Lucibufagin

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Lucibufagin
Lucibufagin C.png
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
  • C: InChI=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
    Key: DVEVNJSTCHVUOO-AXGBFFCYSA-N
  • C: 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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

A lucibufagin is a defensive steroid produced by several species of firefly to make them unpalatable to predators such as spiders and birds.[1] 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.[2] The lucibufagins are a set of three related compounds (Lucibufagin A, B, and C), and are in the same structural class as the bufadienolides.[3]

References[edit]

  1. ^ P.J. Leisch (Summer 2018). "Five things everyone should know about... Fireflies". Grow. 11 (3): 5.
  2. ^ Segelken, Roger. "Lured and liquidated, gullible male fireflies supply 'femmes fatales' with a lifesaving chemical | Cornell Chronicle". news.cornell.edu. Retrieved 5 July 2018.
  3. ^ Eisner, Thomas; Wiemer, David F.; Haynes, LeRoy W.; Meinwald, Jerrold (1978). "Lucibufagins: Defensive steroids from the fireflies Photinus ignitus and P. marginellus (Coleoptera: Lampyridae)". Proc Natl Acad Sci. 75 (2): 905–908. Bibcode:1978PNAS...75..905E. doi:10.1073/pnas.75.2.905. PMC 411366. PMID 16592501.