Machaeriol A
Chemical compound
Machaeriol A
(6aS,9S,10aS)-6,6,9-trimethyl-3-[(E)-2-phenylethenyl]-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol
CAS Number PubChem CID Formula C 24 H 28 O 2 Molar mass 348.486 g·mol−1 3D model (JSmol )
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
InChI=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
Key: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]
Machaeriol B, 377077-53-7[ 11] and Machaeriol C, 565429-89-2 [ 12]
See also
References
^ Muhammad I, Li XC, Dunbar DC, ElSohly MA, Khan IA (October 2001). "Antimalarial (+)-trans-hexahydrodibenzopyran derivatives from Machaerium multiflorum". Journal of Natural Products . 64 (10): 1322–1325. doi :10.1021/np0102861 . PMID 11678659 .
^ Muhammad I, Li XC, Jacob MR, Tekwani BL, Dunbar DC, Ferreira D (June 2003). "Antimicrobial and antiparasitic (+)-trans-hexahydrodibenzopyrans and analogues from Machaerium multiflorum". Journal of Natural Products . 66 (6): 804–809. doi :10.1021/np030045o . PMID 12828466 .
^ Lee HJ, Lee YR, Kim SH (July 2009). "Total Synthesis of (+)‐Machaeriols B and C and of Their Enantiomers with a Cannabinoid Structure". Helvetica Chimica Acta . 92 (7): 1404–1412. doi :10.1002/hlca.200900014 .
^ Klotter F, Studer A (July 2015). "Short and Divergent Total Synthesis of (+)-Machaeriol B, (+)-Machaeriol D, (+)-Δ(8)-THC, and Analogues". Angewandte Chemie . 54 (29): 8547–8550. doi :10.1002/anie.201502595 . PMID 26079816 .
^ Morales P, Reggio PH, Jagerovic N (2017). "An Overview on Medicinal Chemistry of Synthetic and Natural Derivatives of Cannabidiol" . Frontiers in Pharmacology . 8 : 422. doi :10.3389/fphar.2017.00422 . PMC 5487438 . PMID 28701957 .
^ Bloemendal VR, van Hest JC, Rutjes FP (May 2020). "Synthetic pathways to tetrahydrocannabinol (THC): an overview" . Organic & Biomolecular Chemistry . 18 (17): 3203–3215. doi :10.1039/d0ob00464b . hdl :2066/218829 . PMID 32259175 . S2CID 215408648 .
^ Muhammad I, Jacob MR, Ibrahim MA, Raman V, Kumarihamy M, Wang M, et al. (December 2020). "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): 6000. doi :10.3390/molecules25246000 . PMC 7765828 . PMID 33352963 .
^ Haider S, Pandey P, Reddy CR, Lambert JA, Chittiboyina AG (August 2021). "Novel Machaeriol Analogues as Modulators of Cannabinoid Receptors: Structure-Activity Relationships of (+)-Hexahydrocannabinoids and Their Isoform Selectivities" . ACS Omega . 6 (31): 20408–20421. doi :10.1021/acsomega.1c02413 . PMC 8359128 . PMID 34395989 .
^ Kumarihamy M, Tripathi S, Balachandran P, Avula B, Zhao J, Wang M, et al. (October 2022). "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): 6604. doi :10.3390/molecules27196604 . PMC 9570708 . PMID 36235141 .
^ Muhammad I, Ibrahim MA, Kumarihamy M, Lambert JA, Zhang J, Mohammad MH, et al. (May 2023). "Cannabinoid and Opioid Receptor Affinity and Modulation of Cancer-Related Signaling Pathways of Machaeriols and Machaeridiols from Machaerium Pers" . Molecules . 28 (10): 4162. doi :10.3390/molecules28104162 . PMC 10361207 . PMID 37241903 .
^ "Machaeriol B" . PubChem . U.S. National Library of Medicine.
^ "Machaeriol C" . PubChem . U.S. National Library of Medicine.
Phytocannabinoids (comparison )
Cannabibutols Cannabichromenes Cannabicyclols Cannabidiols Cannabielsoins Cannabigerols Cannabiphorols Cannabinols Cannabitriols Cannabivarins Delta-8-tetrahydrocannabinols Delta-9-tetrahydrocannabinols Delta-10-Tetrahydrocannabinols Miscellaneous cannabinoids Active metabolites
Endocannabinoids Synthetic cannabinoid receptor agonists / neocannabinoids
Classical cannabinoids (dibenzopyrans) Non-classical cannabinoids Adamantoylindoles Benzimidazoles Benzoylindoles Cyclohexylphenols Eicosanoids Indazole-3- carboxamides Indole-3-carboxamides Indole-3-carboxylates Naphthoylindazoles Naphthoylindoles Naphthoylpyrroles Naphthylmethylindenes Naphthylmethylindoles Phenylacetylindoles Pyrazolecarboxamides Tetramethylcyclo- propanoylindazoles Tetramethylcyclo- propanoylindoles Others
Allosteric CBR Tooltip Cannabinoid receptor ligands Endocannabinoid enhancers (inactivation inhibitors) Anticannabinoids (antagonists/inverse agonists/antibodies)