Names | |
---|---|
Preferred IUPAC name
(2R,6R)-2-Methyl-6-undecylpiperidine
[1] | |
Other names
Solenopsin A
| |
Identifiers | |
3D model (
JSmol)
|
|
ChemSpider | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C17H35N | |
Molar mass | 253.474 g·mol−1 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Solenopsin is a lipophilic alkaloid with the molecular formula C17H35N found in the venom of fire ants (Solenopsis). It is considered the primary toxin in the venom [2] and may be the component responsible for the cardiorespiratory failure in people who experience excessive fire ant stings. [3]
Structurally solenopsins are a piperidine ring with a methyl group substitution at position 2 and a long hydrophobic chain at position 6. They are typically oily at room temperature, water-insoluble, and present an absorbance peak at 232 nanometers. [4] Fire ant venom contains other chemically related piperidines which make purification of solenopsin from ants difficult. [5] [6] Therefore, solenopsin and related compounds have been the target of organic synthesis from which pure compounds can be produced for individual study. Originally synthesized in 1993, [7] several groups have designed novel and creative methods of synthesizing enantiopure solenopsin and other alkaloidal components of ant venom.
The total synthesis of solenopsin has been described by several methods. [8][ failed verification] A proposed method of synthesis [9](Figure 1) starts with alkylation of 4-chloropyridine with a Grignard reagent derived from 1-bromoundecane, followed by reaction with phenyl chloroformate to form 4-chloro-1-(phenoxycarbonyl)-2-n-undecyl-1,2-dihydropyridine. The phenylcarbamate is converted to the BOC protecting group, and then pyridine is methylated at the 6 position. The pyridine ring is then reduced to a tetrahydropyridine via catalytic hydrogenation with Pd/C and then further reduced with sodium cyanoborohydride to a piperidine ring. The BOC group is finally removed to yield solenopsin. A number of analogs have been synthesized using modifications of this procedure.
A shorter method of synthesis stemming from commercially-available lutidine has been more recently proposed. [10]
Solenopsins are described as toxic against vertebrates and invertebrates. For example, the compound known as isosolenopsin A has been demonstrated to have strong insecticidal effects [11] which may play a central role in the biology of fire ants.
In addition to its toxicity, solenopsis has a number of other biological activities. It inhibits angiogenesis in vitro via the phosphoinositide 3-kinase (PI3K) signaling pathway, [9] inhibits neuronal nitric oxide synthase (nNOS) in a manner that appears to be non-competitive with L-arginine, [12] and inhibits quorum-sensing signaling in some bacteria. [13] The biological activities of solenopsins have led researchers to propose a number of biotechnological and biomedical applications for these compounds. For instance, mentioned anti-bacterial and interference in quorum-sensing signalling apparently provide solenopsins with considerable anti-biofilm activity, which suggests the potential of analogs as new disinfectants and surface-conditioning agents. [14] Also, solenopsins have been demonstrated to inhibit cell division and viability of Trypanosoma cruzi, the cause of Chagas disease, which suggests these alkaloids as potential chemotherapeutic drugs. [15]
Solenopsin and analogs share structural and biological properties with the sphingolipid ceramide, a major endogenous regulator of cell signaling, inducing mitophagy and anti-proliferative effects in different tumor cell lines. [16]
Synthetic analogs of solenopsin are being studied for the potential treatment of psoriasis. [17]
{{
cite book}}
: CS1 maint: location missing publisher (
link)
Names | |
---|---|
Preferred IUPAC name
(2R,6R)-2-Methyl-6-undecylpiperidine
[1] | |
Other names
Solenopsin A
| |
Identifiers | |
3D model (
JSmol)
|
|
ChemSpider | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C17H35N | |
Molar mass | 253.474 g·mol−1 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Solenopsin is a lipophilic alkaloid with the molecular formula C17H35N found in the venom of fire ants (Solenopsis). It is considered the primary toxin in the venom [2] and may be the component responsible for the cardiorespiratory failure in people who experience excessive fire ant stings. [3]
Structurally solenopsins are a piperidine ring with a methyl group substitution at position 2 and a long hydrophobic chain at position 6. They are typically oily at room temperature, water-insoluble, and present an absorbance peak at 232 nanometers. [4] Fire ant venom contains other chemically related piperidines which make purification of solenopsin from ants difficult. [5] [6] Therefore, solenopsin and related compounds have been the target of organic synthesis from which pure compounds can be produced for individual study. Originally synthesized in 1993, [7] several groups have designed novel and creative methods of synthesizing enantiopure solenopsin and other alkaloidal components of ant venom.
The total synthesis of solenopsin has been described by several methods. [8][ failed verification] A proposed method of synthesis [9](Figure 1) starts with alkylation of 4-chloropyridine with a Grignard reagent derived from 1-bromoundecane, followed by reaction with phenyl chloroformate to form 4-chloro-1-(phenoxycarbonyl)-2-n-undecyl-1,2-dihydropyridine. The phenylcarbamate is converted to the BOC protecting group, and then pyridine is methylated at the 6 position. The pyridine ring is then reduced to a tetrahydropyridine via catalytic hydrogenation with Pd/C and then further reduced with sodium cyanoborohydride to a piperidine ring. The BOC group is finally removed to yield solenopsin. A number of analogs have been synthesized using modifications of this procedure.
A shorter method of synthesis stemming from commercially-available lutidine has been more recently proposed. [10]
Solenopsins are described as toxic against vertebrates and invertebrates. For example, the compound known as isosolenopsin A has been demonstrated to have strong insecticidal effects [11] which may play a central role in the biology of fire ants.
In addition to its toxicity, solenopsis has a number of other biological activities. It inhibits angiogenesis in vitro via the phosphoinositide 3-kinase (PI3K) signaling pathway, [9] inhibits neuronal nitric oxide synthase (nNOS) in a manner that appears to be non-competitive with L-arginine, [12] and inhibits quorum-sensing signaling in some bacteria. [13] The biological activities of solenopsins have led researchers to propose a number of biotechnological and biomedical applications for these compounds. For instance, mentioned anti-bacterial and interference in quorum-sensing signalling apparently provide solenopsins with considerable anti-biofilm activity, which suggests the potential of analogs as new disinfectants and surface-conditioning agents. [14] Also, solenopsins have been demonstrated to inhibit cell division and viability of Trypanosoma cruzi, the cause of Chagas disease, which suggests these alkaloids as potential chemotherapeutic drugs. [15]
Solenopsin and analogs share structural and biological properties with the sphingolipid ceramide, a major endogenous regulator of cell signaling, inducing mitophagy and anti-proliferative effects in different tumor cell lines. [16]
Synthetic analogs of solenopsin are being studied for the potential treatment of psoriasis. [17]
{{
cite book}}
: CS1 maint: location missing publisher (
link)