4,8,13-Duvatriene-1,3-diol

There are relatively few reported diterpenoid phytotoxins produced by plants, although there are several potent diterpenes from fungi. The duvatriene-diol diterpenoids from tobacco leaf surfaces are phytotoxic to the serious weed Echinocloa crus-galli.26 Macias et al.32 summarized the effects of various... 

Duvatienediol, a Trichome ", P1NT445 Duvatienediol, P Trichome ", P1NT445 Duvatriene-1-3-diol, p-4-8-13 LfN 5 Elem Lf, Rt, St, Bk,... 

Tobacco leaf has a complicated chemical composition including a variety of polymers and small molecules. The small molecules from tobacco belong to numerous classes of compounds such as hydrocarbons, terpenes, alcohols, phenols, acids, aldehydes, ketones, quinones, esters, nitriles, sulfur compounds, carbohydrates, amino acids, alkaloids, sterols, isoprenoids [48], Amadori compounds, etc. Some of these compounds were studied by pyrolysis techniques. One example of pyrolytic study is that of cuticular wax of tobacco leaf (green and aged), which was studied by Py-GC/MS [49]. By pyrolysis, some portion of cuticular wax may remain undecomposed. The undecomposed waxes consist of eicosyl tetradecanoate, docosyl octadecanoate, etc. The molecules detected in the wax pyrolysates include hydrocarbons (Cz to C34 with a maximum of occurrence of iso-Czi, normal C31 and anti-iso-C32), alcohols (docosanol, eicosanol), acids (hexadecanoic, hexadecenoic, octadecanoic, etc ). The cuticular wax also contains terpenoids such as a- and p-8,13-duvatriene-1,3-diols. By pyrolysis, some of these compounds are not decomposed and others generate closely related products such as seco-cembranoids (5-isopropyl-8,12-dimethyl-3E,8E,12E,14-pentadecatrien-2-one, 3,7,13-trimethyl-10-isopropyl-2,6,11,13-tetradecatrien-1al) and manols. By pyrolysis, c/s-abienol, (12-Z)- -12,14-dien-8a-ol, generates mainly frans-neo-abienol. 

Rowland, R.L. and D.L. Roberts Macrocycylic diterpenes isolated from tobacco, a- and P-3,8,13-Duvatriene-1,5-diols J. Org. Chem. 28 (1963) 1165-1169. Rowland, R.L., A. Rodgman, J.N. Schumacher, D.L. Roberts, L.C. Cook, and W.E. Walker Jr Macrocyclic diterpenes. Hydroxyethers from tobacco and tobacco smoke 17th Tobacco Chemists Research Conference, Program Booklet and Abstracts, Vol. 17, Paper No. 16, 1963, p. 13, for presentation text, see www.rjrtdocs.com 521189981 -9997 Macrocyclic diterpene hydroxyethers from tobacco and cigarette smoke J. Org. Chem. 29... 

Duvatriendiols, primarily a- and 3-4,8,13-duvatrien-1,3-diols (59 and 60), are synthesized in glandular trichomes of the leaves of tobacco. These preformed compounds have antifungal properties. Duvatriendiols inhibit spore germination of Peronospora tabacina with an EC50 of 20 (xg/ml (Kuc, 1992). 

Ripperger H, Schreiber K, Budzikiewicz H (1967b) IsoUerung von Neochlorogenin und Pemiculogenin aus Solarium paniculatum L. Ber 100 1741-1752 Roberts DL, Rowland RL (1962) MacrocycUc diterpenes a- and P-4,8,13-duvatriene-l,3-diols from tobacco. J Oig Chem 27 3989-3995... 

A regular diamond lattice conformation was found for cyclotetradecanone at —157 °C. The structures of sinulariolide (27)" and a plant-growth inhibitor found to be 4,8,13-duvatriene-l,3,-diol(28) have been confirmed using X-ray methods. 

Cuticular extracts used for the isolation of components were obtained from different N. tabacum genotypes that were grown in blocks of 100 plants. Cuticular components were extracted from plant tops using methylene chloride as previously described (75). The extracts from the following tobaccos were used to isolate specific components using the methodology reported by Severson et al.(76) a- and B-4,8,13-duvatriene-l,3-diols (DVT-diols) (97+% by GC, 3 1 a-diol to B-diol) from NC 2326 a- and B-4,8,13-duvatrien-l-ols (DVT-ols) (98+% by GC, 9 1 a-ol to B-ol) from PD 1097 a sucrose ester fraction (SE, 6-O-acetyl-2,3,4-tri-0-acyl-sucrose) (97+%by GC) from PD 1097 labda-12,14-dien-8a-ol (cw-abienol) (98+% as monohydrate, mp 67 C) from NET and labda-13-ene-8a,15-diol(labdenediol) (99+%, mp 126-128 C) from PD 964. 

Figure 1. Probit analyses for survival rates of tobacco aphids that were topically dosed with components isolated from tobacco germplasm sources (N=60 aphids per dose Regression R s Nicotine, 0.75 Sucrose Esters, 0.66 Cw-Abienol, 0.73 a- and B-4,8,13-duvatriene-l,3-diols (DVT-diols), 0.98 a- and B-4,8,13-duvatrien-l-ols (DVT-ols), 0.98 DVT-ols + Cw-abienol, 0.90).

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