Organizing co mmittee

b
), chair-bath type 
15
D
5
,
1
D
14
(
с
) and 
bath-chair type 
15
D
5
,
1
D
14
(
d
) [4]. In 
trans-jointed nonlinear melampolides 
in a ten-membered ring, only type (
c
) 
and 
type 
(
d
) 
were 
found 
experimentally. In structure 
1
, cycle A 
adopts the chair-bath conformation of 
the 
15
D
5
,
1
D
14
type (
c
). 
The 
lactone 
ring 
takes 
the 
conformation of a somewhat distorted 
7α-envelope (

С
S
7
=3.9

).
The cycles in 1 are articulated in the trans-type (torsion angle H6C6C7H7 = 159
o
). 
References 
1. P. Singh, A. Sharma, K. Joshi, J. Jakupovic,F. Bohlmann. 
Phytochemistry
, 
1985
, 
24
, 2023-2028. 
2.A. Rustaiyan, K. Zare, M. Ganj, H. Sadri. 
Phytochemistry
, 
1989
, 
28
, 1535-1536. 
3. A.F. Beechman. 
Tetrahedron
, 
1972
, 
28
, 5543-5554. 
4. Z. Samek, J. Harmatha. 
Coll. Czech. Chem. Commun,
, 
1978
, 
43
, 2779- 2799. 

---

Poster presentation 
48 
NOVEL FLAVONOID FROM SERRATULA CUPULIFORMIS 
 
L.N.Zibareva, О.А.Kotelnikov, V.S.Sidelnikov, D.I. Kazantseva, S.I. Konnova 
National Research Tomsk State University, Russia, 634050, Tomsk region, Tomsk, 
Lenin Ave., 36. 
Previously, the species 
Serratula cupuliformis
Nakai & Kitag. was recommended as 
a new plant source of ecdysteroids - 20-hydroxyecdysone, ecdysone, 2-deoxy-20-
hydroxyecdysone and polypodin B (Zibareva et al., 2017).
The plant material was grown from seeds obtained from the Botanical garden of Jena 
(Germany) and successfully introduced in the Siberian Botanical Garden of Tomsk 
State University. Now this species is presented as a rich source of flavonoids.
In the process of isolation by selective extraction of secondary metabolites from the 
ethanol extract of the aboveground part of 
S.cupuliformis
, chloroform, ethyl acetate, 
butanol fractions were obtained, the yield of which was, respectively, 0.16; 1.61; 1.97% 
of the mass of raw materials. The composition of flavonoids of the ethyl acetate fraction 
was studied, some of which were identified based on HPLC data and comparison with 
the characteristics of standards. The presence of at least 20 flavonoids with different 
absorption maxima – 270/335, 267/344, 251/351, 252/366 nm - was found in the 
aboveground part. The structure of the individual flavonoid isolated by column 
chromatography was established by HPLC-MS and 
1
H and 
13
C NMR methods. The 
value of m/z 315.0 corresponds to the molecular ion [M-H]-, m/z 300.0 corresponds to a 
fragmentary ion formed by the cleavage of a methyl group from a molecular ion. The 
mass spectrum of the sample according to the molecular ion and the nature of 
fragmentation corresponds to a substance with the gross formula С
16
H
12
O
7
.
Fig. 
13
C-NMR spectrum of the studied flavonoid 
According to the results of the studies conducted by liquid chromatography-mass 
spectrometry and NMR spectroscopy, by the mass of the molecular ion, the nature of 
fragmentation, the number of signals and areas of chemical shifts it was found that the 
compound under study corresponds to the substance 2-(2,4-dihydroxyphenyl)-5,7-
dihydroxy-3-methoxy-4H-chromene-4-one. This flavonoid was isolated for the first 
time. 

---

Poster presentation 
49