Two new benzoyl esters of glucose from Lagotis yunnanensis

Two new benzoyl esters of glucose 1-O-(E)-4′-methoxybenzoyl-β-D-glucopyranose (1) and 1-O-(E)-4′-methoxybenzoyl-β-D-gluconic acid (2) were isolated from Lagotis yunnanensis, together with six previously known iridoid glucosides. The structures of these compounds were elucidated on the basis of spectral analysis, including 2D NMR spectroscopy. Published in Khimiya Prirodnykh Soedinenii, No. 6, pp. 529–530, November–December, 2006.     

Isoflavone glycosides from the bark of Amorpha fruticosa

Four known isoflavone glucosides have been isolated from the bark of Amorpha fruticosa, which is a traditional remedy plant, for the first time. They were elucidated as 3′-hydroxy-4′-methoxyisoflavone-7-O-β-D-glucopyranoside (1), 4′,6-dimethoxyisoflavone-7-O-β-D-glucopyranoside (2), 4′-methoxyisoflavone-7-O-β-D-glucopyranoside (3), and 3′,5-dihydroxy-4′-methoxyisoflavone-7-O-β-D-glucopyranoside (4), based on the UV, FT-IR, EIMS, FABMS, HREIMS, and NMR (¹H and ¹³C, DEPT, COSY, NOESY, HMQC, and HMBC) data. Published in Khimiya Prirodnykh Soedinenii, No. 4, pp. 336–338, July–August, 2006.     

Balanoinvolin,a new steroid derivative from <Emphasis Type="Italic">Balanophora involucrate</Emphasis>

A new compound, β-sitosterylglucoside-3′-O-linoleate, named balanoinvolin, and three known compounds coniferin, methylconiferin, and 4-O-β-D-glucopyranosylconiferyl aldehyde, were isolated from Balanophora involucrate Hook. f. and their structures were determined by MS and 1D/2D NMR spectra. Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 315–317, May–June, 2009.     

A new stilbene glycoside from the <Emphasis Type="Italic">n</Emphasis>-butanol fraction of <Emphasis Type="Italic">Veratrum dahuricum</Emphasis>

A new stilbene glycoside, 5-methylresveratrol-3,4′-O-β-D-diglucopyranoside (1), was isolated from the n-butanol fraction of the rhizomes of Veratrum dahuricum, together with five known stilbenoids: resveratrol-3-O-β-D-glycoside (2), 4′-methylresveratrol-3-O-β-D-glycoside (3), oxyresveratrol-4′-O-β-D-glycoside (4), oxyresveratrol-3-O-β-D-glycoside (5), and oxyresveratrol-3,4′-O-β-D-diglycoside (6), and found for the first time in the investigated plant. The structures of six isolates were identified on the basis of 1D and 2D NMR data. Compounds 1–6 showed platelet aggregation inhibition, and compound 1 had an IC₅₀ value of 383.6 μM against platelet aggregation induced by AA. Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 279–282, May–June, 2009.     

Cardiac glycosides from Strophanthus kombe

Twelve cardiac glycosides and aglycons were isolated from Strophanthus kombe seeds. Of these, eight were identified as cymarin, K-strophanthin-β, K-strophanthoside, periplocymarin, 17α-strophadogenin, erysimin (= helveticoside), erysimoside, and neoglucoerysimoside. Four glycosides, preliminarily designated Sk-x, Sk-y, Sk-z, and Sk-20, were new. Their chemical structures were established as 3β-O-β-D-glucopyranosyl-5β,14β,16β-trihydroxy-19-oxo-17α-card-20(22)enolide (17α-strophadogenin-3-O-β-D-glucoside), 3β-O-β-D-cymaropyranosyl-5β,14β,16β-trihydroxy-19-oxo-17α-card-20(22)enolide (17α-strophadogenin-3-O-β-D-cymaroside), 3β-O-β-D-cymaropyranosyl-4′-O-β-D-glucopyranosyl-6″-O-β-D-glucopyranosyl-5β, 14β,16β-trihydroxy-19-oxo-17α-card-20(22)enolide (17α-strophadogenin-3-O-strophanthotrioside), and 3-O-β-D-digitoxopyranosyl-4′-O-β-D-glucopyranosyl-6″-O-β-D-glucopyranosyl-5β,14β, 19-trihydroxy-card-20(22)enolide (strophanthidol-3-O-gentiobiosyldigitoxoside), respectively. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 156–159, March–April, 2006.     

A 2-phenoxychromone from Artemisia rupestris

A 2-phenoxychromone, 6-demethoxy-4′-O-methylcapillarisin, was isolated from Artemisia rupestris L. The structure of this compound was established by analysis of the spectroscopic data. A single-crystal diffraction analysis was performed in order to confirm the proposed structure. Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 14–15, January–February, 2006.     

New glycosidic and other constituents from hulls of <Emphasis Type="Italic">Oryza sativa</Emphasis>

Three new compounds, 4-hydroxymethylene-7-(9,9,13-trimethylcyclohexyl)-heptanyl-3′,7′,7′-trimethylcyclohexa-2′,4′-dien-1′-oate (1), 1-(n-hexadec-7-enoxy)-6-(n-octadecanoxy)-β-D-glucopyranoside (2), and (Z)-12-hydroxy-9-octadecenoic acid-12-β-D-glucopyranoside (3), along with the known compound hexacosanoic acid (4), were isolated and identified from the rice hulls of Oryza sativa. Their structures were elucidated by 1D and 2D NMR spectroscopic techniques (¹H-¹H COSY, ¹H-¹³C HETCOR, DEPT) aided by EIMS, FABMS, HRFABMS, and IR spectra. Published in Khimiya Prirodnykh Soedinenii, No. 4, pp. 344–347, July–August, 2007.     

Phenylethanoid glycosides from the bark of <Emphasis Type="Italic">Fraxinus mandschurica</Emphasis>

The new phenylethanoid glycoside calceolarioside A-2′-α-L-rhamnopyranoside and calceolarioside A and calceolarioside B were isolated from the bark of Fraxinus mandschurica Rupr. for the first time by column chromatography. Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 283–284, May–June, 2009.     

Flavonoids from the aerial part of <Emphasis Type="Italic">Vicia subvillosa</Emphasis>

The new flavone glucoside viscioside, luteolin-4′-O-β-D-galactopyranoside, in addition to the known flavonoids apigenin, luteolin, quercetin, cinaroside, luteolin-4′-O-β-D-glucoside, and isoquercitrin were isolated from the aerial part of Vicia subvillosa. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 30–31, January–February, 2007.     

Hydrolysis of 7,7-Substituted Derivatives of 3-tert-Butyl-3,4-dihydro-2H-thiazolo-[3,2-a][1,3,5]triazin-6(7H)-one

Alkaline hydrolysis of 3-tert-butyl-7,7-bis(hydroxymethyl)-3,4-dihydro-2H-thiazolo[3,2-a][1,3,5]-triazin-6(7H)-one can occur in three directions: with cleavage of the tetrahydrotriazine ring, with cleavage of the thiazolidine ring, and also with opening of both rings. Depending on the process conditions, either the hydrolysis product corresponding to the first direction or the hydrolytic decomposition products corresponding to the second and third directions can be obtained in preparative quantities. Hydrolysis of 3,3′-di-tert-butyl-3′,4′-dihydro-2′ H-spiro[(perhydro-1,3-oxazine)-5,7′-thiazolo[3,2-a][1,3,5]triazin]-6′-one in (NH₄)₂CO₃ solution occurs in two steps: in the first step, cleavage of the tetrahydrotriazine ring occurs; and in the second step, opening of the perhydrooxazine ring occurs. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1089–1097, July, 2005.     

Alkylation of salts ofN-(β-hydroxyalkyl)-N′-hydroxydiazeneN-oxides with alkyl halides and dimethyl sulfate

Salts ofN-(β-hydroxyalkyl)-N′-hydroxydiazeneN-oxides, RCH(OH)CH₂N(O)=NO⁻ M⁺ (R=Me, Prⁱ, or Bu^t; and M=Li, Na, K, Ag, NH₄, or Me₄N), were prepared. Their alkylation with alkyl halides R′X (X=Cl, Br, or I) and dimethyl sulfate was studied. Generally, alkylation afforded mixtures ofN-(β-hydroxyalkyl)-N′-alkoxydiazeneN-oxides RCH(OH)CH₂N(O)=NOR′ andO-alkyl-N-(β-hydroxyalkyl)-N-nitrosohydroxylamines RCH(OH)CH₂N(NO)OR′. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1996–2001, October, 1998.     

A new triterpene from the leaves of Craibiodendron yunnanense

A new triterpene, taraxast-20(30)-en-3β,12β-diol (1), and eight known compounds were isolated from the leaves of Craibiodendron yunnanense. Their structures were established on the basis of spectral evidence. Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 35–37, January–February, 2008.     

Two new isoflavonoid monogalactosides from <Emphasis Type="Italic">Trifolium pratense</Emphasis> roots

Formononetin and the new isoflavonoid glycosides formononetin-7-O-β-D-galactopyranoside and inermin-3-O-β-D-galactopyranoside were isolated from Trifolium pratense L. roots. The structures of the isolated compounds were proved using chemical transformations and UV, PMR, and ¹³C NMR spectra. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 21–23, January–February, 2008.     

Study on the Inclusion Compounds of Eugenol with α-, β-, γ- and Heptakis (2,6-di-O-methyl)-β-cyclodextrins

Several host–guest inclusion compounds of eugenol as a guest molecule and cyclodextrins (α-,β-,γ-CD) and heptakis (2,6-di-O-methyl)-β-cyclodextrin (DMβ-CD) as hosts were investigated in the solid state and in aqueous solution. The one-to-one solid inclusion compounds of eugenol and β-CD or γ-CD were prepared, but those of eugenol with α- or DMβ-CD were not obtained under the same condition. However, the UV-visible absorption spectroscopy data indicated that the liquid guest could form a 1:1 inclusion compound with all four hosts respectively in aqueous solution. The two solid inclusion compounds were characterized by powder X-ray diffraction (XRD), infrared spectroscopy (IR), thermogravimetric analysis (TG), differential scanning calorimetry (DSC) and nuclear magnetic resonance (NMR). The association constants (K), calculated from the modified Benesi–Hidebrand equation, of eugenol with α-, β-, γ- and DMβ-CD is 4.95 × 10⁴, 3.96 × 10⁵, 1.47 × 10⁵ and 9.33 × 10⁴ mol⁻¹ dm³, respectively.     

Study on spectroscopy of two flavonyl glycosides from Andrographis paniculata

To study the bioactive constituents from Andrographis paniculata, two compounds were isolated and purified by column chromatography on AB-8 macro-porous adsorption resin and polyamide. Their structures were determined by various spectroscopic methods, including UV, FABMS, ¹H-NMR, ¹³C-NMR, DQFCOSY, TOCSY, HMQC, HMBC, and NOESY. The ¹H-NMR and ¹³C-NMR signals of the two compounds were assigned. The structures of the two compounds were elucidated as 5,4′-dihydroxy-7-methoxyflavone-6-yl-β-D-glucopyranoside and 5,4′-dihydroxy-7-methoxyflavone-8-yl-β-Dglucopyranoside, respectively. __________ Translated from Acta Chimica Sinica, 2007, 65(14): 1399–1402 [译自: 化学学报]     

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.     

Investigations on 2,3′-biquinolines 22. Novel and convenient method for the synthesis of benzo[5,6]indolizino-[2,1-<Emphasis Type="Italic">b</Emphasis>]quinolinium-13-thiolates and benzo-[5,6]indolizino[1,2-<Emphasis Type="Italic">c</Emphasis>]quinoline-6(5H)-thiones

We have developed a method of synthesis of benzo[5,6]indolizino[2,1-b]quinolinium-13-thiolates and 5,6-dihydrobenzo[5,6]indolizino[1,2-c]quinoline-6-thiones based on the reaction of the corresponding 1′, 2′-dialkyl-1′,2′-dihydro-2,3′-biquinolines and 1′,4′-dialkyl-1′,4′-dihydro-2,3′-biquinolines with sulfur in DMF. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 849–851, June, 2007.     

Preparation of (2′-5′)-oligonucleotides based on 6-<Emphasis Type="Italic">N</Emphasis>-benzylaminopurineriboside using the <Emphasis Type="Italic">Spicaria violacea</Emphasis> fungal enzyme complex

A method for chemico-enzymatic synthesis of (2′-5′)-oligonucleotides with 6-N-benzylaminopurineriboside as the nucleoside units was proposed. The method consisted of enzymatic hydrolysis of the oligonucleotides with mixed (2′-5′)-(3′-5′)-phosphodiesterbonds that were prepared by polymerization of 6-N-benzyladenosine-2′(3′)-monophosphate by using (3′-5′)-specific nuclease and phosphatase contained in the filtrate of culture medium of the mycelial fungus Spicaria violacea. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 64–68, January–February, 2009.     

Phenolic compounds from Filipendula ulmaria

A chromatographically inseparable crystalline mixture of the previously undescribed quercetin-4′-O-β-galactopyranoside and the known quercetin-3-O-β-glucopyranoside (isoquercitrin) in a 7:5 ratio was isolated from the extract of the aerial part of Filipendula ulmaria (L.) Maxim. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 122–124, March–April, 2006.     

The behavior of <Emphasis Type="Italic">p</Emphasis>-bis{3-[N-(3-chloro-buten-2-yl)pyrrolidinio(piperidinio or morpholinio)]propyn-1-yl}benzene dichlorides in an aqueous base medium

In aqueous base medium p-bis{3-[N-(3-chlorobuten-2-yl)pyrrolidinio (piperidinio or morpholinio)]-propyn-1-yl}benzene dichlorides undergo a two-way dehydrochlorination-cyclization reaction to form benzo[5,6-a:5′,6′-c]bis(2,2-tetramethylene- or -2,2-pentamethylene-4-methylisoindolinium) and benzo-[5,6-a:5′,6′-c]bisspiro(4-methylisoindoline-2,4′-morpholinium) dichlorides. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 546–549, April, 2009.