PHYTOCHEMICAL REPORTS
1167
Wood. (500 g) Chromatography (SiO2) of the petrol extract (1 g) gave /3-sitosterol
(0.02 ~o) and of the MeOH extract (5 g) complex mixtures which were not further investi-
gated.
Acknowledgements--The authors wish to thank Dr. Graziella M. Barroso and Dr. T. C. Rizzini for sup-
plying the plant material. A research grant from the Conselho National de Pesquisas is gratefully acknow-
ledged. One of us (CR) is indebted to the Ftmdaf,~o de Amparo a Pesquisa do Estado de S.~o Paulo for a
doctoral fellowship. The technical assistance of Mrs. Kazuko Kajibata Gaeta and of Messrs. Teodomiro
Vieira Santos, Sebasti~o Ribeiro and Alipio Raul de Silva is appreciated.
Phytochemistry 1971, Vol. 10, pp. 1167 to 1169. Pergamon Press. Printed in England.
RUTACEAE
A
Q U I N O L O N E A L K A L O I D FROM O R I C I A S U A V E O L E N S
M. O. ABE and D. A. H. TAYLOR
Department ofChemistry, UniversityofIbadan,Ibadan,Nigeria
(Received 30 June 1970)
Abstract--The timber of Oricia suaveolens has been found to contain 6,7-dimethoxy-N-methylflindersine,
which has been synthesized. Roots of Clausena anisata yielded the known coumarins imperatorin and
coumarrayin.
Oricia suaveolens (Engl.) Verdoon is a small under-storey tree locally common in West
Africa, belonging to the family Rutaceae. In the course of work designed to find new
limonoids, we extracted the timber of this tree. Chromatography of the fight petroleum
extract gave a new compound which we call oricine, m.p. 150-155°. The mass spectral
molecular weight was 301; elemental analysis suggested the formula CtTHtgO4N. The
N-MR spectrum showed two methoxy groups at about 8 4.0, a methyl group at 8 3.7, two
coupled vinyl protons (J = 10 cycles/sec) at 8 5.48 and 6.75, two single proton singiets at
8 6.73 and 7.31, and a six proton singlet at 8 1-53. Catalytic hydrogenation gave dihydro-
oricine, m.p. 150°, in which the two vinyl doublets were missing, being replaced by two
triplets at 8 1.83, 2.65 each corresponding to two hydrogen atoms. The i.r. spectrum of
oricine (Vma~ 1630 cm -a) suggested a quinolone, the u.v. spectrum (~max 260, 355, 373 rim)
was similar to that of flindersine (Ia)?
Since the two aromatic protons are not strongly coupled, we assumed they were para
to each other, which means the methoxy groups must be at positions 6 and 7 of the benzene
ring. The final methyl group can be accommodated as an N-methyl group, which is shifted
downiield from the usual position of an amide methyl by the deshielding due to the aromatic
nucleus. Consequently we concluded that oricine was 6,7-dimethoxy-N-methylflindersine
fib).
1 R. F. C. BROWN et aL, Australian J. Chem. 7, 348 (1954).
Abe,M.O.
