Flavonoids of Acacia dealbata and Filipendula vulgaris Growing in Azerbaijan

Full text of DOI:10.1007/s10600-017-2111-3

DOI 10.1007/s10600-017-2111-3
Chemistry of Natural Compounds, Vol. 53, No. 4, July, 2017
FLAVONOIDS OF Acacia dealbata AND Filipendula vulgaris
GROWING IN AZERBAIJAN
1
1,2*
3
I. S. Movsumov, E. E. Garaev,
G. Herbette,
2
2
2
B. Baghdikian, E. Ollivier, R. Elias,
T. A. Suleimanov, and E. A. Garaev
1
1
Flowers of Acacia dealbata Link (Fabaceae) and leaves and stems of Filipendula vulgaris Moench (Rosaceae Juss.)
growing in Azerbaijan were studied in a search for possible new sources of biologically active compounds [1, 2].
Previously, flowers of A. dealbata yielded naringenin, naringenin diglucoside, robinetin, rutin, quercetin, and other
flavonoids [3]. Several flavonoids and oleanolic acid were isolated from flowers of F. vulgaris [4].
Flowers (0.8 kg) of A. dealbata that were collected at the end of March 2015 were extracted (2ꢀ) with EtOH (80%)
for 24 h. The extracts were condensed in an IKARV8 rotary evaporator (Germany) to an aqueous residue that was washed
with CHCl and EtOAc. The EtOAc washings were evaporated to a dry residue that was dissolved in H O (100 mL) and
3
2
extracted with EtOAc–hexane (1:1) and with a gradually increasing amount of EtOAc. The extraction was monitored using
paper chromatography (BAW solvent system, 4:1:5, Filtrak FN5 paper).
Identical extracts were combined, evaporated, and recrystallized from aqueous EtOH to afford 1 and 2.
Leaves and stems (without flowers) (0.6 kg) of F. vulgaris were extracted with EtOH (80%). The extract was evaporated
to an aqueous residue that was extracted with CHCl and EtOAc–hexane (9:1). Evaporation of the EtOAc–hexane extract and
3
recrystallization of the residue from EtOH produced 3. Other flavonoids were not detected in the extract.
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Compound 1, C H O 42H O, mp 226–228°C (aq. EtOH), [ꢁ] –60° (c 0.4, MeOH). UV spectrum (MeOH,
21 20 12
2
D
1
ꢂ
, nm): 362, 256. Yellow crystals cleaved by acid hydrolysis into quercetin (63.3%) and D-glucose. Í NMR spectrum
max
(600 MHz, DMSO-d , ꢃꢄꢅppm, J/Hz): 3.10 (1H, m, H-5 ), 3.13 (1H, br.t, J = 9.5, H-4 ), 3.23 (1H, br.t, J = 8.5, H-3 ), 3.31 (1H,
6
br.t, J = 8.5, H-2 ), 3.34 (1H, dd, J = 11.9, 6.0, H-6 b), 3.57 (1H, m, H-6 a), 5.44 (1H, d, J = 7.9, H-1 ), 6.20 (1H, d, J = 1.9,
13
H-6), 6.41 (1H, d, J = 1.9, H-8), 6.85 (1H, d, J = 8.8, H-5 ), 7.56 (1H, dd, J = 8.8, 1.9, H-6 ), 7.57 (1H, br.s, H-2 ). C NMR
spectrum (150 MHz, DMSO-d , ꢃ, ppm): 156.6 (Ñ-2), 133.6 (C-3), 177.7 (C-4), 104.2 (C-4à), 161.5 (C-5), 98.9 (C-6), 164.4
6
(C-7), 93.8 (C-8), 156.6 (C-8à), 121.4 (C-1 ), 116.4 (C-2 ), 145.3 (C-3 ), 148.7 (C-4 ), 115.5 (C-5 ), 121.9 (C-6 ), 101.1 (C-1 ),
74.3 (C-2 ), 76.7 (C-3 ), 70.1 (C-4 ), 77.7 (C-5 ), 61.3 (C-6 ). Compound 1 was identified as quercetin-3-O-ꢆ-D-
glucopyranoside (isoquercitrin) [5, 6].
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Compound 2, C H O , mp 258–260°C (aq. EtOH), [ꢁ] –50° (c 0.58, DMF). UV spectrum (MeOH, ꢂ , nm):
21 20 13
D
max
1
364, 262. Dark-yellow powder cleaved by acid hydrolysis into myricetin (64.0%) and D-glucose. Í NMR spectrum
(600 MHz, DMSO-d , ꢃꢄꢅppm, J/Hz): 3.10 (1H, m, H-5 ), 3.13 (1H, br.t, J = 9.5, H-4 ), 3.23 (1H, br.t, J = 8.5, H-3 ), 3.31
6
(1H, br.t, J = 8.5, H-2 ), 3.34 (1H, dd, J = 11.9, 6.0, H-6 b), 3.57 (1H, m, H-6 a), 5.44 (1H, d, J = 7.9, H-1 ), 6.19 (1H, d,
13
J = 1.9, H-6), 6.38 (1H, d, J = 1.9, H-8), 7.19 (2H, s, H-2 , 6 ). C NMR spectrum (150 MHz, DMSO-d , ꢃ, ppmꢇ: 156.5
6
(Ñ-2), 133.7 (C-3), 177.7 (C-4), 104.2 (C-4à), 161.5 (C-5), 98.9 (C-6), 164.4 (C-7), 93.7 (C-8), 156.5 (C-8à), 120.2 (C-1 ),
108.8 (C-2 , 6 ), 145.6 (C-3 ), 136.7 (C-4 , 5 ), 101.1 (C-1 ), 74.2 (C-2 ), 76.8 (C-3 ), 70.1 (C-4 ), 77.7 (C-5 ), 61.3
(C-6 ).
1) Azerbaijan Medical University, Baku AZ 1000, Azerbaijan, e-mail: eldargar@mail.ru; 2) UMR-MD3, Laboratoire
de Pharmacognosie et Ethnopharmacologie, Faculte de Pharmacie, Aix Marseille Univ. 27 Boulevard Jean Moulin, CS30064,
13385, Marseille Cedex 5, France; 3) Spectropole, FR 1739, Aix Marseille Univ. Campus Scientifique Saint Jerome, Service
511, 13397 Marseille Cedex 20, France, e-mail: gaetan.herbette@univ-amu.fr. Translated from Khimiya Prirodnykh Soedinenii,
No. 4, July–August, 2017, p. 643. Original article submitted November 4, 2016.
©
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0009-3130/17/5304-0754 2017 Springer Science+Business Media New York

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Compound 3, C H O , mp 234–236°C (EtOH), [ꢁ] –58° (c 0.1, MeOH). UV spectrum (MeOH, ꢂ , nm):
21 20 12
D
max
13
354, 265, 255. Light-yellow crystals cleaved by acid hydrolysis into quercetin (63.3%) and D-galactose. PMR and C NMR
spectra of 3 were identical to those of quercetin-3-O-ꢆ-D-galactopyranoside (hyperoside) [5, 6].
Isoquercitrin and isomyricitrin were not detected previously in A. dealbata.
REFERENCES
1.
2.
Flora of Azerbaijan [in Russian], Vol. V, Baku, 1954, 579 pp.
Plant Resources. Flowering Plants, Their Chemical Composition, Use. Fam. Hydrangeaceae–Haloragaceae
[in Russian], Nauka, Leningrad, 1986, 334 pp.
3.
4.
I. S. Movsumov and E. A. Garaev, Khim. Rastit. Syr ya, No. 3, 159 (2011).
P. Pakudina and A. S. Sadikov, Distribution in Plants and Physicochemical Properties of Flavones, Flavonols, and
Their Glycosides [in Russian], Tashkent, 1970, 94 pp.
5.
6.
S. Scharbert, N. Holzmann, and T. Hoffmann, J. Agric. Food Chem., 52 (11), 3498 (2004).
S. S. Azimova and V. I. Vinogradova (eds.), Natural Compounds – Flavonoids, Springer Science Media,
New York, 2013, pp. 201, 205.
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