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Contryphan

The contryphans (conus + tryptophan) are a family of peptides that are active constituents of the potent venom produced by cone snail (genus Conus). The two amino acid cysteine residues in contryphans are linked by a disulfide bond. In addition, contryphans undergo an unusual degree of post-translational modification including epimerization of leucine and tryptophan, tryptophan bromination, amidation of the C-terminus, and proline hydroxylation. In the broader scheme of genetic conotoxin classification, contryphans are members of "Conotoxin Superfamily O2."

Family members

Contryphan family members include:

Peptide	Sequence	Species	Reference
Des(Gly1)contryphan-R	COwEPWC-NH2	C. radiatus	vauthors = Jimenéz EC, Olivera BM, Gray WR, Cruz LJ	title = Contryphan is a D-tryptophan-containing Conus peptide	journal = The Journal of Biological Chemistry	volume = 271	issue = 45	pages = 28002–5	date = November 1996	pmid = 8910408	doi = 10.1074/jbc.271.45.28002	doi-access = free }}
Contryphan-R	GCOwEPWC-NH2	Conus radiatus
Bromocontyphan-R	GCOwEPXC-NH2	C. radiatus	vauthors = Jimenez EC, Craig AG, Watkins M, Hillyard DR, Gray WR, Gulyas J, Rivier JE, Cruz LJ, Olivera BM	title = Bromocontryphan: post-translational bromination of tryptophan	journal = Biochemistry	volume = 36	issue = 5	pages = 989–94	date = February 1997	pmid = 9033387	doi = 10.1021/bi962840p }}
Contryphan-Sm	GCOwQPWC-NH2	Conus stercusmuscarum	vauthors = Jacobsen R, Jimenez EC, Grilley M, Watkins M, Hillyard D, Cruz LJ, Olivera BM	title = The contryphans, a D-tryptophan-containing family of Conus peptides: interconversion between conformers	journal = The Journal of Peptide Research	volume = 51	issue = 3	pages = 173–9	date = March 1998	pmid = 9531419	doi = 10.1111/j.1399-3011.1998.tb01213.x }}
Contryphan-P	GCOwDPWC-NH2	C. purpurascens
Contryphan-R/Tx	GCOwEPWC-NH2	Conus textile
Contryphan-Tx	GCOWQPYC-NH2	Conus textile
Contryphan-Vn	GDCPwKPWC-NH2	Conus ventricosus	vauthors = Massilia GR, Schininà ME, Ascenzi P, Polticelli F	title = Contryphan-Vn: a novel peptide from the venom of the Mediterranean snail Conus ventricosus	journal = Biochemical and Biophysical Research Communications	volume = 288	issue = 4	pages = 908–13	date = November 2001	pmid = 11688995	doi = 10.1006/bbrc.2001.5833	bibcode = 2001BBRC..288..908M }}
Leu-contryphan-P	GCVlLPWC-OH	Conus purpurascens	vauthors = Jacobsen RB, Jimenez EC, De la Cruz RG, Gray WR, Cruz LJ, Olivera BM	title = A novel D-leucine-containing Conus peptide: diverse conformational dynamics in the contryphan family	journal = The Journal of Peptide Research	volume = 54	issue = 2	pages = 93–9	date = August 1999	pmid = 10461743	doi = 10.1034/j.1399-3011.1999.00093.x }}
Leu-contryphan-Tx	CVlYPWC-NH2	Conus textile
Glaconryphan-M	NγSγCPWHPWC-NH2	Conus marmoreus

where the sequence abbreviations stand for:

O = 4-trans-hydroxyproline,
l = D-leucine, L = L-leucine,
w = D-tryptophan, W = L-tryptophan,
γ = gamma-carboxyglutamic acid,
NH2 = C-terminal amidation and the remainder of the letters refer to the standard one letter abbreviations for amino acids.

Mechanism of toxicity

The venom of cone snails cause paralysis of their fish prey. The molecular target has not been determined for all contryphan peptides, however it is known that contryphan-Vn is a Ca2+-dependent K+ channel modulator, while glacontryphan-M is a L-type calcium channel blocker.

References

(June 2004). "Solution structure of the cyclic peptide contryphan-Vn, a Ca²⁺-dependent K⁺ channel modulator". Biopolymers.
(July 2004). "The first gamma-carboxyglutamic acid-containing contryphan. A selective L-type calcium ion channel blocker isolated from the venom of Conus marmoreus". The Journal of Biological Chemistry.
(December 2014). "Conotoxin gene superfamilies". Marine Drugs.
(November 1996). "Contryphan is a D-tryptophan-containing Conus peptide". The Journal of Biological Chemistry.
(February 1997). "Bromocontryphan: post-translational bromination of tryptophan". Biochemistry.
(March 1998). "The contryphans, a D-tryptophan-containing family of Conus peptides: interconversion between conformers". The Journal of Peptide Research.
(November 2001). "Contryphan-Vn: a novel peptide from the venom of the Mediterranean snail Conus ventricosus". Biochemical and Biophysical Research Communications.
(August 1999). "A novel D-leucine-containing Conus peptide: diverse conformational dynamics in the contryphan family". The Journal of Peptide Research.

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neurotoxins ion-channel-toxins snail-toxins

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