Stenusin

Last updated
Stenusin
Stenusin Image.png
Names
IUPAC name
1-Ethyl-3-(2-methylbutyl)-piperidine
Other names
  • N-Ethyl-3-(2-methylbutyl)piperidine
  • Stenusine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
MeSH stenusin
PubChem CID
  • InChI=DYZADDXQHPDPNW-UHFFFAOYSA-N
  • CCC(C)CC1CCCN(C1)CC
Properties
C12H25N
Molar mass 183.339 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Stenusin is a piperidine alkaloid molecule synthesized by rove beetles of the genus Stenus . By lowering its abdomen and releasing stenusin, this genus of rove beetle are able to quickly escape predators through a process called skimming. [1] Skimming is caused by the low surface tension of stenusin, which rapidly spreads over water surfaces when emitted and allows the beetle to glide away from danger. [2]

Biosynthesis

Stenusin is biosynthesized in the pygidial glands of Stenus Latreille, located in the last three segments of the beetles' abdomen. This molecule is the enzymatic product of several reactions that utilize L-lysine, L-isoleucine, and an acetate source. First, both L-lysine and L-isoleucine undergo separate decarboxylation reactions followed by oxidative deamination. The product created from L-lysine undergoes intramolecular Schiff base formation to create the piperidine ring found in stenusin. The two amino acid products then combine through a Stork enamine alkylation reaction and are further acylated and reduced to form stenusin. [1]

Stenusin biosynthesis Stenusin Biosynthesis.png
Stenusin biosynthesis

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Stenus is a genus of semiaquatic rove beetles in the subfamily Steninae, and one of the largest genera in the kingdom Animalia, with some 2700 known species worldwide. They are predators of Collembola and other small arthropods. Adults have a protrusible labium with a sticky tip used in prey capture. To overcome the rapid escape of Collembola, the labium is protruded at high speed by hemolymph pressure, and immediately withdrawn, pulling the prey within the range of the mandibles. However, the labium tip does not easily stick to prey covered in scales or setae or that have a large body size. Stenus comma is more likely to catch such prey by lunging forward and grabbing them directly with its mandibles rather than using its labium. Stenus species are also known for "skimming" on the water surface using their pygidial gland secretions that act as a surfactant and rapidly propel the beetle fast forward, a phenomenon known as the Marangoni effect. Stenus comma has been seen to achieve a velocity of 0.75 m/s, and to cover a distance of up to 15 m if the secretion is continuous.

<i>Paederus</i> Genus of beetles

Paederus is a genus of small beetles of the family Staphylinidae. With 622 valid species assigned by 1987 to the subtribe Paederina, and with all but 148 within Paederus itself, the genus is large. Due to toxins in the hemolymph of some species within this genus, it has given its name to paederus dermatitis, a characteristic skin irritation that occurs if one of the insects is crushed against skin. That name, Paederus dermatitis, is a poor choice because, decades earlier, the affliction had been called dermatitis linearis, a name that works in all languages, not just English, because of its Latin origin; the name Paederus dermatitis is also inappropriate because it has shown to be caused by (a) only a few species of the genus Paederus, but (b) also a few species that belong to closely related genera within the subtribe Paederina. A scholarly paper in 2002 suggested that a Paederus species could have been responsible for some of the ten Plagues of Egypt described in the Bible's Book of Exodus.

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<i>Stenus melanarius</i> Species of beetle

Stenus melanarius is a species of rove beetle widely spread in Asia and Europe. It is a natural predator of the pest, Cnaphalocrocis medinalis.

Stenus solutus is a species of rove beetle widely spread in Asia and England.

References

  1. 1 2 Lusebrink, Inka; Dettner, Konrad; Seifert, Karlheinz. Biosynthesis of Stenusine. Journal of Natural Products. 2008, 71 (5), 743-745.doi:10.1021/np070310w
  2. Lusebrink, Inka; Dettner, Konrad; Seifert, Karlheinz. Stenusine, an antimicrobial agent in the rove beetle genus Stenus (Coleoptera, Staphylinidae). Naturwissenschaften. 2008, 95, 751-755. doi : 10.1007/s00114-008-0374-z