Chemistry of Natural Compounds, Vol. 46, No. 2, 2010
COMPONENTS OF Laser trilobum
Yu. M. Azizov and S. V. Serkerov*
UDC 547.314
Laser trilobum L. Borkh. is known to contain sesquiterpene lactones [1, 2].
The isolation of the sesquiterpene lactone lasolide, a coumarin derivative of hydroxypeucedanine, crocatone (latifolone),
and an ester (laserine) from roots of L. trilobum collected in Khyzin Region of the Republic of Azerbaidzhan during fruiting
was reported earlier [3, 4].
During separation of total extracted compounds of L. trilobum, we isolated a phenylpropanoid of formula C H O
21 26
7
as an ester. Although the IR spectrum of the newly isolated aromatic ester coincided in details with that of an aromatic ester
from Ferula oopoda [5], nevertheless the PMR spectrum of the studied compound in the methyl range (except for ester
methyls) contained two doublets characteristic of two secondary methyls at 1.14 (J = 6.5 Hz) and 1.24 ppm (J = 6.5 Hz) with
resonances having the same area. This suggested that we were probably dealing with a mixture of two epimeric compounds
such as 2-epilaserine (1) and laserine (2). An analogous mixture in a 2:1 ratio was isolated earlier from Seseli vayredanum [6].
O
O
O
5'
O
5'
H CO 3'
3
H CO 3'
3
6'
2
H
O
H
CH
6'
2
H
H
CH
1'
1'
H C 4''
3
3
3
1
1
HO
3''
O
1''
CH
3
OH
2''CH
O
3
5''
O
CH
3
1, 2
3, 4
2ꢂ (1, 3); 2ꢃ (2, 4)
In fact, integration of the NMR spectrum established that the compound isolated by us consisted of a mixture of two
components in a 1:1 ratio and had the following PMR spectrum (300 MHz, CDCl , ꢀ, ppm): 1.14 (3H, s, CH ), 1.24 (3H, s,
3
3
CH ), 1.80–2.1 (24H, m, H C–CH=, H C–CH=), 3.87 (6H, s, 2 ꢁ OCH ), 5.75 (1H, s, H-1), 5.90 (1H, s, H-1), 5.25–5.40 (2H,
3
3
3
3
m, 2 ꢁ H-2), 5.93 and 5.94 (2H, s, 2 ꢁ OCH O), 6.00–6.15 (4H, m, 4 ꢁ –CH=), 6.54 (2H, s, 2 ꢁ H-2), 6.56 (2H, s, 2 ꢁ H-6).
2
Saponification of the studied compound by base (5% KOH:EtOH) produced angelic acid, which was identified by its
IR spectrum, and a mixture of diols 3 and 4. The IR spectra of 3 and 4 (3400, 1632, 1510, 1370, 1323, 1195, 1130, 1090, 1041,
–1
932, 753 cm ), saponified products of a mixture of 2-epilaserine and laserine [6], and helmanticine [7] were comparable.
A comparison of PMR spectra of 2-epilaserine and laserine [6] and the aromatic ester isolated from L. trilobum
confirmed that the last consisted of a mixture of 2-epilaserine and laserine in a 1:1 ratio. Resonances of the ester and SSCC of
the adjacent resonances were not given.
REFERENCES
1.
2.
3.
4.
5.
6.
7.
K. S. Rybalko, Natural Sesquiterpene Lactones [in Russian], Moscow, 1978.
M. Holub, R. Groote, V. Herout, and F. Sorm, Collect. Czech. Chem. Commun., 33, 2911 (1968).
Yu. M. Azizov and S. V. Serkerov, Tr. Inst. Bot. Nats. Akad. Nauk Az., 28, 373 (2008).
Yu. M. Azizov and S. V. Serkerov, Tr. Inst. Bot. Nats. Akad. Nauk Az., 29, 399 (2009).
S. V. Serkerov, Khim. Prir. Soedin., 552 (1972).
F. B. Alejandro, F. Barrero, M. M. Herrador, and P. Arteaga, Phytochemistry, 31, 203 (1992).
T. J. De Pascual, M. De Pascual, A. Arias, J. R. Moran, and M. Grande, Phytochemistry, 24, 1773 (1985).
Institute of Botany, National Academy of Sciences of Azerbaidzhan, AZ1073, Baku, Patamdarskoe shosse, 40, fax:
(99412) 439 33 80, e-mail: s.serkerov@mail.ru. Translated from Khimiya Prirodnykh Soedinenii, No. 2, p. 245, March–
April, 2010. Original article submitted October 8, 2009.
©
0009-3130/10/4602-0291 2010 Springer Science+Business Media, Inc.
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Azizov
