Secoiridoid glycosides from the leaves of <Emphasis Type="Italic">Hydrangea macrophylla</Emphasis> subsp. <Emphasis Type="Italic">serrata</Emphasis>

Seven secoiridoid glycosides, secologanin dimethyl acetal (1), n-butyl vogeloside (2), n-butyl epi-vogeloside (3), (7R)-n-butyl morroniside (4), hydrangenoside A (5), hydrangenoside C (6), and hydrangenoside A dimethyl acetal (7), have been isolated from the leaves of Hydrangea macrophylla subsp. serrata (Thunb.) Makino (Saxifragaceae). The structures were elucidated on the basis of spectral data.     

Studies of the chemical composition of birch bark extracts (<Emphasis Type="Italic">Cortex betula</Emphasis>) from the <Emphasis Type="Italic">Betulaceae</Emphasis> family

This report presents the results obtained from chemical studies of the composition of dried birch bark extracts (DBBE) from Betula pubescens Ehrh. analyzed by GLC, HPLC, and IR and PMR spectroscopy. The extract contained the following groups of natural compounds: terpenoids (75.2%) and their esters (fatty acid esters of betulinol and lupeol, 4.4%), ether oils (0.08%), hydrocarbons (6.3%) and their epoxides (1.0%), steroids (β-sitosterol, 2.7%), tannins (2.1%), flavonoids (1.56%-mainly kaempferol, its 7-methyl ester, quercetin, the 4-methyl ester of naringenin, etc.), hydroxycoumarins (0.85%-umbelliferone, esculetin, etc.), and a number of unidentified compounds (about 4.0%). The major components of DBBE were triterpenoids and hydrocarbons. Preparative chromatographic separation of fractions containing triterpenoids and hydrocarbons yielded isolated samples which allowed the following compounds to be identified: the terpenoids betulinol, isobetulinol, lupeol, lupenone, betulonic aldehyde, betulonic acid, betulinic acid, and platanic acid, and the hydrocarbons α-santalene, β-trans-bergamotene, and α-trans-bergamotene, and their epoxy derivatives. The chemical composition of DBBE varied depending on the preparation method used, this particularly affecting the content of the major component betulinol, which varied from 54 to 82%. These studies led to the development of a contemporary preparative technology for betulinol with a yield of 95%, along with production of many of its acyl derivatives (for example, the diacetate, succinate, benzoate, etc.) with quite high yields (95–98%); betulinic acid was synthesized in mild conditions with a yield of at least 99.0%. These compounds are currently subject to pharmacological studies. __________ Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 41, No. 8, pp. 22–26, August, 2007.     

Standardization of homeopathic <Emphasis Type="Italic">Coffea arabica</Emphasis> (<Emphasis Type="Italic">Coffea cruda</Emphasis>) and <Emphasis Type="Italic">Coffea tosta</Emphasis> matrix tinctures

Methods of standardization and quality control of homeopathic matrix tinctures of Coffea arabica and Coffea tosta obtained using green and roasted coffee beans are described. They include the organoleptic characteristics, qualitative reactions, TLC, quantitative estimation of caffeine and total phenolcarboxylic acids (calculated as caffeic acid), relative density, and percentage of dry residue. The period of expiration on storage is established at two years. These methods are included in drafts of pharmacopoeial monographs for homeopathic matrix tinctures of Coffea arabica and Coffea tosta. Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 42, No. 11, pp. 45–48, November, 2008.     

Chemical composition of the above-ground part of <Emphasis Type="Italic">Coriandrum sativum</Emphasis>

The composition of c (Coriandrum sativum L.) has been studied. The results of HPLC showed the presence of 43 substances, among which 21 phenolic compounds were identified. These components represent mainly flavonoids, coumarins, and phenolcarboxylic acids. Some of these compounds, including apigenin, luteolin, hyperoside, hesperidin, vicenin, diosmin, orientine, dihydroquercetin, chrysoeriol, catechin, ferulic acid, gallic acid, salicylic acid, dicoumarin, 4-hydroxycoumarin, esculin, esculetin, maleic acid, tartaric acid, and arbutin were identified in this plant for the first time. The elemental and amino acid analyses of coriander, which were also performed for the first time, showed that the prevailing elements are potassium, sodium, calcium and phosphorus, while the prevailing amino acids are glutamine, asparagine, and arginine. __________ Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 41, No. 3, pp. 30–34, March, 2007.     

Chemical studies on monoterpenoid indole alkaloids from medicinal plant resources <Emphasis Type="Italic">Gelsemium</Emphasis> and <Emphasis Type="Italic">Ophiorrhiza</Emphasis>

We have proved that the plant of origin of “Yakatsu”, one of the ancient medicines stored in Shosoin Repository, is Gelsemium elegans (Loganiaceae). Exhaustive investigation of the alkaloids in this plant as well as its closely related plant, G. sempervirens, resulted in the isolation of more than 50 compounds, including new gelsedine-, sarpagine-, and yohimbane-type alkaloids. Pharmacological study of representative and new Gelsemium alkaloids revealed that the gelsedine-type alkaloids exhibit potent cytotoxic activity against the A431 human epidermoid carcinoma cell line. It was found that Ophiorrhiza pumila (Rubiaceae) produces a remarkable anti-tumor alkaloid, camptothecin, and its related alkaloids, including new compounds that might be the biogenetic precursors of camptothecin. Chemical investigation of callus cultures, regenerated plants, and hairy roots of O. pumila revealed that the regenerated plants and the hairy roots produce almost the same alkaloids, including camptothecin, as do the wild-type plants.     

Novel cycloartane-type triterpenoid from the fruits of <Emphasis Type="Italic">Nandina</Emphasis><Emphasis Type="Italic">domestica</Emphasis>

A novel cycloartane-type triterpenoid was isolated from the fruits of Nandina domestica (Berberidaceae). The structure was characterized as 24-methylene-3-oxocycloartane 13-carboxylic acid on the basis of NMR spectroscopic data.     

Chemical constituents of <Emphasis Type="Italic">Polyalthia parviflora</Emphasis> stem

From the stem of Polyalthia parviflora, four compounds were isolated, including p-hydroxyphenylethyl p-coumarate (1), p-hydroxyphenylethyl ferulate (2), dehydrodiscretamine (3) and (−)-discretamine (4). Complete ¹H and ¹³C NMR assignments were obtained for 1, 3 and 4 for the first time.     

Antileishmanial amides and lignans from <Emphasis Type="Italic">Piper cubeba</Emphasis> and <Emphasis Type="Italic">Piper retrofractum</Emphasis>

The n-hexane, ethyl acetate, methanol, and acetone extracts of Piper cubeba Linn. and P. retrofractum Vahl. (Piperaceae) were evaluated in vitro against promastigotes of Leishmania donovani, and all exhibited significant in vitro activity at 100 μg/ml. Two lignans, cubebin and hinokinin, were isolated from the hexane extract of P. cubeba; and one bis-epoxy lignan, (−)-sesamin, and two amides, pellitorine and piplartine, were isolated from the hexane and methanol extracts of P. retrofractum. Cubebin and piplartine showed significant antileishmanial activity in vitro at 100 μM and were further tested in vivo in a hamster model of visceral leishmaniasis. Piplartine showed activity at 30 mg/kg dose. This is the first report of antileishmanial activity of these two plants and their isolated constituents. NIPER Communication No. 395.     

Synthesis and antimicrobial activity of 1<Emphasis Type="Italic">H</Emphasis>,10<Emphasis Type="Italic">H</Emphasis>-benzo[<Emphasis Type="Italic">e</Emphasis>]pyrrolo[3,2-g]indole derivatives

We have synthesized a series of new phenylazo derivatives of 1H,10H-benzo[e]pyrrolo[3, 2-g]indole containing 3-(p-bromophenylazo) (II), 3-(p-iodophenylazo) (III), 3-(p-sulfamidophenylazo) (IV), 3-formyl (V), 3,8-diformyl (VI), 3-phenylazo (VII), 3-(p-chlorophenylazo) (VIII), 3-(p-nitrophenylazo) (IX), 2,9-di(adamantylaminocarbonyl) (X), 2,9-di(p-benzenesulfamidoaminocarbonyl) (XI), 2,9-di(isonicotinoylhydrazidecarbonyl) (XII), and 2,9-di(carbohydrazide) (XIII) substituents. The antimicrobial, antifungal, and antituberculosis activity was investigated in vitro with respect to various microorganisms including conditionally pathogenic mycobacteria and pathogenic fungi. It is established that the tested compounds possess high antimicrobial activity. The synthesized compounds are of great interest for further, more thorough investigations and experiments on animals with the corresponding infectious diseases. Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 43, No. 2, pp. 23–25, February, 2009.     

(<Emphasis Type="Italic">Z</Emphasis>)-3-Hexenyl diglycosides from <Emphasis Type="Italic">Spermacoce laevis</Emphasis> Roxb.

A new (Z)-3-hexenyl O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside was isolated from the aerial part of Spermacoce laevis, along with 17 known compounds: (6S,9R)-roseoside, (Z)-3-hexenyl O-β-d-glucopyranoside, (Z)-3-hexenyl O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside, (Z)-3-hexenyl O-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranoside, phenyethyl O-β-d-glucopyranoside, phenyethyl O-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranoside, phenyethyl O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside, benzyl O-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranoside, benzyl O-β-d-xylopyranosyl-(1→6)-β-d-glucopyranoside, asperuloside, 6α-hydroxyadoxoside, asperulosidic acid, kaempferol 3-O-β-d-glucopyranoside, kaempferol 3-O-rutinoside, quercetin 3-O-β-d-galactopyranoside, quercetin 3-O-α-l-rhamnopyranosyl-(1→6)-β-d-galactopyranoside, and rutin. The structure determinations were based on physical data and spectroscopic evidence.     

Two novel A-<Emphasis Type="Italic">seco</Emphasis>-rearranged lanostane triterpenoids from <Emphasis Type="Italic">Abies sachalinensis</Emphasis>

Further chemical study led to two new A-seco-rearranged lanostane triterpenoid derivatives (1–2) and one known compound Abiesanolide C (3) from the ethyl acetate (EtOAc) soluble fraction of the MeOH extract of Abies sachalinensis needles. The new compounds were identified as 3,4-seco-8-(14→13R)abeo-17,13-friedo-9β-lanosta-4(28), 7, 14, 24-tetraen-26,23-olide-23-hydroxy-3-oic acid and methyl-3,4-seco-8-(14→13R) abeo-17,13-friedo-9β-lanosta-4(28), 7, 14, 24-tetraen-26,23-olide-23-hydroxy-3-oate, respectively. Structural determination of these compounds were carried out by the spectral studies especially by the two digital (2D)-NMR and high-resolution (HR)-MS experiences.     

Chemical composition and pharmacological activity of anthraquinones from <Emphasis Type="Italic">Rubia cordifolia</Emphasis> cell culture

The results of qualitative and quantitative determination of anthraquinones in Indian madder (Rubia cordifolia L.) cell culture are presented. According to the ¹H and ¹³C NMR, UV, IR, and mass-spectroscopic data, seven anthraquinones have been identified, in which munjistin and purpurin are predominant. The cell culture preparation exhibits antiinflammatory activity, which is manifested by an antiexudative effect and antiproliferative action during the rapid development of a model edema. Adecrease in the antioxidant state without significant suppression of enzymatic activity is demonstrated. __________ Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 41, No. 11, pp. 38–41, November, 2007.     

Polygosumic acid,a new cadinane sesquiterpene from <Emphasis Type="Italic">Polygonum viscosum</Emphasis>, inhibits the growth of drug-resistant <Emphasis Type="Italic">Escherichia coli</Emphasis> and <Emphasis Type="Italic">Staphylococcus aureus</Emphasis> (MRSA) in vitro

Three new sesquiterpenes, 6-hydroxy-7-(1-methylethyl)-3,3a,6,7,8,8a-hexahydroazulene-1,4-dicarboxylic acid methyl ester (1, named viscozulenic acid methyl ester), 7-(1-methylethyl)-3,3a,6,7,8,8a-hexahydroazulene-1,4-dicarboxylic acid 1-methyl ester (2, named viscoazucinic acid) and 3-oxo-1-epi-sclerosporin (3, named polygosumic acid), have been isolated from the chloroform extract of the aerial parts of Polygonum viscosum by reversed-phase preparative high performance liquid chromatography (HPLC). The structures of these compounds were established conclusively by ultraviolet (UV), mass spectrometry (MS) and a series of 1D and 2D nuclear magnetic resonance (NMR) analyses. The anti-bacterial properties of 1–3 against 12 pathogenic bacterial strains have also been assessed by the rapid and robust microtitre-plate-based serial dilution method incorporating resazurin as an indicator of cell growth. Polygosumic acid was the most active among the sesquiterpenes and inhibited the growth of penicillin-resistant Escherichia coli (minimum inhibitory concentration, MIC=0.05 mg/ml) and methicillin-resistant Staphylococcus aureus (MRSA) (MIC=0.10 mg/ml).     

Extraction,composition and the antioxidant and anticomplement activities of high molecular weight fractions from the leaves of <Emphasis Type="Italic">Symphytum asperum</Emphasis> and <Emphasis Type="Italic">S. caucasicum</Emphasis>

High molecular weight fractions (> 1000 kDal) from the leaves of Symphytum asperum and S. caucasicum had anticomplement activity, were able to inhibit luminol- and lucigenin-dependent chemiluminescence (CL_lum and CL_luc respectively) induced by human polymorphonuclear neutrophils (PMN) after stimulation with opsonized zymosan, and could decrease the CL_luc signal induced by superoxide anion formation in a cell-free hypoxanthine/xanthine oxidase system. The anticomplement and antioxidant activities of the high molecular weight fractions (> 1000 kDal) from the leaves of Symphytum asperum and S. caucasicum indicate that they might be used as anti-inflammatory and wound-healing agents.     

Prenylated xanthones from <Emphasis Type="Italic">Hypericum ascyron</Emphasis>

Three new prenylated xanthones, 1,3,5-trihydroxy-6,7-[2′-(1-methylethenyl)-dihydrofurano]-xanthone (1), 1,3,5-trihydroxy-6,7-[2′-(1-hydroxy-1-methylethyl)-dihydrofurano]-xanthone (2), and 1,3,5-trihydroxy-6-O-prenyl-xanthone (3), together with eight known compounds were isolated from the leaves of Hypericum ascyron. Compound 3 has an O-prenyl moiety, and therefore represents the first reported xanthone to have an O-prenyl moiety from genus Hypericum. The structures of the isolated compounds were established based on spectroscopic data and on a comparison with values for previously identified analogues.     

Secoiridoid and iridoid glucosides from the leaves of <Emphasis Type="Italic">Fraxinus griffithii</Emphasis>

Phytochemical investigation of the dried leaves of Fraxinus griffithii collected in Okinawa has led to the isolation of three new secoiridoid glucosides, griffithosides A–C (1–3), and one new iridoid glucoside, 7-epi-7-O-(E)-caffeoylloganic acid (4), along with eight known secoiridoid glucosides (5–12). The structures of these compounds were elucidated by means of NMR, MS, and other spectroscopic techniques, as well as comparison with literature data. The isolated compounds were tested for radical-scavenging activity. Among them, compounds 3, 4, and 7 exhibited substantial radical-scavenging activity.     

Therapeutic effect of phenolic compounds isolated from <Emphasis Type="Italic">Rhododendron ungernii</Emphasis> leaves

The sum of phenolic compounds was obtained from the leaves of Caucasian endemic plant Rhododendron ungernii (Trautv.) in the amount of 7%. The extract contains flavonoids, catechins, and anthocyanidins, in particular, quercetin, isoquercetin, quercitrin, hyperin, rutin, (+)-catechin, (−)-epicatechin, (+)-gallocatechin, and leucoanthocyanidins. The sum of phenolic compounds from Rhododendron ungernii completely inhibits Herpes simplex virus reproduction in a bioassay. A new medicinal preparation (Rhodopes) in the form of a 5% ointment was created on the basis of this extract and tested under clinical conditions at a dental clinic and three other specialized medical departments. The results showed a high therapeutic efficacy: Rhodopes favorably influenced the state of patients and caused neither mucosa irritation nor allergic and other adverse reactions. Rhodopes has received State Registration and is recommended for the treatment of all forms of herpetic disorders. __________ Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 41, No. 1, pp. 10–13, January, 2007.     

Tropane alkaloids from <Emphasis Type="Italic">Erythroxylum emarginatum</Emphasis>

A tropane alkaloid, anhydroecgonine methyl ester N-oxide (2), was isolated for the first time as a naturally occurring compound, with anhydroecgonine methyl ester (1) from the bark of Erythroxylum emarginatum. Compound 1 was also isolated from the twigs. Their structures were elucidated mainly by spectroscopic methods.     

Studies of the chemical constituents of the flower buds of <Emphasis Type="Italic">Magnolia kobus</Emphasis> and <Emphasis Type="Italic">M. salicifolia</Emphasis>

The constituents of the flower buds of Magnolia kobus DC. and M. salicifolia MAXIM. have been investigated. We isolated and identified six bis-tetrahydrofuran-type and three tetrahydrofuran-type lignan derivatives from M. kobus, and one bis-tetrahydrofuran-type lignan and eight phenylpropanoid-type derivatives from M. salicifolia. The structures of these compounds were elucidated on the basis of chemical and spectroscopic evidence.