Cannabioxepane, a novel tetracyclic cannabinoid from hemp, Cannabis sativa L.

Alberto Pagani; Fernando Scala; Giuseppina Chianese; Gianpaolo Grassi; Giovanni Appendino; Orazio Taglialatela-Scafati

doi:10.1016/j.tet.2011.03.062

Cannabioxepane, a novel tetracyclic cannabinoid from hemp, Cannabis sativa L.

Alberto Pagani
, Fernando Scala
, Giuseppina Chianese
, Gianpaolo Grassi
, Giovanni Appendino
, Orazio Taglialatela-Scafati

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

Abstract

Apart from large amounts of cannabidiol, the known stilbenoids 1-4 and the oxylipins 7 and 8, a fibre cultivar of Cannabis sativa derived from the historical Carmagnola variety gave the novel spiranic stilbenoid isocannabispiradienone (5) and the biphenyl-type cannabinoid cannabioxepane (CBX, 6), a tetracyclic compound characterized by an unprecedented C-5/C-8′ oxygen bridge and devoid of cannabinoid activity. Structures were established by analysis of MS and NMR data, and the biogenetic derivation of the new compounds is discussed.

Lingua originale	Inglese
pagine (da-a)	3369-3373
Numero di pagine	5
Rivista	Tetrahedron
Volume	67
Numero di pubblicazione	19
DOI	https://doi.org/10.1016/j.tet.2011.03.062
Stato di pubblicazione	Pubblicato - 13 mag 2011
Pubblicato esternamente	Sì

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@article{39183573f49e43fabe784aa2c607c03a,

title = "Cannabioxepane, a novel tetracyclic cannabinoid from hemp, Cannabis sativa L.",

abstract = "Apart from large amounts of cannabidiol, the known stilbenoids 1-4 and the oxylipins 7 and 8, a fibre cultivar of Cannabis sativa derived from the historical Carmagnola variety gave the novel spiranic stilbenoid isocannabispiradienone (5) and the biphenyl-type cannabinoid cannabioxepane (CBX, 6), a tetracyclic compound characterized by an unprecedented C-5/C-8′ oxygen bridge and devoid of cannabinoid activity. Structures were established by analysis of MS and NMR data, and the biogenetic derivation of the new compounds is discussed.",

keywords = "Cannabinoids, Cannabioxepane, Cannabis sativa, Stilbenoids, Structure elucidation",

author = "Alberto Pagani and Fernando Scala and Giuseppina Chianese and Gianpaolo Grassi and Giovanni Appendino and Orazio Taglialatela-Scafati",

year = "2011",

month = may,

day = "13",

doi = "10.1016/j.tet.2011.03.062",

language = "English",

volume = "67",

pages = "3369--3373",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

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TY - JOUR

T1 - Cannabioxepane, a novel tetracyclic cannabinoid from hemp, Cannabis sativa L.

AU - Pagani, Alberto

AU - Scala, Fernando

AU - Chianese, Giuseppina

AU - Grassi, Gianpaolo

AU - Appendino, Giovanni

AU - Taglialatela-Scafati, Orazio

PY - 2011/5/13

Y1 - 2011/5/13

N2 - Apart from large amounts of cannabidiol, the known stilbenoids 1-4 and the oxylipins 7 and 8, a fibre cultivar of Cannabis sativa derived from the historical Carmagnola variety gave the novel spiranic stilbenoid isocannabispiradienone (5) and the biphenyl-type cannabinoid cannabioxepane (CBX, 6), a tetracyclic compound characterized by an unprecedented C-5/C-8′ oxygen bridge and devoid of cannabinoid activity. Structures were established by analysis of MS and NMR data, and the biogenetic derivation of the new compounds is discussed.

AB - Apart from large amounts of cannabidiol, the known stilbenoids 1-4 and the oxylipins 7 and 8, a fibre cultivar of Cannabis sativa derived from the historical Carmagnola variety gave the novel spiranic stilbenoid isocannabispiradienone (5) and the biphenyl-type cannabinoid cannabioxepane (CBX, 6), a tetracyclic compound characterized by an unprecedented C-5/C-8′ oxygen bridge and devoid of cannabinoid activity. Structures were established by analysis of MS and NMR data, and the biogenetic derivation of the new compounds is discussed.

KW - Cannabinoids

KW - Cannabioxepane

KW - Cannabis sativa

KW - Stilbenoids

KW - Structure elucidation

UR - https://www.scopus.com/pages/publications/79955047924

U2 - 10.1016/j.tet.2011.03.062

DO - 10.1016/j.tet.2011.03.062

M3 - Article

SN - 0040-4020

VL - 67

SP - 3369

EP - 3373

JO - Tetrahedron

JF - Tetrahedron

IS - 19

ER -

Cannabioxepane, a novel tetracyclic cannabinoid from hemp, Cannabis sativa L.

Abstract

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