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研究生:李逸潔
研究生(外文):Yi-Chieh Lee
論文名稱:馬氏濱藜 (Atriplex maximowicziana) 衍生真菌株Alternaria alstroemeriae Km2286之成分研究
論文名稱(外文):Chemical constituents from Atriplex maximowicziana-derived fungus Alternaria alstroemeriae Km2286
指導教授:李宗徽李宗徽引用關係
指導教授(外文):Tzong-Huei Lee
學位類別:碩士
校院名稱:國立臺灣大學
系所名稱:漁業科學研究所
學門:農業科學學門
學類:漁業學類
論文種類:學術論文
論文出版年:2022
畢業學年度:110
語文別:中文
論文頁數:217
中文關鍵詞:馬氏濱藜Alternaria alstroemeriaealtertromin抗病毒抗發炎
外文關鍵詞:Atriplex maximowiczianaAlternaria alstroemeriaealtertrominanti-EBVanti-inflammation
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致謝 I
中文摘要 II
英文摘要 III
表目錄 IX
圖目錄 X
縮寫表 XIV
第一章 緒論與研究目的 1
第二章 文獻回顧 4
2.1 真菌株之分類學與介紹 4
2.2 鏈格孢菌屬 (Alternaria spp.) 真菌成份之文獻回顧 4
第三章 實驗結果 78
3.1 真菌液態醱酵萃取液分離流程 78
3.2 天然物結構解析 80
3.2.1 Altertromin A (1) 之結構解析 80
3.2.2 Altertromin B (2) 之結構解析 91
3.2.3 Altertromin C (3) 之結構解析 102
3.2.4 Altertromin D (4) 之結構解析 117
3.2.5 Altertoxin IV (5) 之結構解析 129
3.2.6 Altertoxin VIII (6) 之結構解析 142
3.2.7 Stemphyperylenol (7) 之結構解析 153
3.2.8 Tenuazonic acid (8) 之結構解析 157
3.2.9 allo-Tenuazonic acid (9) 之結構解析 161
3.3 各成分之物理數據 165
3.4 化合物活性平台測試 169
3.4.1 抗病毒實驗結果 169
3.4.2 一氧化氮抑制與細胞存活率之實驗結果 171
第四章 實驗部分 173
4.1 儀器設備與試劑 173
4.1.1 化合物之物理性質測定儀器 173
4.1.2 管柱層析膠體 173
4.1.3 試劑耗材與溶劑 174
4.1.4 真菌培養基 174
4.2 實驗材料 174
4.2.1 真菌材料 174
4.2.2 菌種分子鑑定 174
4.2.3 真菌菌株分離與篩選 177
4.3 抗病毒活性篩選 177
4.4 真菌培養與成分分離 177
4.4.1 培養基配製 177
4.4.2 真菌菌種保存 178
4.4.3 真菌液態醱酵液萃取 178
4.4.4 真菌液態醱酵液之成分分離與純化 179
4.4.5 ECD之計算 181
4.5 抗病毒活性評估 181
4.6 抗發炎活性評估 181
4.6.1 細胞培養 181
4.6.2 Griess reagent assay 182
4.6.3 MTT assay 182
第五章 討論 183
第六章 參考文獻 187
第七章 附錄 215
1.Cragg, G. M.; Newman, D. J.; Snader, K. M. Natural products in drug discovery and development. J. Nat. Prod. 1997, 60 (1), 52-60, DOI: 10.1021/np9604893
2.Harvey, A. Strategies for discovering drugs from previously unexplored natural products. Drug Discov. Today 2000, 5 (7), 294-300, DOI: 10.1016/s1359-6446(00)01511-7
3.Calixto, J. B. The role of natural products in modern drug discovery. An. Acad. Bras. Cienc. 2019, 91 (Suppl. 3), e20190105, DOI: 10.1590/0001-3765201920190105
4.Butler, M. S. The role of natural product chemistry in drug discovery. J. Nat. Prod. 2004, 67 (12), 2141-2153, DOI: 10.1021/np040106y
5.Newman, D. J.; Cragg, G. M. Natural products as sources of new drugs over the nearly four decades from 01/1981 to 09/2019. J. Nat. Prod. 2020, 83 (3), 770-803, DOI: 10.1021/acs.jnatprod.9b01285
6.Sarwari, N. M.; Khoury, J. D.; Hernandez, C. M. R. Chronic Epstein Barr virus infection leading to classical Hodgkin lymphoma. BMC Hematol. 2016, 16 (1), 19, DOI: 10.1186/s12878-016-0059-3
7.Cohen, J. I. Erratum: Epstein-Barr virus vaccines. Clin. Transl. Immunol. 2015, 4 (4), e36-e36, DOI: 10.1038/cti.2015.4
8.Hjalgrim, H.; Askling, J.; Rostgaard, K.; Hamilton Dutoit, S.; Frisch, M.; Zhang, J. S.; Madsen, M.; Rosdahl, N.; Konradsen, H. B.; Storm, H. H.; Melbye, M. Characteristics of hodgkin's lymphoma after infectious mononucleosis. N. Engl. J. Med. 2003, 349 (14), 1324-1332, DOI: 10.1056/NEJMoa023141
9.Kerr, J. R. Epstein-Barr virus (EBV) reactivation and therapeutic inhibitors. J. Clin. Pathol. 2019, 72 (10), 651 - 658, DOI: 10.1136/jclinpath-2019-205822
10.Cheung, F. TCM: Made in China. Nature 2011, 480 (7378), S82-S83, DOI: 10.1038/480S82a
11.Wilson, D. Endophyte: The evolution of a term, and clarification of its use and definition. Oikos 1995, 73 (2), 274-276, DOI: 10.2307/3545919
12.Porras-Alfaro, A.; Bayman, P. Hidden fungi, emergent properties: Endophytes and microbiomes. Annu. Rev. Phytopathol. 2011, 49 (1), 291-315, DOI: 10.1146/annurev-phyto-080508-081831
13.Jadulco, R.; Edrada, R. A.; Ebel, R.; Berg, A.; Schaumann, K.; Wray, V.; Steube, K.; Proksch, P. New communesin derivatives from the fungus penicillium sp. Derived from the mediterranean sponge Axinella verrucosa. J. Nat. Prod. 2004, 67 (1), 78-81, DOI: 10.1021/np030271y
14.Xu, D. X.; Sun, P.; Kurtán, T.; Mándi, A.; Tang, H.; Liu, B.; Gerwick, W. H.; Wang, Z. W.; Zhang, W. Polyhydroxy cyclohexanols from a Dendrodochium sp. fungus associated with the sea cucumber Holothuria nobilis Selenka. J. Nat. Prod. 2014, 77 (5), 1179-1184, DOI: 10.1021/np500024r
15.Parikesit, A. A. Drug design - novel advances in the omics field and applications. ed.; IntechOpen: 2020, ISBN: 9781789847536
16.Carroll, A. R.; Copp, B. R.; Davis, R. A.; Keyzers, R. A.; Prinsep, M. R. Marine natural products. Nat. Prod. Rep. 2021, 38 (2), 362-413, DOI: 10.1039/D0NP00089B
17.Woudenberg, J. H. C.; Groenewald, J. Z.; Binder, M.; Crous, P. W. Alternaria redefined. Stud. Mycol. 2013, 75 (1), 171-212, DOI: 10.3114/sim0015
18.ChfBkowski, J.; Visconti, A. Alternaria: Biology, plant diseases and metabolites. ed.; Elsevier Science: 1992; Vol. 1, ISBN: 9780444889980
19.D′Mello, J. P. F. Handbook of plant and fungal toxicants. ed.; CRC Press: Boca Raton, 1997; p 19, ISBN: 9780429281952
20.Shinha, K. K.; Bhatnagar, D. Mycotoxins in agriculture and food safety. ed.; CRC Press: Boca Raton, 1998; p 520, ISBN: 9780429079702
21.Miller, J.; Trenholm, H. Mycotoxin in grain. Rev. Inst. Med. Trop. Sao Paulo 1994, 36 (5), DOI: 10.1590/S0036-46651994000500017
22.Magan, N.; Olsen, M. Mycotoxins in food. ed.; CRC Press: Boca Raton, 2004; p 471, ISBN: 9781855737334
23.Ostry, V. Alternaria mycotoxins: an overview of chemical characterization, producers, toxicity, analysis and occurrence in foodstuffs. World Mycotoxin J. 2008, 1 (2), 175-188, DOI: 10.3920/WMJ2008.x013
24.Scott, P. M. Analysis of agricultural commodities and foods for Alternaria mycotoxins. J. AOAC Int. 2019, 84 (6), 1809-1817, DOI: 10.1093/jaoac/84.6.1809
25.Liu, S.; Liu, M.; Wu, H.; Wang, Q.; Li, W.; Huang, S.; Feng, J. A new isomer and other metabolites isolated from Alternaria alternata. Chem. Nat. Compd. 2021, 57 (5), 844-847, DOI: 10.1007/s10600-021-03495-8
26.Ding, H.; Zhang, D.; Zhou, B.; Ma, Z. Inhibitors of BRD4 protein from a marine-derived fungus Alternaria sp. NH-F6. Mar. Drugs 2017, 15 (3), 76, DOI: 10.3390/md15030076
27.Tan, X.; Wang, Y.; Liu, Z.; Liu, L.; Yu, M.; Ding, G. Systematical NMR analysis of swainsonine, a mycotoxin from endophytic fungus Alternaria oxytropis. Magn. Reson. Chem. 2021, 59 (1), 16-22, DOI: 10.1002/mrc.5098
28.Wang, W.; Wang, Y.; Tao, H.; Peng, X.; Liu, P.; Zhu, W. Cerebrosides of the halotolerant fungus Alternaria raphani Isolated from a sea salt field. J. Nat. Prod. 2009, 72 (9), 1695-1698, DOI: 10.1021/np9002299
29.Hellwig, V.; Grothe, T.; Mayer Bartschmid, A.; Endermann, R.; Geschke, F. U.; Henkel, T.; Stadler, M. Altersetin, a new antibiotic from cultures of endophytic Alternaria spp. taxonomy, fermentation, isolation, structure elucidation and biological activities. J. Antibiot. 2002, 55 (10), 881-92, DOI: 10.1002/chin.200312204
30.Chadwick, D. J.; Easton, I. W. 2-Acetyl-4(3H)-quinazolinone, C10H8N2O2. Acta Crystallogr. Sect. C 1983, 39 (4), 454-456, DOI: 10.1107/S0108270183005090
31.Stierle, A.; Hershenhorn, J.; Strobel, G. Zinniol-related phytotoxins from Alternaria cichorii. Phytochemistry 1993, 32 (5), 1145-1149, DOI: 10.1016/S0031-9422(00)95080-5
32.Phuwapraisirisan, P.; Rangsan, J.; Siripong, P.; Tip-pyang, S. New antitumour fungal metabolites from Alternaria porri. Nat. Prod. Res. 2009, 23 (12), 1063-1071, DOI: 10.1080/14786410802265415
33.Rosett, T.; Sankhala, R. H.; Stickings, C. E.; Taylor, M. E. U.; Thomas, R. Studies in the biochemistry of micro-organisms. 103. Metabolites of Alternaria tenuis Auct.: culture filtrate products. Biochem. J. 1957, 67 (3), 390-400, DOI: 10.1042/bj0670390
34.Mahmoud, M. M.; Abdel-Razek, A. S.; Soliman, H. S. M.; Ponomareva, L. V.; Thorson, J. S.; Shaaban, K. A.; Shaaban, M. Diverse polyketides from the marine endophytic Alternaria sp. LV52: Structure determination and cytotoxic activities. Biotechnol. Rep. 2022, 33, e00628, DOI: 10.1016/j.btre.2021.e00628
35.Kellogg, J. J.; Todd, D. A.; Egan, J. M.; Raja, H. A.; Oberlies, N. H.; Kvalheim, O. M.; Cech, N. B. Biochemometrics for natural products research: Comparison of data analysis approaches and application to identification of bioactive compounds. J. Nat. Prod. 2016, 79 (2), 376-386, DOI: 10.1021/acs.jnatprod.5b01014
36.Aly, A. H.; Edrada-Ebel, R.; Indriani, I. D.; Wray, V.; Müller, W. E. G.; Totzke, F.; Zirrgiebel, U.; Schächtele, C.; Kubbutat, M. H. G.; Lin, W. H.; Proksch, P.; Ebel, R. Cytotoxic metabolites from the fungal endophyte Alternaria sp. and their subsequent detection in its host plant Polygonum senegalense. J. Nat. Prod. 2008, 71 (6), 972-980, DOI: 10.1021/np070447m
37.Browne, L. M.; Conn, K. L.; Ayert, W. A.; Tewari, J. P. The camalexins: New phytoalexins produced in the leaves of Camelina sativa (cruciferae). Tetrahedron 1991, 47 (24), 3909-3914, DOI: 10.1016/S0040-4020(01)86431-0
38.Tian, L. L.; Ren, H.; Xi, J. M.; Fang, J.; Zhang, J. Z.; Wu, Q. X. Diverse anti-inflammation and anti-cancer polyketides isolated from the endophytic fungi Alternaria sp. MG1. Fitoterapia 2021, 153, 105000, DOI: 10.1016/j.fitote.2021.105000
39.Ma, Y. T.; Qiao, L. R.; Shi, W. Q.; Zhang, A. L.; Gao, J. M. Metabolites produced by an endophyte Alternaria alternata isolated from Maytenus hookeri. Chem. Nat. Compd. 2010, 46 (3), 504-506, DOI: 10.1007/s10600-010-9662-x
40.Dahiya, J. S.; Tewari, J. P. Plant growth factors produced by the fungus Alternaria brassicae. Phytochemistry 1991, 30 (9), 2825-2828, DOI: 10.1016/S0031-9422(00)98206-2
41.Zhang, A. H.; Jiang, N.; Gu, W.; Ma, J.; Wang, Y. R.; Song, Y. C.; Tan, R. X. Characterization, synthesis and self-aggregation of (−)-alternarlactam: A new fungal cytotoxin with cyclopentenone and isoquinolinone scaffolds. Chem. – Eur. J. 2010, 16 (48), 14479-14485, DOI: 10.1002/chem.201002205
42.Yang, H.; Qi, B.; Ding, N.; Jiang, F.; Jia, F.; Luo, Y.; Xu, X.; Wang, L.; Zhu, Z.; Liu, X.; Tu, P.; Shi, S. Polyketides from Alternaria alternata MT-47, an endophytic fungus isolated from Huperzia serrata. Fitoterapia 2019, 137, 104282, DOI: 10.1016/j.fitote.2019.104282
43.Suemitsu, R.; Ohnishi, K.; Morikawa, Y.; Nagatomo, S. Zinnimidine and 5-(3′,3′-dimethylallyloxy)-7-methoxy-6-methylphthalide from Alternaria porri. Phytochemistry 1995, 38 (2), 495-497, DOI: 10.1016/0031-9422(94)00546-6
44.Horiuchi, M.; Maoka, T.; Iwase, N.; Ohnishi, K. Reinvestigation of structure of porritoxin, a phytotoxin of Alternaria porri. J. Nat. Prod. 2002, 65 (8), 1204-1205, DOI: 10.1021/np020072z
45.Horiuchi, M.; Ohnishi, K.; Iwase, N.; Nakajima, Y.; Tounai, K.; Yamashita, M.; Yamada, Y. A novel isoindoline, porritoxin sulfonic acid, from Alternaria porri and the structure-phytotoxicity correlation of its related compounds. Biosci., Biotechnol., Biochem. 2003, 67 (7), 1580-1583, DOI: 10.1271/bbb.67.1580
46.Ranganathan, N.; Mahalingam, G. Secondary metabolite as therapeutic agent from endophytic fungi Alternaria longipes strain VITN14G of mangrove plant Avicennia officinalis. J. Cell. Biochem. 2019, 120 (3), 4021-4031, DOI: 10.1002/jcb.27686
47.Masi, M.; Di-Lecce, R.; Maddau, L.; Marsico, G.; Superchi, S.; Evidente, A. Argyrotoxins A-C, a trisubstituted dihydroisobenzofuranone, a tetrasubstituted 2-hydroxyethylbenzamide and a tetrasubstitutedphenyl trisubstitutedbutyl ether produced by Alternaria argyroxiphii, the causal agent of leaf spot on African mahogany trees (Khaya senegalensis). Phytochemistry 2021, 191, 112921, DOI: 10.1016/j.phytochem.2021.112921
48.Shen, Y.; Xu, Q. L.; Cheng, P.; Liu, C. L.; Lu, Z. Y.; Li, W.; Wang, T. T.; Lu, Y. H.; Tan, R. X.; Ge, H. M.; Jiao, R. H. Aromatic polyketides from a caterpillar associated Alternaria sp. Tetrahedron Lett. 2017, 58 (31), 3069-3072, DOI: 10.1016/j.tetlet.2017.06.071
49.Suemitsu, R.; Ohnishi, K.; Horiuchi, M.; Kitaguchi, A.; Odamura, K. Porritoxin, a phytotoxin of Alternaria porri. Phytochemistry 1992, 31 (7), 2325-2326, DOI: 10.1016/0031-9422(92)83273-2
50.Cai, S.; King, J. B.; Du, L.; Powell, D. R.; Cichewicz, R. H. Bioactive sulfur-containing sulochrin dimers and other metabolites from an Alternaria sp. isolate from a Hawaiian soil sample. J. Nat. Prod. 2014, 77 (10), 2280-2287, DOI: 10.1021/np5005449
51.Huang, Y. F.; Li, L. H.; Tian, L.; Qiao, L.; Hua, H. M.; Pei, Y. H. Sg17-1-4, a novel isocoumarin from a marine fungus Alternaria tenuis Sg17-1. J. Antibiot. 2006, 59 (6), 355-357, DOI: 10.1038/ja.2006.50
52.Liakopoulou-Kyriakides, M.; Lagopodi, A. L.; Thanassoulopoulos, C. C.; Stavropoulos, G. S.; Magafa, V. Isolation and synthesis of a host-selective toxin produced by Alternaria alternata. Phytochemistry 1997, 45 (1), 37-40, DOI: 10.1016/S0031-9422(96)00789-3
53.Nakashima, T.; Ueno, T.; Fukami, H.; Taga, T.; Masuda, H.; Osaki, K.; Otani, H.; Kohmoto, K.; Nishimura, S. Isolation and structures of AK-Toxin I and II, host-specific phytotoxic metabolites produced by Alternaria alternata Japanese pear pathotype. Agric. Biol. Chem. 1985, 49 (3), 807-815, DOI: 10.1271/bbb1961.49.807
54.Nakashima, T.; Ueno, T.; Fukami, H. Structure elucidation of AK-toxins, host-specific phytotoxic metabolites produced by Alternaria kikuchiana Tanaka. Tetrahedron Lett. 1982, 23 (43), 4469-4472, DOI: 10.1016/S0040-4039(00)85630-0
55.King, J. B.; Carter, A. C.; Dai, W.; Lee, J. W.; Kil, Y. S.; Du, L.; Helff, S. K.; Cai, S.; Huddle, B. C.; Cichewicz, R. H. Design and application of a high-throughput, high-content screening system for natural product inhibitors of the human parasite Trichomonas vaginalis. ACS Infect. Dis. 2019, 5 (8), 1456-1470, DOI: 10.1021/acsinfecdis.9b00156
56.Yamada, T.; Kikuchi, T.; Tanaka, R. Altercrasin A, a novel decalin derivative with spirotetramic acid, produced by a sea urchin-derived Alternaria sp. Tetrahedron Lett. 2015, 56 (10), 1229-1232, DOI: 10.1016/j.tetlet.2015.01.066
57.Nakajima, S. Studies on the metabolites of phytotoxic fungi. I. isolation of macrosporin and 6-methylxanthopurpurin 3-methyl ether from Alternaria bataticola IKATA ex YAMAMOTO. Chem. Pharm. Bull. 1973, 21 (9), 2083-2085, DOI: 10.1248/cpb.21.2083
58.Suemitsu, R.; Iwai, J.; Kawaguchi, K. Isolation and identification of physcion, 4, 5-dihydroxy-7-methoxy-2-methylanthraquinone, from the mycelium of Alternaria porri. Agric. Biol. Chem. 1975, 39 (11), 2249-2250, DOI: 10.1271/bbb1961.39.2249
59.Suemitsu, R.; Kida, A.; Horiuchi, K.-i.; Hiura, M. Isolation and identification of 2-methylxanthopurpurin-7-methylether from the mycelium of Alternaria porri. Agric. Biol. Chem. 1974, 38 (11), 2277-2278, DOI: 10.1271/bbb1961.38.2277
60.Noboru, S.; Choji, K.; Makoto, Y.; Toki, S.; Ryotaro, M. Altenin. I. The isolation of altenin from Alternaria Kikuchiana Tanaka. Bull. Chem. Soc. Jpn. 1966, 39 (7), 1573-1577, DOI: 10.1246/bcsj.39.1573
61.Huang, C. H.; Pan, J. H.; Chen, B.; Yu, M.; Huang, H. B.; Zhu, X.; Lu, Y. J.; She, Z. G.; Lin, Y. C. Three bianthraquinone derivatives from the mangrove endophytic fungus Alternaria sp. ZJ9-6B from the south China sea. Mar. Drugs 2011, 9 (5), 832-843, DOI: 10.3390/md9050832
62.Chen, B.; Shen, Q.; Zhu, X.; Lin, Y. The anthraquinone derivatives from the fungus Alternaria sp. XZSBG-1 from the saline lake in Bange, Tibet, China. Molecules 2014, 19 (10), 16529-16542, DOI: 10.3390/molecules191016529
63.Suemitsu, R.; Kitagawa, N.; Shinomaru, H.; Tomoyoshi, T. Isolation and identification of 3,4,5-trihydroxy-7-methoxy-2-methyl-anthraquinone from the mycelium of Alternaria porri (Ellis) Ciferri. Agric. Biol. Chem. 1977, 41 (1), 207-207, DOI: 10.1271/bbb1961.41.207
64.Suemitsu, R.; Iwai, J.; Kawaguchi, K.; Haitani, N.; Kitagawa, N. Isolation and identification of erythroglaucin (1,4,5-trihydroxy-7-methoxy-2-methylanthraquinone) from the mycelium of Alternaria porri (Ellis) Ciferri. Agric. Biol. Chem. 1977, 41 (11), 2289-2290, DOI: 10.1271/bbb1961.41.2289
65.Zhang, N.; Zhang, C.; Xiao, X.; Zhang, Q.; Huang, B. New cytotoxic compounds of endophytic fungus Alternaria sp. isolated from Broussonetia papyrifera (L.) Vent. Fitoterapia 2016, 110, 173-180, DOI: 10.1016/j.fitote.2016.03.014
66.Stoessl, A.; Stothers, J. B. Tetrahydroaltersolanol B, a hexahydroanthronol from Alternaria solani. Can. J. Chem. 1983, 61 (2), 378-382, DOI: 10.1139/v83-068
67.Suemitsu, R.; Nakamura, A. Isolation and identification of altersolanol A from the culture liquid of Alternaria porri (Ellis) Ciferri. Agric. Biol. Chem. 1981, 45 (10), 2363-2364, DOI: 10.1080/00021369.1981.10864889
68.Yagi, A.; Okamura, N.; Haraguchi, H.; Abot, T.; Hashimoto, K. Antimicrobial tetrahydroanthraquinones from a strain of Alternaria solani. Phytochemistry 1993, 33 (1), 87-91, DOI: 10.1016/0031-9422(93)85401-C
69.Suemitsu, R.; Kitagawa, N.; Horie, S.; Kazawa, K.; Harada, T. Isolation and identification of altersolanol B (7-methoxy-2-methyl-(2R,3S)-1,2,3,4-tetrahydro-2,3,5-trihydroxyanthraquinone) from the mycelium of Alternaria porri (Ellis) Ciferri. Agric. Biol. Chem. 1978, 42 (9), 1801-1802, DOI: 10.1271/bbb1961.42.1801
70.Suemitsu, R.; Nakamura, A.; Isono, F.; Sano, T. Isolation and identification of dactylariol from the culture liquid of Alternaria porri (Ellis) Ciferri. Agric. Biol. Chem. 1982, 46 (6), 1693-1694, DOI: 10.1271/bbb1961.46.1693
71.Okamura, N.; Haraguchi, H.; Hashimoto, K.; Yagi, A. Altersolanol-related antimicrobial compounds from a strain of Alternaria solani. Phytochemistry 1993, 34 (4), 1005-1009, DOI: 10.1016/S0031-9422(00)90703-9
72.Stevens, K. L.; Badar-Ud, D.; Ahmad, A.; Ahmad, M. The antibiotic bostrycin from Alternaria eichhorniae. Phytochemistry 1979, 18 (9), 1579-1580, DOI: 10.1016/S0031-9422(00)98507-8
73.Okamura, N.; Mimura, K.; Haraguchi, H.; Shingu, K.; Miyahara, K.; Yagi, A. Altersolanol-related compounds from the culture liquid of Alternaria solani. Phytochemistry 1996, 42 (1), 77-80, DOI: 10.1016/0031-9422(95)00861-6
74.Suemitsu, R.; Yamamoto, T.; Miyai, T.; Ueshima, T. Alterporriol A: A modified bianthraquinone from Alternaria porri. Phytochemistry 1987, 26 (12), 3221-3224, DOI: 10.1016/S0031-9422(00)82473-5
75.Suemitsu, R.; Sano, T.; Yamamoto, M.; Arimoto, Y.; Morimatsu, F.; Nabeshima, T. Structural elucidation of alterporriol B, a novel metabolic pigment produced by Alternaria porri (Ellis) Ciferri. Agric. Biol. Chem. 1984, 48 (10), 2611-2613, DOI: 10.1271/bbb1961.48.2611
76.Suemitsu, R.; Ueshima, T.; Yamamoto, T.; Yanagawase, S. Alterporriol C: A modified bianthraquinone from Alternaria porri. Phytochemistry 1988, 27 (10), 3251-3254, DOI: 10.1016/0031-9422(88)80036-0
77.Suemitsu, R.; Sakurai, Y.; Nakachi, K.; Miyoshi, I.; Kubota, M.; Ohnishi, K. Alterporriol D and E, modified bianthraquinones from Alternaria porri (Ellis) Ciferri. Agric. Biol. Chem. 1989, 53 (5), 1301-1304, DOI: 10.1080/00021369.1989.10869452
78.Liebermann, B.; Ihn, W.; Tresselt, D.; Baumann, E. Isolierung und strukturaufklärung von zwei cyclischen peptiden aus kulturfiltraten des pilzes Alternaria alternata. Z. Chem. 1987, 27 (5), 173-173, DOI: 10.1002/zfch.19870270505
79.Guo, D. L.; Zhao, M.; Xiao, S. J.; Xia, B.; Wan, B.; Gu, Y. C.; Ding, L. S.; Zhou, Y. Two new diketopiperazines and a new glucosyl sesterterpene from Alternaria alternata, an endophytic fungi from Ceratostigma griffithii. Phytochem. Lett. 2015, 14, 260-264, DOI: 10.1016/j.phytol.2015.10.024
80.Abdou, R.; Dawoud, M. Cytotoxic metabolites of Alternaria alternata, an endophyte of the medicinal plant Bidens bipinnata. Int. J. Pharm. Pharm. Sci. 2020, 12 (3), 42-48, DOI: 10.22159/ijpps.2020v12i3.36317
81.Liebermann, B.; Ihn, W.; Baumann, E.; Tresselt, D. Dihydrotentoxin and a related dipeptide produced by Alternaria alternata. Phytochemistry 1988, 27 (2), 357-359, DOI: 10.1016/0031-9422(88)83097-8
82.Kono, Y.; Gardner, J. M.; Takeuchi, S. Nonselective phytotoxins simultaneously produced with host-selective ACTG-toxins by a pathotype of Alternaria citri causing brown spot disease of mandarins. Agric. Biol. Chem. 1986, 50 (9), 2401-2403, DOI: 10.1080/00021369.1986.10867757
83.Suemitsu, R.; Ohnishi, K.; Nobuhara, T.; Horiuchi, M.; Horiuchi, K. Isolation and identification of tentoxin from Alternaria porri (Ellis) Ciferri. Agric. Biol. Chem. 1990, 54 (9), 2449-2450, DOI: 10.1271/bbb1961.54.2449
84.Suemitsu, R.; Horiuchi, K.; Horiuchi, M.; Hanabata, M. Detection of tentoxin by Alternaria solani, A. cucumerina, A. bataticola and A. japonica. Biosci., Biotechnol., Biochem. 1992, 56 (1), 139-139, DOI: 10.1271/bbb.56.139
85.Kim, M. Y.; Sohn, J. H.; Ahn, J. S.; Oh, H. Alternaramide, a cyclic depsipeptide from the marine-derived fungus Alternaria sp. SF-5016. J. Nat. Prod. 2009, 72 (11), 2065-2068, DOI: 10.1021/np900464p
86.Soledade, M.; Pedras, C.; Smith, K. C. Sinalexin, a phytoalexin from white mustard elicited by destruxin B and Alternaria brassicae. Phytochemistry 1997, 46 (5), 833-837, DOI: 10.1016/S0031-9422(97)00362-2
87.Buchwaldt, L.; Jensen, J. S. HPLC purification of destruxins produced by Alternaria brassicae in culture and leaves of Brassica napus. Phytochemistry 1991, 30 (7), 2311-2316, DOI: 10.1016/0031-9422(91)83638-2
88.Suemitsu, R.; Ohnishi, K.; Horiuchi, M.; Morikawa, Y.; Sakaki, Y.; Matsumoto, Y. Structure of porriolide, a new metabolite from Alternaria porri. Biosci., Biotechnol., Biochem. 1993, 57 (2), 334-335, DOI: 10.1271/bbb.57.334
89.Pang, X.; Lin, X.; Wang, P.; Zhou, X.; Yang, B.; Wang, J.; Liu, Y. Perylenequione derivatives with anticancer activities isolated from the marine sponge-derived fungus, Alternaria sp. SCSIO41014. Mar. Drugs 2018, 16 (8), 280, DOI: 10.3390/md16080280
90.Gamboa-Angulo, M. M.; Escalante-Erosa, F.; García-Sosa, K.; Alejos-González, F.; Delgado-Lamas, G.; Peña-Rodríguez, L. M. Natural zinniol derivatives from Alternaria tagetica. Isolation, synthesis, and structure-activity correlation. J. Agric. Food Chem. 2002, 50 (5), 1053-1058, DOI: 10.1021/jf010641t
91.Suemitsu, R.; Ohnishi, K.; Horiuchi, M.; Morikawa, Y. Isolation and identification of 6-(3′,3′-dimethylallyloxy)-4-methoxy-5-methylphthalide from Alternaria porri. Biosci., Biotechnol., Biochem. 1992, 56 (6), 986-986, DOI: 10.1271/bbb.56.986
92.Ichihara, A.; Tazaki, H.; Sakamura, S. The structure of zinnolide, a new phytotoxin from Alternaria solani. Agric. Biol. Chem. 1985, 49 (9), 2811-2812, DOI: 10.1271/bbb1961.49.2811
93.Suemitsu, R.; Ohnishi, K.; Morikawa, Y.; Ideguchi, I.; Uno, H. Porritoxinol, a phytotoxin of Alternaria porri. Phytochemistry 1994, 35 (3), 603-605, DOI: 10.1016/S0031-9422(00)90570-3
94.Zhao, S.; Tian, K.; Li, Y.; Ji, W.; Liu, F.; Khan, B.; Yan, W.; Ye, Y. Enantiomeric dibenzo-α-pyrone derivatives from Alternaria alternata ZHJG5 and their potential as agrochemicals. J. Agric. Food Chem. 2020, 68 (51), 15115-15122, DOI: 10.1021/acs.jafc.0c04106
95.Zhao, S.; Xiao, C.; Wang, J.; Tian, K.; Ji, W.; Yang, T.; Khan, B.; Qian, G.; Yan, W.; Ye, Y. Discovery of natural FabH inhibitors using an immobilized enzyme column and their antibacterial activity against Xanthomonas oryzae pv. oryzae. J. Agric. Food Chem. 2020, 68 (48), 14204-14211, DOI: 10.1021/acs.jafc.0c06363
96.Wang, Y.; Yang, M. H.; Wang, X. B.; Li, T. X.; Kong, L. Y. Bioactive metabolites from the endophytic fungus Alternaria alternata. Fitoterapia 2014, 99, 153-158, DOI: 10.1016/j.fitote.2014.09.015
97.Kono, Y.; Gardner, J. M.; Suzuki, Y.; Takeuchi, S. Plant pathotoxins from Alternaria citri: The minor ACRL toxins. Phytochemistry 1985, 24 (12), 2869-2874, DOI: 10.1016/0031-9422(85)80016-9
98.Gardner, J. M.; Kono, Y.; Tatum, J. H.; Suzuki, Y.; Takeuchi, S. Structure of the major component of ACRL-toxins, host-specific pathotoxic compounds produced by Alternaria citri. Agric. Biol. Chem. 1985, 49 (4), 1235-1238, DOI: 10.1080/00021369.1985.10866886
99.Tabuchi, H.; Oikawa, H.; Ichihara, A. Biosynthetic study of alternaric acid: isolation of plausible biosynthetic intermediates and origins of the hydrogen and oxygen atoms. J. Chem. Soc., Perkin Trans. 1 1994, (19), 2833-2839, DOI: 10.1039/P19940002833
100.Tabuchi, H.; Ichihara, A. Structures and stereochemistries of new compounds related to alternaric acid. J. Chem. Soc., Perkin Trans. 1 1994, (1), 125-133, DOI: 10.1039/P19940000125
101.Grove, J. F. 774. Alternaric acid. Part I. Purification and characterisation. J. Chem. Soc. 1952, (0), 4056-4059, DOI: 10.1039/JR9520004056
102.Brian, P. W.; Curtis, P. J.; Hemming, H. G.; Unwin, C. H.; Wright, J. M. Alternaric acid, a biologically active metabolic product of the fungus Alternaria solani. Nature 1949, 164 (4169), 534-534, DOI: 10.1038/164534a0
103.Liu, G.; Niu, S.; Liu, L. Alterchromanone A, one new chromanone derivative from the mangrove endophytic fungus Alternaria longipes. J. Antibiot. 2021, 74 (2), 152-155, DOI: 10.1038/s41429-020-00364-4
104.Bashyal, B. P.; Wijeratne, E. M. K.; Tillotson, J.; Arnold, A. E.; Chapman, E.; Gunatilaka, A. A. L. Chlorinated dehydrocurvularins and alterperylenepoxide A from Alternaria sp. AST0039, a fungal endophyte of Astragalus lentiginosus. J. Nat. Prod. 2017, 80 (2), 427-433, DOI: 10.1021/acs.jnatprod.6b00960
105.Liu, Y.; Li, Z.; Vederas, J. C. Biosynthetic incorporation of advanced precursors into dehydrocurvularin, a polyketide phytotoxin from Alternaria cinerariae. Tetrahedron 1998, 54 (52), 15937-15958, DOI: 10.1016/S0040-4020(98)01003-5
106.Arai, K.; Rawlings, B. J.; Yoshizawa, Y.; Vederas, J. C. Biosyntheses of antibiotic A26771B by Penicillium turbatum and dehydrocurvularin by Alternaria cinerariae: comparison of stereochemistry of polyketide and fatty acid enoyl thiol ester reductases. J. Am. Chem. Soc. 1989, 111 (9), 3391-3399, DOI: 10.1021/ja00191a042
107.Hyeon, S. B.; Ozaki, A.; Suzuki, A.; Tamura, S. Isolation of .ALPHA..BETA.-dehydrocurvularin and .BETA.-hydroxycurvularin from Alternaria tomato as sporulation-suppressing factors. Agric. Biol. Chem. 1976, 40 (8), 1663-1664, DOI: 10.1271/bbb1961.40.1663
108.Zhao, D. L.; Cao, F.; Wang, C. Y.; Yang, L. J.; Shi, T.; Wang, K. L.; Shao, C. L.; Wang, C. Y. Alternatone A, an unusual perylenequinone-related compound from a soft-coral-derived strain of the fungus Alternaria alternata. J. Nat. Prod. 2019, 82 (11), 3201-3204, DOI: 10.1021/acs.jnatprod.9b00905
109.Zhao, D. L.; Wang, D.; Tian, X. Y.; Cao, F.; Li, Y. Q.; Zhang, C. S. Anti-phytopathogenic and cytotoxic activities of crude extracts and secondary metabolites of marine-derived fungi. Mar. Drugs 2018, 16 (1), 36, DOI: 10.3390/md16010036
110.Idris, A.; Tantry, M. A.; Ganai, B. A.; Kamili, A. N.; Williamson, J. S. Reduced perylenequinone derivatives from an endophytic Alternaria sp. isolated from Pinus ponderosa. Phytochem. Lett. 2015, 11, 264-269, DOI: 10.1016/j.phytol.2015.01.008
111.Hradil, C. M.; Hallock, Y. F.; Clardy, J.; Kenfield, D. S.; Strobel, G. Phytotoxins from Alternaria cassiae. Phytochemistry 1989, 28 (1), 73-75, DOI: 10.1016/0031-9422(89)85011-3
112.Okuno, T.; Natsume, I.; Sawai, K.; Sawamura, K.; Furusaki, A.; Matsumoto, T. Structure of antifungal and phytotoxic pigments produced by Alternaria sps. Tetrahedron Lett. 1983, 24 (50), 5653-5656, DOI: 10.1016/S0040-4039(00)94165-0
113.Lee, C.; Li, W.; Bang, S.; Lee, S. J.; Kang, N. y.; Kim, S.; Kim, T. I.; Go, Y.; Shim, S. H. Secondary metabolites of the endophytic fungus Alternaria alternata JS0515 isolated from Vitex rotundifolia and their effects on pyruvate dehydrogenase activity. Molecules 2019, 24 (24), 4450, DOI: 10.3390/molecules24244450
114.Kjer, J.; Wray, V.; Edrada-Ebel, R.; Ebel, R.; Pretsch, A.; Lin, W.; Proksch, P. Xanalteric acids I and II and related phenolic compounds from an endophytic Alternaria sp. isolated from the mangrove plant Sonneratia alba. J. Nat. Prod. 2009, 72 (11), 2053-2057, DOI: 10.1021/np900417g
115.Stinson, E. E.; Osman, S. F.; Pfeffer, P. E. Structure of altertoxin I, a mycotoxin from Alternaria. J. Org. Chem 1982, 47 (21), 4110-4113, DOI: 10.1021/jo00142a020
116.Bashyal, B. P.; Wellensiek, B. P.; Ramakrishnan, R.; Faeth, S. H.; Ahmad, N.; Gunatilaka, A. A. L. Altertoxins with potent anti-HIV activity from Alternaria tenuissima QUE1Se, a fungal endophyte of Quercus emoryi. Bioorg. Med. Chem. 2014, 22 (21), 6112-6116, DOI: 10.1016/j.bmc.2014.08.039
117.Wu, W. B.; Yue, G. C.; Huang, Q. L.; Sun, L. L.; Zhang, W. A new compound from an endophytic fungus Alternaria tenuissima. J. Asian Nat. Prod. Res. 2014, 16 (7), 777-782, DOI: 10.1080/10286020.2014.896343
118.Kong, F. D.; Yi, T. F.; Ma, Q. Y.; Xie, Q. Y.; Zhou, L. M.; Chen, J. P.; Dai, H. F.; Wu, Y. G.; Zhao, Y. X. Biphenyl metabolites from the patchouli endophytic fungus Alternaria sp. PfuH1. Fitoterapia 2020, 146, 104708, DOI: 10.1016/j.fitote.2020.104708
119.Hou, Z.; Sun, C.; Chen, X.; Zhang, G.; Che, Q.; Li, D.; Zhu, T. Xanalterate A, altertoxin VIII and IX, perylenequinone derivatives from antarctica-sponge-derived fungus Alternaria sp. HDN19-690. Tetrahedron Lett. 2022, 96, 153778, DOI: 10.1016/j.tetlet.2022.153778
120.Tantry, M. A.; Idris, A. S.; Williamson, J. S.; Shafi, T.; Dar, J. S.; Malik, T. A.; Ganai, B. A.; Shawl, A. S. Perylenequinones from an endophytic Alternaria sp. of Pinus ponderosa. Heliyon 2018, 4 (12), e01046, DOI: 10.1016/j.heliyon.2018.e01046
121.Stierle, A. C.; Caddlina, J. H.; Strobel, G. A. Phytotoxins from Alternaria alternata, A Pathogen of spotted knapweed. J. Nat. Prod. 1989, 52 (1), 42-47, DOI: 10.1021/np50061a003
122.Robeson, D.; Strobel, G.; Matusumoto, G. K.; Fisher, E. L.; Chen, M. H.; Clardy, J. Alteichin: an unusual phytotoxin from Alternaria eichorniae, a fungal pathogen of water hyacinth. Experientia 1984, 40 (11), 1248-1250, DOI: 10.1007/BF01946657
123.Stack, M. E.; Mazzola, E. P. Stemphyltoxin III from Altenaria alternata. J. Nat. Prod. 1989, 52 (2), 426-427, DOI: 10.1021/np50062a042
124.Chagas, F. O.; Dias, L. G.; Pupo, M. T. New perylenequinone derivatives from the endophytic fungus Alternaria tenuissima SS77. Tetrahedron Lett. 2016, 57 (29), 3185-3189, DOI: 10.1016/j.tetlet.2016.06.035
125.Zhang, S. Y.; Li, Z. L.; Bai, J.; Wang, Y.; Zhang, L. M.; Wu, X.; Hua, H. M. A new perylenequinone from a halotolerant fungus, Alternaria sp. M6. Chin. J. Nat. Med. 2012, 10 (1), 68-71, DOI: 10.1016/S1875-5364(12)60015-6
126.Gamboa-Angulo, M. M.; García-Sosa, K.; Alejos-González, F.; Escalante-Erosa, F.; Delgado-Lamas, G.; Peña-Rodríguez, L. M. Tagetolone and tagetenolone:  Two phytotoxic polyketides from Alternaria tagetica. J. Agric. Food Chem. 2001, 49 (3), 1228-1232, DOI: 10.1021/jf000872k
127.Noboru, S.; Choji, K.; Makoto, Y.; Ryotaro, M. Altenin, a new phytopathologically-toxic metabolite from Alternaria Kikuchiana. Bull. Chem. Soc. Jpn. 1965, 38 (11), 2028-2028, DOI: 10.1246/bcsj.38.2028
128.Stoessl, A.; Stothers, J. B. 2-Epi- and 15-dihydro-2-epilubimin: new stress compounds from the potato. Can. J. Chem. 1980, 58 (19), 2069-2072, DOI: 10.1139/v80-329
129.He, J. W.; Chen, G. D.; Gao, H.; Yang, F.; Li, X. X.; Peng, T.; Guo, L. D.; Yao, X. S. Heptaketides with antiviral activity from three endolichenic fungal strains Nigrospora sp., Alternaria sp. and Phialophora sp. Fitoterapia 2012, 83 (6), 1087-1091, DOI: 10.1016/j.fitote.2012.05.002
130.Ai, H. L.; Zhang, L. M.; Chen, Y. P.; Zi, S. H.; Xiang, H.; Zhao, D. K.; Shen, Y. Two new compounds from an endophytic fungus Alternaria solani. J. Asian Nat. Prod. Res. 2012, 14 (12), 1144-1148, DOI: 10.1080/10286020.2012.733701
131.Crocoll, C.; Kettner, J.; Dörffling, K. Abscisic acid in saprophytic and parasitic species of fungi. Phytochemistry 1991, 30 (4), 1059-1060, DOI: 10.1016/S0031-9422(00)95171-9
132.Dahiya, J. S.; Tewari, J. P.; Woods, D. L. Abscisic acid from Alternaria brassicae. Phytochemistry 1988, 27 (9), 2983-2984, DOI: 10.1016/0031-9422(88)80702-7
133.Robeson, D. J.; Strobel, G. A. Zinniol induces chlorophyll retention in barley leaves: the selective action of a non host-specific phytotoxin. Phytochemistry 1984, 23 (8), 1597-1599, DOI: 10.1016/S0031-9422(00)83447-0
134.Gamboa-Angulo, M. M.; Alejos-González, F.; Escalante-Erosa, F.; García-Sosa, K.; Delgado-Lamas, G.; Peña-Rodríguez, L. M. Novel dimeric metabolites from Alternaria tagetica. J. Nat. Prod. 2000, 63 (8), 1117-1120, DOI: 10.1021/np990422q
135.Stoessl, A.; Unwin, C. H.; Stothers, J. B. On the biosynthesis of some polyketide metabolites in Alternaria solani: 13C and 2Hmr studies. Can. J. Chem. 1983, 61 (2), 372-377, DOI: 10.1139/v83-067
136.Xu, X.; Zhao, S.; Wei, J.; Fang, N.; Yin, L.; Sun, J. Porric acid D from marine-derived fungus Alternaria sp. isolated from Bohai Sea. Chem. Nat. Compd. 2012, 47 (6), 893-895, DOI: 10.1007/s10600-012-0097-4
137.Kameda, K.; Aoki, H.; Namiki, M.; Overeem, J. C. An alternative structure for botrallin a metabolite of Botrytis allii. Tetrahedron Lett. 1974, 15 (1), 103-106, DOI: 10.1016/S0040-4039(01)82147-X
138.Berestetskiy, A.; Cimmino, A.; Sofronova, J.; Dalinova, A.; Avolio, F.; Evidente, M.; Chisty, L.; Krivorotov, D.; Evidente, A. Alternethanoxins C–E, further polycyclic ethanones produced by Alternaria sonchi, a potential mycoherbicide for Sonchus arvensis Biocontrol. J. Agric. Food Chem. 2015, 63 (4), 1196-1199, DOI: 10.1021/jf5054595
139.Evidente, A.; Punzo, B.; Andolfi, A.; Berestetskiy, A.; Motta, A. Alternethanoxins A and B, polycyclic ethanones produced by Alternaria sonchi, potential mycoherbicides for Sonchus arvensis biocontrol. J. Agric. Food Chem. 2009, 57 (15), 6656-6660, DOI: 10.1021/jf9014944
140.Gardner, J. M.; Kono, Y.; Tatum, J. H.; Suzuki, Y.; Takeuchi, S. Plant pathotoxins from Alternaria citri: The major toxin specific for rough lemon plants. Phytochemistry 1985, 24 (12), 2861-2867, DOI: 10.1016/0031-9422(85)80015-7
141.Kono, Y.; Gardner, J. M.; Takeuchi, S. Structure of the host-selective toxins produced by a pathotype of Alternaria citri causing brown spot disease of mandarins. Agric. Biol. Chem. 1986, 50 (3), 801-804, DOI: 10.1271/bbb1961.50.801
142.Kono, Y.; Gardner, J. M.; Suzuki, Y.; Takeuchi, S. Studies on host-selective toxins produced by a pathotype of Alternaria citri causing brown spot disease of mandarins. Agric. Biol. Chem. 1986, 50 (6), 1597-1606, DOI: 10.1080/00021369.1986.10867585
143.Zhang, G.; Wu, G.; Zhu, T.; Kurtán, T.; Mándi, A.; Jiao, J.; Li, J.; Qi, X.; Gu, Q.; Li, D. Meroterpenoids with diverse ring systems from the sponge-associated fungus Alternaria sp. JJY-32. J. Nat. Prod. 2013, 76 (10), 1946-1957, DOI: 10.1021/np4005757
144.Kodoma, M.; Wada, H.; Otani, H.; Kohmoto, K.; Kimura, Y. 3,5-Di-O-caffeoylquinic acid, an infection-inhibiting factor from Pyrus pyrifolia induced by infection with Alternaria alternata. Phytochemistry 1998, 47 (3), 371-373, DOI: 10.1016/S0031-9422(97)00621-3
145.Oikawa, H.; Matsuda, I.; Kagawa, T.; Ichihara, A.; Kohmoto, K. Absolute configuration of main chain of AAL-toxins. Tetrahedron 1994, 50 (47), 13347-13368, DOI: 10.1016/S0040-4020(01)89343-1
146.Tal, B.; Robeson, D. J.; Burke, B. A.; Aasen, A. J. Phytotoxins from Alternaria helianthi: radicinin, and the structures of deoxyradicinol and radianthin. Phytochemistry 1985, 24 (4), 729-731, DOI: 10.1016/S0031-9422(00)84885-2
147.Robeson, D. J.; Strobel, G. A. Deoxyradicinin, a novel phytotoxin from Alternaria helianthi. Phytochemistry 1982, 21 (7), 1821-1823, DOI: 10.1016/S0031-9422(82)85081-4
148.Chen, Q. F.; Zhou, M.; Yang, T.; Chen, X. Z.; Wang, C.; Zhang, G. L.; Li, G. Y. Secondary metabolites from fungus Alternaria sp. CIB 108. Chin. Chem. Lett. 2011, 22 (10), 1226-1228, DOI: 10.1016/j.cclet.2011.05.036
149.Clarke, D. D.; Nord, F. F. Radicinin: A new pigment from Stemphylium radicinum. Arch. Biochem. Biophys. 1953, 45 (2), 469-470, DOI: 10.1016/S0003-9861(53)80025-1
150.Robeson, D. J.; Strobel, G. A. 3-Epideoxyradicinol and the biosynthesis of deoxyradicinin. Phytochemistry 1984, 23 (4), 767-768, DOI: 10.1016/S0031-9422(00)85021-9
151.Robeson, D. J.; Gray, G. R.; Strobel, G. A. Production of the phytotoxins radicinin and radicinol by Alternaria chrysanthemi. Phytochemistry 1982, 21 (9), 2359-2362, DOI: 10.1016/0031-9422(82)85205-9
152.Sheridan, H.; Canning, A. M. Novel radicinol derivatives from long-term cultures of Alternaria chrysanthemi. J. Nat. Prod. 1999, 62 (11), 1568-1569, DOI: 10.1021/np990154w
153.Solfrizzo, M.; Vitti, C.; De Girolamo, A.; Visconti, A.; Logrieco, A.; Fanizzi, F. P. Radicinols and radicinin phytotoxins produced by Alternaria radicina on carrots. J. Agric. Food Chem. 2004, 52 (11), 3655-3660, DOI: 10.1021/jf035254t
154.Kimura, Y.; Mizuno, T.; Nakajima, H.; Hamasaki, T. Altechromones A and B, new plant growth regulators produced by the fungus, Alternaria sp. Biosci., Biotechnol., Biochem. 1992, 56 (10), 1664-1665, DOI: 10.1271/bbb.56.1664
155.Christensen, K. B.; Van Klink, J. W.; Weavers, R. T.; Larsen, T. O.; Andersen, B.; Phipps, R. K. Novel chemotaxonomic markers of the Alternaria infectoria species-group. J. Agric. Food Chem. 2005, 53 (24), 9431-9435, DOI: 10.1021/jf0513213
156.Pedras, M. S. C.; Chumala, P. B.; Jin, W.; Islam, M. S.; Hauck, D. W. The phytopathogenic fungus Alternaria brassicicola: Phytotoxin production and phytoalexin elicitation. Phytochemistry 2009, 70 (3), 394-402, DOI: 10.1016/j.phytochem.2009.01.005
157.Ostenfeld-Larsen, T.; Perry, N. B.; Andersen, B. Infectopyrone, a potential mycotoxin from Alternaria infectoria. Tetrahedron Lett. 2003, 44 (24), 4511-4513, DOI: 10.1016/S0040-4039(03)01018-9
158.Tang, J.; Huang, L.; Liu, Y.; Toshmatov, Z.; Zhang, C.; Shao, H. Two phytotoxins isolated from the pathogenic fungus of the invasive weed Xanthium italicum. Chem. Biodivers. 2020, 17 (4), e2000043, DOI: 10.1002/cbdv.202000043
159.Wang, X. Z.; Luo, X. H.; Xiao, J.; Zhai, M. M.; Yuan, Y.; Zhu, Y.; Crews, P.; Yuan, C. S.; Wu, Q. X. Pyrone derivatives from the endophytic fungus Alternaria tenuissima SP-07 of Chinese herbal medicine Salvia przewalskii. Fitoterapia 2014, 99, 184-190, DOI: 10.1016/j.fitote.2014.09.017
160.Gatenbeck, S.; Hermodsson, S. Enzymic synthesis of the aromatic product alternariol. Acta Chem. Scand. 1965, 19, 65-71, DOI: 10.3891/acta.chem.scand.19-0065
161.Thomas, R. Studies in the biosynthesis of fungal metabolites. 4. Alternariol monomethyl ether and its relation to other phenolic metabolites of Alternaria tenuis. Biochem. J. 1961, 80 (2), 234-240, DOI: 10.1042/bj0800234
162.Carter, A. C.; King, J. B.; Mattes, A. O.; Cai, S.; Singh, N.; Cichewicz, R. H. Natural-product-inspired compounds as countermeasures against the liver carcinogen aflatoxin B1. J. Nat. Prod. 2019, 82 (6), 1694-1703, DOI: 10.1021/acs.jnatprod.9b00290
163.Bradburn, N.; Coker, R. D.; Blunden, G.; Turner, C. H.; Crabb, T. A. 5′-Epialtenuene and neoaltenuene, dibenzo-α-pyrones from Alternaria alternata cultured on rice. Phytochemistry 1994, 35 (3), 665-669, DOI: 10.1016/S0031-9422(00)90583-1
164.Chadwick, D. J.; Easton, I. W.; Johnstone, R. A. W. Fungal metabolites Part 9. Isolation and X-Ray structure determination of alternarian acid from Alternaria mali Sp. Tetrahedron 1984, 40 (13), 2451-2455, DOI: 10.1016/S0040-4020(01)83496-7
165.Ichihara, A.; Tazaki, H.; Sakamura, S. Solanapyrones A, B and C, phytotoxic metabolites from the fungus Alternaria solani. Tetrahedron Lett. 1983, 24 (48), 5373-5376, DOI: 10.1016/S0040-4039(00)87872-7
166.Oikawa, H.; Yokota, T.; Sakano, C.; Suzuki, Y.; Naya, A.; Ichihara, A. Solanapyrones, phytotoxins produced by Alternaria solani: Biosynthesis and isolation of minor components. Biosci., Biotechnol., Biochem. 1998, 62 (10), 2016-2022, DOI: 10.1271/bbb.62.2016
167.Ichihara, A.; Miki, M.; Sakamura, S. Absolute configuration of (−)-solanapyrone A. Tetrahedron Lett. 1985, 26 (20), 2453-2454, DOI: 10.1016/S0040-4039(00)94851-2
168.Tang, J. W.; Xu, H. C.; Wang, W. G.; Hu, K.; Zhou, Y. F.; Chen, R.; Li, X. N.; Du, X.; Sun, H. D.; Puno, P. T. (+)- and (−)-Alternarilactone A: Enantiomers with a diepoxy-cage-like scaffold from an endophytic Alternaria sp. J. Nat. Prod. 2019, 82 (4), 735-740, DOI: 10.1021/acs.jnatprod.8b00571
169.Starratt, A. N. Sterols of Alternaria kikuchiana. Phytochemistry 1976, 15 (12), 2002-2003, DOI: 10.1016/S0031-9422(00)88878-0
170.Yuan, L.; Zhao, P. J.; Ma, J.; Li, G. H.; Shen, Y. M. Tricycloalternarenes A – E: Five new mixed terpenoids from the endophytic fungal strain Alternaria alternata Ly83. Helv. Chim. Acta 2008, 91 (8), 1588-1594, DOI: 10.1002/hlca.200890172
171.Wang, L.; Jiao, J.; Liu, D.; Zhang, X.; Li, J.; Che, Q.; Zhu, T.; Zhang, G.; Li, D. Cytotoxic meroterpenoids from the fungus Alternaria sp. JJY-32. Chem. Biodivers. 2020, 17 (7), e2000226, DOI: 10.1002/cbdv.202000226
172.Liebermann, B.; Ellinger, R.; Günther, W.; Ihn, W.; Gallander, H. Tricycloalternarenes produced by Alternaria alternata related to ACTG-toxins. Phytochemistry 1997, 46 (2), 297-303, DOI: 10.1016/S0031-9422(97)00278-1
173.Nussbaum, R. P.; Günther, W.; Heinze, S.; Liebermann, B. New tricycloalternarenes produced by the phytopathogenic fungus Alternaria alternata. Phytochemistry 1999, 52 (4), 593-599, DOI: 10.1016/S0031-9422(99)00275-7
174.Li, F.; Lin, S.; Zhang, S.; Pan, L.; Chai, C.; Su, J. C.; Yang, B.; Liu, J.; Wang, J.; Hu, Z.; Zhang, Y. Modified fusicoccane-type diterpenoids from Alternaria brassicicola. J. Nat. Prod. 2020, 83 (6), 1931-1938, DOI: 10.1021/acs.jnatprod.0c00165
175.Shi, Z. Z.; Yin, X. L.; Fang, S. T.; Miao, F. P.; Ji, N. Y. Two new isomeric tricycloalternarenes from the marine alga-epiphytic fungus Alternaria alternata k23-3. Magn. Reson. Chem. 2018, 56 (3), 210-215, DOI: 10.1002/mrc.4676
176.Liebermann, B.; Nussbaum, R. P.; Günther, W. Bicycloalternarenes produced by the phytopathogenic fungus Alternaria alternata. Phytochemistry 2000, 55 (8), 987-992, DOI: 10.1016/S0031-9422(00)00268-5
177.MacKinnon, S. L.; Keifer, P.; Ayer, W. A. Components from the phytotoxic extract of Alternaria brassicicola, a black spot pathogen of canola. Phytochemistry 1999, 51 (2), 215-221, DOI: 10.1016/S0031-9422(98)00732-8
178.Minami, A.; Tajima, N.; Higuchi, Y.; Toyomasu, T.; Sassa, T.; Kato, N.; Dairi, T. Identification and functional analysis of brassicicene C biosynthetic gene cluster in Alternaria brassicicola. Bioorg. Med. Chem. Lett. 2009, 19 (3), 870-874, DOI: 10.1016/j.bmcl.2008.11.108
179.Oikawa, H.; Suzuki, Y.; Naya, A.; Katayama, K.; Ichihara, A. First direct evidence in biological diels-alder reaction of incorporation of diene-dienophile precursors in the biosynthesis of solanapyrones. J. Am. Chem. Soc. 1994, 116 (8), 3605-3606, DOI: 10.1021/ja00087a059
180.Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Petersson, G. A.; Nakatsuji, H.; Li, X.; Caricato, M.; Marenich, A. V.; Bloino, J.; Janesko, B. G.; Gomperts, R.; Mennucci, B.; Hratchian, H. P.; Ortiz, J. V.; Izmaylov, A. F.; Sonnenberg, J. L.; Williams; Ding, F.; Lipparini, F.; Egidi, F.; Goings, J.; Peng, B.; Petrone, A.; Henderson, T.; Ranasinghe, D.; Zakrzewski, V. G.; Gao, J.; Rega, N.; Zheng, G.; Liang, W.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Throssell, K.; Montgomery Jr., J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M. J.; Heyd, J. J.; Brothers, E. N.; Kudin, K. N.; Staroverov, V. N.; Keith, T. A.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A. P.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Millam, J. M.; Klene, M.; Adamo, C.; Cammi, R.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Farkas, O.; Foresman, J. B.; Fox, D. J. Gaussian 16 Rev. C.01, Wallingford, CT, 2016.
181.Zheng, C. J.; Fu, X. M.; Zhang, X. L.; Kong, W. W.; Wang, C. Y. Bioactive perylene derivatives from a soft coral-derived fungus Alternaria sp. (ZJ-2008017). Chem. Nat. Compd. 2015, 51 (4), 766-768, DOI: 10.1007/s10600-015-1406-5
182.Arnone, A.; Nasini, G.; Merlini, L.; Assante, G. Secondary mould metabolites. Part 16. Stemphyltoxins, new reduced perylenequinone metabolites from Stemphylium botryosum var. Lactucum. J. Chem. Soc., Perkin Trans. 1 1986, (0), 525-530, DOI: 10.1039/P19860000525
183.Sternhell, S. Correlation of interproton spin–spin coupling constants with structure. Chem. Soc. Rev. 1969, 23 (2), 236-270, DOI: 10.1039/QR9692300236
184.Rabideau, P. W.; Paschal, J. W.; Marshall, J. L. Conformational analysis of cyclohexa-1,4-dienes by nuclear magnetic resonance. J. Chem. Soc., Perkin Trans. 2 1977, (6), 842-844, DOI: 10.1039/P29770000842
185.Grossel, M. C.; Perkins, M. J. Proton nuclear magnetic resonance spectra and conformation in 1,4-dihydrobenzenes and 9,10-dihydroanthracenes. J. Chem. Soc., Perkin Trans. 2 1975, (14), 1544-1549, DOI: 10.1039/P29750001544
186.Grossel, M. C.; Hayward, R. C. Homoallylic coupling in 1,4-dihydronaphthalenes. J. Chem. Soc., Perkin Trans. 2 1976, (7), 851-854, DOI: 10.1039/P29760000851
187.Kurz, M.; Herrmann, M.; Toti, L.; Vertesy, L. Hydroperylene derivatives, and production thereof, for the treatment of platelet aggregation-associated disease. WO 03/045905 Al, 2003.
188.Krohn, K.; Biele, C.; Aust, H.-J.; Draeger, S.; Schulz, B. Herbarulide, a ketodivinyllactone steroid with an unprecedented homo-6-oxaergostane skeleton from the endophytic fungus Pleospora herbarum. J. Nat. Prod. 1999, 62 (4), 629-630, DOI: 10.1021/np980422a
189.Schobert, R.; Jagusch, C.; Melanophy, C.; Mullen, G. Synthesis and reactions of polymer-bound Ph3P=C=C=O: a quick route to tenuazonic acid and other optically pure 5-substituted tetramates. Org. Biomol. Chem. 2004, 2 (23), 3524-3529, DOI: 10.1039/B412779J
190.Poncet, J.; Jouin, P.; Castro, B.; Nicolas, L.; Boutar, M.; Gaudemer, A. Tetramic acid chemistry. Part 1. Reinvestigation of racemisation during the synthesis of tetramic acids via Dieckmann cyclisation. J. Chem. Soc., Perkin Trans. 1 1990, (3), 611-616, DOI: 10.1039/P19900000611
191.Hu, J.; Sarrami, F.; Li, H.; Zhang, G.; Stubbs, K. A.; Lacey, E.; Stewart, S. G.; Karton, A.; Piggott, Andrew M.; Chooi, Y.-H. Heterologous biosynthesis of elsinochrome A sheds light on the formation of the photosensitive perylenequinone system. Chem. Sci. 2019, 10 (5), 1457-1465, DOI: 10.1039/C8SC02870B
192.Gao, J.; Wenderoth, M.; Doppler, M.; Schuhmacher, R.; Marko, D.; Fischer, R.; Pietro, A. D. Fungal melanin biosynthesis pathway as source for fungal toxins. mBio 2022, 13 (3), e00219-22, DOI: 10.1128/mbio.00219-22
193.Khiralla, A.; Mohammed, A. O.; Yagi, S. Fungal perylenequinones. Mycol. Prog. 2022, 21 (3), 38, DOI: 10.1007/s11557-022-01790-4
194.Weiss, U.; Merlini, L.; Nasini, G., Naturally occurring perylenequinones. In Fortschritte der chemie organischer naturstoffe / Progress in the chemistry of organic natural products, Springer Vienna: Vienna, 1987; Vol. 70, pp 1-71, ISBN: 9783709189061
195.Ubuka, T.; Ohta, J.; Akagi, R.; Hosaki, Y.; Ishimoto, Y.; Kiguchi, S.; Ikeda, T.; Ishino, K. Metabolism of L-cysteine via transamination pathway (3-mercaptopyruvate pathway). Amino Acids 1992, 3 (3), 243-252, DOI: 10.1007/BF00805999
196.Wróbel, M.; Ubuka, T.; Yao, W. B.; Abe, T. L-cysteine metabolism in guinea pig and rat tissues. Comp. Biochem. Physiol. Part B: Biochem. Mol. Biol. 1997, 116 (2), 223-226, DOI: 10.1016/S0305-0491(96)00216-7
197.Kim, M. J.; Whitesides, G. M. L-Lactate dehydrogenase: substrate specificity and use as a catalyst in the synthesis of homochiral 2-hydroxy acids. J. Am. Chem. Soc. 1988, 110 (9), 2959-2964, DOI: 10.1021/ja00217a044
198.Adelin, E.; Martin, M. T.; Bricot, M. F.; Cortial, S.; Retailleau, P.; Ouazzani, J. Biotransformation of natural compounds: Unexpected thio conjugation of Sch-642305 with 3-mercaptolactate catalyzed by Aspergillus niger ATCC 16404 cells. Phytochemistry 2012, 84, 135-140, DOI: 10.1016/j.phytochem.2012.08.002
199.Sonaimuthu, V.; Parihar, S.; Thankur, J. P.; Luqman, S.; Saikia, D.; Chanotiya, C. S.; Jhonpaul, M.; Singh Negi, A. Tenuazonic acid: a promising antitubercular principle from Alternaria alternata. Microbiol. Res. 2011, 2 (2), 63-65, DOI: 10.4081/mr.2011.e17
200.Griffin, G. F.; Chu, F. S. Toxicity of the Alternaria metabolites alternariol, alternariol methyl ether, altenuene, and tenuazonic acid in the chicken embryo assay. Appl. Environ. Microbiol. 1983, 46 (6), 1420-1422, DOI: 10.1128/aem.46.6.1420-1422.1983
201.Zhang, H.; Bai, X.; Wang, H. Isolation and identification of an antimicrobial and cytotoxic chlorated perylenequinone from the symbiotic fungus Aspergillus fumigatus D. Biochem. Pharmacol. 2017, 139, 110, DOI: 10.1016/j.bcp.2017.06.066
202.Lou, J.; Fu, L.; Peng, Y.; Zhou, L. Metabolites from Alternaria Fungi and their bioactivities. Molecules 2013, 18 (5), 5891-5935, DOI: 10.3390/molecules18055891
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