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DOI: 10.1055/s-2008-1034311
© Georg Thieme Verlag KG Stuttgart · New York
Isolation and Characterization of New Cannabis Constituents from a High Potency Variety
Publikationsverlauf
Received: October 16, 2007
Revised: December 10, 2007
Accepted: January 16, 2008
Publikationsdatum:
18. Februar 2008 (online)
![](https://www.thieme-connect.de/media/plantamedica/200803/lookinside/thumbnails/10.1055-s-2008-1034311-1.jpg)
Abstract
Phytochemical investigation of a high potency variety of Cannabis sativa L. resulted in the isolation of six new metabolites, (±)-6,7-trans-epoxycannabigerolic acid (2), (±)-6,7-cis-epoxycannabigerolic acid (3), (±)-6,7-cis-epoxycannabigerol (4), (±)-6,7-trans-epoxycannabigerol (5), 5′-methyl-4-pentylbiphenyl-2,2′,6-triol (7), and 7-methoxycannabispirone (8), along with seven known compounds namely, cannabigerolic acid (1), 5′-methoxycannabigerolic acid (6), cannabispirone (9), β-cannabispiranol (10), dehydrocannabifuran (11), cannflavin B (12) and cannabigerol (13). The antimicrobial as well as the antileishmanial activities were investigated.
Abbreviations
CBG:cannabigerol
CBD:cannabidiol
FID:flame ionization detector
Δ9-THC:Δ9-tetrahydrocannabinol
VLC:vacuum liquid chromatography
Key words
Cannabis sativa - Cannabaceae - epoxy cannabigerolic acid - cannabispirone - antimicrobial activity - antileishmanial activity
References
- 1 El-Sohly M A, Slade D. Chemical constituents of Marijuana: The complex mixture of natural cannabinoids. Life Sci. 2005; 78 539-48
- 2 Williamson E M, Evans F J. Cannabinoids in clinical practice. Drugs. 2000; 60 1303-14
- 3 El-Sohly M A, Ross S A, Mehmedic Z, Arafat R, Yi B, Banahan B F. Potancy trends of Δ9-THC and other cannabinoids in confiscated Marijuana from 1980 - 1997. J Forensic Sci. 2000; 45 24-30
- 4 Bharate S B, Khan S I, Yunus N A, Chaulhe S K, Jacob M R, Tekwani B. et al . Antiprotozoal and antimicrobial activities of O-alkylated and formylated acylphloroglucinols. Bioorg Med Chem. 2007; 15 87-96
- 5 Radwan M M, Manly S P, Ross S A. Two new sulfated sterols from the marine sponge Lendenfeldia dendyi. . Nat Prod Comm. 2007; 2 901-4
- 6 Yang C R, Zhang Y, Jacob M R, Khan S I, Zhang Y J, Li X C. Antifungal activity of C-27 steroidal saponins. Antimicrob Agents Chemother. 2006; 50 1710-4
- 7 Mechoulam R, Gaoni Y. The isolation and structure of cannabinolic, cannabidiolic and cannabigerolic acids. Tetrahedron. 1965; 21 1223-9
- 8 Hevesi L, Nagy J B, Derouane E G. H and C studies of alkenes, epoxides and cyclic thionocarbonates. Org Magn Reson. 1977; 10 14-9
- 9 Choi Y H, Hazekamp A, Peltenburg-Looman A G, Frederich M, Erkelens C, Lefeber A M. et al . NMR assignments of the major cannabinoids and cannabiflavonoids isolated from flowers of cannabis sativa. Phytochem Anal. 2004; 15 345-54
- 10 Shoyama Y, Yamauchi T, Nishioka I. Cannabis V, cannabigerolic acid monomethyl ether and cannabinolic acid. Chem Pharm Bull. 1970; 18 1327-32
- 11 McClanahan R, Robertson L W. Microbial transformation of olivetol by Fusarium roseum. J Nat Prod. 1985; 48 660-3
- 12 El-Feraly F S, El-sherei M M, Muhtadi F J. Spiro-indans from Cannabis sativa. Phytochemistry. 1986; 25 1992-4
- 13 Bercht C A, Dongen J P, Heerma W, Lousberg R C, Kuppers F J. Cannabispirone and cannabispirenone, two naturally occurring spiro-compounds. Tetrahedron. 1976; 32 2939-43
- 14 El-Feraly F S, Chan Y M. Total synthesis of cannabispiran and (±)-dehydrocannabispiran. J Nat Prod. 1981; 44 557-61
- 15 Boeren E G, El-Sohly M A, Turner C E, Salemink C A. β-Cannabispiranol: a non-cannabinoid phenol from Cannabis sativa L. Experientia. 1977; 33 848
- 16 Papadakis D P, Salemink C A. Isolation and identification of new cannabinoids in cannabis smoke. Tetrahedron. 1983; 39 2223-5
- 17 Jorapur V S, Duffley R P, Radzan R K. A biogenetic- type synthesis of cannabifuran and dehydrocannabifuran. Synth Commun. 1984; 14 203-7
Dr. Samir A. Ross
National Center for Natural Products Research
School of Pharmacy
The University of Mississippi
University
MS 38677
USA
Telefon: +1-662-915-1031
Fax: +1-662-915-7989
eMail: sross@olemiss.edu