Abstract
Chrysogenamide A (1), a new member of the macfortine group of alkaloids, along with four known compounds (2~5) were identified from Penicillium chrysogenum No. 005, an endophytic fungus associated with Cistanche deserticola Y. C. Ma. The new structure was elucidated on the basis of comprehensive spectral analysis. 1 exhibited a neurocyte protection effect against oxidative stress-induced cell death in SH-SY5Y cells.
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Li LL, Wang XW, Wang XF . Antilipid peroxidation and antiradiative action of glycosides in herba Cistanches. China J Chin Mater Med 22: 364–367 ( 1997)
Xie JH, Wu CF . Effect of ethanolic extract of Cistanche deserticola on the contents of monoamine neurotransmitters in rat brain. Chin Trad Herb Drugs 24: 417–419 ( 1993)
Dai JR, Carte BK, Sidebottom PJ, Yew ALS, Ng SB, Huang Y, Butler MS . Circumdatin G, a new alkaloid from the fungus Aspergillus ochraceus. J Nat Prod 64: 125–126 ( 2001)
Kettering M, Sterner O, Anke T . Antibiotics in the chemical communication of fungi. Zeitschrift fuer Naturforschung, C: Journal of Biosciences 59: 816–823 ( 2004)
Trifonov LS, Bieri JH, Prewo R, Dreiding AS, Hoesch L, Rast DM . Isolation and structure elucidation of three metabolites from Verticillium intertextum: sorbicillin, dihydrosorbicillin and bisvertinoquinol. Tetrahedron 39: 4243–4256 ( 1983)
Zhang GL, Xing QY, Zhang MZ . Glycolipids from Mirabilis himalaica. Phytochemistry 45: 1213–1215 ( 1997)
Polonsky J, Merrien MA, Prange T, Pascard C, Moreau S . Isolation and structure (X-ray analysis) of marcfortine A, a new alkaloid from Penicillium roqueforti. J C S Chem Comm 13: 601–602 ( 1980)
Lee BH, Kornis GI, Cialdella JI, Clothier MF, Marshall VP, Martin DG, McNally PL, Mizsak SA, Whaley HA, Wiley VH . Microbiological hydroxylation at six individual carbon atoms of marcfortine A. J Nat Prod 60: 1139–1142 ( 1997)
Whyte AC, Gloer JB, Wicklow DT, Dowd PF . Sclerotiamide: A new member of the paraherquamide class with potent antiinsectan activity from the sclerotia of Aspergillus sclerotiorum. J Nat Prod 59: 1093–1095 ( 1996)
Kato H, Yoshida T, Tokue T, Nojiri Y, Hirota H, Ohta T, Williams RM, Tsukamoto S . Notoamides A~D: prenylated indole alkaloids isolated from a marine-derived fungus, Aspergillus sp. Angew Chem Int Ed 46: 2254–2256 ( 2007)
Williams RM, Kwast E, Coffman H, Glinka T . Remarkable, enantio-divergent biogenesis of brevianamide A and B. J Am Chem Soc 111: 3064–3065 ( 1989)
Banks RM, Blanchflower SE, Everett JR, Manger BR, Reading C . Novel anthelmintic metabolites from an Aspergillus species: the aspergillimides. J Antibiot 50: 840–846 ( 1997)
Qian-Cutrone J, Haung S, Shu YZ, Vyas D, Fairchild C, Menendez A, Krampitz K, Dalterio R, Klohr SE, Gao Q . Stephacidin A and B: Two structurally novel, selective inhibitors of the testosterone-dependent prostate LNCaP cells. J Am Chem Soc 124: 14556–14557 ( 2002)
Wilson BJ, Yang DTC, Harris TM . Production, isolation, and preliminary toxicity studies of brevianamide A from cultures of Penicillium Viridicatum. Appl Microbiol 26: 633–635 ( 1973)
Birch AJ, Russell RA . Studies in relation to biosynthesiss XLIV. Structural elucidations of brevianamides B, C, D and F. Tetrahedron 28: 2999–3008 ( 1972)
Liesch JM, Wichmann CF . Novel antinematodal and antiparasitic agents from Penicillium charlesii. II. Structure determination of paraherquamides B, C, D, E, F, and G. J Antibiot 43: 1380–1386 ( 1990)
Martinez-Luis S, Rodriguez R, Acevedo L, Gonzalez MC, Lira-Rocha A, Mata R . Malbrancheamide, a new calmodulin inhibitor from the fungus Malbranchea aurantiaca. Tetrahedron 62: 1817–1822 ( 2006)
Mugishima T, Tsuda M, Kasa Y, Ishiyama H, Fukushi E, Kawabata J, Watanabe M, Akao K, Kobayashi J . Absolute stereochemistry of citrinadins A and B from marine-derived fungus. J Org Chem 70: 9430–9435 ( 2005)
Lopez-Gresa MP, Gonzalez MC, Ciavatta L, Ayala I, Moya P, Primo J . Insecticidal activity of paraherquamides, paraherquamides, including paraherquamide H and paraherquamide I, Two New Alkaloids Isolated from Penicillium cluniae. J Agric Food Chem 54: 2921–2925 ( 2006)
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Lin, Z., Wen, J., Zhu, T. et al. Chrysogenamide A from an Endophytic Fungus Associated with Cistanche deserticola and Its Neuroprotective Effect on SH-SY5Y Cells. J Antibiot 61, 81–85 (2008). https://doi.org/10.1038/ja.2008.114
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DOI: https://doi.org/10.1038/ja.2008.114
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