Lamiide from Phlomis cancellata
7.
8.
9.
~. D. Levin, B. Denisov, and R.Z. Pen, The Complex Processing of the Larch, [in
Russian], Lesnaya Prom-st', Moscow (1978), p. 224,
Hnadbook of Terpenoids, CRC Press, Boca Raton, Florida, Vol. !i (1985), p. 158.
G . F . Chernenko, I. Yu. Bagryanskaya, and ~. N. Shmidt, Khim. Prir. Soedin., No. 5, 641
(1990).
LAMIIDE FROM Phlomis cancellata
G. A. Fokina and T. V. Bukreeva
UDC 547.918:547.192
We have detected compound (I) of iridoid nature, in the epigeal part of the plant
Phlomis cancellata Bunge (family Lamiaceae) collected in April, 1988 in the south-western
Kopet Dagh.
The air-dry comminuted raw material (1.2 kg) was extracted at room temperature with 70%
ethanol until extraction was complete.
The concentrated extract (i liter) was freed from
lipophilic substances with diethyl ether (3 × 1 liter) and chloroform (3 × 1 liter) and then,
to eliminate the phenolic compounds, was passed through a column of neutral alumina that had
previously been washed with water. The column was eluted with water until the reaction for
iridoid glycosides was negative, and the aqueous eluate ws evaporated under reduced pressure.
Ground activated carbon (750 g) was added to the concentrated extract until the iridoid glycosides had been adsorbed completely.
The resulting suspension was placed in a column and was
washed with water (15 liters) and then with aqueous alcoholic mixtures with increasing concentrations of ethanol.
The fraction containing 20% of ethanol afforded an individual compound (I) (yield on the
air-dry raw material 1.5%) in the form of awhite amorphous substance C17H2~Oz2, [~]~5-122°(c 1.0,
CH3OH), ACH~
max OH nm: 230 (log 4.15); ~max, cm-Z: 1700 (C=O); 1635 (C=C); z3CNMR (5~.33 MHz, D20);
94.46 (C-l), 152.67 (C-3), 114.21 (C-4), 68.71 (C-5), 45.80 (C-6), 77.14 (C-7), 79.14 (C-8),
56.86 (C-9), 19.60 (C-10), 169.00 (C-If), 99.14 (C-I'), 52.61 (CH30).
Substance (I) (0.3 g) was acetylated with acetic anhydride at room temperature for a
month. The reaction products were chromatographed on a column of silica gel with elution by
the chloroform--methanol (9:1) system. This gave 180 mg of the pentaacetate (II) C27H36Oz~,
mp 186-188°C (from ethanol), [a]~5--76 ° (c 0.5; CHCL 3) and 75 mg of the hexaacetate (III),
C ~ g H ~ O I 8 mp 203-204°C (ethanol), [a]~s _ 5 4 ° (c 1.0; CHCI~).
From the physicochemical constants and spectral characteristics of substance (I) and its
derivatives (II) and (III), the compound isolated from Phlomis cancellata was identified as
lamiide, an iridoid glucoside of the loganin group [i, 2].
LITERATURE CITED
1.
2.
M. L. Scarpati and M. Guiso, Gazz. Chim. Ital., 99, 1150 (1969).
A. Bianco, P. Caciola, M. Guiso, C. Iavarone, and C. Trogolo, Gazz, Chim. Ital., IIi,
201 (1981).
Botanical Institute, Academy of Sciences of the USSR, Leningrad.
Translated from
Khimiya Prirodnykh Soedinenii, No. 6, pp. 834-835, November-December, 1990. Original article
submitted March 15, 1990.
0009-3130/90/2606-0715512.50
©1991 Plenum Publishing Corporation
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