Hodgkinsine Explained

Hodgkinsine is an alkaloid found in plants of the genus Psychotria, particularly Psychotria colorata,^[1] although it is also found in Psychotria lyciiflora^[2] and probably other species in this family,^[3]

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,^[4] both of which are mechanisms of action shared with commonly used painkillers (morphine and ketamine respectively, and which occur concurrently in the clinical analgesics methadone and levorphanol).

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.^{[5] [6] [7]}

See also

• Psychotridine

Notes and References

1. Verotta L, Pilati T, Tatò M, Elisabetsky E, Amador TA, Nunes DS . Pyrrolidinoindoline Alkaloids from Psychotria colorata1 . Journal of Natural Products . 61 . 3 . 392–6 . March 1998 . 9548883 . 10.1021/np9701642 .
2. Jannic V, Guéritte F, Laprévote O, Serani L, Martin MT, Sévenet T, Potier P . Pyrrolidinoindoline alkaloids from Psychotria oleoides and Psychotria lyciiflora . Journal of Natural Products . 62 . 6 . 838–43 . June 1999 . 10395499 . 10.1021/np9805387 .
3. Saad HE, el-Sharkawy SH, Shier WT . Biological activities of pyrrolidinoindoline alkaloids from Calycodendron milnei . Planta Medica . 61 . 4 . 313–6 . August 1995 . 7480176 . 10.1055/s-2006-958090 . 260250178 .
4. Amador TA, Verotta L, Nunes DS, Elisabetsky E . Antinociceptive profile of hodgkinsine . Planta Medica . 66 . 8 . 770–2 . December 2000 . 11199142 . 10.1055/s-2000-9604 . 260283293 .
5. Verotta L, Orsini F, Sbacchi M, Scheildler MA, Amador TA, Elisabetsky E . Synthesis and antinociceptive activity of chimonanthines and pyrrolidinoindoline-type alkaloids . Bioorganic & Medicinal Chemistry . 10 . 7 . 2133–42 . July 2002 . 11983509 . 10.1016/s0968-0896(02)00078-0 .
6. Kodanko JJ, Overman LE . Enantioselective total syntheses of the cyclotryptamine alkaloids hodgkinsine and hodgkinsine B . Angewandte Chemie . 42 . 22 . 2528–31 . June 2003 . 12800178 . 10.1002/anie.200351261 .
7. Kodanko JJ, Hiebert S, Peterson EA, Sung L, Overman LE, de Moura Linck V, Goerck GC, Amador TA, Leal MB, Elisabetsky E . 6 . Synthesis of all low-energy stereoisomers of the tris(pyrrolidinoindoline) alkaloid hodgkinsine and preliminary assessment of their antinociceptive activity . The Journal of Organic Chemistry . 72 . 21 . 7909–14 . October 2007 . 17887704 . 10.1021/jo7013643 .