Four new iridoid glucosides from Ajuga reptans

Four new iridoid glucosides were isolated from the whole plant of Ajuga reptans L. (Labiatae) along with four known iridoid glucosides, one known diterpenoid glycoside, one known aliphatic alcohol glycoside, and three known ecdysteroids. Their chemical structures were determined on the basis of spectroscopic data and chemical evidence. The diterpenoid glycoside exhibited 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and H?O? scavenging activities.     

Two diterpene rhamnosides, mimosasides B and C, from Mimosa hostilis

Two new diterpene rhamnosides, mimosasides B and C (1, 2) were isolated together with mimosaside A (3), a known diterpene rhamnoside (4), four known flavones (5-8), five known flavanones (9-13), and four known chalcones (14-17) from the leaves and twigs of a Brazilian medicinal plant, Mimosa hostilis.     

Cytotoxic Diarylheptanoids from Pericarps of Juglans Cathayensis Dode

A novel diarylheptanoid, named Jugcathanin（1）, along with two known diarylheptanoids（2,3）, were isolated from the fresh pericarps ofduglans Cathayensis Dode. A known triterpene（4） and a known aphthaoquinone（5） were also isolated from the plant. Their structures were elucidated on the basis of spectroscopic studies. All the compounds exhibited moderate cytotoxicities against human Hela, HepG2, and HL-60 cell lines.     

Novel abietane diterpenoids and aromatic compounds from Cladonia rangiferina and their antimicrobial activity against antibiotics resistant bacteria

From Cladonia rangiferina were isolated two novel abietane diterpenoids, hanagokenols A (1) and B (2). Also in this investigation, four known abitetane diterpenoids (3-6), four known labdane diterpenoids (7-10), one known isopimarane diterpenoid (11), and six known aromatic compounds were isolated. These structures were elucidated primarily through extensive NMR experiments. Hanagokenol A (1) was a unique abietane diterpene having an ether linkage between C-6 and C-18 of sugiol. Hanagokenol B (2) is also a unique secoabietane diterpene, having gamma-lactone which occurred by cleavage and subsequently oxidation between C-6/C-7 of 12-hydroxydehydroabietinol. Furthermore, all the isolated compounds (1-17) were tested for the antimicrobial activity against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococci (VRE).     

Saponins and other constituents from the leaves of Aralia elata

A new triterpenoid saponin, together with five known saponins, were isolated from the nonpolar n-hexane fraction of the leaves of Aralia elata. The structure of the new saponin, durupcoside C, was elucidated as hederagenin 3-O-beta-D-glucopyranosyl(1-->3)-beta-D-glucopyranosyl(1-->3)-alpha-L-arabinopyranoside on the basis of spectroscopic analysis. The known saponins were characterized as 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl hederagenin 28-O-beta-D-xylopyranosyl(1-->6)-beta-D-glucopyranosyl ester, hederagenin 3-O-beta-D-glucopyranosyl(1-->3)-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside, oleanolic acid 3-O-beta-D-glucopyranosyl(1-->3)-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside, hederagenin 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside (alpha-hederin), and hederagenin 3-O-beta-D-glucopyranosyl(1-->3)-alpha-L-arabinopyranoside (collinsonidin). In addition, two known lipids, Arisaema glyceride 3 and ceramide mixtures were also isolated and characterized. Collinsonidin and two known lipids were isolated for the first time from this plant.     

New iridoid glucosides from the aerial parts of Verbena brasiliensis

Two new iridoid glucosides, verbenabraside A (1) and verbenabraside B (2), were isolated from the aerial parts of Verbena brasiliensis VELL., along with six known iridoid glucosides, gelsemiol 3-O-beta-D-glucoside (3), verbraside (4), 9-hydroxysemperoside (5), griselinoside (6), aralidioside (7), and 6alpha-hydroxyforsythide dimethyl ester (8), three known phenylethanoid glycosides, 2-phenylethyl O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucopyranoside (9), acteoside (10), and leucosceptoside A (11), two known lignan glucosides, dihydroxymethyl-bis(3,5-dimethoxy-4-hydroxyphenyl) tetrahydrofuran-9 (or 9')-O-beta-glucopyranoside (12) and (+)-lyoniresinol 3alpha-O-beta-D-glucopyranoside (13), a known methyl salicylate glucoside, methyl 2-O-beta-D-glucopyranosylbenzoate (14), and two known sterols, beta-sitosterol 3-O-beta-D-glucopyranoside (15) and beta-sitosterol (16). Their chemical structures were determined on the basis of spectroscopic data. Compound 1 exhibited stronger scavenging effect on the stable free radical 1,1-diphenyl-2-picrylhydrazyl than that of alpha-tocopherol.     

Studies on Chemical Constituents of Polygonum Ciliinerve Ohwi

Three new apianen lactones Maomailiaoine I ( 1 ), Maomailiaoine II ( 2 ) and Maoimaliaoine III ( 3 ), together with one known apianen lactone, five known flavonoids and three other known compounds were isolated from Polgonum ciliinerve Ohwi. Their structures were deduced from spectroscopic methods and 2D NMR techniques.     

Complete 1H and 13C data assignments of two new guaianolides isolated from Ainsliaea fragrans

Two new guaianolides, 8alpha-hydroxy-11alpha,13-dihydroglucozaluzanin C and 11alpha,13-dihydroglucozaluzanin C, were isolated from Ainsliaea fragrans, along with two known guaianolides, 8alpha-hydroxy-11alpha,13-dihydrozaluzanin C and glucozaluzanin C. The structures of the new compounds were unambiguously established by HR-ESI-MS, one-dimensional (1D) (DEPT), two-dimensional (2D) ((1)H-(1)H COSY, HSQC, HMBC, ROESY) NMR experiments and by comparison with structurally related compounds. The known compounds were identified by comparison of spectral data with published references. Some NMR data of the known compounds were reported for the first time.     

A new highly hydroxylated triterpene from Salvia atropatana Bunge

One new triterpenoid olean-18-ene-1β, 2α, 3β-triol (1) along with four known compounds were isolated from the chloroform extract of the aerial part of Salvia atropatana Bunge. The known compounds were two flavonoids, 5-hydroxy-7,4'-dimethoxyflavone (2) and 5-hydroxy-6,7,4'-trimethoxyflavone (3), an abietane-type diterpene namely taxodione (4) and a phytosterol namely γ -sitosterol (5). The structure of (1) was elucidated by comprehensive spectroscopic analysis including electron ionization-mass spectra (EI-MS), (1)H NMR, (13)C NMR, distortionless enhancement by polarization transfer (DEPT), H,H correlation spectroscopy (COSY), heteronuclear multiple quantum coherence (HMQC) and heteronuclear multiple bond correlation (HMBC). The structure of known compounds 2-5 were identified by comparison of their spectral data with those reported in the literature.     

Phomosines H-J, novel highly substituted biaryl ethers, isolated from the endophytic fungus Phomopsis sp. from Ligustrum vulgare

From the endophytic fungus Phomosis sp., four known phomosines A-D (1-4) and three new phomosines H-J (5-7) have been isolated. The structures of the new compounds were determined on the basis of their spectroscopic data analysis (1H, 13C, 1H-1H COSY, HMQC, and HMBC NMR, as well as mass spectrometry). The structures of phomosine H (5) and J (7) were also confirmed by semisynthesis from phomosine A (1). The remaining four known compounds [phomosines A-D (1-4)] were identified by comparing their spectroscopic data with those reported in the literature. The four known metabolites were biologically active. Of the novel metabolites, only 6 was antifungal and antibacterial.     

A novel agarofuran sesquiterpene, celahin D from Celastrus hindsii Benth

A novel agarofuran sesquiterpene polyol ester, 1beta,2beta,6alpha,15beta-tetracetoxy-8 beta,9alpha-dibenzoyloxy-beta- dihydroagarofuran (celahin D) (1), two known analogues of 1,1beta-acetoxy-8beta,9alpha-dibenzoyloxy-4al pha6alpha-dihydroxy-2beta(alphamethylbutanoyloxy)-beta-++ +dihydroagarofuran (2) and beta-acetoxy-8beta,9alpha-dibenzoyloxy-6alpha-hy droxy-2beta(alpha -methylbutanoyloxy)-beta-dihydroagarofuran (3), and a known cytotoxic sesquiterpene pyridine alkaloid, emarginatine E (4) were isolated from the stems of Celastrus hindsii Benth. Three known triterpenes, loranthol (5), lupenone (6) and friedelinol (7) were also obtained from the titled plant. Structural elucidation of compound 1 was established by 2D NMR spectra.     

Terpenoids and bibenzyls from three Argentine liverworts

A new rosane diterpenoid, 3a-hydroxy-5,15-rosadien-11-one (3), was isolated, together with a known rosane diterpenoid, 5,15-rosadiene-3,11-dione (4), and an aromadendrane sesquiterpenoid, ent-cyclocolorenone (5), from the Et(2)O extract of an unidentified Argentine liverwort Anastrophyllum species. Moreover, four known sesquiterpene lactones 6-9 and two known bibenzyls 10, 11 were isolated from the Et(2)O extracts of Argentine Frullania brasiliensis and Radula voluta, respectively. The structures of compounds 3-11 were determined by the use of NMR techniques.     

Chemical constituents of Blumea balsamifera of Indonesia and their protein tyrosine phosphatase 1B inhibitory activity

A methanol extract of the leaves of Blumea balsamifera (L.) DC. (Asteraceae) afforded a new guaian-type sesquiterpene, epiblumeaene K (1), together with four known guaian-type sesquiterpenes (2-5), three known sesquiterpenes (6-8), and nine known flavonoids (9-17) by a combination of chromatography and preparative TLC techniques. Their structures were elucidated by extensive spectroscopic methods and comparison with the literature data. Among the isolated compounds, a known sesquiterpene, beta-caryophyllene 8R,9R-oxide (6), exhibited a significant PTP1B inhibitory activity in a dose-dependent manner, with an IC50 value of 25.8 microM (5.62 microg/mL).     

Two new iridoid glycosides from the Tibetan folk medicine Swertia franchetiana

Two new iridoid glycosides designated as senburiside III (2) and senburiside IV (3), together with one known iridoid glycoside senburiside I (1) and three known secoiridoid glucosides swertiamarin (4), gentiopicroside (5) and sweroside (6), were isolated from the whole plant of Swertia franchetiana. The structures of the two new compounds were elucidated by spectroscopic methods.     

Phytochemical Investigation of Artemisia pallens

Two new eudesmanolides, pallensin ( 1 ) and 4‐epipallensin ( 2 ), along with a known eudesmanolide, santonin, and a known flavone, 4‐epivalgarin, have been isolated from the aerial part of A. pallens. Their structures were established by detailed spectral studies (1D and 2D) and by comparison of their spectroscopic data with those of known compounds.     

Constituents of the leaves of Woodfordia fruticosa Kurz. I. Isolation, structure, and proton and carbon-13 nuclear magnetic resonance signal assignments of woodfruticosin (woodfordin C), an inhibitor of deoxyribonucleic acid topoisomerase II

Woodfruticosin (woodfordin C), a new cyclic dimeric hydrolyzable tannin having an inhibitory activity toward deoxyribonucleic acid (DNA) topoisomerase II, has been isolated from the leaves of Woodfordia fruticosa Kurz (Lythraceae) along with three known flavonol glycosides and three known flavonol glycoside gallates. The structure of wood fruticosin (woodfordin C) was determined by the use of two-dimensional nuclear magnetic resonance (2-D NMR) spectroscopy including heteronuclear multiple quantum coherence (HMQC) and heteronuclear multiple bond connectivity (HMBC) techniques. Detailed analyses of the proton and carbon-13 NMR (1H- and 13C-NMR) spectra of six known flavonoids were performed.     

Dihydrophenanthrenes from Bletilla formosana

Three new dihydrophenanthrenes, 4-methoxy-9,10-dihydrophenanthrene-1,2,7-triol (1), 1-(4-hydroxybenzyl)-4,7-dimethoxy-9,10-dihydrophenanthrene-2-ol (2), and 1,3,6-tri(4-hydroxybenzyl)-4-methoxydihydrophenanthrene-2,7-diol (3) together with seven known phenanthrene derivatives, six known flavonoids, a bibenzyl and three phenolic compounds were isolated from the whole plant of Bletilla formosana. Their structures were elucidated by spectroscopic, mainly 2D NMR spectrometry and chemical methods.     

Phenolic compounds from Scorzonera latifolia (Fisch. & Mey.) DC

A new 3-benzylphthalide, scorzoveratrin 4'-O-β-glucoside (1), together with the known 3-benzylphthalides, scorzoveratrin (2) and scorzoveratrozit (3), the caffeoyl derivatives, chlorogenic acid methyl ester (4), 4,5-dicaffeoylquinic acid (5), 4,5-dicaffeoylquinic acid methyl ester (6), 3,5-dicaffeoylquinic acid (7) and caffeic acid (8) were isolated from the subaerial parts of Scorzonera latifolia (Fisch. & Mey.) DC. All secondary metabolites were assigned using physicochemical and spectroscopic data. The known compounds 2-8 were isolated for the first time from this species.     

苔藓植物短肋羽藓Thuidium kanedae sak 中的双二氢黄酮类化合物

A new bidihydroflavonoid, thuidinin 1, together with 5 known compounds including one known biflavonoid 3＇,3＂＇-binaringenin （2） and four other known natural products pentadecane （3）, methyl β-orcinolarboxylate （4）, β-sitosterol （5） and daucostenol （6）, were isolated from leaves of Thuidium kanedae Sak. Their structures were established on the basis of 1D and 2D spectroscopic analysis. The absolute stereochemistry of compounds 1 and 2 was determined by CD spectra.     

Iridoid and lignan glycosides from Citharexylum spinosum L

From the aerial parts of Citharexylum spinosum L., one new iridoid glucoside, the 7-ss-O-acetate (1) of lamiide, along with four known iridoid glucosides, lamiide (2), lamiidoside (3), duranterectoside C (4), 8-epiloganin (5) and one known lignan glucoside (+)-lyonirenisol-3a-O-ss-D-glucopyranoside (6) were isolated. The compound structures were established by one- and two-dimensional 1H- and 13C-NMR as well as by ESI-MS spectra.