Phalloidin

Structural formula
General
Surname	Phalloidin
Molecular formula	C 35 H 48 N 8 O 11 S
Brief description	white solid
External identifiers / databases
CAS number 17466-45-4 EC number 241-484-5 ECHA InfoCard 100,037,697 PubChem 441542 Wikidata Q2266164
properties
Molar mass	788.88 g mol −1
Physical state	firmly
Melting point	280-282 ° C
solubility	hydrolyzed in water (5 g l −1 at 20 ° C) soluble in ethanol and methanol
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 300-310-330 P: 260-264-280-284-301 + 310-302 + 350
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Phalloidin is the main representative of the phallotoxins and one of the toxins of the green amanita mushroom ( Amanita phalloides ). It is a cyclopeptide made up of seven amino acids , two of which are connected as tryptathionine via an additional sulfide cross-bridge, creating a bicyclic heptapeptide. These structural features indicate all Phallotoxine and are similar only in the eight amino acids constructed Amatoxinen before where the Trp - Cys -Querbrücke as sulfoxide is formed.

history

Phalloidin was first presented in crystallized form by Feodor Lynen and Ulrich Wieland in 1937 ; its structure was later determined by Theodor Wieland .

Occurrence

Phalloidin, along with other phallotoxins and amatoxins, was found in various types of death cap mushrooms . The Amanita virosa ( Amanita virosa ) also contains Virotoxine , the Phallotoxinen similar monocyclic heptapeptides, which lack an internal cross-bridge. The yellow cap mushroom ( Amanita citrina ), on the other hand, which also occurs as a white variant, only contains bufotenin .

properties

When taken orally , phalloidin is ineffective as it is not absorbed by the healthy intestine. But when injected, it changes the cells of the liver in particular due to its irreversible binding to polymerized actin and can be fatal within a few hours; the LD ₅₀ ( mouse i.p. ) is 2 mg / kg.

The high affinity for filamentous (F-) actin can be used in specific molecular biological staining techniques to make parts of the cytoskeleton visible. Phalloidin, to which a fluorescent dye is bound, is used. The light it emits is captured with high resolution in fluorescence microscopy and information about the distribution of F-actin in a cell is obtained.

Individual evidence

1. ↑ ^{a b c d e f} Entry for CAS no. 17466-45-4 in the GESTIS substance database of the IFA , accessed on May 3, 2017(JavaScript required) .
2. ^ William M. Haynes: CRC Handbook of Chemistry and Physics, 97th Edition . CRC Press, 2016, ISBN 978-1-4987-5429-3 , pp. 444 ( limited preview in Google Book search).
3. ^ Peptides: Advances in Research and Application: 2011 Edition . ScholarlyEditions, 2012, ISBN 978-1-4649-2309-8 , pp. 4 ( limited preview in Google Book search).
4. ↑ Theodor Wieland: Modern natural product chemistry using the example of the fungal poison phalloidin, presented at the meeting on April 25, 1981 . Springer-Verlag, 2013, ISBN 978-3-642-46451-5 , p. 22 ( limited preview in Google Book search).
5. ↑ Bernd Gutte: Peptides Synthesis, Structures, and Applications . Academic Press, 1995, ISBN 978-0-08-053859-4 , pp. 33 ( limited preview in Google Book search).
6. ↑ E. Benk, A. Th. Czaja, W. Bötticher, H. Drews, J. Gutschmidt, K. Herrmann, AS Kovacs, F. Martens, H. Mohler, P. Nehring, F. Reiff, H. Sulser: Fruit, vegetables, potatoes, mushrooms 2nd part . Springer-Verlag, 2013, ISBN 978-3-642-87680-6 , p. 521 ( limited preview in Google Book search).
7. ↑ Entry on phalloidin in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on May 3, 2017.