The isolation and characterization of 19
new alkaloids from the bark of Galbulimima species is described. After some
corrections to previous work, the number of alkaloids from this source now
stands at 28.
The extractives of the
barks and leaves of Alphitonia excelsa, A. petriei,
and A. whitei,
and of the wood, bark, and leaves of A. macrocarpa have been examined. Ceanothic,
betulinic, and alphitolic
acids were isolated from all species, but A. macrocarpa was exceptional in
that its wood contained no benzylhydroxycoumarone
derivative, characteristic of the other species, and its leaves gave a small
yield of the alkaloid, adouetine X. From the bark of A. excelsa a new
triterpene, alphitexolide, was isolated in very small
amount. By spectroscopic methods and a partial synthesis its structure was
established as(1).
Treibs and Rungel prepared four trans-cisoid-trans-perhydroanthracenols via their nitrate esters. Two of these alcohols (Ia and IV of ref.1) were identified as isomers of trans-cisoid-trans-anthracen-9-01 since each could be oxidized to transcisoid-trans-anthracen-9-one. This paper describes the preparation and identification of trans-cisoid-trans-perhydroanthracen-2-01 which was found to correspond to "Alkohol VII" of the above authors and was shown to have an equatorial hydroxyl group.The alcohol was prepared by oral administration of trans-cisoid-trans-perhydroanthracene to rabbits. Previous investigations233 had indicated that such a hydrocarbon would be hydroxylated in vivo at a carbon atom j 3 to the ring junction, and this indeed occurred.
ExperimentalMelting points are uncorrected. Where a specific reference is not given, the melting points were taken from ref. 4 This compound was prepared by hydrogenation of anthracene a t 100 atm and 180" with W-7 Raney nickel in ethanol. After isolation and purification, the product had m.p. 72-75" (lit. 78").The n.m.r. spectrum showed a singlet a t 6 6.71, a broad singlet a t 6 2.66, and a multiplet a t 8 1.72.Compound (1) (1 0 g) was suspended in diaminoethane (1 50 ml) under nitrogen. Lithium (10 g) was added in small pieces over 2 hr After gentle refluxing for 2 hr, the reaction mixture was left overnight. Ice-water was carefully added, and then dilute HC1, with stirring. The product was extracted with ether; g.1.c. showed complete absence of starting material. Removal of the ether
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