Physcion

ID 2: 497

Toxin: n

Trivial name:

Anthraquinone, 1,​8-​dihydroxy-​3-​methoxy-​6-​methyl- (8CI); Chrysophanic acid, 6-​methoxy- (4CI); 1,​8-​Dihydroxy-​3-​methoxy-​6-​methylanthraquinone; 1,​8-​Dihydroxy-​3-​methyl-​6-​methoxyanthraquinone; 1,​8-​Dihydroxy-​6-​methoxy-​3-​methyl anthraquinone; 6-​O-​Methylemodin; Emodin 3-​methyl ether; NSC 251670; Parietin; Physcion; Physcione; Rheochrysidin

Systematic name:

9,​10-​Anthracenedione, 1,​8-​dihydroxy-​3-​methoxy-​6-​methyl-

Molecular formulae: 

C₁₆H₁₂O₅

Molecular weight: 284.26

Chemical abstract number: 521-61-9

Literature reference:

• Production of polyhydroxyanthraquinones by the lower fungi (molds). Raistrick, Harold. Enzymologia (1937), 4, 76-8.
  Metabolic products of Aspergillus chevalieri. Kitamura, Jiro; Kurimoto, Uzuhiko; Yokoyama, Matatsugu. Yakugaku Zasshi (1956), 76, 972-3.
  Eurotium (Aspergillus) repens metabolites and their biological activity. Podojil, M.; Sedmera, P.; Vokoun, J.; Betina, V.; Barathova, H.; Durackova, Z.; Horakova, K.; Nemec, P. Folia Microbiologica (Prague, Czech Republic) (1978), 23(6), 438-43.
  Iron chelating capability of physcion, a yellow pigment from Aspergillus ruber. Engstrom, George W.; McDorman, Donald J.; Maroney, Michael J. Journal of Agricultural and Food Chemistry (1980), 28(6), 1139-41.
  Aspergillus fumigatus CY018, an endophytic fungus in Cynodon dactylon as a versatile producer of new and bioactive metabolites. Liu J Y; Song Y C; Zhang Z; Wang L; Guo Z J; Zou W X; Tan R X. Journal of biotechnology (2004), 114(3), 279-87.
  Two new cytotoxic quinone type compounds from the halotolerant fungus Aspergillus variecolor. Wang, Wenliang; Zhu, Tianjiao; Tao, Hongwen; Lu, Zhenyu; Fang, Yuchun; Gu, Qianqun; Zhu, Weiming. Journal of Antibiotics (2007), 60(10), 603-607.
  A new spiroketal from Aspergillus terreus, an endophytic fungus in Opuntia ficusindica Mill. Wu Shao-Hua; Chen You-Wei; Qin Sheng; Huang Rong. Journal of basic microbiology (2008), 48(2), 140-2.
  Antioxidant metabolites from marine alga-​derived fungus Aspergillus wentii EN-​48. Li, Xin; Li, Xiao-Ming; Xu, Gang-Ming; Li, Chun-Shun; Wang, Bin-Gui. Phytochemistry Letters (2014), 7, 120-123.

References URL: 

• http://pubchem.ncbi.nlm.nih.gov/compound/10639
• http://pubs.acs.org/doi/pdf/10.1021/jf60232a017?source=chemport&cookieSet=1&cookieSet=1&cookieSet=1&cookieSet=1
• http://onlinelibrary.wiley.com/doi/10.1002/jobm.200700363/abstract

Aspergillus Species known to produce this metabolite:

• /species/a-glaucus
• /species/a-chevalieri
• /species/eurotium-repens
• /species/a-ruber
• /species/a-fumigatus
• /species/a-variecolor
• /species/a-terreus
• /species/a-wentii

Toxicity:

mouse LD50 intraperitoneal 10mg/kg (10mg/kg) EFFECT: GASTROINTESTINAL: OTHER CHANGES
Journal of Agricultural and Food Chemistry. Vol. 27, Pg. 1342, 1979. Link to PubMed

Date uploaded: 2008-07-14 09:47:52

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Mycotoxin & Metabolites

Mycotoxin & Metabolite database

Aspergillus species produce a large number of secondary metabolites, sometimes referred to as extrolites. We attempt to list them all here and we also collect published papers.

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