DOI 10.1007/s10600-015-1463-9
Chemistry of Natural Compounds, Vol. 51, No. 5, September, 2015
BIOLOGICALLY ACTIVE COMPOUNDS FROM
Lepidium campestre AND PULP FROM
LEMON-JUICE PRODUCTION
1
1
1*
D. Yu. Yusifova, I. S. Movsumov, E. A. Garaev,
2
2
3
V. Mahiou-Leddet, F. Mabrouki, G. Herbette,
B. Baghdikian, and E. Ollivier
2
2
In continuation of the search for possible new sources of biologically active compounds, we studied the aerial parts
of Lepidium campestre (L.) W.T.Aiton of the family Cruciferae Juss. that was growing in Azerbaijan [1] and fruit of Citrus
limon Burm. of the family Rutaceae Juss. [2, 3].
Aerial parts of L. campestre were collected during full flowering in the middle of July 2012 in the vicinity of Kubinsky
District, Azerbaijan Republic. Pulp was produced during lemon-juice production at facilities in Lenkaransky Districts in
autumn 2014. Air-dried ground aerial parts (1.0 kg) of L. campestre were extracted with EtOH (95%). The extracts were
evaporated to 150–200 mL, diluted with H O (150 mL), and evaporated to an aqueous residue that was worked up sequentially
2
with CHCl , EtOAc:hexane, and EtOAc.
3
The EtOAc–hexane extract afforded compound 1, C H O , mp 275–277°C (EtOH), tetraacetate mp 182–184°C
1
5 10 6
(
(
CHCl –MeOH).
3
1
Kaempferol (3,5,7,4ꢀ-tetrahydroxyflavone) (1). Í NMR spectrum (600 MHz, DMSO-d , ꢁꢂꢃppm, J/Hz): 6.18
6
1
3
1Í, d, Í-6), 6.39 (1Í, d, Í-8), 8.08 (1Í, d, Í-2ꢀ), 6.90 (2Í, d, Í-3ꢀ, 5ꢀ), 8.08 (1Í, d, Í-6ꢀ). C NMR spectrum (150 MHz,
DMSO-d , ꢁꢂꢃppm): 148.1 (Ñ-2), 137.1 (Ñ-3), 177.4 (Ñ-4), 162.5 (Ñ-5), 99.3 (Ñ-6), 165.6 (Ñ-7), 94.5 (Ñ-8), 158.3 (Ñ-9),
6
1
04.5 (Ñ-10), 123.7 (Ñ-1ꢀ), 130.7 (Ñ-2ꢀ), 116.2 (Ñ-3ꢀ), 160.0 (Ñ-4ꢀ), 116.2 (Ñ-5ꢀ), 130.7 (Ñ-6ꢀ) [4].
Compound 2 was isolated from the EtOAc extract and was a flavonoid [5] of formula C H O , mp 210–212°C
2
6 28 14
(
EtOH). Acid hydrolysis cleaved 2 into kaempferol (48%), L-arabinose, and L-rhamnose. The attachment site of the sugars to
the aglycon was determined as before [6]. Alkaline hydrolysis of 2 (aqueous KOH solution, 0.5%, 2 h) produced kaempferol-
3
2
-O-ꢄ-L-arabinopyranoside (juglanin) of formula C H O , mp 224–226°C (EtOH). UV spectrum (MeOH, ꢅmax, nm):
20 18 10
66, 350. Stepwise acid hydrolysis (15% AcOH, 2 h) of 2 produced the intermediate monoglycoside kaempferol-7-O-ꢄ-L-
rhamnopyranoside (rhamnoisorobinin) of formula C H O , mp 170–173°C (EtOH).
2
1 20 10
Kaempferol-3-O-ꢄ-L-arabinopyranoside-7-O-ꢄ-L-rhamnopyranoside (2). 1Í NMR spectrum (600 MHz,
DMSO-d , ꢁꢂꢃppm, J/Hz): 6.45 (1Í, d, J = 2.2, Í-6), 6.83 (1Í, d, J = 2.2, Í-8), 8.12 (1Í, d, J = 8.8, Í-2ꢀ, 6ꢀ), 6.9 (1Í, d,
6
J = 8.8, Í-3ꢀ, 5ꢀ), 5.35 (1Í, d, J = 5.5, Í-1ꢀꢀ), 3.75 (1Í, dd, J = 6.9, 5.5, Í-2ꢀꢀ), 3.53 (1Í, dd, J = 6.9, 3.0, Í-3ꢀꢀ), 3.66 (1Í, m,
Í-4ꢀꢀ), 3.58 (2Í, dd, J = 11.6, 5.5, Í-5ꢀꢀ), 3.22 (2Í, dd, J = 11.6, 2.2, Í-5ꢀꢀ), 5.56 (1Í, d, J = 1.7, Í-1ꢀꢀꢀ), 3.85 (1Í, br.s, Í-2ꢀꢀꢀ),
3
.64 (1Í, dd, J = 9.4, 3.3, Í-3ꢀꢀꢀ), 3.30 (1Í, br.t, J = 9.4, Í-4ꢀꢀꢀ), 3.43 (1Í, dq, J = 9.4, 6.2, Í-5ꢀꢀꢀ), 1.12 (3Í, d, J = 6.1, Í-6ꢀꢀꢀ).
1
3
C NMR spectrum (150 MHz, DMSO-d , ꢁꢂꢃppm): 160.2 (Ñ-2), 133.9 (Ñ-3), 177.7 (Ñ-4), 160.9 (Ñ-5), 99.4 (Ñ-6), 161.6
6
(
(
(
Ñ-7), 94.6 (Ñ-8), 155.9 (Ñ-9), 105.6 (Ñ-10), 120.6 (Ñ-1ꢀ), 131.1 (Ñ-2ꢀ, 6ꢀ), 115.3 (Ñ-3ꢀ, 5ꢀ), 156.8 (Ñ-4ꢀ), 101.2 (Ñ-1ꢀꢀ), 70.8
Ñ-2ꢀꢀ), 71.5 (Ñ-3ꢀꢀ), 66.0 (Ñ-4ꢀꢀ), 64.2 (Ñ-5ꢀꢀ), 98.4 (Ñ-1ꢀꢀꢀ), 69.8 (Ñ-2ꢀꢀꢀ), 70.1 (Ñ-3ꢀꢀꢀ), 71.6 (Ñ-4ꢀꢀꢀ), 69.8 (Ñ-5ꢀꢀꢀ), 17.9
Ñ-6ꢀꢀꢀ) [7].
1
) Azerbaijan Medical University, Ul. Bakikhanova, 21, Baku, AZ 1022, Azerbaijan, e-mail: eldargar@mail.ru;
2
) UMR-MD3, Laboratoire de Pharmacognosie et Ethnopharmacologie, Faculteꢀ de Pharmacie, Aix-Marseille Universite, 27
Boulevard Sean Monlin, CS 30064, 13385 Marseille Cedex 5, France; 3) Spectropole, FR 1739, Aix-Marseille Universiteꢀ
Campus Scientitique Saint Jerome, Servise 511, 13397 Marseille Cedex 20, France, e-mail: gaetan.herbette@univ-amu.fr.
Translated from Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2015, pp. 826–827. Original article submitted
April 21, 2015.
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0009-3130/15/5105-0964 ©2015 Springer Science+Business Media New York