Isolation and Characterization of New Cannabis Constituents from a High Potency Variety

Radwan, Mohamed M.; Rosenberg, S A; Slade, Desmond; Ahmed, SA; Zulfiqar, Fazila; Ma, Erni

doi:10.1055/s-2008-1075211

Cited by 18 publications

(25 citation statements)

References 7 publications

(7 reference statements)

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“…Δ 9 -THC, 26 Δ 9 -THCA, 26 CBNA, 30 and CBGA 28 were identified by comparison with published data; however, this is the first time full NMR data are reported for CBNA. 2815, 1716, 1636, 1541, 1457, 1418, 1067 cm −1; 1 H NMR and 13 C NMR, see …”

Section: Extraction and Isolationmentioning

confidence: 89%

“…28 The 1 H NMR spectrum for 11 displayed three methyl resonances at δ 1.58 (3H, s, H-8), 1.68 (3H, s, H-9), and 1.83 (3H, s, H-10), three methylenes at δ 2.11 (2H, m, H-5), 2.21 (2H, m, H-4), and 3.44 (2H, d, J) 7.0 Hz, H-1), and two olefinic proton resonances at δ 5.07 (1H, t, J) 6.4 Hz, H-6) and 5.28 (1H, t, J = 7.0 Hz, H-2), attributed to a geranyl substituent. It also displayed an aromatic proton signal at δ 6.23 (1H, s, H-4′).…”

Section: Hhs Public Accessmentioning

confidence: 99%

“…28 methine, and one quaternary carbon, indicating that 11 is a sesquiterpenol CBGA ester. GC-MS analysis spontaneously hydrolyzed and decarboxylated 11 to give CBG and a sesquiterpenol.…”

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confidence: 99%

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Cannabinoid Ester Constituents from High-PotencyCannabis sativa

et al. 2008

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Eleven new cannabinoid esters, together with three known cannabinoid acids and Δ 9 -tetrahydrocannabinol (Δ 9 -THC), were isolated from a high-potency variety of Cannabis sativa. The structures were determined by extensive spectroscopic analyses to be β-fenchyl Δ 9 -tetrahydrocannabinolate (1), epi-bornyl Δ 9 -tetrahydrocannabinolate (2), α-terpenyl Δ 9 -tetrahydrocannabinolate (3), 4-terpenyl Δ 9 -tetrahydrocannabinolate (4), α-cadinyl Δ 9 -tetrahydrocannabinolate (5), γ-eudesmyl Δ 9 -tetrahydrocannabinolate (6), γ-eudesmyl cannabigerolate (7), 4-terpenyl cannabinolate (8), bornyl Δ 9 -tetrahydrocannabinolate (9), α-fenchyl Δ 9 -tetrahydrocannabinolate (10), α-cadinyl cannabigerolate (11), Δ 9 -tetrahydrocannabinol (Δ 9 -THC), Δ 9 -tetrahydrocannabinolic acid A (Δ 9 -THCA), cannabinolic acid A (CBNA), and cannabigerolic acid (CBGA). Compound 8 showed moderate antimicrobial activity against Candida albicans ATCC 90028 with an IC 50 value of 8.5 μg/mL. CB-1 receptor assay indicated that the esters, as well as the parent acids, are not active.The family Cannabaceae is currently recognized as containing only one genus, namely, Cannabis, which includes only one highly variable species: Cannabis sativa L. Other previously reported species include Cannabis indica Lam. and Cannabis ruderalis Janisch. Plants considered to have belonged to these species are now recognized as varieties of C. sativa L. (var. indica and var. ruderalis, respectively). C. sativa L. has been used by humans for thousands of years, providing fiber for spinning and making paper, seed for human and animal consumption, and aromatic resin for medicinal use. The chemotypes of C. sativa L.can be divided into drug type (marijuana), intermediate type, and fiber type (hemp), with the tetrahydrocannabinol (Δ 9 -THC) content ranging from 1 to 20%, 0.3-1.0%, and <0.3%, respectively. 1-3 Supporting Information Available: HRESIMS, GC-MS, GC-MS trimethylsilyl derivatization, 1 H NMR, 13 C NMR, and selected 2D NMR spectra for compound 1. HPLC chromatograms of isolated compounds. GC-MS data of isolated compounds. This material is available free of charge via the Internet at http://pubs.acs.org. Cannabis is very complex in its chemistry due to the vast number of its constituents and their possible interaction with one another. The compounds reported include many natural product classes, e.g., mono-and sesquiterpenes, sugars, hydrocarbons, steroids, flavonoids, nitrogenous compounds, and amino acids. [4][5][6][7][8][9][10] The best-known and the most specific group of compounds found in cannabis is the C 21 terpenophenolics, the cannabinoids, with (−)-Δ 9 -trans-(6aR,10aR)-tetrahydrocannabinol (Δ 9 -THC) being the most psychoactive constituent. 11 The development of synthetic cannabinoids and the discovery of chemically different endogenous cannabinoid receptor ligands (endocannabinoids) have prompted the use of the term "phytocannabinoids" to describe these compounds. 12 The class cannabinoids can be divided into 11 groups: cannabigerol type (7 known), ca...

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Section: Extraction and Isolationmentioning

confidence: 89%

Section: Hhs Public Accessmentioning

confidence: 99%

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Cannabinoid Ester Constituents from High-PotencyCannabis sativa

et al. 2008

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“…Currently, 86 cannabinoids have been isolated from cannabis ElSohly and Slade, 2005 ;Radwan et al, 2008 ). Non-cannabinoid constituents isolated from cannabis include flavonoids, spiroindans, dihydrostilbenes, dihydrophenanthrenes, sterols and alkaloids, among others ( Ross and ElSohly, 1995 ;Turner et al, 1980 ).…”

Section: Introductionmentioning

confidence: 99%

“…Non-cannabinoid constituents isolated from cannabis include flavonoids, spiroindans, dihydrostilbenes, dihydrophenanthrenes, sterols and alkaloids, among others ( Ross and ElSohly, 1995 ;Turner et al, 1980 ). As part of our program to study the constituents of high potency cannabis and their pharmacology Radwan et al, 2008 ), we herein report the isolation and structure elucidation of eleven non-cannabinoid constituents including six new (1-6) and five known (7-11) compounds as well as their antimicrobial, antileishmanial, antimalarial and antioxidant activities. The analgesic activities of 2-4 are also reported.…”

Section: Introductionmentioning

confidence: 99%

Non-cannabinoid constituents from a high potency Cannabis sativa variety

Radwan¹,

ElSohly²,

Slade³

et al. 2008

Planta Med

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Six new non-cannabinoid constituents were isolated from a high potency Cannabis sativa L.variety, namely 5-acetoxy-6-geranyl-3-n-pentyl-1,4-benzoquinone (1), 4,5-dihydroxy-2,3,6-trimethoxy-9,10-dihydrophenanthrene (2), 4-hydroxy-2,3,6,7-tetramethoxy-9,10-dihydrophenanthrene (3), 4,7-dimethoxy-1,2,5-trihydroxyphenanthrene (4), cannflavin C (5) and β-sitosteryl-3-O-β-D-glucopyranoside-2'-O-palmitate (6). In addition, five known compounds, α-cannabispiranol (7), chrysoeriol (8), 6-prenylapigenin (9), cannflavin A (10) and β-acetyl cannabispiranol (11) were identified, with 8 and 9 being reported for the first time from cannabis. Some isolates displayed weak to strong antimicrobial, antileishmanial, antimalarial and antioxidant activities. Compounds 2-4 were inactive as analgesics.

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Antiparasitic Activity of C‐Geranyl Flavonoids from Mimulus bigelovii

Salem

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Rito

et al. 2011

Phytotherapy Research

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Bioactivity-directed fractionation of the MeOH fraction of the extract of Mimulus bigelovii by means of an axenic Leishmania amastigote assay and chromatographic techniques resulted in the isolation of four C-geranyl flavanones, diplacone (1), 3'-O-methyldiplacone (2), 4'-O-methyldiplacone (3), 3'-O-methyldiplacol (4), together with a geranylated flavone, cannflavin A (5). These compounds were separated from M. bigelovii for the first time. All compounds showed moderate antileishmanial activity against axenic Leishmania donovani amastigotes with IC(50) values ranging from 4.8 to 14.6 μg/mL. The compounds were also tested against the related kinetoplastid parasite Trypanosoma brucei brucei and they showed activity with IC(50) values ranging from 1.4 to 7.2 μg/mL.

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Isolation and Characterization of New Cannabis Constituents from a High Potency Variety

Cited by 18 publications

References 7 publications

Cannabinoid Ester Constituents from High-PotencyCannabis sativa

Cannabinoid Ester Constituents from High-PotencyCannabis sativa

Non-cannabinoid constituents from a high potency Cannabis sativa variety

Antiparasitic Activity of C‐Geranyl Flavonoids from Mimulus bigelovii

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