Easterfiei.d. — Chemist ri/ of tlte Sew Zeithiiul Floni. 53 



Art. VIII. — Studies on the Chemistry of the Neiv Zealand Flora. 



By T. H. Easterfield, Victoria College, Wellington. 



[Read before the Wellinijion Philosophical Society, 5th Octol)er, 1010.] 



PART IV.— THE CHEMISTRY OF THE PODOCARPI. 



The present paper summarizes, for the use of New Zealand readers, work 

 which has been carried on for several years in the Victoria College labora- 

 tories on various species of New Zealand Podocarpi. The full details have in 

 part already appeared in the " Transactions of the Chemical Society," and 

 others ^will shortly be forwarded for publication in that journal. These 

 details are of too technical a nature to be of interest to any except the 

 highly trained specialist, who can readily refer to the journal in question,, 

 which is taken in the library of each of the University Colleges. 



(1.) The Miro (Podocarpus ferrugineus). 



The miro appears to be the only New Zealand member of the family which 

 weeps drops of resin when the bark is incised {Ueberwallungsharz). The resin 

 thus obtained is valued by bushmen for the treatment of cuts and sores. 

 A quantity of this resin collected in Westland was steain-distilled, and the 

 volatile oil resulting from this process was dried and distilled several times 

 in contact with metallic sodium. The highly refractive colourless oil was 

 proved by analysis to have the formula C^KjH^g, and the boiling-point, 

 specific gravity, specific rotation, and refractive index showed conclusively 

 that the substance was a mixture of dextro- and laevo-rotary pinene. 



The water in which the resin had been boiled was only faintly acid, and 

 contained traces only of matter in solution. 



The non-volatile portion of the resin was neutral in reaction, and under- 

 went no hydrolysis when boiled with alcoholic potash ; it therefore con- 

 tains neither esters nor lactones. After drying it can be distilled without 

 decomposition under reduced pressure (15-20 mm.). The distillate sets on 

 cooling to a glassy mass which has hitherto resisted all attempts to make 

 it crystallize. The substance has a characteristic smell, recalling that of 

 cannabinol, and is easily soluble in all ordinary organic solvents. Analvses 

 of different preparations agree with the formula Cj^gHj^gO. 



(2.) The Kahikatea (Podocarpus dacrydioides). 



It is well known that large logs of white-pine are frequently flawed by 

 heart-shakes filled to a greater or less extent with a hard white or yellowish 

 deposit, which also saturates and hardens the woody tissue in the neigh- 

 bourhood of the cracks. A quantity of this deposit was dissolved in alcohol 

 and crystallized by the cautious addition of water until a permanent 

 opalescence resulted. In a few hours the whole solution was filled with 

 colourless crystals, which when completely purified melted at 192° C, 

 showed a specific rotation of -1-136°, and upon analysis and titration gave 

 numbers agreeing sharply with the formula C^-HooOg. This is the formula 

 for podocarpic acid discovered by Oudemans C" Annalen der Chemie," 1873, 

 vol. 170, p. 213) in the heart-resin of Podocarpus cupressinus var. imbricatus 

 (a tree common on the mountains of Java at a height of 4,000 ft. and up- 

 wards), and not since recorded in any other plant. By the kindness of 



