Three new phenanthrenone constituents from Trigonostemonlii

Three new phenanthrenone constituents, trigoxyphins U–W (1, 7 and 9), together with eight known ones, trigoxyphin M (2), 6,9-O-dimethyltrigonostemone (3), trigonstemone (4), thrigonosomone B (5), trigonochinene E (6), actephiiol A (8), epiactephilol A (10) and neoboutomannin (11), were obtained from the methanol extract of the leaves and stems of Trigonostemonlii. The structures of the new metabolites were elucidated by analysing the spectroscopic data (1D NMR, 2D NMR, HR-ESI-MS and IR). Compounds 1–6 were evaluated for their cytotoxic activities on five human tumour cell lines by using the MTT method, and compound 1 exhibited inhibitory activity against HL-60, SMMC-7721, A-549, MCF-7 and SW480 with IC₅₀ values ranging from 3.77 to 14.51 μM.     

Isolation of a new lycodine alkaloid from Lycopodium japonicum

A new lycodine alkaloid, N-methylhydroxypropyllycodine (1), was isolated from the club moss Lycopodium japonicum Thunb, together with five known compounds, N-methyllycodine (2), huperzinine (3), β-obscurine (4), α-obscurine (5) and des-N-methyl-α-obscurine (6). Their structures were elucidated by spectroscopic analyses, including 2D NMR techniques.     

A new sesquiterpene from Kalimeris integrifolia

A new sesquiterpene kalinturoside A (1), and 17 known compounds friedelan-3-ol (2), 24-ethyl-5a-cholesta-7, 22(E)-dien-3-one (3), friedelin (4), syringaresinol (5), α-spinasterol (6), ciwujiatone (7), syringic acid (8), scopoletin (9), apocynin (10), 1-(3-hydroxy-4, 5-dimethoxyphenyl)ethan-1-one (11), apigenin (12), 5-hydroxymethylfurfural (13), stigmasterol-3-O-β-d-glucopy-ranoside (14), bidenoside C (15), citrusin (16), irioresinol A (17) and syringaresinol-4-O-β-d-glucopyranoside (18) were isolated from the herbs of Kalimeris integrifolia. The structures of these compounds were elucidated using spectroscopic techniques such as NMR and MS. All of the compounds were isolated from this genus for the first time.     

Balanochalcone,a new chalcone from Balanophora laxiflora Hemsl.

A new chalcone named as balanochalcone (1) together with eight known compounds, methyl caffeate (2), β-hydroxydihydrochalcone (3), methyl gallate (4), dimethyl-6,9,10-trihydroxybenzo[kl]xanthene-1,2-dicarboxylate (5), p-coumaric acid (6), quercetin (7), scopoletin (8) and pinoresinol (9) have been isolated from the ethyl acetate extract of Vietnamese Balanophora laxiflora Hemsl. Their structures were characterised by IR, UV, HR-ESI-MS, 1D and 2D NMR and CD spectroscopies. Compounds 2 and 5 showed moderate cytotoxicity against four cancer cell lines, KB (a human epidermal carcinoma), MCF7 (human breast carcinoma), SK-LU-1 (human lung carcinoma) and HepG2 (hepatocellular carcinoma). In addition, compounds 1 and 5 showed moderate antioxidant activity.     

A new di-C-prenylated coumarin from Sophora interrupta

A new di-C-prenylated coumarin, 7-methoxy-6,8-bis-(2,3-dihydroxy-3-methylbutyl)-coumarin (1), together with seven known compounds, isopimpinellin (2), an arylbenzofuran (3), three flavonoids (4–6), (+)-maackianin (7) and echinoisoflavanone (8), were isolated from the leaves of Sophora interrupta Bedd. The structure of the new compound 1 as well as known compounds was elucidated by extensive 1D and 2D NMR spectral studies.     

A new arbutin derivative from the leaves of Vaccinium dunalianum wight

A new arbutin derivative, namely dunalianosides J (1), along with six known compounds, arbutin (2), robustaside A (3), 6′-O-caffeoylarbutin (4), dunalianoside D (5), kaempferol 3-O-β-D-glucopyranoside (6) and kaempferol 3-O-β-D-sambubioside (7) were isolated from the leaves of Vaccinium dunalianum Wight (Ericaceae). The structure of 1 was elucidated by extensive 1D and 2D NMR, HR-MS and CD spectroscopic analyses. In which, kaempferol 3-O-β-D-sambubioside (7) was isolated from the genus Vaccinium for the first time.     

A new coruleoellagic acid derivative from stems of Rhodamnia dumetorum

A new coruleoellagic acid derivative, 3,3′,4,4′,5′-pentamethylcoruleoellagic acid (1) together with nine known compounds, hexamethylcoruleoellagic acid (2), 3,4,3′-tri-O-methylellagic acid (3), heptaphylline (4), 7-methoxymukonal (5), dentatin (6), sinapaldehyde (7), gallic acid (8), 2,6-dimethoxy-4H-pyran-4-one (9) and β-sitosterol (10) were isolated from the stems of Rhodamnia dumetorum. Their structures were identified by physical and spectroscopic data (IR, 1D and 2D NMR, and MS). Compounds 1, 2 and 7-10 were tested for antibacterial activity against six pathogenic bacterial strains (Bacillus cereus, Escherichia coli, Pseudomonas aeruginosa, Salmonella enterica serovar Typhimurium, Staphylococcus aureus, and Methicillin resistant S. aureus (MRSA)).     

A new xanthone glycoside from Pyrrosia sheareri

A new xanthone glycoside, 3,5,7,8-tetramethoxyxanthone-1-O-β-D-glucopyranoside (1), along with five known compounds, mangiferin (2), kaempferol (3), quercetin (4), chlorogenic acid (5) and diploptene (6), was isolated from the whole plants of Pyrrosia sheareri (Bak.) Ching. The structure of compound 1 was established on the basis of extensive spectroscopic analyses and chemical methods.     

A new labdane diterpene from the rhizomes of Alpinia officinarum

A new labdane diterpene, (Z)-12,14-labdadien-15(16)-olide-17-oic acid (1), and a new natural cadinane sesquiterpene, 4-isopropyl-6-methyl-1-naphthalenemethanol (2), were isolated from the ethanolic extract of the rhizomes of Alpinia officinarum, together with three other products, galangin (3), kaempferol (4) and quercetin (5). Their structures were elucidated by using extensive spectroscopic methods. Compounds 1 and 2 showed no remarkable cytotoxic activity against HeLa and HepG2 cancer cell lines with IC₅₀>50 μg mL^? 1.     

A new oxo-sterol derivative from the rhizomes of Costus speciosus

Chemical investigation of the rhizomes of Costus speciosus led to the isolation of a new compound, 22-ketocholesteryl palmitate (1) along with four known compounds, 24-methylenecycloartanol (2), cycloartanol (3), stigmasterol (4) and linoleic acid (5). The structure of new compound was characterised by extensive 1D-, 2D-NMR and mass spectrometry (GC-MS and HR-ESI-MS) techniques.     

A new acylated triterpene with antimicrobial activity from the leaves of <Emphasis Type="Italic">Rauvolfia vomitoria</Emphasis>

A new acylated tritrepene, 3β-hexadecanoyloxy-lup-20(29)-en-21-ol (1), along with seven known compounds, lupeol (2), betulinic acid (3), ursonic acid (4), -sitosterol (5), β-stigmasterol (6), 3-O-β-D-glucopyranosyl-β-stigmasterol (7), and palmitic acid (8), were isolated from the leaves of Rauvolfia vomitoria (Apocynaceae). Their structures were established on the basis of spectroscopic analysis and chemical evidence. The new acylated triterpene exhibited interesting antimicrobial activity against Candida albicans (a yeast) with the MIC value 64 μg/mL.     

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.     

Pseudolycorine N-oxide,a new N-oxide from Narcissus tazetta

Abstract

A new N-oxide, Pseudolycorine N-oxide (1) was characterised along with eleven known alkaloids homolycorine (2), O-methylmaritidine (3), 8-O-demethylhomolycorine (4), homolycorine N-oxide (5), lycorine (6), narciclasine (7), pseudolycorine (8), ungeremine (9), 8-O-demethylmaritidine (10), zefbetaine (11) and lycorine N-oxide (12), from Narcissus tazetta. Their structures were established on the basis of spectroscopic data analysis. The extract, fractions and isolated compounds were screened for in vitro cytotoxicity against two human cancer cell lines, human cervical cancer (SiHa) and human epidermoid carcinoma (KB) cells. The study demonstrated the cytotoxic potential of extract and its chloroform and n-butanol fractions. Further, the results revealed the bioactive potential of narciclasine, pseudolycorine and homolycorine alkaloids. However, new N-oxide (1) was not active against these cell lines.     

Two new dammarane-type triterpene sapogenins from Chinese red ginseng

Two new dammarane-type triterpene sapogenins were isolated from the Chinese red ginseng. The new sapogenins were named as 24,26-dihydroxy-panaxdiol (1) and 24-hydroxy-panaxdiol (2). Their structures were elucidated by the combined analysis of NMR and mass spectrometry as 20(S),25(R)-epoxydammarane-3β,12β,24β,26-tetraol (1) and 20(S),25-epoxydammarane-3β,12β,24α-triol (2). The complete signal assignments of the two compounds were carried out by 2D NMR spectral and NOE differential spectroscopy analysis.     

A new 9,10-dihydrophenanthrene from Dendrobium moniliforme

A new 9,10-dihydrophenanthrene,1,5-dihydroxy-3,4,7-trimethoxy-9,10-dihydrophenanthrene (1) was isolated and identified from the whole plants of Dendrobium moniliforme, as well as 24 known compounds including hircinol (2), (2R^*,3S^*)-3-hydroxymethyl-9-methoxy-2-(4′-hydroxy-3′,5′-dimethoxyphenyl)-2,3,6,7-tetrahydro-phenanthro[4,3-b]furan-5,11-diol (3), diospyrosin (4), aloifol I (5), moscatilin (6), 3,4′-dihydroxy-3′,4,5-trimethoxybibenzyl (7), gigantol (8), 3,3′-dihydroxy-4,5-dimethoxybibenzyl (9), longicornuol A (10), N-trans-cinnamoyltyramine (11), paprazine (12), N-trans-feruloyl 3′-O-methyldopamine (13), moupinamide (14), dihydroconiferyl dihydro-p-coumarate (15), dihydrosinapyl dihydro-p-coumarate (16), 3-isopropyl-5-acetoxycyclohexene-2-one-1 (17), p-hydroxybenzaldehyde (18), vanillin (19), p-hydroxyphenylpropionic acid (20), vanillic acid (21), protocatechuic acid (22), (+)-syringaresinol (23), β-sitosterol (24) and daucosterol (25). Compounds 3, 4, 13, 16, 17 and 20 were isolated from the Dendrobium genus for the first time, and compounds 2, 5, 7, 9–12, 14, 15, 18, 21 and 22 were originally obtained from D. moniliforme.     

Two new monoterpenoid indole alkaloids from Alstonia rostrata

Two new indole alkaloids, winphyllines A (1) and B (4), along with four known alkaloids, N_b-demethylechitamine (2), 17-O-acetylnorechitamine (3), 12-methoxyechitamidine (5), and N(4)-demethylastogustine (6), were isolated from the methanol extract of the twigs of Alstonia rostrata. The structures of 1 and 4 were elucidated by means of HRMS and NMR spectroscopic methods. The in vitro cytotoxic activity of the isolated alkaloids against several human cancer cell lines was evaluated.     

A new naphthoquinone and a new neolignan from <Emphasis Type="Italic">Ligularia vellerea</Emphasis> rhizomes

In the course of phytochemical investigations of Ligularia vellerea rhizomes, a new naphthoquinone, 2,5-dihydroxy-6,7-dimethylnaphthoquinone (1), and a new neolignan, 4-[(3',4'-dihydroxycinnamoyl)-oxy]methyl cinnamate (2), have been isolated and characterized on the basis of spectroscopic methods (¹H NMR, ¹³C NMR, 2D NMR, and MS).     

A new flavonoid from Cudrania cochinchinensis

Chemical investigation of the ethanol extract of the roots of Cudrania cochinchinensis led to the isolation of a new flavonoid, (6S,12S,13R)-1-methoxy cyanomaclurin (1), together with seven known compounds, 1,3,5-trihydroxy-4-(3′-hydroxy-3′-methylbutyl)xanthone (2), 1,3,6-trihydroxy-4-prenylxanthone (3), 1,3,6,7-tetrahydroxyxanthone (4), 1,3,5,6-tetrahydroxyxanthone (5), 1,3,6-trihydroxy-5-methoxyxanthone (6), resveratrol (7) and oxyresveratrol (8). The structure of compound 1 was elucidated on the basis of 1D and 2D NMR spectra and the HR-ESI-MS data. The absolute stereochemistry was deduced via Rh₂(OCOCF₃)₄-induced CD and NOESY spectra.     

Two new labdane diterpenoids from the rhizomes of Isodon yuennanensis

Two new labdane diterpenoids, s-trans-8(17),12E,14-labdatrien-20-oic acid (1), s-trans-12E,14-labdadien-20,8β-olide (2), along with 10 known compounds, hinokiol (3), ursonic acid (4), 2α,3α-dihydroxyolean-12-en-28-oic acid (5), 2α,3β,23-trihydroxyolean-12-en-28-oic acid (6), ethyl 3-(3,4-dihydroxyphenyl)lactate (7), ethyl rosmarinate (8), (Z,E)-2-(3,4-dihydroxyphenyl)ethenyl caffeic ester (9), tridecanoic acid (10), β-sitosterol (11) and daucosterol (12), were isolated from the 70% acetone extract of the rhizomes of Isodon yuennanensis. Their structures were elucidated based on the analyses of extensive spectroscopic data and physicochemical properties.     

A new proline-containing flavonol glycoside from Caragana leucophloea Pojark

One new proline-containing flavonol glycoside, namely kaempferol-3-O-methyl-7-O-β-d-glucopyranosyl-8-(1-methyleneproline)-4′-O-β-d-glucopyranoside (1), together with 15 known flavonoids, 3-O-methylkaempferol (2), 3-O-methylquercetin (3), quercetin (4), kaempferol (5), apigenin (6), rhamnazin (7), astragalin (8), alquds (9), quercitrin (10), rutin (11), isoquercitrin (12), apigetrin (13), myricitrin (14), hesperidin (15) and calycosin-7-O-β-d-glucopyranoside (16) were isolated from the aerial parts of Caragana leucophloea Pojark. (Leguminosae). Their structures were determined on the basis of spectroscopic analyses and by comparison with literature data. Compounds 2–4 revealed a strong antimicrobial activity with minimum inhibitory concentration values of 12.5–150 μg/mL and median inhibitory concentration (IC₅₀) values of 7.42–76.61 μg/mL. Compounds 3, 4, 6–8, 10–12 and 14 showed strong antioxidant activity. Compounds 2–7 exhibited moderate antinematodal activity on Caenorhabditis elegans with IC₅₀ values of 40.51–68.05 μg/mL.