Coumarin and terpenoids from Perezia alamani var. oolepis

Isoparvifolinone (2a), 8-hydroxypereflorine (3a) and diperezone (5) and the known sesquiterpenes cyperene and parvifoline (1a) were isolated from the roots of Perezia alamani var. oolepis. The structures of the new compounds were deduced from spectral data and tested by chemical correlation. Thus diperezone (5) was identical to the dimerization product of perezone (4a), isoparvifolinone (2a) was partially synthesized from parvifoline (1a) and 8-hydroxypereflorine (3a) was converted into the known 8-methoxypereflorine (3b).     

Bioactive styryllactones,two new naphthoquinones and one new styryllactone,and other constituents from Goniothalamus scortechinii

Two new naphthoquinones, goniothalaminone A (1) and B (2), and a new styryllactone, (?)-8-epi-9-deoxygoniopypyrone acetate (12) together with one known naphthoquinone (3), one known indolequinone (4), one known 1-azaanthraquinone (5), six known styryllactones (6–11) and one known sesquiterpene (13) were isolated from the roots and leaves of Goniothalamus scortechinii. The structures of the new compounds were elucidated by spectroscopic analysis and of the known compounds by comparison of their physical, UV, IR, ¹H and ¹³C NMR data with those of published compounds. Antiplasmodial, antimycobacterial and cytotoxic activities of the styryllactones were evaluated. Compounds 6–10 exhibited cytotoxic against human cancer cell lines, KB, BC and NCI-H187 with IC₅₀ values ranging from 0.13 to 11.7 μg/ml.     

Two new labdane diterpenoids and one new β-lactam from the aerial parts of Roylea cinerea

Two new labdane diterpenoids cinereanoid C (1), cinereanoid D (2), a new β-lactam, cinerealactam E (3) as well as six known flavonoid glycosides (4–9) were isolated from the aerial parts of Roylea cinerea (Lamiaceae). The structures of (1–9) were all determined by MS, IR and NMR spectroscopy. The structure of cinereanoid D (2) was further proven by single crystal X-ray diffraction. Six known flavonoid glycosides (4–9) were also isolated for the first time from this plant. 2, 5, 6 and 7 were found to significantly inhibit the ATP binding of a tumour growth-promoting heat shock protein, Hsp90.     

Antiproliferative terpenoids and alkaloids from the roots of Maytenus vitis-idaea and Maytenus spinosa

Investigation of the organic extracts of the roots of Maytenus vitis-idaea and Maytenus spinosa, collected in the province of Salta, Argentina, led to isolation of eighteen compounds belonging to several classes. From M. vitis-idaea, eight methylenequinone celastroids (1–8) were isolated, four of which (4–7) were hitherto unknown. Additionally, from M. spinosa, two known celastroids, a known celastroid dimer (9), three pentacyclic triterpenoids (10–12) and six β-dihydroagarofuran sesquiterpenoid alkaloids (13–18) were identified. Compounds 4–7 were active against six solid tumor cell lines at micromolar concentrations.     

O-Prenylated flavonoids from Dalbergia sissoo

A chalcone, 2,3-dimethoxy-4′-γ,γ-dimethylallyloxy-2′-hydroxychalcone (1) and an isoflavone, 7-γ,γ-dimethylallyloxy-5-hydroxy-4′-methoxyisoflavone (2) together with a known flavone, 7-hydroxy-6-methoxyflavone (3), a known isoflavone, biochanin A (4) and a known rotenoid, dehydroamorphigenin (5) were isolated from the root bark of Dalbergia sissoo. The structures of compounds 1–5 were elucidated on the basis of spectral and chemical studies.     

Sesquiterpenoids from the Chinese endangered plant Manglietia aromatica

One new bourbonane-type (1) and one new cadinane-type (2) sesquiterpenoids, along with one known aromodendrane-type (3) and five known megastigmane-type (4–8) compounds, were isolated from the leaves and twigs of Manglietia aromatica, a Chinese endangered plant that has not been previously phytochemically investigated. The structures and absolute configurations of the new isolates, (1R,4S,5S,6S,7S,10S)-4-hydroxy-bourbon-8-one (1) and (1R,6S,7S)-1-hydroxy- cadin-4,9-dien-8-one (2), were established by means of spectroscopic methods and a combination of experimental and calculated electronic circular dichroism (ECD). Among the isolates, compound 2 was found to show a moderate inhibitory effect against the human protein tyrosine phosphatase 1 B (PTP1B) enzyme, a target for the treatment of type-II diabetes and obesity, with an IC₅₀ value of 83.5 μM.     

Anthraquinone derivatives from the mangrove-derived fungus Phomopsis sp. PSU-MA214

One new tetrahydroanthraquinone derivative, (2R,3S)-7-ethyl-1,2,3,4-tetrahydro-2,3,8-trihydroxy-6-methoxy-3-methyl-9,10-anthracenedione (1), together with five known anthraquinones (2–6), two known phenylethyl alcohols (7–8) and one known butanamide (9), were isolated from the mangrove-derived fungus Phomopsis sp. PSU-MA214. Their structures were established by spectroscopic evidence. Compound 1 is a rare ethyltetrahydroanthraquinone and exhibited weak cytotoxicity against breast cancer (MCF-7) cell lines and antibacterial activity against the standard Staphylococcus aureus ATCC25923 and methicillin-resistant S. aureus SK1.     

New flavonoids from the fruits of Cornus mas,Cornaceae

One new β-hydroxychalcone, 4-acetoxy-5,2′,4′,6′,β-pentahydroxy-3-methoxychalcone (1), one new flavanone, 7,3′-dihydroxy-5,4′-dimethoxyflavanone (2) and seven known compounds, 2R, 3R-trans-aromadendrin (3), naringenin-7-O-methylether (4), myricetin (5), quercetin-3-O-rutinoside (6), ursolic acid (7), gallic acid (8) and d-glucose (9) were isolated from the methanolic fruit extract of Cornus mas L. (=Cornus mascula L.), Cornaceae. The structures of the new compounds were elucidated on the basis of extensive spectroscopic methods, including 2D NMR experiments and of known compounds by comparison of physical and spectral data with literature.     

Cytotoxic quinazoline alkaloids from the seeds of Peganum harmala

Seventeen quinazoline alkaloids and derivatives, containing two pairs of new epimers, named as (S)- and (R)-1-(2-aminobenzyl)-3-hydroxypyrrolidin-2-one β-d-glucopyranosyl-(1?→?6)-β-d-glucopyranoside (1, 2), (S)- and (R)-vasicinone β-d-glucopyranosyl-(1?→?6)-β-d-glucopyranoside (3, 4), and a new enantiomer (12b), together with six known ones (5–8, 10, and 12a), and three pairs of known enantiomers (9, 11, and 13), were isolated from the ethanol extracts of the seeds of Peganum harmala L.. Their structures including the absolute configuration were elucidated by using 1D and 2D NMR, and ECD calculation approaches. The cytotoxic activities of all isolated compounds were evaluated. 11 showed moderate cytotoxicity against PC-3 cells with an IC₅₀ value of 15.41?μM.     

Diarylpentanoids from Diplomorpha canescens and Diplomorpha ganpi

Two new α-hydroxy ketone type diarylpentanoids, diplomorphanone A, 2(S)-hydroxy-1-(4-hydroxyphenyl)-5-phenyl-1-pentanone (1) and diplomorphanone B, 2(R)-hydroxy-1,5-diphenyl-1-pentanone (2) were isolated from aerial parts of Diplomorpha canescens (Meisn.) C.A. Meyer and roots of Diplomorpha ganpi (Sieb. et Zucc.) Nakai, respectively. Nine known compounds including diarylpentanoids (3–6), phenylpropanoid derivatives (7–9), (+)-afzelechin (10) and apiosylskimmin (11) were also isolated for the first time from D. ganpi. Structures of these compounds were elucidated on the basis of spectroscopic data.     

Triterpene saponins from Fagonia scabra Forssk and other Fagonia species

This article reports on the structure of triterpenoids saponins (1–49) isolated from Fagonia species. In addition, it describes one known flavonoid (50) with luteolin as aglycone and seven known triterpenoid saponins (26, 51–56) isolated from the aerial parts of Fagonia scabra Forssk. Compounds 50–56, were isolated for the first time from the genus Fagonia, while compounds 50–53, 55–56 have never been encountered in the Zygophyllaceae family. The chemotaxonomic relationship between F. scabra and other Fagonia species was also discussed.     

A new triterpenic diester from the aerial parts of Chrysanthemum macrocarpum

A new triterpenic diester, 3,21-dipalmitoyloxy-16β,21α-dihydroxy-β-amyrine (1), along with two natural cyclitols, conduritol C (2) and viburnitol (3), four known triterpenes (4–7), and seven known flavonoids (8–14) were isolated from the aerial parts of Chrysanthemum macrocarpum. Their structures were established on the basis of extensive 1D and 2D NMR (¹H, ¹³C, COSY, HMBC, HSQC, and ROESY) and ESIMS studies. The chloroform fraction, taraxasterol (4) and β-sitosterol (7) were investigated for their antibacterial activity against Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, Pseudomonas aeruginosa and Klebsiella pneumoniae. The chloroform fraction and taraxasterol (4) showed a weak antibacterial activity and were evaluated for their cytotoxic activity against human colon cancer HT-29 cells and human prostate carcinoma PC3 cells. The results indicated that both the chloroform fraction and taraxasterol (4) inhibited cell proliferation of both PC3 and HT-29 cells.     

Six new dammarane-type triterpene saponins from the processed leaves of Panax notoginseng

Six new dammarane-type triterpenoid saponins, notoginsenosides SFt₅–SFt₁₀ (1–6) were isolated from the processed leaves of Panax notoginseng (Burk.) F.H.Chen (Araliaceae), together with eight known notoginsenosides (7–14), fourteen known ginsenosides (15−28), two known vinaginsenosides (29−30), and one known gypenoside (31). Their structures were established by detailed spectroscopic analysis (NMR, UV, IR, HRESI-MS) and acidic hydrolysis. Four compounds notoginsenoside SFt₁ (7), ginsenosides Rg₅ (17), C-Mc (23) and 20(R)–Rg₃ (25) have significant protective effects against L-glutamate-induced SH–SY5Y nerve injury (10 μM).     

Alkaloids from Galanthus rizehensis

Two new Amaryllidaceae alkaloid N-oxides, incartine N-oxide (1) and lycorine N-oxide (2) together with one β-carboline alkaloid, 1-acetyl-β-carboline (3) and six known alkaloids namely, incartine (4), N-trans feruloyltyramine (5), lycorine (6), O-methylnorbelladine (7), vittatine (8) and 11-hydroxyvittatine (9) were isolated from Galanthus rizehensis Stern (Amaryllidaceae). The structures of the alkaloids were elucidated by spectroscopic analyses (UV, IR, MS, 1D and 2D NMR). Acetylcholinesterase inhibitory activity potentials of the compounds were also determined.     

Neoflavanoids of Dalbergia melanoxylon

The heartwood of Dalbergia melanoxylon has yielded new examples of known neoflavanoid types. The isolates included 4-phenylcoumarins, (S)-4-methoxydalbergiones and benzophenones which have the corresponding oxygenation pattern. The structures of the extractives have been examined by physical methods, and confirmed by conversion to known compounds or by independent synthesis. A 2-cinnamylphenol (6) and 3-cinnamylflavan (7) were the only products in a condensation reaction in the attempted synthesis of the 4-methoxydalbergione (1b).     

New antibacterial sesquiterpene aminoquinones from a Vietnamese marine sponge of Spongia sp.

Two new sesquiterpene aminoquinones, langcoquinones A (1) and B (2), together with seven known meroterpenoids (3⿿9), were isolated from the marine sponge Spongia sp. collected in Vietnam. Their structures were determined on the basis of spectroscopic analyses and comparisons with published data. The antibacterial activities of the isolated compounds (1⿿9) were investigated against four bacterial strains. Among these, the new sesquiterpene aminoquinones (1 and 2) and the known related compounds (3, 5, 6, 8, and 9) exhibited significant antibacterial activities against Staphylococcus aureus and Bacillus subtilis, with MICs ranging from 6.25 to 12.5 μM.     

Anthraquinone derivatives from Rumex plants and endophytic Aspergillus fumigatus and their effects on diabetic nephropathy

Two new oxanthrone C-glycosides, patientosides A (14) and B (15), together with three known ones (11–13), were isolated from Rumex patientia. Their structures were identified on the basis of spectroscopic methods. The absolute configuration for 14 and 15 were deduced by analysis of their CD spectra and comparison with those of known similar compounds. Compounds 11–15, and 14 known anthraquinones (1–4, 6–10, 16–20) previously isolated from Rumex nepalensis, Rumex hastatus, and endophytic Aspergillus fumigatus, respectively, as well as a commercially available compound rhein (5) were evaluated for their inhibitory effects on IL-6 and extracellular matrix production in mesangial cells.     

Lipoxygenase inhibitors derived from marine macroalgae

The solvent extracts from the algae Sargassum thunbergii (Sargassaceae) and Odonthalia corymbifera (Rhodomelaceae) were subjected to soybean lipoxygenase inhibitory screening. Two hydrophobic inhibitors were obtained from the extracts of S. thunbergii through inhibitory assay-guided fractionation. The inhibitors were identified as known exo-methylenic alkapolyenes (6Z,9Z,12Z,15Z)-1,6,9,12,15-henicosapentaene (1) and (6Z,9Z,12Z,15Z,18Z)-1,6,9,12,15,18-henicosahexaene (2). The alkapolyenes 1 and 2 showed higher inhibitory activity than the known inhibitor nordihydroguaiaretic acid (NDGA). Pheophytin a (3) was obtained from the extract of O. corymbifera. The inhibitor 3 also showed higher inhibitory activity than NDGA. This is the first report on lipoxygenase inhibition of exo-methylenic alkapolyenes and a chlorophyll a-related substance.     

New amides from the roots of Anisodus tanguticus

Two new amides (1 and 2) and four known analogues (3–6) were isolated from the roots of Anisodus tanguticus (Maxim.) Pascher. Their structures were determined by extensive spectroscopic analyses. The absolute configuration of compound 1 was determined by comparison of the calculated optical rotation (OR) value with the experimental OR value. All known amides were isolated from the genus Anisodus for the first time, of which compounds 3, 5, and 6 were first reported from the family Solanaceae. Furthermore, the chemotaxonomic significance of these secondary metabolites is discussed.     

Two new diterpenoids from the roots of Pygmacopremna herbacea

Two new diterpenoids, neobharangi-δ-lactone (1) and bharangi quinone (2) along with two known compounds neobharangin (3) and bharangin (4) were isolated from the ethyl acetate extract of root nodules of Pygmacopremna herbacea. The structures of the new compounds were established by 1D and 2D NMR spectroscopic data.