Nepetalactol

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Nepetalactol
Nepetalactol.svg
Names
IUPAC name
(4aS,7S,7aR)-4,7-Dimethyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-ol
Identifiers
  • 183071-73-04 stereocentres specified
3D model (JSmol)
3DMet
ChEBI
ChemSpider
KEGG
PubChem CID
  • InChI=1S/C10H16O2/c1-6-3-4-8-7(2)5-12-10(11)9(6)8/h5-6,8-11H,3-4H2,1-2H3/t6-,8+,9+,10?/m0/s1
    Key: OJGPEAXUHQRLNC-CEPLBNANSA-N
  • InChI=1/C10H16O2/c1-6-3-4-8-7(2)5-12-10(11)9(6)8/h5-6,8-11H,3-4H2,1-2H3/t6-,8+,9+,10u/m0/s1
    Key: OJGPEAXUHQRLNC-XUFCCMHBBP
  • C[C@H]1CC[C@H]2[C@@H]1C(OC=C2C)O
Properties
C10H16O2
Molar mass 168.236 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Nepetalactol is an iridoid. It is produced from 8-oxogeranial by the enzyme iridoid synthase. [1] Nepetalactol is a substrate for the enzyme iridoid oxidase (IO) which produces 7-deoxyloganetic acid. It has been identified in Actinidia polygama (the silver vine) as a major cat attractant, and a mosquito repellent. The fact that mosquitos bite less often cats with nepetalactol on their fur may explain why cats are attracted to silver vine in the first place. [2]

Related Research Articles

Nepetalactone Chemical compound

Nepetalactone is a name for multiple iridoid analog stereoisomers. Nepetalactones are produced by Nepeta cataria (catnip) and a many other plants belonging to the genus Nepeta, in which they protect these plants from herbivorous insects by functioning as insect repellents. They are also produced by many aphids, in which they are sex pheromones. Nepetalactones are cat attractants, and cause the behavioral effects that catnip induces in domestic cats. However, they affect visibly only about 2/3 of adult cats. They produce similar behavioral effects in many other Felidae, especially in lions and jaguars. McElvain and colleagues were the first to extract and name nepetalactones, which they did in 1941.

Ribonucleotide reductase (RNR), also known as ribonucleotide diphosphate reductase (rNDP), is an enzyme that catalyzes the formation of deoxyribonucleotides from ribonucleotides. It catalyzes this formation by removing the 2'-hydroxyl group of the ribose ring of nucleoside diphosphates. This reduction produces deoxyribonucleotides. Deoxyribonucleotides in turn are used in the synthesis of DNA. The reaction catalyzed by RNR is strictly conserved in all living organisms. Furthermore, RNR plays a critical role in regulating the total rate of DNA synthesis so that DNA to cell mass is maintained at a constant ratio during cell division and DNA repair. A somewhat unusual feature of the RNR enzyme is that it catalyzes a reaction that proceeds via a free radical mechanism of action. The substrates for RNR are ADP, GDP, CDP and UDP. dTDP is synthesized by another enzyme from dTMP.

<i>Junonia coenia</i> Species of insect (butterfly)

Junonia coenia, known as the common buckeye or buckeye, is a butterfly in the family Nymphalidae. It is found in all parts of the United States except the northwest, and is especially common in the South, the California coast, and throughout Central America. Its habitat is open areas with low vegetation and some bare ground. Its original ancestry has been traced to Africa, which then experiences divergence in Asia.

Beta-glucuronidase

Beta-glucuronidases are members of the glycosidase family of enzymes that catalyze breakdown of complex carbohydrates. Human β-glucuronidase is a type of glucuronidase that catalyzes hydrolysis of β-D-glucuronic acid residues from the non-reducing end of mucopolysaccharides such as heparan sulfate. Human β-glucuronidase is located in the lysosome. In the gut, brush border β-glucuronidase converts conjugated bilirubin to the unconjugated form for reabsorption. Beta-glucuronidase is also present in breast milk, which contributes to neonatal jaundice. The protein is encoded by the GUSB gene in humans and by the uidA gene in bacteria.

Actinidine Chemical compound

Actinidine is an iridoid produced in nature by a wide variety of plants and animals. It was the first cyclopentanoid monoterpene alkaloid to be discovered. It is one of several compounds that may be extracted from the valerian root and silver vine, as well as several types of insects in the larval and imaginal stages. Actinidine is a cat attractant, with effects like those of nepetalactone, the active compound found in catnip.

Stearoyl-CoA desaturase-1

Stearoyl-CoA desaturase (Δ-9-desaturase) is an endoplasmic reticulum enzyme that catalyzes the rate-limiting step in the formation of monounsaturated fatty acids (MUFAs), specifically oleate and palmitoleate from stearoyl-CoA and palmitoyl-CoA. Oleate and palmitoleate are major components of membrane phospholipids, cholesterol esters and alkyl-diacylglycerol. In humans, the enzyme is encoded by the SCD gene.

Iridoid

Iridoids are a type of monoterpenoids in the general form of cyclopentanopyran, found in a wide variety of plants and some animals. They are biosynthetically derived from 8-oxogeranial. Iridoids are typically found in plants as glycosides, most often bound to glucose.

Cat pheromones are pheromones that are used by cats and other felids for cat communication.

Cauxin is a carboxylesterase that is excreted in large amounts in cat urine. There is also evidence that it can serve as a peptide hydrolase in the production of cat pheromone precursors. Cauxin has a mass of 70 kilodaltons and is composed of 545 amino acids. The protein can also exist as a multimeric protein complex connected by disulfide bonds with a mass of 300-350 kilodaltons. This is its primary form in non-reducing conditions. The proximal tubules of epithelial cells in the kidney express cauxin. This protein is secreted into the urine from the renal tubular cells. The gene for the protein is also found in several other mammalian genomes in various organs. However, the only mammals that have cauxin present in urine are cats. It is also the first carboxylesterase to be found in urine.

UBE2C

Ubiquitin-conjugating enzyme E2 C is a protein that in humans is encoded by the UBE2C gene.

Catnip Nepeta cataria; species of plant

Nepeta cataria, commonly known as catnip, catswort, catwort, and catmint, is a species of the genus Nepeta in the family Lamiaceae, native to southern and eastern Europe, the Middle East, Central Asia, and parts of China. It is widely naturalized in northern Europe, New Zealand, and North America. The common name catmint can also refer to the genus as a whole.

<i>Actinidia polygama</i> Species of plant

Actinidia polygama is a species of kiwifruit in the Actinidiaceae family. It grows in the mountainous areas of Japan and China at elevations between 500 and 1,900 metres.

Tetrahydrodeoxycorticosterone

Tetrahydrodeoxycorticosterone, also referred to as allotetrahydrocorticosterone, is an endogenous neurosteroid. It is synthesized from the adrenal hormone deoxycorticosterone by the action of two enzymes, 5α-reductase type I and 3α-hydroxysteroid dehydrogenase. THDOC is a potent positive allosteric modulator of the GABAA receptor, and has sedative, anxiolytic and anticonvulsant effects. Changes in the normal levels of this steroid particularly during pregnancy and menstruation may be involved in some types of epilepsy and premenstrual syndrome, as well as stress, anxiety and depression.

Genetically modified animal

Genetically modified animals are animals that have been genetically modified for a variety of purposes including producing drugs, enhancing yields, increasing resistance to disease, etc. The vast majority of genetically modified animals are at the research stage while the number close to entering the market remains small.

Aucubin Chemical compound

Aucubin is an iridoid glycoside. Iridoids are commonly found in plants and function as defensive compounds. Iridoids decrease the growth rates of many generalist herbivores.

Genetically modified mammal

Genetically modified mammals are mammals that have been genetically engineered. They are an important category of genetically modified organisms. The majority of research involving genetically modified mammals involves mice with attempts to produce knockout animals in other mammalian species limited by the inability to derive and stably culture embryonic stem cells.

Secologanin Chemical compound

Secologanin is a secoiridoid monoterpene synthesized from geranyl pyrophosphate in the mevalonate pathway. Secologanin then proceeds with dopamine or tryptamine to form ipecac and terpene indole alkaloids, respectively.

Enzyme promiscuity is the ability of an enzyme to catalyse a fortuitous side reaction in addition to its main reaction. Although enzymes are remarkably specific catalysts, they can often perform side reactions in addition to their main, native catalytic activity. These promiscuous activities are usually slow relative to the main activity and are under neutral selection. Despite ordinarily being physiologically irrelevant, under new selective pressures these activities may confer a fitness benefit therefore prompting the evolution of the formerly promiscuous activity to become the new main activity. An example of this is the atrazine chlorohydrolase from Pseudomonas sp. ADP that evolved from melamine deaminase, which has very small promiscuous activity toward atrazine, a man-made chemical.

8-Oxogeranial Chemical compound

8-Oxogeranial, also incorrectly called 10-oxogeranial, is a monoterpene. The terpenoid is produced by 8-hydroxygeraniol dehydrogenase which uses 8-hydroxygeraniol as its substrate. 8-Oxogeranial is itself a substrate for iridoid synthase which synthesizes cis–trans-iridodial and cis–trans-nepetalactol.

Iridodial Chemical compound

Iridodial is an iridoid. It is produced from 8-oxogeranial by the enzyme iridoid synthase (IS). Iridodial is one of the substrates for the enzyme iridoid oxidase (IO) which produces 7-deoxyloganetic acid.

References

  1. Geu-Flores, Fernando; Sherden, Nathaniel H.; Courdavault, Vincent; Burlat, Vincent; Glenn, Weslee S.; Wu, Cen; Nims, Ezekiel; Cui, Yuehua; o’Connor, Sarah E. (2012). "An alternative route to cyclic terpenes by reductive cyclization in iridoid biosynthesis". Nature. 492 (7427): 138–42. Bibcode:2012Natur.492..138G. doi:10.1038/nature11692. PMID   23172143. S2CID   4431685.
  2. Uenoyama, Reiko; Miyazaki, Tamako; Hurst, Jane L.; Beynon, Robert J.; Adachi, Masaatsu; Murooka, Takanobu; Onoda, Ibuki; Miyazawa, Yu; Katayama, Rieko; Yamashita, Tetsuro; Kaneko, Shuji; Nishikawa, Toshio; Miyazaki, Masao (2021). "The characteristic response of domestic cats to plant iridoids allows them to gain chemical defense against mosquitoes". Science Advances. 7 (4): eabd9135. doi: 10.1126/sciadv.abd9135 . PMC   7817105 . PMID   33523929. S2CID   231681044.