Tobacco Chemistry. 59. Six New Cembratrienetriols from Tobacco.

Wahlberg, Inger; Arndt, Rolf; Wallin, Ingrid; Vogt, Carmen; Nishida, Toshiaki; Enzell, Curt R.

doi:10.3891/acta.chem.scand.38b-0021

Cited by 17 publications

(13 citation statements)

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“…The identified cembranoids and labdanoids in this study are summarized in Tables 1 and 2. Comparing these compounds with the previously reports, some have already been found 25–35, but new compounds were present, which were deduced from the mass spectrum and need to be further confirmed by authentic references. The bold in two tables probably were unreported diterpenoids, including three cembranoids and seven labdanoids.…”

Section: Resultssupporting

confidence: 65%

Separation and detection of polar cuticular components from Oriental tobacco leaf by integration of normal‐phase liquid chromatography fractionation with reversed‐phase liquid chromatography‐mass spectrometry

Ding¹,

Xie²,

Xu³

et al. 2010

J of Separation Science

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Integration of normal-phase LC (NPLC) fractionation with RPLC-ESI/MS was established to detect the polar fractions of cuticular components from Oriental tobacco leaf. NPLC was selected for the fractionation of polar components of cuticular leaf extract, after being concentrated with rotary evaporator, each of the enriched fractions was further analyzed by RPLC-ESI/MS. In total, 83 compounds were finally detected including 45 cembranoids, 15 labdanoids, 20 sucrose esters, and 3 glucose esters (or fructose esters). Three cembranoids and seven labdanoids possibly are new diterpenoids. Glucose esters (or fructose esters) are also reported in Nicotiana tobacco for the first time.

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Section: Resultssupporting

confidence: 65%

Separation and detection of polar cuticular components from Oriental tobacco leaf by integration of normal‐phase liquid chromatography fractionation with reversed‐phase liquid chromatography‐mass spectrometry

Ding¹,

Xie²,

Xu³

et al. 2010

J of Separation Science

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“…In agreement with this, the 4S,6R-diol [2] reacted smoothly with singlet oxygen at the 11,12 double bond giving, after reduction of the initially generated hydroperoxides using triethyl phosphite, two 4,6,11-triols [ 8, .9J and two 4,6,12-triols [ 12,13] in the ratio 63:1:31:5 (12). The generation of both major triols [ 8,12] may be accounted for by reactions taking place with conformer a of the 4S,6R-diol [2] (Scheme 3).…”

supporting

confidence: 51%

“…All four products [ 8,9,12,13] are formed by syn ene reactions, i.e. hydrogen abstraction occurs solely from the 1,2-disubstituted side of the trisubstituted double bond (Scheme 4).…”

mentioning

confidence: 99%

“…Scheme 13). An alternative pathway, validated by photooxygenation experiments, involves oxidation of the 11,12 double bond in the 4R, 8S-diol [22] (12). , also a tobacco constituent (3,16), is obtainable by an acid-induced cyclization of the 4S,6R,11$-triol [8J (cf.…”

mentioning

confidence: 99%

“…The generation of both major triols [ 8,12] may be accounted for by reactions taking place with conformer a of the 4S,6R-diol [2] (Scheme 3). Thus oxygen attachment to C-11 and rearrangement of a hydrogen from C-20 would yield the hydroperoxide precursor of the 4S,6R,11S-triol, whereas the hydroperoxide precursor of the 4S,6R,12S-triol would arise by oxygen attachment to C-12 and migration of the pro-R-hydrogen from C-10.…”

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confidence: 99%

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Tobacco Cembranoids

Wahlberg¹,

Enzell²

1984

Beiträge Zur Tabakforschung / Contributions to Tobacco Research

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The discovery of the first diterpenoids of the cembrane type in tobacco dates back to the early 1960's. Since then some forty tobacco cembranoids have been encountered. Most of these have a hydroxyl substituent at C-4 and are commonly divided into two series: those having a 4R- and those having a 4S-configuration. Additional oxygenation is found at C-6, C-7, C-8, C-11 or C-12. These compounds, which are present in the gummy exudate of the tobacco leaf and flower, are susceptible to biodegradation thus accounting for the presence of the large number of odoriferous norcembranoids in tobacco. They are also reported to include representatives having growth inhibiting and insect resistance properties. A considerable insight into the biological transformations of the tobacco cembranoids has been obtained by isolation and determination of the stereostructures of new compounds and by biomimetic experiments. The latter have involved singlet oxygen reactions, epoxidations and acid- and base-induced rearrangements. The results obtained support the importance of the (1S,2 E,4R,6R,7E,11 E)- and (1 S,2 E,4 S,6R,7 E,11 E)-2,7,11-cembratriene-4,6-diols, the major tobacco cembranoids, as key metabolites in the biogenesis of the other cembranic compounds. An account of these biogenetic reactions will be given and the isolation of a few new cembranoids will be reported.

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