Machaeriol A Explained

Iupac Name:(6aS,9S,10aS)-6,6,9-trimethyl-3-[(E)-2-phenylethenyl]-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol
Width:240
Cas Number:377077-52-6
Pubchem:10089121
C:24
H:28
O:2
Smiles:C[C@H]1CC[C@H]2[C@H](C1)C3=C(C=C(C=C3OC2(C)C)/C=C/C4=CC=CC=C4)O
Stdinchi:1S/C24H28O2/c1-16-9-12-20-19(13-16)23-21(25)14-18(15-22(23)26-24(20,2)3)11-10-17-7-5-4-6-8-17/h4-8,10-11,14-16,19-20,25H,9,12-13H2,1-3H3/b11-10+/t16-,19-,20-/m0/s1
Stdinchikey:KCNFZTIIENBEPU-TUCATBTLSA-N

Machaeriol A is one of a number of phytocannabinoids with a hexahydrocannabinol backbone, found in plants from the Machaerium family such as Machaerium multiflorum. While they are related in structure to tetrahydrocannabinols such as those from cannabis, the machaeriol compounds have opposite trans stereochemistry from THC and have no affinity for the psychoactive CB1 receptor. However, some derivatives are active at CB2, and they have also been found to have antibacterial, antifungal and antiparasitic actions, and have been investigated as lead compounds for the development of potential anti-cancer drugs.[1] [2] [3] [4] [5] [6] [7] [8] [9] [10]

See also

Notes and References

  1. Muhammad I, Li XC, Dunbar DC, ElSohly MA, Khan IA . Antimalarial (+)-trans-hexahydrodibenzopyran derivatives from Machaerium multiflorum . Journal of Natural Products . 64 . 10 . 1322–1325 . October 2001 . 11678659 . 10.1021/np0102861 .
  2. Muhammad I, Li XC, Jacob MR, Tekwani BL, Dunbar DC, Ferreira D . Antimicrobial and antiparasitic (+)-trans-hexahydrodibenzopyrans and analogues from Machaerium multiflorum . Journal of Natural Products . 66 . 6 . 804–809 . June 2003 . 12828466 . 10.1021/np030045o .
  3. Lee HJ, Lee YR, Kim SH . Total Synthesis of (+)‐Machaeriols B and C and of Their Enantiomers with a Cannabinoid Structure. . Helvetica Chimica Acta . July 2009 . 92 . 7 . 1404–1412 . 10.1002/hlca.200900014 .
  4. Klotter F, Studer A . Short and Divergent Total Synthesis of (+)-Machaeriol B, (+)-Machaeriol D, (+)-Δ(8)-THC, and Analogues . Angewandte Chemie . 54 . 29 . 8547–8550 . July 2015 . 26079816 . 10.1002/anie.201502595 .
  5. Morales P, Reggio PH, Jagerovic N . An Overview on Medicinal Chemistry of Synthetic and Natural Derivatives of Cannabidiol . Frontiers in Pharmacology . 8 . 422 . 2017 . 28701957 . 5487438 . 10.3389/fphar.2017.00422 . free .
  6. Bloemendal VR, van Hest JC, Rutjes FP . Synthetic pathways to tetrahydrocannabinol (THC): an overview . Organic & Biomolecular Chemistry . 18 . 17 . 3203–3215 . May 2020 . 32259175 . 10.1039/d0ob00464b . 215408648 . free . 2066/218829 . free .
  7. Muhammad I, Jacob MR, Ibrahim MA, Raman V, Kumarihamy M, Wang M, Al-Adhami T, Hind C, Clifford M, Martin B, Zhao J, Sutton JM, Rahman KM . 6 . Antimicrobial Constituents from Machaerium Pers.: Inhibitory Activities and Synergism of Machaeriols and Machaeridiols against Methicillin-Resistant Staphylococcus aureus, Vancomycin-Resistant Enterococcus faecium, and Permeabilized Gram-Negative Pathogens . Molecules . 25 . 24 . December 2020 . 6000 . 33352963 . 7765828 . 10.3390/molecules25246000 . free .
  8. Haider S, Pandey P, Reddy CR, Lambert JA, Chittiboyina AG . Novel Machaeriol Analogues as Modulators of Cannabinoid Receptors: Structure-Activity Relationships of (+)-Hexahydrocannabinoids and Their Isoform Selectivities . ACS Omega . 6 . 31 . 20408–20421 . August 2021 . 34395989 . 8359128 . 10.1021/acsomega.1c02413 .
  9. Kumarihamy M, Tripathi S, Balachandran P, Avula B, Zhao J, Wang M, Bennett MM, Zhang J, Carr MA, Lovell KM, Wellington OI, Marquart ME, Nanayakkara NP, Muhammad I . 6 . Synthesis and Inhibitory Activity of Machaeridiol-Based Novel Anti-MRSA and Anti-VRE Compounds and Their Profiling for Cancer-Related Signaling Pathways . Molecules . 27 . 19 . October 2022 . 6604 . 36235141 . 9570708 . 10.3390/molecules27196604 . free .
  10. Muhammad I, Ibrahim MA, Kumarihamy M, Lambert JA, Zhang J, Mohammad MH, Khan SI, Pasco DS, Balachandran P . 6 . Cannabinoid and Opioid Receptor Affinity and Modulation of Cancer-Related Signaling Pathways of Machaeriols and Machaeridiols from Machaerium Pers . Molecules . 28 . 10 . May 2023 . 4162 . 37241903 . 10361207 . 10.3390/molecules28104162 . free .

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