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.
Similar content being viewed by others
Log in or create a free account to read this content
Gain free access to this article, as well as selected content from this journal and more on nature.com
or
References
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)
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
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
Received:
Accepted:
Issue date:
DOI: https://doi.org/10.1038/ja.2008.114
Keywords
This article is cited by
-
Bioactive compounds and biomedical applications of endophytic fungi: a recent review
Microbial Cell Factories (2023)
-
Structural basis of the stereoselective formation of the spirooxindole ring in the biosynthesis of citrinadins
Nature Communications (2021)
-
Total synthesis of brevianamide A
Nature Chemistry (2020)
-
Endophytic Penicillium species and their agricultural, biotechnological, and pharmaceutical applications
3 Biotech (2020)
-
Antifungal potential of secondary metabolites involved in the interaction between citrus pathogens
Scientific Reports (2019)
