Macrocyclic Diterpene Hydroxy Ethers from Tobacco and Cigarette Smoke

Rowland, R. L.; Rodgman, Alan; Schumacher, J. N.; Roberts, Donald L.; Cook, Lawrence C.; Walker, W. E.

doi:10.1021/jo01024a003

Cited by 27 publications

(4 citation statements)

References 5 publications

(8 reference statements)

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“…The data presented are consistent with the structure proposed in the text; however, additional spectral and chemical information is clearly required. Reports of diterpenes possessing 14-membered carbocyclic rings are becoming increasingly numerous (e.g., Rowland et al, 1964;Kimland and Norin, 1968). All of the compounds appear to possess the carbon skeleton of the hydrocarbon cembrene (V) which itself is found in certain pine species (Dauben et al, 1965;Kobayashi and Akiyoshi, 1963).…”

Section: Discussionmentioning

confidence: 99%

Biosynthesis of cyclic diterpenes in extracts from seedlings of Ricinus communis. I. Identification of diterpene hydrocarbons formed from mevalonate

Robinson¹,

West²

1970

Biochemistry

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Section: Discussionmentioning

confidence: 99%

Biosynthesis of cyclic diterpenes in extracts from seedlings of Ricinus communis. I. Identification of diterpene hydrocarbons formed from mevalonate

Robinson¹,

West²

1970

Biochemistry

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“…< The saturated aliphatic hydrocarbons a , the phytosterols b , and terpenoids c (such as solanesol and its long-chained aliphatic esters) in tobacco, were demonstrated to be major precursors of PAHs in CSC in a 1979 study by Severson et al (842) of the United States Department of Agriculture and in a 1958 study in which the levels of each category in the cigarette tobacco were doubled and tripled (843). < In 1963 and 1964, Rowland et al (844) described the conversion of a cyclotetradecane derivative to a phenanthrene derivative. A cholesterol pyrolysate was demonstrated to be tumorigenic in 1928 by Kennaway and Sampson (343), in 1945 by Beck et al (846), and again in 1949 by Falk et al (845).…”

Section: Controversies Over the Roffo Investigationsmentioning

confidence: 99%

The Chemical Components Identified in Tobacco and Tobacco Smoke Prior to 1954: A Chronology of Classical Chemistry

Rodgman¹,

Perfetti²

2009

Beiträge Zur Tabakforschung International/Contributions to Tobacco Research

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Because of the excellent fractionation and identification technologies developed during the early-1950s, the compositions of tobacco and tobacco smoke, both classified as highly complex mixtures, have been defined more completely than the composition of any other highly complex commercial product such as coffee. By year-end 1953, the many years of research by scientists using classical chemical techniques to define the composition of tobacco and its smoke provided meaningful information on the nature of over 300 tobacco components and fewer than 100 tobacco smoke components. Those involved in the pre-1954 research not only provided the cornerstone of our knowledge of the two compositions but also deserve the gratitude of their successors for the early information generated on tobacco and its smoke. This article is our tribute to those researchers who generated much meaningful knowledge on the composition of tobacco and tobacco smoke prior to 1954 despite the now known fractionation and analytical limitations of the so-called classical chemical techniques. It also notes the similarity of some of the early and more recent research results obtained on the chemical and biological properties of smoke condensate and several of its components from tobacco with those obtained by Roffo in the 1930s on a destructive distillate of tobacco.

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“…But at the 50 pg and 100 pg dose levels of B(a)P, the combined action of B(a)P and tobacco extract (GrlO and G r l l ) as well as of B(a)P and betel nut extract (Gr13 and Gr14), in terms of tumor incidence tended to be synergistic in nature, i.e., the tumor incidences in GrlO, G r l l , Gr13 and Gr14 were respectively much higher than the expected summation of the tumor incidence rates seen in Gr4-plus-Gr6, Gr5-plus-Gr6, Gr4-plus-Gr7 and Gr5-plus-Gr7 combinations. It also should be noted that between tobacco and betel nut, the former was obviously more effective not only in yielding tumors on its own merit, but also in synergistically enhancing the carcinogenic action of higher doses of B(a)P. Extracts of tobacco leaf have been shown to possess tumor-promoting activity in mouse skin and this may be due to the presence of macrocyclic diterpenes similar in structure to phorbol, a tumor promoter (Bock et al, 1964;Rowland et al, 1964).…”

Section: Discussionmentioning

confidence: 99%

Modifying influences of betel quid ingredients on B(a)P‐induced carcinogenesis in the buccal pouch of hamster

Rao¹

1984

Intl Journal of Cancer

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The present study evaluates the incidence of tumors in hamster buccal pouches following short-term (10 days) and long-term (6 months) topical exposures to graded doses of benzo(a)pyrene, B(a)P (25 micrograms, 50 micrograms and 100 micrograms per pouch either daily for 10 days or thrice weekly for 6 months) alone or in combination with extract of tobacco (1 mg/pouch, twice daily), betel nut (1 mg/pouch, twice daily) or betel leaf (5 mg/pouch, twice daily). Given alone, the three doses of B(a)P respectively yielded, 6 months after the last treatment, 4%, 8.7% and 16.7% tumors in the short-term study, and 20%, 35% and 61% tumors in the long-term study. Short-term treatments with individual ingredients of betel quid did not produce any tumors while long-term treatments produced tumors only with tobacco (17.6%) and betel nut (10.5%). When B(a)P, and betel quid ingredients were painted concomitantly for 10 days, there was, depending upon the dose of B(a)P, complete or partial suppression of tumor production. But when B(a)P-plus-tobacco or B(a)P-plus-betel nut treatments were given for 6 months, there was a considerable increase in tumor incidence. Betel leaf extract, in both short-term and long-term studies, expressed its inhibitory influence on B(a)P-induced tumorigenesis.

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Macrocyclic Diterpene Hydroxy Ethers from Tobacco and Cigarette Smoke

Cited by 27 publications

References 5 publications

Biosynthesis of cyclic diterpenes in extracts from seedlings of Ricinus communis. I. Identification of diterpene hydrocarbons formed from mevalonate

Biosynthesis of cyclic diterpenes in extracts from seedlings of Ricinus communis. I. Identification of diterpene hydrocarbons formed from mevalonate

The Chemical Components Identified in Tobacco and Tobacco Smoke Prior to 1954: A Chronology of Classical Chemistry

Modifying influences of betel quid ingredients on B(a)P‐induced carcinogenesis in the buccal pouch of hamster

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