Chemistry of Natural Compounds, Vol. 38, No. 3, 2002
COMPONENTS OF Aerva lanata
A. A. Yuldashev,1 M. P. Yuldashev,2
and V. N. Abdullabekova1
UDC 547.972
The aerial part of
Juss has yielded O-acylglycosides, β-sitosterol, daucosterol, syringic acid, vanillic acid,
Aerva lanata
feruloylthyramine, feruloylhomovanillylamine, narcissin, and aervitrine [1-4].
Ground and air-dried raw material (1.3 kg) collected during flowering (August 1999) in the Mid-Chirchiksk region
(Tashkent district, Republic of Uzbekistan) was extracted with water. The aqueous extract was condensed in vacuo and treated
with n-butanol. The solvent was removed to yield a butanol fraction (14.0 g) that was chromatographed over a silica-gel column
with gradient elution by CHCl —CH OH (97:3—80:20). Preparative TLC of the individual fractions isolated 1-5, which were
3
3
identified using PMR, UV, IR, and mass spectra, chemical transformations, and comparison with authentic samples.
Compounds 1-3 were identified as vanillic, syringic, and ferulic acids, respectively, by examining their physicochemical
properties and spectra [2-6].
Isorhamnetin-3-O-β-D-glucoside (4), C22H22O12, mp 162-164°C. UV spectrum (EtOH, λmax, nm): 257, 267, 360.
The IR spectrum contains absorption bands of hydroxyls (3394 cm-1), methoxyl (2935), carbonyl of γ-pyrone (1655), aromatic
C=C (1611, 1578, 1513), and glycoside C–O (1076, 1025).
The PMR spectrum (100 MHz, C D N, δ, ppm, J/Hz) contains signals at 3.50-4.52 (sugar protons), 3.82 (3H, s, OCH ),
5
5
3
6.00 (1H, d, J = 7.0, H-1″), 6.48 (1H, d, J = 2.0, H-6), 6.65 (1H, d, J = 2.0, H-8), 7.12 (1H, d, J = 8.0, H-5′), 7.65 (1H, dd,
J = 2.0 and J = 8.0, H-6′), 8.15 (1H, d, J = 2.0, H-2′).
+
Acid hydrolysis of 4 produced isorhamnetin (C16H12O7, mp 305-307°C, M 316) and D-glucose. Acetylation of 4 by
acetic anhydride in pyridine gave the heptaacetyl derivative. The mass spectrum of this derivative contains a peak for the
molecular ion with m/z 772 and strong peaks for fragments of the tetraacetylhexose with m/z 331, 329, 271, and 169 [7-9].
Narcissin (5) (isorhamnetin-7-O-rutinoside), C28H32O16, mp 177-179°C. UV spectrum (EtOH, λmax, nm): 254, 265sh,
305sh, 356. The IR spectrum contains absorption bands for hydroxyls (3370 cm-1), methoxyl (2928), carbonyl of γ-pyrone
(1656), aromatic C C (1608, 1508), and glycoside C–O (1075, 1017).
The PMR spectrum (100 MHz, C D N, δ, ppm, J/Hz) contains signals at 1.35 (3H, d, J = 6.0, CH ), 3.50-4.50 (10H,
5
5
3
sugar), 3.80 (3H, s, OCH ), 4.80 (1H, br.s, H-1″′), 5.78 (1H, d, J = 7.0, H-1″), 6.56 (1H, d, J = 2.5, H-6), 6.73 (1H, d, J = 2.5,
3
H-8), 7.25 (1H, d, J = 8.0, H-5′), 7.80 (1H, dd, J = 2.5 and J = 8.0, H-6′), 8.26 (1H, d, J = 2.5, H-2′).
Acid hydrolysis of 5 produced isorhamnetin, D-glucose, and L-rhamnose. Acetylation of 5 by acetic anhydride in
+
pyridine gave the nonaacetyl derivative with mp 118-120°C. The mass spectrum (1002, [M] ) contains strong peaks for
fragments of the terminal rhamnose with m/z 273 (100%), 213, 153, and the acylated biose with m/z 561 [4, 7, 8].
Compounds 3 and 4 are isolated from Aerva lanata for the first time.
REFERENCES
1.
A. M. Zadorozhnyi, G. G. Zapesochnaya, L. N. Pervykh, A. V. Shchavlinskii, L. S. Kovtun, and N. V. Svanidze,
Khim.-Farm. Zh., 20, 855 (1986).
2.
3.
G. G. Zapesochnaya, V. A. Kurkin, and L. N. Pervykh, Khim. Prir. Soedin., 694 (1990).
G. G. Zapesochnaya, L. N. Pervykh, and V. A. Kurkin, Khim. Prir. Soedin., 388 (1991).
1) Tashkent Pharmaceutical Institute, Tashkent, fax (99871)-256-08-18; 2) S. Yu. Yunusov Institute of the Chemistry
of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (99871) 120 64 75. Translated from
Khimiya Prirodnykh Soedinenii, No. 3, p. 245, May-June, 2002. Original article submitted June 10, 2002.
0009-3130/02/3803-0293$27.00 ©2002 Plenum Publishing Corporation
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