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.     

(<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.     

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.     

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.     

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.     

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).     

A new kaempferol trioside from <Emphasis Type="Italic">Solidago altissima</Emphasis> L.

A new kaempferol trioside [kaempferol 3-O-rutinoside 7-O-β-d-apiofuranoside, (1)] was isolated together with nine phenolic compounds, trans-tiliroside (2), caffeic acid (3), chlorogenic acid (4), 3-O-caffeoylquinic acid (5), 4-O-caffeoylquinic acid (6), 3-O-coumaroylquinic acid (7), 4-O-coumaroylquinic acid (8), 3,5-di-O-caffeoylquinic acid (9) and 4,5-dicaffeoylquinic acid (10) from the leaves of Solidago altissima L. The structure elucidations of the compounds were based on the analyses of spectroscopic data.     

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.     

A new phenylethanoid glycoside from the fruits of <Emphasis Type="Italic">Callicarpa japonica</Emphasis> Thunb. var. <Emphasis Type="Italic">luxurians</Emphasis> Rehd.

A new phenylethanoid glycoside, named acetyl forsythoside B (1), was isolated from the fruits of Callicarpa japonica Thunb. var. luxurians Rehd. (Verbenaceae) along with forsythoside B (2), brandioside (3), poliumoside (4), actioside (5), and apigenin 7-galacturonide (6). The structures of 1–6 were determined on the basis of spectroscopic data. In addition, the antioxidative activity of 1–4 and 6 was evaluated by the ferric thiocyanate method. All of the tested compounds except 6 exhibited almost the same activity as 3-tert-butyl-4-hydroxyanisole. The radical-scavenging effect of 1–6 on the stable free radical 1,1-diphenyl-2-picrylhydrazyl was also examined. Compounds 1–5 showed almost twice the activity compared to α-tocopherol.     

Megastigmane glucoside from <Emphasis Type="Italic">Asystasia gangetica</Emphasis> (L.) T. Anderson

A 5,11-epoxymegastigmane glucoside (asysgangoside) was isolated from the aerial parts of Asystasia gangetica together with the known compounds, salidroside, benzyl β-d-glucopyranoside, (6S,9R)-roseoside, ajugol, apigenin 7-O-β-d-glucopyranoside, apigenin 7-O-neohesperidoside, and apigenin 7-O-β-d-glucopyranosyl (1→6)-β-d-glucopyranoside. The structure elucidations were based on spectroscopic evidence.     

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.     

Antinociceptive properties of conocarpan and orientin obtained from <Emphasis Type="Italic">Piper solmsianum</Emphasis> C. DC. var. <Emphasis Type="Italic">solmsianum</Emphasis> (Piperaceae)

The antinociceptive properties of some fractions and two pure compounds, conocarpan and orientin, obtained from P. solmsianum leaves were investigated in several models of pain in mice. The results indicated that this plant exhibits a promising antinociceptive profile, as it produces active principles which are several times more active than some reference drugs used for comparison. The main compound tested, orientin, caused potent and dose-dependent effects against acetic acid-induced writhing and capsaicin- and glutamate-induced nociception, being more effective against the first one, with an ID₅₀ value of 6.5 mg/kg (14.5 μmol/kg). Orientin was about 20-fold more potent than acetylsalicylic acid and 3.5-fold more active than indomethacin. The antinociceptive effects of this plant may be attributed, at least partially, to the presence of conocarpan and, in particular, to the flavonoid orientin.     

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.