Indole

ID 2: 56

Toxin: n

Trivial name:

Indole (8CI); 1-​Azaindene; 1-​Benzazole; 2,​3-​Benzopyrrole; Benzo[b]​pyrrole; Ketole; NSC 1964

Systematic name:

1H-Indole

Molecular formulae: 

C₈H₇N

Molecular weight: 117.15

Chemical abstract number: 120-72-9

Literature reference:

• The formation of flavin-​type pigments in liquid cultures of Aspergillus niger. Knobloch, H.; Sellmann, R. Zentralblatt fuer Bakteriologie, Parasitenkunde, Infektionskrankheiten und Hygiene, Abteilung 2, Naturwissenschaftliche: Allgemeine, Landwirtschaftliche und Technische Mikrobiologie (1941), 103, 277-80.
  Chemical studies of the Aspergillus glaucus group. XI. Echinulin. Quilico, Adolfo. Cesare Cardani, and Franco Piozzi. Gazz. chim. ital. (1955), 85, 3-33.
  Neoechinuline: a new indole metabolite from Aspergillus amstelodami. Barbetta, Marco; Casnati, Giuseppe; Pochini, A.; Selva, A. Tetrahedron Letters (1969), 51, 4457-60.
  Effect of tryptophan and related compounds on alkaloid formation in Aspergillus fumigatus. Rao, K. K.; Patel, V. P. Lloydia (1974), 37(4), 608-10.
  Isolation and structure elucidation of a new indole metabolite from Aspergillus ruber. Nagasawa, Hiromichi; Isogai, Akira; Ikeda, Katsutoshi; Sato, Shouhachi; Murakoshi, Shigeo; Suzuki, Akinori; Tamura, Saburo. Agricultural and Biological Chemistry (1975), 39(9), 1901-2.
  Indole metabolites from a strain of Aspergillus flavus. Cole, Richard J.; Dorner, Joe W.; Springer, James P.; Cox, Richard H. Journal of Agricultural and Food Chemistry (1981), 29(2), 293-5.
  Identification of some volatile constituents of Aspergillus clavatus. Seifert, Richard M.; King, A. Douglas, Jr. Journal of Agricultural and Food Chemistry (1982), 30(4), 786-90.
  Synthesis of 2-​(indol-​3-​yl)​methyl-​5-​methylpyrazines, the skeleton of astechrome. Ohta, Akihiro; Jing, Hao; Maeda, Atsushi; Arai, Yasuyo; Goto, Mikiko; Aoyagi, Yutaka. Heterocycles (1992), 34(1), 111-19.
  Identification of the active-​site peptide of 2,​3-​dihydroxybenzoic acid decarboxylase from Aspergillus oryzae. Santha R; Rao N A; Vaidyanathan C S. Biochimica et biophysica acta (1996), 1293(2), 191-200.
  Production of indole diterpenes by Aspergillus alliaceus. Junker B; Walker A; Connors N; Seeley A; Masurekar P; Hesse M. Biotechnology and bioengineering (2006), 95(5), 919-37.
  Characterization of melanin pigment produced by Aspergillus nidulans. Goncalves, R. C. R.; Lisboa, H. C. F.; Pombeiro-Sponchiado, S. R. World Journal of Microbiology & Biotechnology (2012), 28(4), 1467-1474.

References URL: 

• http://pubchem.ncbi.nlm.nih.gov/compound/798
• https://www.jstage.jst.go.jp/article/bbb1961/39/9/39_9_1901/_article
• http://pubs.acs.org/doi/pdf/10.1021/jf00104a019?source=chemport&cookieSet=1&cookieSet=1&cookieSet=1&cookieSet=1
• http://pubs.acs.org/doi/pdf/10.1021/jf00112a044?source=chemport&cookieSet=1&cookieSet=1&cookieSet=1&cookieSet=1
• http://www.heterocycles.jp/newlibrary/payments/form/04510/PDF
• http://www.sciencedirect.com/science?_ob=ArticleListURL&_method=list&_ArticleListID=-605036189&_sort=r&_st=13&view=c&md5=69b752aea5693dfca508ce8e497b5204&searchtype=a
• http://onlinelibrary.wiley.com/doi/10.1002/bit.21053/abstract
• http://search.proquest.com/shibboleth?accountid=12253

Aspergillus Species known to produce this metabolite:

• /species/a-niger
• /species/a-glaucus
• /species/a-amstelodami
• /species/a-fumigatus
• /species/a-ruber
• /species/a-flavus
• /species/clavatus
• /species/a-terreus
• /species/a-oryzae
• /species/alliaceus
• /species/a-nidulans

Toxicity:

Tremorgenic

Date uploaded: 2008-07-07 16:30:55

---

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.

Search Metabolite papers here