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.     

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.     

A new alloside from <Emphasis Type="Italic">Neocheiropteris palmatopedata</Emphasis>

A new compound, 2,4,6-trihydroxybenzoic acid 4-O-β-D-allopyranoside (1), together with four known compounds, sucrose (2), fructose (3), ecdysterone (4), and β-sitosterol (5) was isolated from the roots of Neocheiropteris palmatopedata (Baker) Christ. The new compound was identified based on extensive spectroscopic studies including HR-ESI-MS, FAB-MS, ¹H NMR, ¹³C NMR, DEPT, ¹H–¹H COSY, HSQC, HMBC, and NOESY spectra, and the known compounds were identified by their spectroscopic data analysis, comparison with reports in the literature, and co-chromatography with authentic standards. Compounds 2, 3, and 5 were obtained from the Neocheiropteris genus for the first time, and 4 was originally isolated from the plant.     

Alkaloids ofCorydalis stricta

The alkaloids of the epigeal part and roots ofCorydalis stricta have been studied. Of the 23 alkaloids isolated, N-methylcorypalline proved to be new, and its structure has been determined. Stilopine hydroxymethylate and pycnarrhine have been isolated from the genusCorydalis for the first time, and cheilanthiofoline isocorypalmine, scoulerine, isoboldine, reticuline, N-methylcoclaurine, coreximine, juziphine, pancorydine, corypalline, wilsonirine, stilopine, adlumidine, dihydrosanguinarine, adlumine, and bicucculine have been isolated from this species of plant for the first time.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 490–493, July–August, 1983.     

Furostanol Glycosides from leaves of the Chinese plant <Emphasis Type="Italic">Tribulus terrestris</Emphasis>

The structures of five furostanol glycosides (1–5), of which the 26-O-β-D-glucopyranosyl-(25S),5α-furost20(22)-en-12-one-2α,3β,26-triol-3-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (1) was new, from the leaves of Tribulus terrestris L. were established using chemical and NMR spectroscopic methods.     

Two novel phenolic compounds from <Emphasis Type="Italic">Stenoloma chusanum</Emphasis> and their antifungal activity

Two new phenolic compounds, 4-O-β-D-(6-O-gentisoylglucopyranosyl) vanillic acid (1), 2-O-β-D-(6-O-gentisoylglucopyranosyl) gentisic acid (2), together with three known compounds, vanillic acid (3), syringic acid (4), and gentisic acid (5), were isolated from the whole part of Stenoloma chusanum (L.) Ching. Structures of the two new compounds 1, 2 were elucidated on the basis of spectroscopic methods, including twodimensional NMR techniques and HR ESI-MS analysis. The compounds′ activities against Candida albicans, Cryptococcus neoformans, Trichophyton rubrum, Trichophyton mentagrophytes, Microsporum canis, Epidermophyton floccosum, and Aspergillus niger were determined, and the minimal inhibitory concentrations (MIC) were 25–100 μg/mL. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 161–164, March–April, 2009.     

Synthesis of diblock copolymers with cellulose derivatives. 3. Cellulose derivatives carrying a single pyrene group at the reducing-end and fluorescent studies of their self-assembly systems in aqueous NaOH solutions

Novel cellobiose and cellulose (DP _n =ca. 30) derivatives, N-(1-pyrenebutyloyl)-4-O-(β-d-glucopyranosyl)-β-d-glucopyranosylamine (6), N-(15-(1-pyrenebutyloylamino)-pentadecanoyl)-4-O-(β-d-glucopyranosyl)-β-d-glucopyranosylamine (7), N-(1-pyrenebutyloyl)-β-cellulosylamine (13), N-(15-(1-pyrenebutyloylamino)-pentadecanoyl)-β-cellulosylamine (14) carrying a pyrene group as a single fluorescent probe at the reducing end, were prepared in order to investigate their self-assembly systems in solutions. The relative intensity of the excimer emission at ca. 480 nm due to dimerized pyrenes (intensity I _E) to the monomer emission at ca. 380 nm due to isolated pyrene (intensity I _M), i.e., I _E/I _M, was monitored in various solutions. In water/dimethyl sulfoxide (DMSO) mixed solvent (0–98%, v/v), the ratio I _E/I _M remained low (0.04) for compound 6 over the range of water concentrations, indicating that pyrenes at C-1 position of compound 6 were diffused. On the other hand, the ratio I _E/I _M increased (0.04–4.96) for compound 7 with the increase in water concentration, indicating that pyrenes at C-1 position were associated. In aqueous NaOH solutions (4.4–17.5%, w/w), compound 14 showed a large increase in the ratio I _E/I _M (0.84–8.14) with the increase in NaOH concentration, compared to compound 13 (0.06–0.41). It was found that the association of hydrophobic groups at the reducing-end of cellulose could be controlled by the hydrophilic–hydrophobic balance of compounds and the solvent polarity.     

A new triterpene glycoside from <Emphasis Type="Italic">Premna microphylla</Emphasis>

A new triterpene glycoside, namely 28-O-α-L-rhamnopyranosyl (1→2)-β-D-glucopyranoside tormentic acid ester, was isolated from the leaves of Premna microphylla, together with two known triterpenes, i.e., arjunolic acid (2) and hyptatic acid A (3). Its structure was established by mass-spectrometric and spectroscopic methods, especially 2D NMR techniques. This is the first report of the isolation of triterpenes from this plant. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 173–174, March–April, 2009.     

A new ceramide from the root of <Emphasis Type="Italic">Isatis Indigotica</Emphasis> and its cytotoxic activity

In addition to two ceramides 1-O-β-D-glucopyranosyl-(2S,3R)-N-(2'-hydroxyhexadecanoyl)-octadeca-4E,8Esphingenine (2) and (2S,3S,4R)-N-(2'-hydroxytetracosanoyl)-octadecasphingenine (3), which separated for the first time, a new ceramide 1-O-β-D-glucopyranosyl-(2S,3R)-N-(2'-hydroxyhexacosanoyl)octadecasphingenine (1) was isolated from the traditional Chinese medicinal herb Isatis indigotica. Their cytotoxic effects were evaluated by the MTT method.     

Isoquinoline alkaloids from <Emphasis Type="Italic">Broussonetia papyrifera</Emphasis> fruits

A new isoquinoline alkaloid, named broussonpapyrine (1), along with three other known isoquinoline alkaloids, namely nitidine (2), oxyavicine (3), and liriodenine (4), were isolated from Broussonetia papyrifera fruits. The structures of these compounds were determined by 1D and 2D NMR, MS techniques, and chemical methods. This is the first report of the isoquinoline alkaloids isolated from this plant. Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 83–84, January–February, 2007.     

New triterpenoid glycosides fromThalictrum minus L.

Two triterpenoid diglycosides of the cycloartane series were isolated from the terrestrial part ofThalictrum minus L. (Ranunculaceae). Genins of these glycosides are side-chain structural isomers—3-O-β-d-galactopyranosyl-29-O-β-d-glucopyranosyl-9β, 19-cyclo-20(S)-lanost-24(Z)-ene-3β, 16β, 22(S), 26, 29-pentaol and 3-O-β-d-galactopyranosyl-29-O-β-d-glucopyranosyl-9β, 19-cyclo-20(S)-lanost-25-ene-3β, 16β,22(S), 24ζ, 29-pentaol. The structures of these glycosides were established using 1D and 2D NMR spectroscopy and FAB mass spectrometry. For Part 9, see Ref. 1. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1434–1437, July, 1998.     

A new flavanone glycoside from <Emphasis Type="Italic">Clausena pentaphylla</Emphasis>

From the ethyl acetate extract of the roots of Clausena pentaphylla, a flavanone glycoside, 5,7-dihydroxy3',4'-dimethoxyflavanone 6-C-[α-rhamnopyranosyl-(1 → 6)]-β-glucopyranoside (1), was isolated. The isolated compound was characterized by UV, IR, and NMR (¹H, ¹³C) studies.     

New alkaloids from <Emphasis Type="Italic">Casimiroa edulis</Emphasis> fruits and their pharmacological activity

The extract of Casimiroa edulis was investigated for antihypertensive activity. The ethanol and total alkaloids (in chloroform) extracts were found to have antihypertensive properties at doses of 500 and 200 mg/kg, respectively. Four quinolinone alkaloids were isolated and identified as: 2-(2′-hydroxy-4′-methoxyphenyl)-5,8-dimethoxy-3-propyl-1H-quinolin-4-one (1), 5,8-dimethoxy-2-(3′-methoxyphenyl)-3-propyl-1H-quinolin-4-one (2), 5,8-dimethoxy-2-(3′,4′-dimethoxyphenyl)-3-propyl-1H-quinolin-4-one (3), and 5,6-dimethoxy-2-(2′,5′,6′-trimethoxyphenyl)-1H-quinolin-4-one (4). Interestingly, compounds 1, 2, and 3 were found to be new alkaloids. The four isolated alkaloids showed antihypertensive activity at doses of 50, 100, 200, and 300 mg/kg, respectively. Published in Khimiya Prirodnykh Soedinenii, No. 5, pp. 473–476, September–October, 2007.     

Alkaloids ofDicentra

Methanolic extraction ofDicentra spectabilis L., collected in the flowering period in the botanical garden of Pyatigorsk Pharmaceutical Institute, has yielded 0.17% of combined alkaloids from the epigeal part and 0.25% from the roots. By the separation of these materials, dihydrosanguinarine, sanguinarine, scoulerine, cheilanthifoline, corydine, and protopine have been obtained.Dicentra peregrina Rudolph, collected in the flowering period on the island of Sakhalin, has yielded 1.8% of combined alkaloids from the epigeal part and 1.51% from the roots. From these combined materials have been isolated isocorydine, corydine, dicentrine, protopine, dihydrosanguinarine, sanguinarine, cheilanthifoline, bicuculline, lederine, scoulerine, isoboldine, predicentrine, reticuline, and allocryptopine.Institute of the Chemistry of Plant Substances. Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 79–81, January–February, 1984.     

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.     

A new alkaloid from Lysimachia patungensis

A new pyridine alkaloid and six known compounds were isolated from the whole plant of Lysimachia patungensis Hand.-Mazz. The structure of the new alkaloid, named patungensin, was characterized as (17R, E)-2-hydroxy-4,6-dimethoxy-17-acetoxy-cyclopentadeca-1, 3-diene[1,2-b]pyridine, and the six known compounds were identified as octacosanoic acid (1), palmic acid (2), stigmasterol (3), ardisiacrispin A (5), isorhamnetin 3-β-D-galactopyranoside (6), and isorhamnetin 3-robinobioside (7), respectively. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 141–142, March–April, 2007.     

Triterpene Glycosides from <Emphasis Type="Italic">Cussonia paniculata</Emphasis>. II. Acetylated Glycosides from Leaves

Structures of 13 new acetylated triterpene glycosides from leaves of Cussonia paniculata (Araliaceae) were established as 28-O-(2-O-acetyl- and 3-O-acetyl-α-L-rhamnopyranosyl)-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β -D-glucopyranosides of 23-hydroxybetulinic acid (1a and 1b) and hederagenin (2a and 2b), 3-O-α-L-arabinopyranosyl-28-O-(2-O-acetyl- and 3-O-acetyl-a-L-rhamnopyranosyl)-(1→ 4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glycopyranosides of oleanic (3a and 3b) and ursolic (3c and 3d) acids, 3-O-α-L-arabinopyranosyl-28-O-(4-O-acetyl-, 2-O-acetyl-, and 3-O-acetyl-α-L-rhamnopyranosyl)-(1→4)-O-β-D-glucopyranosyl-(1→ 6)-O-β-D-glucopyranosides of hederagenin (4, d5a and 5b), and 3-O-β-D-glucopyranosyl-(1→2)-O-α-L-arabinopyranosyl-28-O-(2-O-acetyl- and 3-O-acetyl-α-L-rhamnopyranosyl)-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D- glucopyranosides of oleanic acid (6a and 6b). The structures of the compounds were established using chemical methods and NMR spectroscopy. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 351–356, July–August, 2005.     

Ellagic acid glycosides from the stem bark of <Emphasis Type="Italic">Aphananthe aspera</Emphasis>

Five ellagic acid glycosides were isolated from Aphananthe aspera and their structures were identified as 3-O-methylellagic acid-4′-O-α-L-rhamnopyranoside (1), 3-O-methylellagic acid-4′-O-β-D-xylopyranoside (2), 3,3′-di-O-methylellagic acid-4′-O-β-D-xylopyranoside (3), 3,3′, 4-tri-O-methylellagic acid-4′-O-β-D-glucopyranoside (4), and 3,3′-di-O-methylellagic acid-4′-O-α-L-rhamnopyranoside (5) on the basis of spectroscopic analysis. Compound 1 is new, and all the compounds were isolated for the first time from the title plant. Published in Khimiya Prirodnykh Soedinenii, No. 5, pp. 458–459, September–October, 2007.     

New oligomeric proanthocyanidin glycosides platanoside-A and platanoside-B from <Emphasis Type="Italic">Platanus orientalis</Emphasis> trunk bark

Two new oligomeric proanthocyanidin glycosides were isolated from trunk bark of Platanus orientalis. Their structures and relative configurations were found to be 7-O-β-D-Glcp-(–)-epicatechin-(4β-8)-(–)-epicatechin(4β-8)-(–)-epicatechin-3-O-gallate (platanoside-A) and 7-O-β-D-Glc \textp\xrightarrow6 {\text{p}}\xrightarrow{6} galloyl-(+)-catechin-3-O-gallate(4α-8)-(–)-epicatechin-3-O-gallate-(4β-8)-(–)-epicatechin-3-O-gallate-(4β-8)-5-O-β-D-Glcp-(–)epicatechin-3-O-gallate (platanoside-B).     

Synthesis of 20S-protopanaxadiol 20-O-β-D-glucopyranoside, a metabolite of Panax ginseng glycosides, and compounds related to it

A preparative semi-synthetic method was developed to prepare 20S-protopanaxadiol 20-O-β-Dglucopyranoside (1), a metabolite of Panax ginseng glycosides. The 20-O-•-D-glucopyranosides of 20S-hydroxydammar-24-en-3,12-dione, 3β,20S-dihydroxydammar-24-en-12-one, and 3β,12α, 20S-trihydroxydammar-24-ene were synthesized for the first time. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 364–369, July–August, 2006.