Machaeriol A

Machaeriol A
Identifiers
	IUPAC name (6aS,9S,10aS)-6,6,9-trimethyl-3-[(E)-2-phenylethenyl]-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol;
CAS Number	377077-52-6;
PubChem CID	10089121;
Chemical and physical data
Formula	C24H28O2
Molar mass	348.486 g·mol−1
3D model (JSmol)	Interactive image;
	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;
	InChI 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]

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.

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[pmid11678659-1] 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.

[pmid12828466-2] 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.

[3] 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.

[pmid26079816-4] 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.

[pmid28701957-5] 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.

[pmid32259175-6] 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.

[pmid33352963-7] 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.

[pmid34395989-8] 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.

[pmid36235141-9] 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.

[pmid37241903-10] 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.

[11] "Machaeriol B". PubChem. U.S. National Library of Medicine.

[12] "Machaeriol C". PubChem. U.S. National Library of Medicine.

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Identifiers

IUPAC name (6aS,9S,10aS)-6,6,9-trimethyl-3-[(E)-2-phenylethenyl]-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol
CAS Number	377077-52-6
PubChem CID	10089121
Chemical and physical data
Formula	C₂₄H₂₈O₂
Molar mass	348.486 g·mol⁻¹
3D model (JSmol)	Interactive image
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
InChI 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

See also

References