Diarylheptanoids from the rhizomes of Alpinia officinarum and their anticancer activity

Two new diarylheptanoids (1, 2), together with two known analogs (3, 4), were isolated from the rhizomes of Alpinia officinarum. The new compounds were elucidated to be (5S)-5-hydroxy-7-(3, 4-dihydroxyphenyl)-1-phenyl-3-heptanone (1) and (5R)-5-hydroxy-7-(3-methoxy-4, 5-dihydroxyphenyl)-1-phenyl-3-heptanone (2) based on their spectral analysis. Compound 4 showed moderate cytotoxicity against human tumor cell lines, HepG2, MCF-7 and SF-268, while no significant effect were found for compounds 1-3.     

Two new nortriterpenoid saponins from Salicornia bigelovii Torr. and their cytotoxic activity

Investigation of characteristic constituents of Salicornia bigelovii Torr. led to isolation of two new 30-nortriterpenoid glycosides, Bigelovii A (1), Bigelovii B (2), together with two known 30-nortriterpenoid glycosides 3-4 and three known oleanane-type triterpenoid glycosides 5-7. The structures of new compounds were elucidated by extensive 1D and 2D NMR, and MS spectroscopic analysis, and chemical evidences. All compounds were isolated for the first time from Chenopodiaceae. Thus compounds 1-4 were evaluated for their cytotoxicity and compouds 1, 3 showed moderate activity against four cell lines, HL-60 (promyelocytic leukemia), MCF-7 (breast carcinoma), HepG2 (liver carcinoma) and A549 (lung carcinoma), with IC(50) values of 6.18, 78.08, 13.64 and >100μM for 1; 31.87, >100, ~100, >100μM for 3, respectively.     

Four new neolignans from the leaves of Tripterygium wilfordii

Four new neolignans, wilfordiols A-D (1-4), together with five known compounds (5-9), were isolated from an aqueous extract of the dried leaves of Tripterygium wilfordii. Their structures were determined by spectroscopic methods, including 1D and 2D NMR, HRESIMS, and CD experiments. The anti-inflammation activities of compounds 1-9 were evaluated by the inhibitory effect on NO production, in vitro.     

Phenolics from Leontopodium leontopodioides inhibiting nitric oxide production

Two new compounds, a neolignan (1), and a benzofuran derivative (2), along with 6 known compounds (3-8), were isolated from the aerial parts of Leontopodium leontopodioides. The structures of the new compounds were elucidated as (7R,8S)-3,5'-dimethoxy-4',7-epoxy-8,3'-neolignane-5,9,9'-triol (1) and (2R)-12-hydoxy-4-methoxy-tremeton (2) on the basis of their spectroscopic data, respectively. All of the isolates were evaluated for their effects on the inhibition of nitric oxide (NO) production in lipopolysaccharide-activated RAW264.7 macrophages and compounds 1 and 8 exhibited inhibitory activity with IC(50) values of 35.80 and 24.41 μM, respectively.     

Three new antibacterial active diarylheptanoids from Alpinia officinarum

Three new diarylheptanoids, together with ten known ones, were isolated from the ethanol extract from the rhizomes of Alpinia officinarum Hance. The structural identification of these compounds was mainly achieved by spectroscopic methods. The new compounds were elucidated as 7-(4″, 5″-dihydroxy-3″-methoxyphenyl)-1-phenyl -4-heptene-3-one (1), 1, 7-diphenyl-5-heptene-3-one (2) and 4-phenethyl-1, 7-diphenyl -1-heptene-3, 5-dione (3), respectively. All of the compounds showed antibacterial activity against Helicobactor pylori. Especially, the three new compounds showed strong antibacterial activity against Hp-Sydney strain 1 with the MIC values of 9–12 μg/mL, and against Hp-F44 with the MIC values of 25–30 μg/mL.     

Anti-neuroinflammatory constituents from Polygala tricornis Gagnep

Two new compounds (S)-(+)-butyl-4-methylene-5-oxo-pyrrolidin-2-carboxylate (1) and (5-formylfuran-2-yl)methyl 4-hydroxy-2-methylenebutanoate (2), together with four known compounds (3-6) were isolated from the roots of Polygala tricornis Gagnep. Their structures were determined on the basis of 1D- and 2D-NMR experiments and by comparison with physical data of known compounds. All the isolated compounds were examined for their inhibitory effect on the nitric oxide (NO) production induced by lipopolysaccharide (LPS) in BV-2 microglial cells, and compounds 1 and 2 exhibited pronounced inhibition on the NO production with IC(50) values of 14.1 μM and 1.77 μM, respectively.     

Benzophenone glycosides and epicatechin derivatives from Malania oleifera

A new benzophenone C-glycoside, malaferin A (1), and two new epicatechin derivatives, malaferin B (2) and malaferin C (3), together with five known compounds were isolated from Malania oleifera. In addition, (-)-epicatechin-3-O-benzoate (6) was isolated for the first time from a natural resource. Structures of 1-3 were determined on the basis of their spectroscopic methods, including 1D and 2D NMR techniques. All of the compounds were evaluated for anti-HIV activities.     

New cytotoxic quinolone alkaloids from fruits of Evodia rutaecarpa

Three new quinolone alkaloids, 1-methyl-2-[7-hydroxy-(E)-9-tridecenyl]-4(1H)-quinolone (1), 1-methyl-2-[(Z)-4-nonenyl]-4(1H)-quinolone (2), 1-methyl-2-[(1E,5Z)-1,5-undecadienyl]-4(1H)-quinolone (3) and one new natural product, 1-methyl-2-[(E)-1-undecenyl]-4(1H)-quinolone (4), were isolated from the dried and nearly ripe fruits of Evodia rutaecarpa (Juss.) Benth., along with thirteen known compounds (5-17). In addition, one new artificial product, 1-methyl-2-[7-carbonyl-(E)-9-tridecenyl]-4(1H)-quinolone (1A) was also obtained. The structures of these compounds were determined by spectroscopic analyses. The cytotoxic activities of all of the compounds against the human cancer cell lines HL-60, N-87, H-460, and Hep G(2) cells were evaluated by MTT assay. The results showed that these alkaloids inhibited cell proliferation with IC(50) values between 14μM and 22μM.     

Norditerpenoids from Salvia castanea Diels f. pubescens

Three new norditerpenoids, castanol A-C (1-3), along with eighteen known diterpenoids, were isolated from Salvia castanea Diels f. pubescens. Their structures were elucidated by extensive spectroscopic analysis. All compounds were evaluated for their cytotoxic activities against five human cancer cell lines. The known compounds neo-tanshinlactone (12) and methyltanshinoate (17) exhibited significant cytotoxic activities against some cells.     

Anti-acetylcholinesterase, anti-α-glucosidase, anti-leishmanial and anti-fungal activities of chemical constituents of Beilschmiedia species

Phytochemical investigation of Beilschmiedia alloiophylla has resulted in the isolation of one new alkaloid, 2-hydroxy-9-methoxyaporphine (1), and ten known natural products, laurotetanine (2), liriodenine (3), boldine (4), secoboldine (5), isoboldine (6), asimilobine (7), oreobeiline (8), 6-epioreobeiline (9), β-amyrone (10), and (S)-3-methoxynordomesticine (11). Chemical studies on the bark of B. kunstleri afforded compounds 2 and 4 along with one bisbenzylisoquinoline alkaloid, N-dimethylphyllocryptine (12). Structures of compounds 1-12 were elucidated on the basis of spectroscopic methods. All of these isolates were evaluated for their anti-acetylcholinesterase (AChE), anti-α-glucosidase, anti-leishmanial and anti-fungal activities. Compounds 1-12 exhibited strong to moderate bioactivities in aforementioned bioassays.     

Heptaketides with antiviral activity from three endolichenic fungal strains Nigrospora sp., Alternaria sp. and Phialophora sp

Two new heptaketides, (+)-(2S,3S,4aS)-altenuene (1a) and (-)-(2S,3S,4aR)-isoaltenuene (2a), together with six known compounds, (-)-(2R,3R,4aR)-altenuene (1b), (+)-(2R,3R,4aS)-isoaltenuene (2b), 5'-methoxy-6-methyl-biphenyl-3,4,3'-triol (3), alternariol (4), alternariol-9-methyl ether (5), and 4-hydroxyalternariol-9-methyl ether (6) were isolated from the EtOAc extract of an endolichenic fungal strain Nigrospora sphaerica (No.83-1-1-2). Compounds 1a and 1b were separated from enantiomers 1 by chiral HPLC, and so were 2a and 2b from enantiomers 2. Interestingly, 1-6 were also obtained from other two endolichenic fungal strains Alternaria alternata (No.58-8-4-1) and Phialophora sp. (No.96-1-8-1). The structures of 1-6 were elucidated by means of MS, HR-MS, NMR, and X-ray diffraction. Furthermore, the absolute configurations of 1a-2b were determined by CD experiments and CD calculation. Of these compounds, 4 and 5 showed antiviral activity against herpes simplex virus (HSV) in vitro, with IC(50) values of 13.5 and 21.3 μM, and with selective index (SI) values of 26.5 and 17.1, respectively.     

Five new furostanol saponins from the rhizomes of Tupistra chinensis

Five new furostanol saponins (1-5), together with three known compounds (6-8) were obtained from the n-butanol soluble fraction of ethanol extract from Tupistra chinensis. Their structures were determined on the basis of chemical methods and spectral data. The isolated compounds were tested in vitro for their cytotoxic activities against the A549, HepG 2 and Caski cancer cell lines. Among them, compounds 6, 7, and 8 showed cytotoxicity against A549 cancer cell lines with IC(50) values of 6.6, 6.7 and 29.1 μM, respectively.     

Iridoid, phenylethanoid and flavonoid glycosides from Sideritis trojana

From the MeOH extract of Sideritis trojana, a new iridoid glycoside, 10-O-(E)-feruloylmelittoside (1) was obtained in addition to four known iridoid glycosides [melittoside (2), 10-O-(E)-p-coumaroylmelittoside (3), stachysosides E (4) and G (5)]. Moreover, five phenylethanoid glycosides [verbascoside (6), isoacteoside (7), lamalboside (8), leonoside A (9), isolavandulifolioside (10), three flavone glycosides (isoscutellarein 7-O-[6'-O-acetyl-β-allopyranosyl-(1→2)]-β-glucopyranoside (11), 4'-O-methyisoscutellarein 7-O-[6'-O-acetyl-β-allopyranosyl-(1→2)]-β-glucopyranoside (12), 3'-hydroxy-4'-O-methyisoscutellarein 7-O-[6'-O-acetyl-β-allopyranosyl-(1→2)]-β-glucopyranoside (13) and a benzylalcohol derivative (di-O-methylcrenatin) were obtained and identified. The structures were elucidated on the basis of NMR and HRMS data. All compounds were tested for their antioxidant activity by in vitro TEAC assay and some of them exhibited moderate activity (0.97-1.44 mM) when compared with the reference compound (quercetin 1.86 mM). Glycosides 6-13, the most active compounds in the TEAC assay, were also tested by flow cytometry to evaluate their ability to affect the levels of reactive oxygen species (ROS) in human prostate cancer cells (PC3).     

Chemical constituents from the fruits of Gardenia jasminoides Ellis

A new lignan glucoside, (+)-(7S,8R,8'R)-lyoniresinol 9-O-β-D-(6″-O-trans-sinapoyl)glucopyranoside (1), and a new iridoid glucoside, 10-O-trans-sinapoylgeniposide (2), together with eight known compounds, were isolated from the fruits of Gardenia jasminoides Ellis. The structures of the isolates were elucidated by extensive spectroscopic studies, including UV, IR, 1D and 2D NMR, ESI-MS, HR-ESI-MS, and CD experiments. The short-term-memory-enhancement activities of some compounds were evaluated on an Aβ transgenic drosophila model.     

Phenolics from Bidens bipinnata and their amylase inhibitory properties

A new chlorinated flavonoid, 3, 6, 8-trichloro-5, 7, 3', 4'-tetrahydroxyflavone (1), a new biscoumaric acid derivative, 4-O-(2″, 3″-O-diacetyl-6″-O-p-coumaroyl-β-d-glucopyranosyl)-p-coumaric acid (2), and 8, 3', 4'-trihydroxyflavone-7-O-β-d-glucopyranoside (3) together with twenty-four known compounds (4-27) were isolated from the whole plant of Bidens bipinnata. All chemical structures were established on the basis of UV-, MS- and NMR ((1)H, (13)C, (1)H-(1)H COSY, HMQC and HMBC) spectroscopic data. Some of the isolated compounds were tested for the inhibition of α-amylase. The result showed that isookanin (6) was a potent inhibitor of α-amylase (IC(50)=0.447mg/ml).     

Cytotoxic sesquiterpenes and lignans from Saussurea deltoidea

Two new sesquiterpenes deltoiden A (1) and deltoiden B (2), and two new lignans deltoignan A (9) and deltoignan B (10), together with 14 known compounds, including six sesquiterpenes 3-8 and three lignans 11-13, were isolated from the whole plant of Saussurea deltoidea. Compounds 3-8 and 11-17 were isolated for the first time from this plant. Their structures were established by spectroscopic analysis, including 2D-NMR spectroscopic techniques. Cytotoxicities of compounds 1-13 were tested against three cancer cell lines A549, Hela and SMMC-7721. Results showed that 5, 6 and 7 exhibited cytotoxicity against SMMC-7721 with the IC(50) values of 6.49, 9.53, 1.23 μg/ml, 5 and 7 against A549 with the IC(50) values of 4.99 and 5.35 μg/ml, 5, 6, 7, 13 against Hela with the IC(50) values of 1.40, 4.75, 0.93 and 5.42 μg/ml, respectively. The structure-activity relationships of sesquiterpenes 1-8 were discussed on the base of cytotoxic results.     

Bioactive polar compounds from stem bark of Magnolia officinalis

Two new phenylethanoid glycosides magnoloside D (1) and E (2), together with nine known compounds, were isolated from the polar part of methanol extract of the stem bark of Magnolia officinalis. The structures of the new compounds were established on the basis of spectral analysis. Anti-spasmodic activity of four major constituents (3, 4, 9 and 11) was tested in isolated colon of rat, compounds 3, 4, and 9 showed inhibition against acetylcholine, with the effect similar to that of magnolol and honokiol. At the same time, antioxidant activity of the isolated compounds was investigated using a DPPH and an ORAC assay. All of the compounds, except compound 8 showed potent antioxidant capacity in the ORAC assay, while compounds 1-5 and 11 exhibited potent antioxidant activity in the DPPH assay.     

Cycloartane triterpenoids from the stems of Schisandra glaucescens and their bioactivity

Five new cycloartane triterpenoids, schiglausins K-O (1-5), including one hexanortriterpenoid (1) and one octanortriterpenoid (2), as well as two known compounds (6-7), were isolated from the stems of Schisandra glaucescens Diels. Their structures were elucidated on the basis of spectroscopic methods, including extensive NMR spectra. Compounds 2-7 were tested for their FXR agonistic and antagonistic effects. Compound 7 exhibited significant antagonistic effect against FXR with IC(50) of 1.50 μM.     

Triterpene saponins from the roots of Dipsacus asper and their protective effects against the Aβ(25-35) induced cytotoxicity in PC12 cells

Three new triterpene saponins, named asperosaponin A-C (1-3), together with seven known triterpene saponins (4-10) were isolated from the roots of Dipsacus asper. The structures of compounds 1-3 were elucidated on the basis of detailed spectroscopic analysis and chemical methods. Compounds 1-3, 6-10 had significantly protective effects in PC12 cells against the Aβ(25-35) induced cytotoxicity. All the compounds isolated showed no cytotoxic activity against three human cancer cell lines, A-549, Bel-7402 and BGC-823.     

Solanum incanum and S. heteracanthum as sources of biologically active steroid glycosides: confirmation of their synonymy

A new spirostanol saponin (1), along with four known saponins, dioscin (2), protodioscin (3), methyl-protodioscin (4), and indioside D (5), and one known steroid glycoalkaloid solamargine (6) were isolated from the two synonymous species, Solanum incanum and S. heteracanthum. The structure of the new saponin was established as (23S,25R)-spirost-5-en-3β,23-diol 3-O-{β-D-xylopyranosyl-(1→2)-O-α-L-rhamnopyranosyl-(1→4)-[O-α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside}, by using a combination of 1D and 2D NMR techniques including (1)H, (13)C, COSY, TOCSY, NOESY, HSQC and HMBC experiments and by mass spectrometry. The compounds 1, 3, 4 and 5 were evaluated for cytotoxicity against five cancer cell lines and for antioxidant and cytoprotective activity.