Lucibufagin

{{Chembox

|ImageFile = Lucibufagin C.png

|ImageCaption = Lucibufagin C

|Section1={{Chembox Identifiers

|index3_label=C

| PubChem3 = 15924888

| ChEBI3 = 134224

| ChEMBL3 = 485697

| ChemSpiderID3 = 24702088

| InChI3=1S/C28H36O10/c1-14(29)37-19-11-25(3)22-18(7-9-27(25,34)12-20(19)38-15(2)30)28(35)10-8-17(16-5-6-21(31)36-13-16)26(28,4)24(33)23(22)32/h5-6,13,17-20,22-23,32,34-35H,7-12H2,1-4H3/t17-,18-,19+,20-,22-,23+,25-,26+,27+,28+/m1/s1

| InChIKey3 = DVEVNJSTCHVUOO-AXGBFFCYSA-N

| SMILES3 = C=1(C=CC(OC1)=O)[C@@H]2[C@]3(C([C@H]([C@@]4([C@]5(C[C@@H]([C@@H](C[C@]5(CC[C@]4([C@]3(CC2)O)[H])O)OC(=O)C)OC(=O)C)C)[H])O)=O)C

}}

}}

Lucibufagins are a group of defensive steroids produced by several species of firefly to make them unpalatable to predators such as spiders and birds.{{cite journal|title=Five things everyone should know about... Fireflies|author=P.J. Leisch|journal=Grow|volume=11|issue=3|page=5|date=Summer 2018|url=https://grow.cals.wisc.edu/departments/on-henry-mall/five-things-everyone-should-know-about-fireflies}} Certain species of firefly that do not themselves produce lucibufagins have been observed to eat other species of firefly that do produce the steroid to gain the defensive properties for themselves.{{cite web |last1=Segelken |first1=Roger |title=Lured and liquidated, gullible male fireflies supply 'femmes fatales' with a lifesaving chemical {{!}} Cornell Chronicle |url=http://news.cornell.edu/stories/1997/09/cornell-biologists-report-mimicry-and-murder-night |website=news.cornell.edu |access-date=5 July 2018 |language=en}} The lucibufagins are a set of three related compounds (lucibufagin A, B, and C), and are in the same structural class as the bufadienolides.{{cite journal |journal= Proc Natl Acad Sci |year= 1978 |volume= 75 |issue= 2 |pages= 905–908 |title= Lucibufagins: Defensive steroids from the fireflies Photinus ignitus and P. marginellus (Coleoptera: Lampyridae) |first1= Thomas |last1= Eisner |first2= David F. |last2= Wiemer |first3= LeRoy W. |last3= Haynes |first4= Jerrold |last4= Meinwald |pmid= 16592501 |doi= 10.1073/pnas.75.2.905 |pmc= 411366 |bibcode= 1978PNAS...75..905E |doi-access= free }}