A compound with a structure similar to that of 1 was isolated from suspension culture of Chenopodium rubrum.
However, the glucose in this phenylpropanoid was bonded to the carboxyl [9].
Thus, lavandoside (1) that was isolated from L. spica flowers was a new natural compound with the structure
4-hydroxy-3-methoxycinnamic acid 4-O-b-D-glucopyranoside.
EXPERIMENTAL
Flowers of Lavandula spica collected in Moroccoin a valleyofthe Atlas Mountains (2006) and dried in air in the shade
were used as starting material for the investigation.
Lavender flowers (200 g) were extracted exhaustively with ethanol (70%) by combining grinding (24 h) with
subsequent thermal extraction at 85-90°C. The aqueous alcohol extracts were evaporated in vacuo to a thick residue (about
50 mL). The condensed extract was dried over silica gel (L 40/100) to produce a powder (extract + silica gel) that was placed
on a layer of silica gel that was pretreated with CHCl . The chromatography column was eluted with CHCl and
3
3
CHCl :C H OH in various ratios (97:3, 95:5, 93:7, 90:10, 88:12, 85:15, 80:20, 70:30). The separation was monitored byTLC.
3
2 5
Fractions containing 1 were combined and placed on Woelm polyamide for further purification. The dry powder
(extract + polyamide) was transferred to a chromatographycolumn (sorbent height 4.0 cm, diameter 5 cm) that was eluted with
water and aqueous ethanol (20, 40, 70, 96%). The purification over polyamide columns produced 1 (water eluent) that was
purified additionally by rechromatography over Sephadex LH-20 with elution by CHCl and CHCl :C H OH in various ratios
3
3
2 5
(95:5, 93:7, 90:10, 88:12, 85:15, 80:20, 70:30).
UV spectra of 1 and its aglycon (2) were recorded on a Specord 40 spectrophotometer (Analytik, Jena). PMR spectra
of 1 were recorded on a Bruker 250 spectrometer. Mass spectra were obtained in a Finnigan LXQ LC—MS/MS. Enzymatic
hydrolysis of 1 was carried out using b-glucosidase (Fluka, Hungary) at 38°C for 12 h.
Compound 1, amorphous light-yellow compound, C H O , mass spectrum (m/z, %): 195.01 (24.71) [M (aglycon)
21 20 10
+
+
+
+ H] , 176.98 (100.00) [M (aglycon) - H O + H] , 152.97 (28.60) [M (algycon) - COO + H] . UV spectrum (EtOH, l
, nm):
max
2
281, 313. PMR spectrum (250 MHz, CD OD, d, ppm, J/Hz): 3.3-4.0 (6H, glucose), 3.86 (3H, s, OCH ), 5.00 (1H, d, J = 7.0,
3
3
glucopyranose H-1¢), 6.44 (1H, d, J = 16.05, H-8), 6.67 (1H, dd, J = 2.33, 8.61, H-6), 6.88 (1H, J = 2.33, H-2), 7.60 (1H, d,
J = 8.61, H-5), 8.08 (1H, d, J = 16.05, H-7).
PMR spectrum (250 MHz, CH CN:C D , d, ppm, J/Hz): 3.20-3.60 (4H, glucose), 3.64 (1H, dd, J = 5, 12, H-6¢), 3.76
3
6 6
(3H, s, OCH ), 3.84 (1H, dd, J = 1.86, 12.10, H-6¢), 4.98 (1H, d, J = 7.21, glucopyranose H-1¢), 6.43 (1H, d, J = 16.05, H-8),
3
6.57 (1H, dd, J = 2.33, 8.61, H-6), 6.80 (1H, J = 2.33, H-2), 7.52 (1H, d, J = 8.61, H-5), 8.04 (1H, d, J = 16.05, H-7).
Compound 2, light-yellow crystals, C H O , mp 167-170°C (aqueous alcohol). UV spectrum (EtOH,
, nm):
max
10 10
4
240, 290sh, 318.
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1.
V. A. Kurkin, Pharmacognosy: Textbook for Students of Pharmacy Schools [in Russian], 2nd Ed., Revised and
Supplemented, OOO Ofort, GOU VPO SamGMU, Samara (2007).
2.
3.
4.
5.
State Registry of Drugs [in Russian], Vol. 1, Official Ed., Meditsina, Moscow (2004).
A. Sejilmassi, Medical Plants in Morocco, Casablanca (1995), 145.
A. T. Nafysi, Review of Traditional Medicine in Iran, Isfahan University Publications, Isfahan (1989), 122.
H. Wagner, Pharmazeutische Biologie, Drogen und ihre Inhaltsstoffe, Gustav Fischer Verlag, Stuttgart-New York
(1993).
6.
7.
V. A. Kurkin and M. Lamrini, Khim. Prir. Soedin., 582 (2007).
J. B. Harborne, Comparative Biochemistry of the Flavonoids—Phytochemical Unit, The Hartley Botanical
Laboratories, The University of Liverpool, England (1967), 217.
8.
9.
V. A. Kurkin, G. G. Zapesochnaya, A. G. Dubichev, E. D. Vorontsov, I. V. Aleksandrova, and R. V. Panova,
Khim. Prir. Soedin., 481 (1991).
D. Strack and M. Bokern, Z. Naturforsch. C: J. Biosci., 39, No. 9/10, 902 (1984).
170