Full text of DOI:10.1016/0031-9422(71)85046-X

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9 7 1 , Vol. 1 0 , pp. 1 6 6 9 t o 1 6 7 0 .
Prin t ed in En glan d.
SHORT COMMUNICATION
MANSONONE C IN ELM WOOD
V.
Department of Chemistry, University of Delhi, Delhi-7, India
and
R. H. T H O M S O N
Department of Chemistry, University of Aberdeen, Old Aberdeen, Scotland
(Received 29 October 1970)
HAS been
recently that young branches of Ulmus hollandica (Ulmaceae) produce
mansonones E and F after inoculation with Ceratocystis ulmi. Previously mansonones
there are 10)’ had been found only in wood (Sterculiaceae). In view of this we
wish to report the existence of mansonone C (I) as a normal constituent of the heartwood
of This seemed to us likely when the hydroxynaphthaldehydes (II) and (III)
were discovered in this wood, as all three compounds have the same cadalene skeleton
(
3
and a similar oxidation level, and in fact extraction of
yielded (I), (II) and (III). Synthetic (I), obtained from
with Fremy’s salt, was identical with the natural pigment.
heartwood with light petroleum
by oxidation
7-Hydroxycadalene is also
in glabra and rubra and may be a biogenetic
intermediate, nuclear or side chain oxidation leading to (I) and (II), respectively. Further
investigation of Ulmus and Mansonia heartwoods may reveal other examples of the co-
existence of naphthaldehydes and naphthaquinones. The methoxyaldehyde (III) is the
analogue of mansonone G, while (IV) (another constituent of U.
and U.
corresponds to mansonone B. Since our isolation of mansonone C from U. glabru we
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understand that Dr. J. W. Rowe has found the same quinone in several Ulmus spp.
J. C. OVEREEM and D. M.
9, 1949 (1970).
G. B.
C. G.
and H. IMAMURA, Tetrahedron Letters 2767 (1966); K.
Wood Res. 13,126 (1967); C. GALEFFI, E. M.
Tetrahedron Letters 3583 (1969).
and C. M. 7, 1407 (1968); M.
A. J. Forest Prod. J.
J. W. ROWE, personal communication (1968).
and C.
Tetrahedron Letters 4857 (1965); N. TANAKA,
M.
M.
and H.
and G. B.
MONACHE , C. G.
B. 0 .
J . W. R OWE , R. W.
S. M. FANEGA
,
and J. K.
T
ODA
,
(1968).
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669

1
670
V.
and R. H.
EXPERIMENTAL
Isolation of Mansonone C
Shavings g) of
heartwood were exhaustively extracted
with light petroleum
Removal of the solvent left a pale yellow oily residue which was chromatographed on a silica
gel cohunn. Successive
gave, respectively, oily residues which were discarded, mixtures of the naphthaldehydes (II) and (III), and
mansonone C. Further chromatography afforded pure (II) (25 mg) and (III) (10 Mansonone C was
purified by PLC on silica gel-3% oxalic acid in and from aq. ethanol as
yellow rods, m.p. 134-135” (2 mg), identical with a sample from Mansonia
0 mg of mansonone C obtained from 500 g of heartwood. The
no mansonone C, and none of these was present in the bark.
with light petroleum, light petroleum-benzene (10: to 1:
and benzene,
On a larger scale
contained (II) and (III) but
2
7
-Hydroxycadalene
g) in methanol (200 ml) was treated with Fremy’s salt (3 g) and
in water (200 ml). After 1 hr more water was added, the quinone was extracted with ethyl acetate and
from methanol as orange rods, m.p. 135-137”
C, 78.9; H, identical (mixed
135-136”) (30%) (Found: C, 78.4; H, 7.2.
UV, IR, TLC) with mansonone C.
for
Acknowledgements-We thank Dr. C. G. Casinovi for a specimen of mansonone C and Dr. M. D. Sutherland
for a generous sample of
R. G. LINDAHL, Ann.
Sci. Fennicae AII, No. 48, 7 (1953).