1) Kazan′ State Medical University, 420012, Kazan′, ul. Butlerova, 49, e-mail: nikit@mi.ru; 2) Kazan′ State University.
Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 37-38, January-February, 2005. Original article submitted August
2, 2004.
0009-3130/05/4101-0045
©
2005 Springer Science + Business Media, Inc.
45
O
O
CH
2
OH
CH
3
CO
CH
3
CO
O
O
O
OH
CH
3
CO
CH
3
CO
CH
3
O
O
O
OH
CH
3
CO
CH
2
SCH
2
COCH
3
H
CH
3
CO
O
O
O
O
O
O
SCH
2
COCH
3
1
2
3
HSCH
2
COOCH
3
ZnCl
2
, C
2
H
5
OH, CH
2
Cl
2
17
16
14
3
5
1
7
9
11
13
15
18
19
17
20
19
18
21
22
13
14
15
16
11
20
19
17
18
21
22
14
16
13
11
Chemistry of Natural Compounds, Vol. 41, No. 1, 2005
SYNTHESIS OF S-CONTAINING DERIVATIVES OF
THE SESQUITERPENE LACTONE BRITANIN
N. P. Artemova,
1
L. E. Nikitina,
1
D. A. Yushkov,
1
UDC 547.597
O. G. Shigabutdinova,
1
V. V. Plemenkov,
1
V. V. Klochkov,
2
and B. I. Khairutdinov
2
The optimal method for isolating the sesquiterpene lactone britanin from the aerial part of
Inula britannica
L. (Asteraceae) was developed. Britanin was functionalized by reacting it with methyl mercaptoacetate.
Key words:
Inula britannica
, britanin, sesquiterpene lactones and their S-containing derivatives.
Sesquiterpene lactones of
Inula britannica
L. (Asteraceae) have a variety of structures and pharmacological activities
[1-3]. One of the principal lactones of this species is britanin pseudoguaianolide (
1
), which exhibits antiprotozoic, antibacterial,
and antifungal activities [4]. Terpenoids containing a sulfide exhibit antitumor effects [5] and antimalarial activity [6, 7].
Therefore, chemical modification of britanin is certainly of practical interest.
We investigated the aerial part of
I. britannica
growing in the Volzhsko-Kamsk region as a source of britanin. Three
methods of processing the raw material were investigated in order to select the optimal method of extracting it. These were
water extraction, treatment with hexane followed by water extraction, and chloroform extraction. The first two methods are
more convenient for isolating britanin (the lactone crystallizes from the extract) and give the highest yields (0.125-0.15%). The