Bibenzyl cannabinoid and bisbibenzyl derivative from the liverwort Radula perrottetii

Toyota, Masao; Kinugawa, Tomohide; Asakawa, Y.

doi:10.1016/s0031-9422(00)90371-6

Cited by 71 publications

(53 citation statements)

References 8 publications

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“…9 Furthermore, the neolignans share structural similarity with some highly potent synthetic CB receptor ligands, such as CP55,940 (5), but also plant-derived biaryl CBs. 8,10,11 CB receptors belong to the G protein-coupled receptor (GPCR) superfamily and are divided into two distinct subtypes designated CB 1 and CB 2 , both of which are linked to an inhibition of adenylate cyclase. 12 CB 1 activation mediates analgesia, stimulation of appetite, and euphoria, among other effects.…”

mentioning

confidence: 99%

Magnolia Extract, Magnolol, and Metabolites: Activation of Cannabinoid CB₂ Receptors and Blockade of the Related GPR55

Rempel

Fuchs

Hinz

et al. 2012

ACS Med. Chem. Lett.

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ABSTRACT:The bark of Magnolia of ficinalis is used in Asian traditional medicine for the treatment of anxiety, sleeping disorders, and allergic diseases. We found that the extract and its main bioactive constituents, magnolol and honokiol, can activate cannabinoid (CB) receptors. In cAMP accumulation studies, magnolol behaved as a partial agonist (EC 50 = 3.28 μM) with selectivity for the CB 2 subtype, while honokiol was less potent showing full agonistic activity at CB 1 and antagonistic properties at CB 2 . We subsequently synthesized the major metabolites of magnolol and found that tetrahydromagnolol (7) was 19-fold more potent than magnolol (EC 50 CB 2 = 0.170 μM) exhibiting high selectivity versus CB 1 . Additionally, 7 behaved as an antagonist at GPR55, a CB-related orphan receptor (K B = 13.3 μM, β-arrestin translocation assay). Magnolol and its metabolites may contribute to the biological activities of Magnolia extract via the observed mechanisms of action. Furthermore, the biphenylic compound magnolol provides a simple novel lead structure for the development of agonists for CB receptors and antagonists for the related GPR55.

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confidence: 99%

Magnolia Extract, Magnolol, and Metabolites: Activation of Cannabinoid CB₂ Receptors and Blockade of the Related GPR55

Rempel

Fuchs

Hinz

et al. 2012

ACS Med. Chem. Lett.

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“…29 Natural cannabinoids are restricted to Cannabis sativa and its variants in higher plants, 30,31 and a bibenzyl analogue of ∆ 9 -THC, perrottetinen, had previously been reported from liverwort Radula perrottetii. 32 It is intriguing to note that the antimalarial activity of Peruvian M. multiflorum is contributed by two nonpsychotropic HHDBP derivatives 1 and 2. Recently, antimalarial stilbenes from Artocarpus integer exhibited in vitro activities against multi-drugresistant K1 strain.…”

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confidence: 99%

Antimalarial (+)-trans-Hexahydrodibenzopyran Derivatives from Machaerium multiflorum

Muhammad

Dunbar

et al. 2001

J. Nat. Prod.

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Bioassay-guided fractionation of Machaerium multiflorum yielded the hitherto unreported (+)-trans-hexahydrodibenzopyrans machaeriol A (1) and machaeriol B (2), as well as the known guaiane sesquiterpene (-)-kessane. Structure elucidation was based on (1)H and (13)C NMR data, mainly 2D NMR (1)H-(1)H COSY, (1)H-(13)C HMQC, (1)H-(13)C HMBC, and (1)H-(1)H NOESY experiments. This is the first report of the hexahydrodibenzopyrans from a higher plant other than the genus Cannabis. The cannabimimetic activity was thus evaluated by radioligand binding assay for cannabinoid receptor CB1, which indicated, notably, that both 1 and 2 were inactive. In addition, the cross reactivity of 1 and 2 toward antibodies designed for urinary metabolites of cannabinoids was evaluated with the EMIT and On Line cannabinoids assays. Both compounds showed no response at 100 000 ng/mL in both assays. Machaeriol B (2) demonstrated in vitro antimalarial activity (IC(50) = 120 ng/mL) against Plasmodium falciparum W-2 clone.

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“…However, the bibenzyl cannabinoid, perrottetinene, was isolated in 1994 from the small leafy-stem liverwort, Radula perrottetii. 73 The same compound was found in Radula laxiramea. 74 Later, Toyota et al 75 isolated perrottetinene and its acid, perrottetinenic acid in the New Zealand liverwort Radula marginata.…”

Section: B Cannabinoids From Radula Plantsmentioning

confidence: 63%

Pharmacological and therapeutic secrets of plant and brain (endo)cannabinoids

Hanŭs

2008

Medicinal Research Reviews

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Research on the chemistry and pharmacology of cannabinoids and endocannabinoids has reached enormous proportions, with approximately 15,000 articles on Cannabis sativa L. and cannabinoids and over 2,000 articles on endocannabinoids. The present review deals with the history of the Cannabis sativa L. plant, its uses, constituent compounds and their biogeneses, and similarity to compounds from Radula spp. In addition, details of the pharmacology of natural cannabinoids, as well as synthetic agonists and antagonists are presented. Finally, details regarding the pioneering isolation of the endocannabinoid anandamide, as well as the pharmacology and potential therapeutic uses of endocannabinoid congeners are presented.

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Bibenzyl cannabinoid and bisbibenzyl derivative from the liverwort Radula perrottetii

Cited by 71 publications

References 8 publications

Magnolia Extract, Magnolol, and Metabolites: Activation of Cannabinoid CB₂ Receptors and Blockade of the Related GPR55

Magnolia Extract, Magnolol, and Metabolites: Activation of Cannabinoid CB₂ Receptors and Blockade of the Related GPR55

Antimalarial (+)-trans-Hexahydrodibenzopyran Derivatives from Machaerium multiflorum

Pharmacological and therapeutic secrets of plant and brain (endo)cannabinoids

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Bibenzyl cannabinoid and bisbibenzyl derivative from the liverwort Radula perrottetii

Cited by 71 publications

References 8 publications

Magnolia Extract, Magnolol, and Metabolites: Activation of Cannabinoid CB2 Receptors and Blockade of the Related GPR55

Magnolia Extract, Magnolol, and Metabolites: Activation of Cannabinoid CB2 Receptors and Blockade of the Related GPR55

Antimalarial (+)-trans-Hexahydrodibenzopyran Derivatives from Machaerium multiflorum

Pharmacological and therapeutic secrets of plant and brain (endo)cannabinoids

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Magnolia Extract, Magnolol, and Metabolites: Activation of Cannabinoid CB₂ Receptors and Blockade of the Related GPR55

Magnolia Extract, Magnolol, and Metabolites: Activation of Cannabinoid CB₂ Receptors and Blockade of the Related GPR55