The aerial parts of Cannabis sativa var. Carma afforded a novel polar cannabinoid whose structure was established as rac-6′,7′-dihydro,6′,7′-dihydroxycannabigerol (carmagerol, 1) on the basis of spectroscopic data and semisynthesis from cannabigerol (2a). The dihydroxylation of the ω-double bond was detrimental to the anti-bacterial activity.
PerezJ, RiberaMV. (2008) Managing neuropathic pain with Sativex: a review of pros and cons. Expert Opinions in Pharmacotherapy, 9, 1189–1195.
2.
El-SohlyMA, SladeD. (2005) Chemical constituents from Marijuana: The complex mixture of natural cannabinoids. Life Sciences, 78, 539–548.
3.
MechoulamR, GaoniY (1964) Isolation, structure and partial synthesis of an active constituent of hashish. Journal of American Chemical Society, 86, 1646–1647.
4.
AhmedSA, RossSA, SladeD, RadwanMM, ZulfiquarF, ElsohlyMA. (2008) Cannabinoid ester constituents from high-potency Cannabis sativa. Journal of Natural Products, 71, 536–542.
5.
The name of the famous French revolutionary song “la Carmagnole” was in fact inspired by the trade of this variety of hemp, characterized by very long fibers and insuperable for the manufacture of naval ropes, from Carmagnola and Marseille. See: http://architettura.supereva.com/image/festival/1998/en/bonino.htm
6.
MinassiA, GianaA, Ech ChahadA, AppendinoG. (2008) A regiodivergent synthesis of ring C prenylflavones. Organic Letters, 10, 2257–2270.
7.
ChoiYH, HazekampA, Peltenburg-LoomanAMG, FrédérichM, ErkelensC, LefeberAWM, VerpoorteR. (2004) NMR assignments of the major cannabinoids and cannabiflavonoids isolated from flowers of Cannabis sativa. Phytochemical Analysis, 15, 345–354.
8.
For a related example, see: VidariG, Di RosaA, CastronovoF, ZanoniG. (2000) Enantioselective synthesis of each stereoisomer of the pyranoid linalool oxides: the geraniol route. Tetrahedron Asymmetry, 11, 981–989.
9.
HarveyD, BrownNK. (1990) In vitro metabolism of cannabigerol in several mammalian species. Biomedical & Environmental Mass Spectrometry, 19, 545–553.
10.
A series of cannabigerol derivatives epoxidized on the proximal double bond have recently been reported (RadwanMM, RossSA, SladeD, AhmedSA, ZulfiquarF, ElsohlyMA. (2008) Isolation and characterization of new Cannabis constituents from a high potency variety, Planta Medica, 74, 267–272.
11.
AppendinoG, GibbonsS, GianaA, PaganiA, GrassiG, StavriM, SmithE, Mukhlesur RahmanM. (2008) Antibacterial cannabinoids from Cannabis sativa. A structure-activity study. Journal of Natural Products, 71, 1427–1430.
