The alkaloids of Ochrosia sandwicensis A. Gray

Jordan, Werner Hans Georg
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The endemic Hawaiian tree Ochrosia sandwicensis A. Gray is a member of the family Apocynaceae. Its trivial Hawaiian name is holei and its bark found medicinal use in ancient Hawaii. Previous work established the presence of the alkaloids ellipticine, methoxyellipticine, isoreserpiline and N(b)-methylisoreserpilinium chloride (holeinine) in the leaves and/or bark of the tree. Renewed investigation of the bark alone resulted in the isolation of two additional quaternary bases. One of these was isolated in yields of 0.03 % of dry bark, m.p. 322-324° (dec.),[α]D + 10 (water-methanol), [α]D + 44 (water-pyridine), and was only sparingly soluble in most common solvents. It was shown to be identical with hunterburnine α-methochloride of molecular formula C20H27N2O2Cl and structure I, which had recently been isolated from Hunteria eburnea and possesses hypotensive activity, thus accounting for this type of activity observed in crude extracts of O. sandwicensis. The second base was isolated in yields of 0.08 % of dry bark, m.p. 288-289° (dec.),[α]D + 85 (methanol), molecular formula C20H29N2O2Cl, and is tentatively referred to as W.J.-3. Physical data and chemical evidence are in agreement with a proposed structure II. Further work with this compound was precluded because of its unusually high sensitivity under customary reaction conditions. Information gained during work on W.J.-3 made it possible to deduce the stereochemistry of the related alkaloid huntrabrine methochloride. A previously reported yellow base from O. sandwicensis could be identified as ellipticine hydrochloride. Another unknown yellow base found in O. oppositifolia was shown to be methoxyellipticine. A likely position of the methoxyl group in the molecule was derived from spectral analogies. A novel and rapid scheme for the separation of alkaloids from plant material was developed. It promises to be of general utility and involves extraction with dilute aqueous acetic acid, precipitation of the bases with Mayer's reagent and conversion of the Mayer's complex to chlorides by anion exchange. Correlations of 0. sandwicensis with other species of the genus, other genera of the family Apocynaceae and Strictness melinoniana of the family Loganiaceae are discussed.
Thesis (Ph. D.)--University of Hawaii, 1965.
Bibliography: leaves [111]-119.
x, 119 l illus., tables
Alkaloids, Ochrosia sandwicesis
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Theses for the degree of Doctor of Philosophy (University of Hawaii (Honolulu)). Chemistry; no. 66
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