Ophiobolans
Ophiobolanes (also Ophiobolines) are chemical compounds from the group of tricyclic sesterterpene phytotoxins . The name is derived from the pathogen of black- leggedness, the fungus Ophiobolus graminis (now called Gaeumannomyces graminis ), from which the first of the compounds of the class was isolated. They are found in different types of Helminthosporium and Cochliobolus . Ophiobolin A (Ophiobolin, Cochliobolin, Cochliobolin A) is likely responsible for the symptoms of corn burn caused by Helminthosporium maydis .
synthesis
Biosynthesis takes place via a head-to-tail linkage of five isoprene units with the formation of all-trans-geranylfarnesyl pyrophosphate . A total synthesis is also known.
Representative
| Name (synonyms) | Molecular formula | molar mass | Melting point | CAS number |
|---|---|---|---|---|
| Ophiobolin A Cochliobolin A |
C 25 H 36 O 4 | 400.56 | 182 ° C | 4611-05-6 |
| Ophiobolin C zizanine |
C 25 H 38 O 3 | 386.57 | 121 ° C | 19022-51-6 |
| Ophiobolin D cephalonic acid |
C 25 H 36 O 4 | 400.56 | 139 ° C | 24436-08-6 |
| Ophiobolin J. | C 25 H 36 O 4 | 400.56 | oil | 114058-47-8 |
| Ophiobolin K | C 25 H 36 O 3 | 384.56 | 80-82 ° C | 138057-90-6 |
Ophiobolin M is a powerful nematocidal agent.
Individual evidence
- ↑ James R. Hanson: The Chemistry of Fungi . Royal Society of Chemistry, 2008, ISBN 978-1-84755-832-9 , pp. 4 ( limited preview in Google Book search).
- ↑ a b Lexicon of Biochemistry: Ophiobolane - Lexicon of Biochemistry , accessed on July 15, 2019.
- ↑ William G. Dauben, Alan M. Warshawsky: An approach toward the ophiobolane sesterterpenes: synthesis of the ceroplastin nucleus. In: The Journal of Organic Chemistry. 55, 1990, p. 3075, doi : 10.1021 / jo00297a024 .
- ↑ a b Entry on Ophioboline. In: Römpp Online . Georg Thieme Verlag, accessed on July 15, 2019.