Polyprenols from Althaea armeniaca leaves

Van, E. V.; Shakhidoyatov, R. Kh.; Хидырова, Н. К.; Mukarramov, N. I.; Shakhidoyatov, Kh. M.

doi:10.1007/s10600-010-9508-6

Chem Nat Compd

2009

DOI: 10.1007/s10600-010-9508-6

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Polyprenols from Althaea armeniaca leaves

E. V. Van

R. Kh. Shakhidoyatov

Н. К. Хидырова

et al.

Abstract: The accumulation dynamics of polyprenols in leaves of 1-, 2-, and 3-year-old Althaea armeniaca growing in Tashkent were studied according to vegetative phase. Optimal conditions for isolating the polyprenols were determined. It has been shown that the content of polyprenols was highest during fruiting in the second year of growth.

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Cited by 5 publications

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“…Minor components of polyprenols with chain lengths 8, 9, and 14 isoprene units were observed for the first time in plants of the genus Alcea. A total of 28 terpene components of the unsaponified fraction, 26 of which were not previously observed in this species, were determined by GC-MS.Plants of the family Malvaceae are exceptional among leafy plants because of their high content of polyprenols (PPs), which are chemotaxonomic markers [1][2][3][4][5][6]. Such plants also have a characteristically high content of cyclopropane acids, which are practically not observed in plants of other families [7].…”

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Polyprenols and triterpenoids from leaves of Alcea nudiflora

et al. 2012

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Polyprenols and triterpenoids from leaves of Alcea nudiflora were studied for the first time. It was shown that the principal components of the unsaponified fraction were polyprenols, sterols, a phytol, and tocopherols. The composition of the polyprenols from Alcea nudiflora was established. Minor components of polyprenols with chain lengths 8, 9, and 14 isoprene units were observed for the first time in plants of the genus Alcea. A total of 28 terpene components of the unsaponified fraction, 26 of which were not previously observed in this species, were determined by GC-MS.Plants of the family Malvaceae are exceptional among leafy plants because of their high content of polyprenols (PPs), which are chemotaxonomic markers [1][2][3][4][5][6]. Such plants also have a characteristically high content of cyclopropane acids, which are practically not observed in plants of other families [7].Alcea nudiflora belongs to this family, is widely distributed, and is common in the plant cover of the whole Tian-Shan (Chatkal, Kuramin, Ugam, Pskom, etc. ranges) and Pamir-Alai (Alai, Turkestan, Nuratau, Zarafshan, etc. ranges) [8-10]. However, neutral triterpenoids and bioactive PPs from this plant are insufficiently studied [11].Various qualitative and quantitative analytical methods for PPs and dolichols from plant material have been reported. However, each of them has certain shortcomings. Thus, comparison of HPLC analyses of an extract and a chromatographic standard concentrate of PPs does not consider seasonal cycles of the component ratio in plant material according to vegetation periods. Furthermore, PPs and dolichols in certain plant species are present as esters of aliphatic acids that are unsuitable for HPLC analysis [12,13]. HPLC with refractive-index detection also has shortcomings. Normalization to the total peak area in the chromatogram does not consider differences in the extinction or refraction.PMR analysis of polyisoprenoid concentrates also has several shortcomings. A PMR spectrum of a PP sample is a superposition of resonances of similar structural fragments. The regular structure of the PPs produces total resonances that are stronger than those of impurities. This leads to a substantial overestimation of the quantitative characteristics of the studied PP fraction. Solanesol can be cited as an example [14].Use of densitometry of thin-layer chromatograms compared with a standard [15] also usually causes substantial overestimation of quantitative results because accompanying mono-, sesqui-, and diterpene alcohols overlap the spot for the PP fraction. Thus, borneol, cis-abienol, isoabienol, dehydroabietinol, and other alcohols that enhanced the intensity of the PP spot were present as impurities in the total fraction during a study of PPs from conifers [16,17]. Bisabolol was isolated from essential oil of cotton buds [18]. The chromatographic mobility of total extracted compounds depends on the chain length of the PPs in them and their form (as alcohols or esters). Therefore it is practically impossible to choose...

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“…Plants of the family Malvaceae are exceptional among leafy plants because of their high content of polyprenols (PPs), which are chemotaxonomic markers [1][2][3][4][5][6]. Such plants also have a characteristically high content of cyclopropane acids, which are practically not observed in plants of other families [7].…”

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Polyprenols and triterpenoids from leaves of Alcea nudiflora

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“…In particular, the preparation gamapren (OOO GamaVetFarm, Russia) based on moraprenols is manufactured by phosphorylation of polyprenols isolated from Morus spp. The preparation exhibits antiviral action against Herpes viruses by suppressing the synthesis of viral proteins and stimulating the production of interferons [4].In continuation of research on plant polyprenols [5][6][7][8] and in order to compare the quantitative contents of M. alba and M. nigra polyprenols, we present results from a study of polyisoprenols from these two mulberry varieties growing in Tashkent Oblast.Total polyisoprenoids were isolated by the previously published method [9]. Dried and ground leaves (10 g) produced total polyisoprenoids in 2.6 and 3.2% yields.…”

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“…In continuation of research on plant polyprenols [5][6][7][8] and in order to compare the quantitative contents of M. alba and M. nigra polyprenols, we present results from a study of polyisoprenols from these two mulberry varieties growing in Tashkent Oblast.…”

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Polyisoprenoids from leaves of Morus alba and M. nigra

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Trees or bushes of the genus Morus (mulberry) have been cultivated since antiquity. Mainly two species grow in Uzbekistan, M. alba and M. nigra. These species also include little studied varieties such as khasak-tut (used to feed silk worms), balkhi-tut (for fruit), ilon-tut and plakuchaya (as decorative plants), and shotut (M. nigra, for fruit) [1].Three polyisoprenoid alcohols, undeca-and dodecaprenols and solanesol, were isolated from silk-worm cocoons and leaves of M. alba [2]. Solanesol was not observed in the leaves. Moraprenols (polyprenols) from leaves of M. alba growing in Fergan Oblast were studied [3]. However, the quantitative composition of the polyprenologs was not reported. Polyprenols from M. nigra have not been reported.Recently a rather large number of preparations based on the use of polyprenols has appeared. In particular, the preparation gamapren (OOO GamaVetFarm, Russia) based on moraprenols is manufactured by phosphorylation of polyprenols isolated from Morus spp. The preparation exhibits antiviral action against Herpes viruses by suppressing the synthesis of viral proteins and stimulating the production of interferons [4].In continuation of research on plant polyprenols [5][6][7][8] and in order to compare the quantitative contents of M. alba and M. nigra polyprenols, we present results from a study of polyisoprenols from these two mulberry varieties growing in Tashkent Oblast.Total polyisoprenoids were isolated by the previously published method [9]. Dried and ground leaves (10 g) produced total polyisoprenoids in 2.6 and 3.2% yields. The content of total polyprenols was 1.37 and 1.97%, respectively, of the airdried leaf mass. The qualitative and quantitative compositions of the total polyisoprenoids were determined by high-performance TLC (HPTLC, Camag), by densitometry with UV detection at 210 nm, and by other alternate methods. HPTLC analysis used Sorbfil HPTLC-AF-UV plates (10 u 10). Plates were rinsed in distilled CHCl 3 and dried in air at 20-25°C for 10 min. The eluent was toluene:EtOAc (19:1). Compounds (1.0 mg) were dissolved in solvent (1 mL) and sampled (5 PL). The distance from the origin to the solvent front was 70.0 mm. The distance between tracks was 7.7 mm. Plates were dried in air at 20-25°C for 15 min.The standards were authentic samples of polyprenols from leaves of Asimina triloba (at least 96% pure) and those isolated by us from cotton leaves (at least 95% pure) of composition C 50 -C 65 . Standard samples of D-tocopherol and sitosterol were obtained from cotton leaves. Standard samples were prepared as described before [9]. Table 1 presents the results.According to the results, total polyisoprenoids contained polyprenols and D-tocopherol and sitosterol. The sitosterol contents in M. nigra and M. alba were almost identical. However, the amount of D-tocopherol was almost 13 times greater in leaves of M. nigra than in those of M. alba. The homologous composition of polyprenols from both M. nigra and M. alba included deca-, undeca-, and dodecaprenols with undecaprenol do...

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“…The light-yellow oily substance was homogeneous according to TLC and was identified by its IR and PMR spectra and comparison with standards as polyprenols [7,8], which are known to occur in nature as mixtures of isoprenologs. These are natural precursors of dolichols, which play an important role in the protection of cell membranes, the stabilization of cell proteins, and the maintenance of the immune system [9, 10].…”

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Neutral constituents from leaves of plants of the family Malvaceae. I. Abutilon theophrasti

et al. 2012

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The genus Abutilon in the family Malvaceae includes about 160 species. One species, A. theophrasti, grows in the Republic of Uzbekistan and is distributed in Central Asia and the European part of the CIS and in the Caucases, Iran, India, China, Japan, north Africa, etc.Leaves, roots, and flowers of A. theophrasti are used in folk medicine as a substitute for Althea as an expectorant and emollient [1].The chemical composition of A. theophrasti includes 2-3% tanning agents. Leaves contain 24.3 mg% J-carotene, 180-200 mg% vitamin C, and ~0.28% of the air-dried mass of rubber-like substances [2]. Flavonoids [3] and glycosides [4] were reported. Lipophilic components have not been reported.We studied substances extracted from A. theophrasti leaves collected in 2009 in Samarkand Oblast.Leaves that were dried in the shade (10 g) were ground and extracted with EtOH (96%, 100 mL). The extract was evaporated to dryness in a rotary evaporator (2.4 g yield). The resulting resinous (oily) mass was dissolved in petroleum ether (PE) and chromatographed over silica gel with elution by hexane and hexane:CHCl 3 mixtures of increasing polarity. Fractions were monitored by TLC. Identical fractions were combined. Crystallization from hexane isolated four compounds and a homogeneous oily fraction.Compound 1, C 26 H 53 OH, white crystals, mp 78-79°C. Its physicochemical and spectral properties were identical to those of hexacosanol.Compound 2, C 29 H 59 OH, white crystals, mp 80-81°C. Its composition and spectral properties were identical to those of nonacosanol.Compound 3, C 29 H 50 O, white needle-like crystals, mp 135-136°C. Its IR, PMR, and mass spectra corresponded to sitosterol [5].Compound 4, C 29 H 48 O, white needle-like crystals, mp 168-169°C. Its IR and PMR spectra were identical to those of stigmasterol [6].The light-yellow oily substance was homogeneous according to TLC and was identified by its IR and PMR spectra and comparison with standards as polyprenols [7,8], which are known to occur in nature as mixtures of isoprenologs. These are natural precursors of dolichols, which play an important role in the protection of cell membranes, the stabilization of cell proteins, and the maintenance of the immune system [9, 10]. The qualitative and quantitative compositions of the polyprenol fraction were studied using HPLC (Millichrom) with UV detection at 210 nm analogously to polyprenols from sea buckthorn [7]. It was found that A. theophrasti polyprenols, like other representatives of the family Malvaceae, comprised n = 9-13 isoprene units, the percent content of which was 5.9:24.0:45.4:22.6:2.6, respectively, with the deca-, undeca-, and dodecaprenols dominating. The content of the others was insignificant. Additional purification of the polyprenol fraction identified impurities of squalene, D-tocopherol, and phytol by using TLC and their authentic samples. The TLC results were verified using GC-MS.All listed compounds were isolated from A. theophrasti for the first time.

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Polyprenols from Althaea armeniaca leaves

Cited by 5 publications

References 5 publications

Polyprenols and triterpenoids from leaves of Alcea nudiflora

Polyprenols and triterpenoids from leaves of Alcea nudiflora

Polyisoprenoids from leaves of Morus alba and M. nigra

Neutral constituents from leaves of plants of the family Malvaceae. I. Abutilon theophrasti

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