S. M. Adekenov

ESSENTIAL OIL COMPOSITION OF THREE SPECIES OF Achillea FROM KAZAKHSTAN

The chemical composition of essential oils ofAchillea millefoliumL.,A. NobilisL. from Kazakhstan flora andA. GrandifloraBieb introduced in culture at the Karaganda Botanic garden were determined by GC/MS. The main component in the essential oil ofA. MillefoliumL. andA. NobilisL. was found to be camphor, while it was β-pinene for A. grandiflora.

Component composition of essential oils from four species of the genus Achillea growing in Kazakhstan

The component composition of the four species Achillea filipendulina, A. sudetica, A. ledebourii, and A. cartilaginea was studied by GC-MS. It was found that the principal components of the essential oil (%) were santolina alcohol (29.1) and borneol (27.9) for A. filipendulina, linalool (11.8) and caryophyllene (8.9) for A. sudetica, germacrene D (20.55) for A. ledebourii, and α-thujone (26.15) and β-thujone (11.76) for A. cartilaginea. The chemical composition of the essential oils from A. sudetica, A. ledebourii, and A. cartilaginea was studied for the first time.

Calorimetric study of the enthalpies of solution of methyl iodides of dimethylamino grosshemin and diethylamino grosshemin in water and evaluation of the thermodynamic properties of their analogues

The method of isothermal calorimetry at dilutions (moles salt/moles water) of 1:9000, 1:18000, and 1:36000 was applied to study the heats of solution of methyl iodides of dimethyl-and diethylamino grosshemin. The data obtained were used to calculate the standard enthalpies of solution of C18H28O4NI and C20H32O4NI in an infinitely diluted (standard) aqueous solution. The heats of combustion and melting of C18H28O4NI and C20H32O4NI were estimated. The experimental and calculational techniques were combined to calculate the standard heats of formation of methyl iodides of dimethyl-and diethylamino grosshemin and their 66 analogues.

Sesquiterpene lactones and flavonoids from Artemisia albida

The five known lactones matricarin, austricin, canin, and achillin guaianolides and argolide germacranolide and the two flavonoids eupatilin and its 7-O-methyl ester were isolated for the first time from the aerial part of Artemisia albida Willd. The structure of eupatilin was confirmed by an x-ray structure analysis.

Components of Artemisia pontica

Chemical components from the aerial part of the Kazakhstan population of Artemisia pontica, from which the rarely encountered flavonoids 7-O-methyl- and 4′,7-di-O-methyl-esters of apigenin were isolated for the first time, were identified. The complete chemical composition of the essential oil was established using GC-MS.

Essential oil from Kazakhstan Artemisia species

Essential oil from the aerial part of Siberian wild and cultivated Artemisia dracunculus L. (AD, tarragon) was studied previously by GC–MS. The main components were identified as methylhavicol, 1-phenyl-2,4-hexadiyne, spatulenol, and caryophyllene-oxide [1]; from Italy, essential oil contained the main components estragol (70.1%), caryophyllene (14.3), and trans-ocimene (9.4) and was highly active and inhibited aggregation of erythrocytes [2]; from Iran, the main components were anethole (21.1%), -trans-ocimene (20.6), and limonene (12.4) and sedative and anticonvulsive effects were observed [3]. Essential oil from raw material from China contained the main components 3,7-dimethyl-1,3,7-octatriene (38.4%), -pinene (37.0), and 1-methoxy-4-(2-propenyl)benzene (8.6) [4]. According to various researchers, the main components of essential oil from this sage species are estragol and methylhavicol [5–8]; elemicin (50%) and methyleugenol (17.6%) [9]; methylhavicol and methyleugenol [10]. Sabinene (37-85%) and myrcene (8–10) dominated in oil obtained from Kazakhstan raw material [11]. The principal components of A. gmelinii Web. (AG) according to the literature [12] were artemisia ketone and cineole. The composition of oil from various natural populations and introduced species has been studied in detail [13]. According to this study, the principal components of AG essential oil were yomogi alcohol (up to 24%), 1,8-cineole (up to 32), camphor (up to 40), borneol (up to 24), artemisic acetate (up to 20), and chrysanthenylacetate (up to 73). The compositions of essential oils from A. marschalliana Spreng. (AM), A. proceriformis Krasch. (AP), and A. armeniaca Lam. (AA) have not been reported. Raw material for the studies of AD and AP was collected near Yntymak reservoir in Karaganda Oblast on June 15, 2001; of AM and AG, in Karkaralin Region of Karaganda Oblast on June 16, 2001; of AA, in AO SPC Fitokhimiya botanical garden on June 14, 2001. All samples were collected during budding. Samples were identified (Nos. 1999.09.01.02.07, 1984.08.00.02.01, 1996.09.01.02, 2001.06.16.01.04, and 2001.06.16.01, respectively) and preserved in the herbarium voucher of AO SPC Fitokhimiya. Essential oil was obtained from dried and ground aerial parts of the plants by steam distillation in a Clevenger apparatus for 2 h. The yields were 0.2% for AD; 0.2, AM; 0.4, AG; 0.42, AP; and 0.17, AA. GC–MS analysis of essential oil was performed under conditions analogous to those previously reported [14]. Table 1 lists the identified components and their percent content. Table 1 shows that the principal components of AP essential oil were -thujone (66.3) and -thujone (23.4); of AA, spatulenol (30.5), limonene (7.7), and -elemene (6.9); of AD, sabinene (20.2), trans-3(1-butenyl)isocoumarin (10.3), terpinen4-ol (8.7), and myrcene (6.2); of AM, 1,8-cineole (13.5), camphor (9.8), -thujone (5.7), and artemisia ketone (4.4); of AG, 1,8-cineole (28.5), camphor (11.3), borneol (9.3), and -thujone (8.6). Thus, the component composition of five sage species growing in Kazakhstan was investigated. The essential oil compositions of AM, AP, and AA were studied for the first time.

Preparation and structure elucidation of two minor products from reaction of arglabin with chloroform in the presence of a crown ether

A pentachloro derivative, the structure of which was proved by x-ray structure analysis, in addition to a new dichlorocarbene derivative were obtained for the first time by dichlorocyclopropanation of arglabin guaianolide. The stereochemistry of the principal reaction product was established.

Synthesis and Structure of Pinostrobin Oxime and Its Biological Activity

Reaction of pinostrobin with hydroxylamine and hydrazine formed the corresponding oxime and hydrazone with retention of the γ-pyrone ring. The structures of the modified pinostrobin derivatives were established using PMR, 13C NMR, mass spectrometry, and X-ray analysis of pinostrobin oxime. Experiments in vivo revealed high hepatoprotective activity for pinostrobin oxime.

MOLECULAR STRUCTURE OF A NOVEL POLYMORPHIC MODIFICATION OF PINOSTROBIN

Abstract5-Hydroxy-7-methoxyflavanone (pinostrobin) was isolated from buds of balsamic poplar (Populus balsamifieraL.). An x-ray structure analysis of its novel polymorphic modification is performed.

4-Epiashantin from Artemisia sieversiana

Fitokhimiya, 100009, Karaganda, Gazalieva, 4, fax 8(3212) 43 37 73, e-mail: arglabin@phyto.kz; 3) N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, 630090, Novosibirsk, prosp. Akad. Lavrent′eva, 9, fax (3832) 34 47 52, e-mail: raldugin@nioch.nsc.ru. Translated from Khimiya Prirodnykh Soedinenii, No. 2, p. 192, March-April, 2007. Original article submitted October 9, 2006.