Tigilanol tiglate

Tigilanol tiglate
Clinical data
Routes of; administration	injected
Identifiers
CAS Number	943001-56-7 ;
PubChem CID	23627739;
ChemSpider	32079087 ;
UNII	R1ZJT87990;
Chemical and physical data
Formula	C30H42O10
Molar mass	562.647 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC(C)C(=O)O[C@@]12[C@@H](C1(C)C)[C@@H]3[C@H]4[C@](O4)([C@H]([C@]5([C@H]([C@]3([C@@H]([C@H]2OC(=O)/C(=C/C)/C)C)O)C=C(C5=O)C)O)O)CO;
	InChI InChI=1S/C30H42O10/c1-9-13(3)23(33)38-21-16(6)28(36)17-11-15(5)20(32)29(17,37)25(35)27(12-31)22(39-27)18(28)19-26(7,8)30(19,21)40-24(34)14(4)10-2/h9,11,14,16-19,21-22,25,31,35-37H,10,12H2,1-8H3/b13-9+/t14?,16-,17+,18-,19-,21-,22+,25-,27+,28+,29-,30-/m1/s1 ; Key:YLQZMOUMDYVSQR-YUKITULJSA-N ;
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Tigilanol tiglate (USAN),^[1] previously known as EBC-46 is an experimental drug candidate being studied pre-clinically^[2] by the Australian company Ecobiotics (specifically its drug discovery subsidiary Qbiotics). It was discovered through an automated screening process of natural products by selecting increasingly purified fractions of plant extracts, based on their ability to produce the desired activity profile. This is then followed by artificial synthesis of the isolated compound to confirm its chemical structure. EBC-46 is a phorbol ester which, along with other related compounds, acts as a protein kinase C regulator.^[3]

The initial lead came from observation that marsupials found the seed of Fontainea picrosperma unpalatable due to an inflammatory chemical present in reasonably high concentrations. This was identified as 12-tigloyl-13-(2-methylbutanoyl)-6,7-epoxy-4,5,9,12,13,20-hexahydroxy-1-tiglian-3-one.^[4]

EBC-46 is an extract from blushwood berries of Queensland, Australia.^[2]

References

^ "United States Adopted Name (USAN) Drug Finder" (PDF). United States Adopted Names. American Medical Association. Retrieved 20 February 2017.
^ ^a ^b Boyle, G. M.; d'Souza, M. M. A.; Pierce, C. J.; Adams, R. A.; Cantor, A. S.; Johns, J. P.; Maslovskaya, L.; Gordon, V. A.; Reddell, P. W.; Parsons, P. G. (2014). "Intra-Lesional Injection of the Novel PKC Activator EBC-46 Rapidly Ablates Tumors in Mouse Models". PLoS ONE. 9 (10): e108887. doi:10.1371/journal.pone.0108887. PMC 4182759. PMID 25272271.{{cite journal}}: CS1 maint: unflagged free DOI (link)
^ Aitken, A. (1987). "The activation of protein kinase G by daphnane, ingenane and tigliane diterpenoid esters". Botanical Journal of the Linnean Society. 94: 247. doi:10.1111/j.1095-8339.1987.tb01049.x.
^ Tiglian-3-one derivatives. Patent WO 2007/070985

[1] "United States Adopted Name (USAN) Drug Finder" (PDF). United States Adopted Names. American Medical Association. Retrieved 20 February 2017.

[Boyle14-2] Boyle, G. M.; d'Souza, M. M. A.; Pierce, C. J.; Adams, R. A.; Cantor, A. S.; Johns, J. P.; Maslovskaya, L.; Gordon, V. A.; Reddell, P. W.; Parsons, P. G. (2014). "Intra-Lesional Injection of the Novel PKC Activator EBC-46 Rapidly Ablates Tumors in Mouse Models". PLoS ONE. 9 (10): e108887. doi:10.1371/journal.pone.0108887. PMC 4182759. PMID 25272271.{{cite journal}}: CS1 maint: unflagged free DOI (link)

[3] Aitken, A. (1987). "The activation of protein kinase G by daphnane, ingenane and tigliane diterpenoid esters". Botanical Journal of the Linnean Society. 94: 247. doi:10.1111/j.1095-8339.1987.tb01049.x.

[4] Tiglian-3-one derivatives. Patent WO 2007/070985

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See also

References