• Wang B, He B, Chen TY, Li H, Chen LYF, Chen YL, Tian KL, Yang K, Shen DY, Yan W, et al. 2022. Discovery of tropolone stipitaldehyde as a potential agent for controlling phytophthora blight and its action mechanism research. J Agric Food Chem. 70(28):8693–8703.
   PubMed Web of Science ®Google Scholar
• Wang BL, Gao HT, Li WDZ. 2015. Total synthesis of (+)-iresin. J Org Chem. 80(10):5296–5301.
   PubMed Web of Science ®Google Scholar
• Wang M, Liu F, Crous PW, Cai L. 2017. Phylogenetic reassessment of Nigrospora, ubiquitous endophytes, plant and human pathogens. Persoonia. 39:118–142.
   PubMed Web of Science ®Google Scholar
• Wang WX, Silva DD, Moslemi A, Edwards J, Ades PK, Crous PW, Taylor PWJ. 2021. Colletotrichum species causing anthracnose of citrus in Australia. JoF. 7(1):47.
   Google Scholar
• Wen J, Shi Y, Xu YJ, Xiao GS, Zhang YS. 2007. Anti-inflammation and analgesic experimental study on citrus frutis limonoids. Food Sci. 28(11):515–518.
   Google Scholar
• Wu B, Oesker V, Wiese J, Malien S, Schmaljohann R, Imhoff JF. 2014. Spirocyclic drimanes from the marine fungus Stachybotrys sp. strain MF347. Mar Drugs. 12(4):1924–1938.
   PubMed Web of Science ®Google Scholar
• Wu ZH, Xie ZH, Wu ML, Li XQ, Li WL, Ding WJ, She ZG, Li CY. 2018. New antimicrobial cyclopentenones from Nigrospora sphaerica ZMT05, a fungus derived from oxya chinensis Thunber. J Agric Food Chem. 66(21):5368–5372.
   PubMed Web of Science ®Google Scholar
• Xie SS, Wu Y, Zhang N, Guo Y, Wang JP, Xue YB, Zhang YH. 2019. The bioactive secondary metabolites from Phyllanthus glaucus associated fungus Phomopsis sp. TJ507A. Nat Prod Res Dev. 31:61–68.
   Google Scholar
• Xiong DW, Jin DF, Li P, Huang XP. 2018. Screening and culture of citrus Huanglongbing related endophytic bacteria from Gannan navel orange. South China Fruits 2018. 47(04):19–22 + 25.
   Google Scholar
• Yan W, Wei W, Zhang YY, Wang JJ, Ping XF, Xu JY, Ye YH. 2018. Nigrosporanenes C and D, two new cyclohexene derivatives from the enphytic fungus Nigrospora oryzae S4. J Asian Nat Prod Res. 20(10):957–961.
   PubMed Web of Science ®Google Scholar
• Yan ZL, Chen JP, Nong XX, Li X, Luo HY, Wei LL, Ruan JH, Guan XY, Lu S. 2021. Isolation and identification of endophytic fungi from citrus cultivars and their inhibitory activity against Xanthomonas citri subsp. citri causing citrus canker. Guihaia. 41(7):1196–1208.
   Google Scholar
• Yang C, Chen H, Chen HL, Zhong BL, Luo XZ, Chun J. 2017. Antioxidant and anticancer activities of essential oil from Gannan navel orange peel. Molecules. 22(8):1391.
   PubMed Web of Science ®Google Scholar
• Youssef FS, Simal-Gandara J. 2021. Comprehensive overview on the chemistry and biological activities of selected alkaloid producing marine-derived fungi as a valuable reservoir of drug entities. Biomedicines. 9(5):485.
   PubMed Web of Science ®Google Scholar
• Zhang DH, Xiang GL, Kang JS, Choi HD, Jung JH, Son BW. 2007. Redoxcitrinin, a biogenetic precursor of citrinin from marine isolate of fungus Penicillium sp. J Microbiol Biotechnol. 17(5):865–867.
   PubMed Web of Science ®Google Scholar
• Zhang WG, Lu XX, Huo LQ, Zhang S, Chen Y, Zou ZX, Tan HB. 2021. Sesquiterpenes and steroids from an endophytic Eutypella scoparia. J Nat Prod. 84(6):1715–1724.
   PubMed Web of Science ®Google Scholar
• Zhou YJ, Tang YN, Hu CX, Zhan T, Zhang S, Cai MM, Zhao XH. 2021. Soil applied Ca, Mg and B altered phyllosphere and rhizosphere bacterial microbiome and reduced Huanglongbing incidence in Gannan navel orange. Sci Total Environ. 791:148046.
   PubMed Web of Science ®Google Scholar
• Zhu AY, Yang YF, Zhou KP, Wang YX. 2017. Antioxidant activity and phenolic content of Gannan navel orange. Food Sci Tech. 42(4):207–211.
   Google Scholar
• Zhu XW, Chen JQ, Zhu SR, He YY, Ding WJ, Li CY. 2018. Two new compounds from Nigrospora sphaerica ZMT05, a fungus derivated from Oxya chinensis Thunber. Nat Prod Res. 32(20):2375–2381.
   PubMed Web of Science ®Google Scholar