Chemistry of Natural Compounds, Vol. 40, No. 2, 2004
STRUCTURE OF SAMFERINE
K. A. Eshbakova and A. I. Saidkhodzhaev
UDC 547.992.547.37
In continuation ofsystematic research on terpenoids ofplants in the
L. genus (Apiaceae, Carrot) [1], we isolated
Ferula
from roots of
Korov. by chromatographic separation over KSK silica gel with elution by benzine:ethylacetate
F. samarcandica
(6:1) a new compound of formula C H O called samferine.
22 30
5
-1
-1
Its IR spectrum has absorption bands for hydroxyl (3356 cm ), ester carbonyl (1704 cm ), and aromatic rings (1688,
-1
1683, 1609, and 1593 cm ). Its mass spectrum is typical of terpenoid esters with peaks at / 314, 274, 234, 193, 177, 157,
m z
148, 121, 93, 81, and 69 [2].
The PMR spectrum of samferine exhibits signals ( , ppm, J/Hz) at 0.93 and 0.99 (d, 3H each, J = 6, C -2CH ), 1.10
11
3
(s, 3H, C -CH ), 1.70 (br.s, 3H, C -CH ), 3.90 (t, 1H, J = J = 6, C -H), 5.40 (m, 2H, C -H, C -H), 6.95 (d, 2H, J = 9, C -,
1
3
8
3
1
2
2
6
9
3
C -H), 7.95 (d, 2H, J = 9, C -, C -H).
5
2
6
Comparison of spectral data with the literature [2-4] led to the conclusion that samferine is an ester of a sesquiterpene
alcohol of the carotane type with p-hydroxybenzoic acid. Alkaline hydrolysis by aqueous-alcoholic KOH (5%) produced from
the neutral part of the hydrolysate a sesquiterpene alcohol of formula C H O with mp 144-145°C that we called samferol.
15 26
3
We isolated p-hydroxybenzoic acid, C H O , mp 212-213°C, from the acidic part of the hydrolysate.
7
6 3
The PMR spectrum of samferol contains signals (δ, ppm, J/Hz) at 0.84 (t, 6H, J = J = 6.5, C -2CH ), 0.98 (s, 3H,
1
2
11
3
C -CH ), 1.64 (s, 3H, C -CH ), 3.85 (t, 1H, J = J = 6, C -H), 4.45 (sext., 1H, J = J = 10.5, J = 2,5, C -H), 5.30 (t, 1H,
1
3
8
3
1
2
2
1
2
3
6
J = J = 6, C -H).
1
2
9
Comparison ofspectral data for samferine and samferol with those for the esters ferutinol, akichenol, lapidol, lapiferol,
and lapidolinol [5] provides a basis to propose that samferol is a sesquiterpene alcohol of the carotane type with one hydroxyl
located on C and a double bond at C –C .
6
8
9
Signals of two geminal OH protons at 3.85 and 4.45 ppm in the PMR of samferol indicate that two of the three OH
groups are secondaryand one is tertiary. Considering the multiplicityof the C -proton, the onlypossible position for the tertiary
6
OH is C .
4
The position of the second secondary OH in samferine follows from the chemical shift of the angular methyl. The
signal for C -CH in carotane esters without a C -OH appears at 0.75-0.85 ppm [5]. The second secondary OH in samferine
1
3
2
is thought to reside on C according to the chemical shift of C -CH in the spectra of samferine and samferol at 1.10 and 0.98
2
1
3
ppm, respectively.
A sesquiterpene ester isolated from F. communis subsp. communis has been described [6]. Comparison of it and
samferine indicates that the compound isolated byus is an isomer with a different orientation ofthe C -OH for which we propose
2
the following structure as most probable.
OH
HO
H
O C
O
OH
S. Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan,
Tashkent, fax (99871) 120 64 75. Translated from Khimiya Prirodnykh Soedinenii, No. 2, p. 165, March-April, 2004. Original
article submitted March 24, 2003.
0009-3130/04/4002-0194 ©2004 Plenum Publishing Corporation
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