Podocarpus totara

Figure 1.38. The outside surface of the strip hark of Podocarpus totara.

Totarol (102), first isolated from the heartwood of a tree indigenous to New Zealand, Podocarpus totara G. Benn (Podocarpaceae) [158,159], is widely distributed throughout the plant kingdom in various species such as P. nagi (Nagi in Japanese), P. macrophyllus (Southern Yew, Inumaki in... 

Representatives of podocarpanes include podocarpinol in Podocarpus totara, and podocarpic acid, the dominant acidic constituent of podocarpus resin obtained from Javanese P. cupressina (Cupressaceae), as well as the bitter-tasting phenolic compounds nimbiol and nimbione. These are found in the bark and isolated from neem oil expressed from the seed-kernels of the Indian neem tree Azadirachta indica (Meliaceae). Extracts of this bark are added to some mouthwashes and skin creams neem oil is used as an agricultural insect repellant and antifeedant. 

More than 20 quinoid 13,16-cycloabietanes, named as eoleones A-Z, oeeur in the yellow glands in the leaves of Afriean Coleus speeies (Labiatae). Lanugone A isolated from Plectranthus lanuginosis (Labiatae) represents a quinoid n(lS)-abeo-abietane. Totaranes sueh as (-l-)-totarol and the derived biphenyl-type dimer (-t)-podototarine are found in the wood of Podocarpus totara (Cupressaeeae). 

A. grandis, Cedrus libani (Cedar of Lebanon), Tsuga heterophylla (Western hemlock), Pseudotsuga menziesii. Araucaria araucana (Monkey puzzle). Araucaria heterophylla (Norfolk Island pine), Podocarpus totara (Totara), Podocarpus lawrencei (Mountain plum pine), Cupressus macrocarpa (Monterey cypress), Picea sitchensis (Sitka spruce)... 

Pododacric acid (23), isolated from Podocarpus dacrydiodes and P. totara, was shown" to be 12,16,17-trihydroxyabieta-8,ll,13-trien-19-oicacid. This structure was confirmed by a partial synthesis of the tetra-O-methyl derivative from podo-carpic acid demethylation gave the parent acid. 

Pododacric Add. 1,2,3,4,4a, 9,10,lOa-Octahydro-6-hydroxy-7-[2-hydroKy-l-(hydrx>xymethyl)ethyl -t,4a-di-methyl-i -phenanthrenecarboxylic acid 12-hydroxy-13-[2-hydroxy-I-(hydroxymethyl)ethyl]podocarpa-8,11,13-trien-16-oic acid. CMH O, mol wt 348.44. C 68.94%, H 8.10%, O 22.96%. From heart wood of Podocarpus dacrydioides P. totara Briggs et aL, Tetrahedron 7, 270 (1959) Cambie,... 

C17H22O3, Mr 274.36, needle-like cryst., mp. 193-194°C, (a]o +164° (CjHjOH). The compound is isolated mainly from numerous members of the Podo-carpaceae (e. g., Podocarpus cupressina, P. totara, P. dacrydioides, P. hallii). P. is a major component of Podocarpus resin and thus belongs to the group of resin acids. 

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