Secondary metabolites from the aerial parts of <Emphasis Type="Italic">Verbascum dudleyanum</Emphasis> and their biological activities

From the overground parts of Verbascum dudleyanum, six iridoid glycosides, aucubin, ajugol, catalpol, 6-O-α-L-rhamnopyranosylcatalpol, saccatoside, and 6-O-(3″-O-trans-p-coumaroyl)-α-L-rhamnopyranosylcatalpol, and two saponins, ilwensisaponin A and C, as well as a flavonoid, luteolin-7-O-β-glucopyranoside, together with an acetophenone glucoside, picein, were isolated. The structures of isolated compounds were elucidated by spectroscopic methods. These compounds showed biological acitivites. __________ Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 232–234, May–June, 2008.     

New coumarin glucoside from <Emphasis Type="Italic">Angelica dahurica</Emphasis>

A new linear furanocoumarin glycoside named dahurin B (1) was isolated from the fresh roots and rhizomes of Angelica dahurica. The structure of the new compound was elucidated by spectral techniques including ¹H NMR, ¹³C NMR, as well as HSQC, HMBC, and COSY. Published in Khimiya Prirodnykh Soedinenii, No. 4, pp. 330–331, July–August, 2007.     

A new C<Subscript>19</Subscript>-diterpenoid alkaloid,habaenine C,from <Emphasis Type="Italic">Aconitum habaense</Emphasis>

A new C₁₉-diterpenoid alkaloid, habaenine C (1), together with the two known compounds vilmorrianine C and crassicauline A, were isolated from Aconitum habaense. The structure of the new compound was elucidated on the basis of spectral analysis, including 2D NMR spectroscopy. Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 265–266, May–June, 2008.     

New flavonoid-<Emphasis Type="Italic">C</Emphasis>-glycosides from <Emphasis Type="Italic">Triticum aestivum</Emphasis>

Two new flavonoid-C-glycosides named triticuside A (1a) and triticuside B (1b) were isolated from bran of Triticum aestivum L. The structures of the two new compounds were elucidated by spectral techniques including ¹H NMR, ¹³C NMR as well as HSQC, HMBC, and COSY. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 135–137, March–April, 2008.     

A novel sesquiterpenoid from <Emphasis Type="Italic">Ecdysanthera rosea</Emphasis>

A novel sesquiterpenoid was isolated from the whole plant of Ecdysanthera rosea Hook. et Arn. Its structure was elucidated as tricyclo[5,3,1,0^2,4]-3-aldehyde-3,11-dimethyl-8-methanoic acid on the basis of spectral evidence (1D and 2D NMR) and was named ecdysanthblic acid. Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 245–246, May–June, 2008.     

A new compound: Xyloketal H from mangrove fungus <Emphasis Type="Italic">Xylaria</Emphasis> sp. from the South China Sea coast

A new metabolite xyloketal H (1), was isolated from mangrove fungus Xylaria sp. (No.2508) obtained from the South China Sea. By spectroscopic analyses, primarily 2D NMR methods and X-ray diffraction experiments, its structure was elucidated. Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 5–6, January–February, 2008.     

A new iridoid glucoside from <Emphasis Type="Italic">Lamiophlomis rotata</Emphasis>

A new iridoid glucoside and seven known compounds were isolated from the herb of Lamiophlomis rotata (Benth.) Kudo, which is a Tibetan folk medicine. The structure of the new iridoid glucoside was elucidated by spectroscopic methods. The others were lamiophlomiol A, shanzhigenin methyl ester, loganin, 8-O-acetyl-shanzhiside methyl ester, schismoside, phlomiol, and 7,8-dehydropenstemoside. Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 306–307, May–June, 2009.     

Antioxidant flavonoids from <Emphasis Type="Italic">Tamus communis</Emphasis> ssp. <Emphasis Type="Italic">cretica</Emphasis>

A new flavonoid, kaempferol-3,4′-di-O-α-L-rhamnopyranoside (1), and three known flavonoids (2–4) were isolated from the aerial parts of T. communis L. The structure of the new compound was elucidated on the basis of spectroscopic data. Compounds 1 and 2 showed significant antioxidant activity (IC₅₀ 187.151 ± 0.821 μM, and 92.079±0.513 μM, respectively), whereas compounds 3 and 4 showed moderate activity in DPPH free radical scavenging assays. Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 295–297, May–June, 2009.     

Determination of iridoid glycosides in larvae and adults of butterfly<Emphasis Type="Italic"> Melitaea cinxia</Emphasis> by partial filling micellar electrokinetic capillary chromatography—electrospray ionisation mass spectrometry

The iridoid glycosides, methyl catalpol, asperuloside, verbenalin, cinnamoyl catalpol, catalpol and aucubin, were studied from both larvae and adults of butterfly Melitaea cinxia. Special emphasis in the study was put on finding a correlation between the iridoid glycoside content in butterflies and plants. An optimised partial filling micellar electrokinetic capillary chromatographic–electrospray ionisation mass spectrometric (PF-MECC-ESI-MS) method was employed for the separation and identification of the six iridoid glycosides. In this work, the isolation and determination of catalpol and aucubin from extracts of both larvae and adults of Melitaea cinxia butterflies is demonstrated. The PF-MECC-ESI-MS method, using the [M+Na]+, [M+Li]+ and/or [M+NH₄]+ adducts in ESI-MS, was used for quantification of aucubin and catalpol in the insects. In addition, the identification of all analytes was attempted by direct infusion MS/MS analysis. LOQ values for the iridoid glycosides varied between 10 mg/l (for verbenalin) to 50 mg/l (for catalpol and aucubin) corresponding to 0.1% of the sample´s dry mass. A correlation was noticed between the concentrations of iridoid glycosides in plants and the concentrations in larvae feeding on them.     

Configuration and conformation of taibaihenryiin T isolated from <Emphasis Type="Italic">Phlomis umbrosa</Emphasis>

Taibaihenryiin T was isolated for the first time from Phlomis umbrosa Turcz, and its structure was elucidated on the basis of IR and NMR spectra analysis. Its molecular configuration, conformation, and crystal structure were also characterized by X-ray structure analysis. The infrequency of the C–O–O–C group is manifested in this molecular configuration, and hydrogen bonding assembles the molecules into a three-dimensional networking structure in the crystal.     

Components of the heartwood of <Emphasis Type="Italic">Populus euphratica</Emphasis> from an ancient tomb

To probe the organic constituents of over 2000-year-preserved Populus euphratica found in an ancient tomb, a chemical investigation was undertaken, which led to the isolation of a new compound, 2-(4′-hydroxy-3′-methoxyphenyl)-2-oxoacetamide (1), together with 12 known compounds (2–13) by column chromatography. Their structures were elucidated on the basis of spectroscopic evidence. It is the first time that compounds 2–13 were isolated from this plant. Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 7–9, January–February, 2008.     

A furostanol saponin and phytoecdysteroid from roots of <Emphasis Type="Italic">Helleborus orientalis</Emphasis>

A furostanol saponin mixture and a known phytoecdysteroid were isolated from the roots of Helleborus orientalis Lam. Their structures were established as 26-[(β-D-glucopyranosyl)oxy]-22α-hidroxyfurosta-5,25(27)-dien-1β,3β,11α-triol (1a), 26-[(β-D-glucopyranosyl)oxy]-22α-methoxyfurosta-5,25(27)-dien-1β,3β,11α-triol (1b), and 20-hydroxy-β-ecdyson-3-O-β-D-glycoside (2). Acid hydrolysis of 1a,b gave (1β,3β,11α,22α)-22,26-dimethoxyfurosta-5,25(27)-dien-1,3,11-triol (aglycone 1) and of 2 gave 20-hydroxy-β-ecdyson (aglycone 2). Their structures were elucidated by spectral analysis. Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 75–77, January–February, 2007.     

Crystal structure of hinokiol isolated from <Emphasis Type="Italic">Isodon henryi</Emphasis>

Hinokiol was isolated for the first time from Isodon henryi and the structure was elucidated on the basis of IR and NMR spectra analysis. Its molecular configuration, conformation, and crystal structure were also characterized by X-ray structure analysis. The infrequent H-π stacking and hydrogen bonding assemble the molecules of hinokiol into a three-dimensional network structure. Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 229–230, May–June, 2007.     

Brugnanin,a new syn-2,3-dihydrobenzofuran neolignan dioate from the mangrove <Emphasis Type="Italic">Bruguiera gymnorrhiza</Emphasis>

Brugnanin (1), a neolignan dioate, was isolated from a mangrove plant Bruguiera gymnorrhiza. Based on spectroscopic interpretation of MS, IR, and NMR data, 1 was elucidated as (7R*,8S*,E)-3-hydroxy-5,5′-dimethoxy-7-O-4′,8-3′-neolignan-7′-ene-9,9′-dioic acid dioctadecyl ester. MTT assay showed that 1 had weak inhibitory activity against growth of CNE-1 nasopharyngeal carcinoma cell line. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 147–149, March–April, 2008.     

Chemical Constituents of Brown Rice Grain (<Emphasis Type="Italic">Oryza sativa</Emphasis>)

One new compound 3,7,11,15,19-pentamethyl-9α,10α,11α,17α,18α-pentahydroxy-n-tetracosan-1-oxy-p-hydroxycaffeoate (oryzaterpenyl caffeoate) (1), together with three known fatty acids linoleic acid, stearic acid and myristic acid were isolated and identified from the rice grain of Oryza sativa. The structure of the new compound was elucidated by 1D and 2D NMR spectroscopic techniques (¹H-¹HCOSY, ¹H-¹³C HETCOR) aided by EI-MS, and IR spectra. __________ Published in Khimiya Prirodnykh Soedinenii, No. 6, pp. 535–537, November–December, 2005.     

A novel compound from <Emphasis Type="Italic">Flos carthami</Emphasis> and its bioactivity

A novel compound, 4-{1′-hydroxy-1′-mercapto-1′-[1′′-2′′(N→O)-isoquinolyl]}yl-1-benzoic acid (1), together with six known compounds, 6-hydroxykaempferol-3-O-β-D-glucopyranoside (2), rutin (3), quercetin-3-O-β-D-glucopyranoside (4), kaempferol-3-O-β-D-glucopyranoside (5), cartormin (6), hydroxysafflor yellow A (7), were isolated by chromatography from the n-BuOH fraction of 50% ethanol extraction of Flos carthami. Their structures were elucidated on the basis of spectral analysis and comparison with published data. Among them, compound 1 was shown to possess a weak protective effect against cerebral ischemic damage in rats. Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 339–341, May–June, 2009.     

Chemical Components of <Emphasis Type="Italic">Leptopus chinensis</Emphasis>

Six substances were isolated from the branches and leaves of the Chinese herb Leptopus Chinensis (Bunge) Pojark. by column chromatography for the first time. Their structures were elucidated as 3α-hydroxyfriedelan-2-one, saccharose, triacontanol, friedelane-2α,3β-diols, β-sitosterol-3-O-β-D-glucoside, and β -sitosterol on the basis of x-ray, chemical, and spectroscopic methods. __________ Published in Kimiya Prirodnikh Soedinenii, No. 5, pp. 462–464, September–October, 2005.     

Malloapeltic acid,a new benzopyran derivative from <Emphasis Type="Italic">Mallotus apelta</Emphasis>

A new benzopyran derivative, malloapeltic acid (1), along with seven known compounds, was isolated from the roots of Mallotus apelta. The structure of the new compound 1 was elucidated by spectroscopic data analysis. The known compounds 2–8 were identified by comparison of their spectroscopic data with reported values in the literature. Compound 1 showed strong anti-HIV activity in vitro.     

Furofuran lignans from the bark of <Emphasis Type="Italic">Magnolia kobus</Emphasis>

A new furofuran lignan (1) along with four knownones (2-5) were isolated from the bark of Magnolia kobus. Their structures were elucidated as (+)-2α-(3’,4’-dimethoxyphenyl)-6α-(3″-hydroxy-4″,5″-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (1), (+)-sesamin (2), (+)-yangambin (3), (+)-kobusin (4), and (+)-eudesmin (5) on the basis of their comprehensive spectroscopic analysis, including 2D NMR, and by comparison of their spectral data with those of related compounds. Published in Khimiya Prirodnykh Soedinenii, No. 4, pp. 338–341, July–August, 2008.     

Bromination of 9-dimedonyltetrahydroxanthenone as a route to a new type of substituted hydrochromeno[2,3,4-<Emphasis Type="Italic">kl</Emphasis>]xanthenones

Bromination of 9-dimedonyl-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one was carried out to provide a route to a new series of substituted hydrochromeno[2,3,4-kl]xanthenones, which may find application for the synthesis of poorly accessible compounds including the heteroanalogs. A dependence of transformations of dimedonyltetrahydroxanthenone on the nature of the solvent was elucidated: bromination at the α-methylene groups of the dimedonyl substituent is accompanied by heterocyclization involving 1-and 5-oxo groups. Quantum chemical HF/6-311(d,p) ab initio calculations for the proposed mechanism of hemiacetalization and halogenation were carried out. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2191–2194, November, 2007.