Hodgkinsine
Encyclopedia
Hodgkinsine is an alkaloid
found in plants of the Psychotria
genus, particularly Psychotria colorata
, although it is also found in Psychotria lyciiflora and probably other species in this family, as well as in the related species Calycodendron milnei.
Hodgkinsine has antiviral, antibacterial and antifungal
effects, but has mainly been researched for the analgesic
effects that it produces, and is thought to be one of the components responsible for the analgesic effects seen when Psychotria colorata is used in traditional medical practice in humans. It has been found to act as both a mu opioid agonist
and an NMDA antagonist, both of which are mechanisms of action shared with commonly used painkillers (morphine
and ketamine
respectively).
Hodgkinsine is a trimer
composed of three pyrrolidinoindoline subunits, with the monomer
closely resembling another alkaloid eseroline
which has similar bioactivity. Due to its complex structure and multiple chiral centres, hodgkinsine has many stereoisomers and significant research has been undertaken to elucidate the structure-activity relationships of the various isomers and synthetic derivatives structurally derived from hodgkinsine.
Alkaloid
Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...
found in plants of the Psychotria
Psychotria
Psychotria is a plant genus of 1900 species in the family Rubiaceae. Members of the genus are low trees in tropical forests. The distinction between Psychotria and the genus Cephaelis are not well known and many species were formerly placed there....
genus, particularly Psychotria colorata
Psychotria colorata
Psychotria colorata is a species of plant in the Rubiaceae family. It has been documented in an ethnobotanical context among the Ka'apor people of Maranhão, Brazil by Dr. William Balée, the Tulane University anthropologist and historical ecologist:...
, although it is also found in Psychotria lyciiflora and probably other species in this family, as well as in the related species Calycodendron milnei.
Hodgkinsine has antiviral, antibacterial and antifungal
Antimicrobial
An anti-microbial is a substance that kills or inhibits the growth of microorganisms such as bacteria, fungi, or protozoans. Antimicrobial drugs either kill microbes or prevent the growth of microbes...
effects, but has mainly been researched for the analgesic
Analgesic
An analgesic is any member of the group of drugs used to relieve pain . The word analgesic derives from Greek an- and algos ....
effects that it produces, and is thought to be one of the components responsible for the analgesic effects seen when Psychotria colorata is used in traditional medical practice in humans. It has been found to act as both a mu opioid agonist
Mu Opioid receptor
The μ-opioid receptors are a class of opioid receptors with high affinity for enkephalins and beta-endorphin but low affinity for dynorphins. They are also referred to as μ opioid peptide receptors. The prototypical μ receptor agonist is the opium alkaloid morphine; μ refers to morphine...
and an NMDA antagonist, both of which are mechanisms of action shared with commonly used painkillers (morphine
Morphine
Morphine is a potent opiate analgesic medication and is considered to be the prototypical opioid. It was first isolated in 1804 by Friedrich Sertürner, first distributed by same in 1817, and first commercially sold by Merck in 1827, which at the time was a single small chemists' shop. It was more...
and ketamine
Ketamine
Ketamine is a drug used in human and veterinary medicine. Its hydrochloride salt is sold as Ketanest, Ketaset, and Ketalar. Pharmacologically, ketamine is classified as an NMDA receptor antagonist...
respectively).
Hodgkinsine is a trimer
Trimer (biochemistry)
In biochemistry, a trimer is a macromolecular complex formed by three, usually non-covalently bound, macromolecules like proteins or nucleic acids. A homo-trimer would be formed by three identical molecules. A hetero-trimer would be formed by three different macromolecules. Collagen is an example...
composed of three pyrrolidinoindoline subunits, with the monomer
Monomer
A monomer is an atom or a small molecule that may bind chemically to other monomers to form a polymer; the term "monomeric protein" may also be used to describe one of the proteins making up a multiprotein complex...
closely resembling another alkaloid eseroline
Eseroline
Eseroline is a drug which acts as an opioid agonist. It is a metabolite of the acetylcholinesterase inhibitor physostigmine but unlike physostigmine, the acetylcholinesterase inhibition produced by eseroline is weak and easily reversible, and it produces fairly potent analgesic effects mediated...
which has similar bioactivity. Due to its complex structure and multiple chiral centres, hodgkinsine has many stereoisomers and significant research has been undertaken to elucidate the structure-activity relationships of the various isomers and synthetic derivatives structurally derived from hodgkinsine.