Polyphenolic compounds from the leaves of Koelreuteria paniculata Laxm

From the fresh leaves of Koelreuteria paniculata Laxm (Sapindaceae), four new compounds, named ethyl p-trigallate (1), 3"-O-galloyl-4'-O-galloyl-4-O-galloyl-gallic acid (2), ethyl p-heptagallate (3) and 3"-galloylquercitrin (4), together with 12 known compounds namely catechin (5), galloylepicatechin (6), isorhamnetin (7), kaempferol-3-O-arabinopyranoside (8), quercetin-3'-O- g -D-arabinopyranoside (9), quercitrin (10), methyl p-digallate (11), methyl m-digallate (12), p-digalloyl acid (13), m-digalloyl acid (14), hyperin (15) and kaempferol-3-O- f -L-rhamnoside (16) were isolated by extensive column chromatographic separation. Their structures were elucidated on the basis of chemical and spectroscopic methods. Compound 9 was not reported previously with pyranoside of arabinose at C-3'. Compounds 4 and 9 possessed the activity for PTK inhibition.     

A new ferulic acid ester and other constituents from Dracocephalum peregrinum

A new ferulic acid ester, 1′-methyl-2′-hydroxyethyl ferulate (1), together with methylcaffeate (2), 4-hydroxy cinnamic acid (3), ferulic acid (4), caffeic acid (5), diosmetin (6), luteolin (7), 5,3′,4′-trihydroxy-3,7-dimethoxyflavone (8), eriodictyol (9), kaempferol (10), quercetin (11), acacetin-7-O-glcopyranoside (12), 4-(β-glucopyranosyloxy) benzoic acid (13), luteolin-7-O-(6″-feruloyl) glucopyranoside (14), luteolin-7-O-glucopyranoside (15), kaempferide-3-O-rhamnopyranoside (16), quercitrin (17), kaempferol-3-O-glucopyranoside (18), prunasin (19), quercetin-7-O-glucopyranoside (20), quercetin-3-O-glucopyranoside (21), plantaginin (22), linarin (23), luteolin-7-O-rutinoside (24), and chlorogenic acid (25) were isolated from the aerial parts of Dacocephalum peregrinum. The structure of 1 was elucidated on the basis of spectroscopic and HR-ESI-MS analyses. In addition, compound 1 exhibited mild inhibitory effect on NO production in LPS-stimulated RAW264.7 cells.     

Seven new dammarane triterpenes from the floral spikes of Betula platyphylla var. japonica

Seven new dammarane-type triterpenoids, including two 20(S)-hydroxy-25-methoxy-dammar-23-enes (1 and 2), two 20(S),24(R)-epoxydammaranes (3 and 4), a cabralealactone (5), and two 20(S),25-epoxydammaranes (6 and 7), together with seven known triterpenes (8–14), were isolated from the floral spikes of Betula platyphylla var. japonica. The structures for all compounds were elucidated by the analyses of extensive spectroscopic data, as well as chemical examinations.     

Constituents of the roots of <Emphasis Type="Italic">Ligularia dentata</Emphasis> Hara

Nine known compounds, butyrospermol (1), lupeol (2), stigmast-4-en-3-one (3), stigmast-4-ene-3,6-dione (4), (+)-methyl abscisate (5), methyl indole-3-carboxylate (6), vanillin (7), methyl (E)-caffeate (8), and methyl (E)-ferulate (9), and two new compounds, methyl (E)-feruloylglycolate (10), and methyl-7,8-dihydro-(S)-7-methoxyferulate (11), have been isolated from the roots of Ligularia dentata Hara (Compositae). The structures were elucidated on the basis of spectral data.     

Secoiridoid glycosides from the leaves of <Emphasis Type="Italic">Hydrangea macrophylla</Emphasis> subsp. <Emphasis Type="Italic">serrata</Emphasis>

Seven secoiridoid glycosides, secologanin dimethyl acetal (1), n-butyl vogeloside (2), n-butyl epi-vogeloside (3), (7R)-n-butyl morroniside (4), hydrangenoside A (5), hydrangenoside C (6), and hydrangenoside A dimethyl acetal (7), have been isolated from the leaves of Hydrangea macrophylla subsp. serrata (Thunb.) Makino (Saxifragaceae). The structures were elucidated on the basis of spectral data.     

Five new compounds from Dendrobium crystallinum

Five new compounds, dencryol A (1), dencryol B (2), crystalltone (3), crystallinin (4), and 3-hydroxy-2-methoxy-5,6-dimethylbenzoic acid (5), together with six known compounds, dendronobilin B (6), syringic acid (7), apigenin (8), isoviolanthin (9), 6?-glucosyl-vitexin (10), and palmarumycin JC2 (11), have been isolated from the stems of Dendrobium crystallinum, of which compounds 9–11 were isolated from the genus Dendrobium for the first time, and all the other compounds were first obtained from this plant. Their structures were established on the basis of spectroscopic analysis and literature data.     

Two new triterpenoid saponins from the flowers and buds of Lonicera japonica

Two new triterpenoid saponins, loniceroside D (1) and loniceroside E (2), were isolated from the dry flowers and buds of Lonicera japonica Thunb., along with seven known compounds, chlorogenic acid (3), sweroside (4), vogeloside (5), epi-vogeloside (6), loniceroside A (7), loniceroside B (8), and loniceroside C (9). Their structures were elucidated on the basis of spectroscopic data, physicochemical properties, and acid hydrolysis.     

New flavonoids with 2BS cell proliferation promoting effect from the seeds of <Emphasis Type="Italic">Trigonella foenum</Emphasis>-<Emphasis Type="Italic">graecum</Emphasis> L.

Ten flavonoids were isolated from the ethyl acetate-soluble fraction of the ethanolic extract of the seeds of Trigonella foenum-graecum and their structures were elucidated on the basis of spectroscopic methods to be 5,7,3′-trihydroxy-5′-methoxylisoflavone (1), biochanin A (2), formononetin (3), irilone (4), tricin (5), daidzein (6), calycosin (7), orientin-2″-O-p-trans-coumarate (8), vitexin-2″-O-p-trans-coumarate (9), and tricin-7-O-β-d-glucopyranoside (10). Compounds 1 and 8 are new flavonoids, and 8 and 9 strongly promoted 2BS cell proliferation induced by H₂O₂.     

Phenolic compounds from the twigs and leaves of Tara (Caesalpinia spinosa)

Two new homoisoflavans, 4′-hydroxy-7-methoxy-3-benzyl-2H-chromene (1) and 3,4-cis-di-O-3-hydroxy-7-methoxy-3-(4-hydroxybenzyl)-4-ethoxychroman (2), one new coumarin, 7-methoxy-3-(4-hydroxybenzyl)coumarin (4), together with seven known phenolic compounds, bonducellin (3), anemarcoumarin A (5), (+)-syringaresinol (6), curuilignan D (7), scopoletin (8), and p-hydroxybenzaldehyde (9), were isolated from Tara (Caesalpinia spinosa Kuntze). The structures of the new compounds were characterized from their 1D and 2D NMR spectral data. All the compounds were isolated from this plant for the first time.     

Kopsiyunnanines F and isocondylocarpines: new tubotaiwine-type alkaloids from Yunnan <Emphasis Type="Italic">Kopsia arborea</Emphasis>

Five new alkaloids, including three 19,20-epoxytubotaiwine stereoisomers, viz. kopsiyunnanines F1 (1), F2 (2), and F3 (3), (Z)-isocondylocarpine (4), and (Z)-isocondylocarpine N-oxide (5), along with five known tubotaiwine-type indole alkaloids were isolated from the aerial part of Yunnan Kopsia arborea Blume (Apocynaceae). Their structures including absolute configurations were elucidated by spectroscopic and chemical means.     

Free radical scavengers from the aerial parts of <Emphasis Type="Italic">Euphorbia petiolata</Emphasis>

Reversed-phase preparative high-performance liquid chromatography (HPLC) of the methanol extract of the aerial parts of Euphorbia petiolata Banks & Soland, an endemic Iranian medicinal plant, yielded ten free radical scavengers including eight flavonoid glycosides myricetin 3-O-glucoside (1), kaempferol 3-O-(2-O-galloyl)-glucoside (2), myricetin 3-O-rhamnoside (3), quercetin 3-O-glucoside (4), kaempferol 3-O-glucoside (5), quercetin 3-O-rhamnoside (6), kaempferol 3-O-rhamnoside (7), and quercetin 3-O-rutinoside (10), a coumarin esculetin (8) and a phenylpropanoid 2-hydroxydihydrocinnamic acid (9). The structures of these compounds were elucidated conclusively by spectroscopic means and also by direct comparison of their spectroscopic data with respective published data. The free radical scavenging properties of these compounds were assessed by the 2,2-diphenyl-1-picrylhydrazyl assay.     

A new triterpene ester and other chemical constituents from the aerial parts of Anodendron paniculatum and their cytotoxic activity

The aim of the research was to study the active constituents of Anodendron paniculatum Roxb. (Apocynaceae). A new triterpene ester, named anopaniester (1), and cycloartenol (2), ursolic acid (3), esculenic acid (4), bis-(2-ethylhexyl) phthalate (5), desmosterol (6), stigmasterol (7), vaniline (8), and (E)-phytol (9), were isolated from the aerial parts of A. paniculatum. Compounds 3 and 6 showed the significant inhibitory effect (IC₅₀ values ranging from 30.89 ± 3.60 to 44.37 ± 5.40 μg/ml) against tested human cancer cell lines LU-1 and MKN-7. The compounds 1–4, and 6 were isolated from this genus Anodendron for the first time.     

Aspergchromones A and B,two new polyketides from the marine sponge-associated fungus Aspergillus sp. SCSIO XWS03F03

Two new polyketides, aspergchromones A (1) and B (2), together with five known compounds, secalonic acid D (3), noreugenin (4), (3S)-5-hydroxymellein (5), (4S)-6-hydroxyisosclerone (6), and (-)-regiolone (7), were isolated from the ethyl acetate extract of marine sponge-derived fungus Aspergillus sp. SCSIO XWS03F03. Their structures were elucidated by means of spectroscopic techniques (1D and 2D NMR, MS, UV, and IR). The absolute configurations of the new compounds were established by ECD calculations. Compound 3 showed moderate antimicrobial activity.     

Isolation and characterization of secondary metabolites from Plumeria obtusa

Chromatographic purification of the methanolic extract of Plumeria obtusa yielded two new iridoid obtusadoids A (1) and B (2), along with eight known compounds plumieridin A (3), plumieridine (4), 1α-plumieride (5), 15-demethylplumieride (6), rel-(3R,3′S,4R,4′S)-3,3′,4,4′-tetrahydro-6,6′-dimethoxy[3,3′-bi-2H-benzopyran]-4,4′-diol (7), glochiflavanoside B (8), oleanolic acid (9), and methyl coumarate (10). The structures of all the isolates (1–10) were determined by NMR spectroscopy and mass spectrometry. The data of known compounds (3–10) were further compared with the reported data for these compounds.     

甘草酸及其苷元甘草次酸的盐皮质激素样作用研究进展

甘草酸在体内水解成甘草次酸,甘草次酸的化学结构类似于甾体激素,因此甘草酸是甘草次酸的前体药物.甘草酸和甘草次酸是甾体激素代谢失活酶(尤其是Ⅱ型11β-羟化甾体脱氢酶)抑制剂,可提高内源性和外源性皮质激素的活性.甘草酸和甘草次酸又可作为配体,与皮质激素受体结合呈现出糖皮质激素、盐皮质激素样作用.因此长期使用甘草或甘草酸类...     

Alkaloids from the hook-bearing branch of Uncariarhynchophylla and their neuroprotective effects against glutamate-induced HT22 cell death

One new alkaloid, 4-geissoschizine N-oxide methyl ether (1), was isolated from the EtOH extract of the hook-bearing branch of Uncariarhynchophylla, together with 10 known alkaloids, 3-epi-geissoschizine methyl ether (2) isolated from U.rhynchophylla for the first time, geissoschizine methyl ether (3), 4-hirsuteine N-oxide (4), hirsuteine (5), hirsutine (6), 3α-dihydro-cadambine (7), 3β-isodihydro-cadambine (8), cadambine (9), strictosamide (10), and akuammigine (11). The structures were elucidated by spectroscopic methods including UV, ESI-QTOF MS, NMR, and circular dichroism experiments. Neuroprotective effects of 1–9 were investigated against 3 mM glutamate-induced HT22 cell death. The activity assay showed that 2, 3, 5, and 6 exhibited potent neuroprotective effects against glutamate-induced HT22 cell death. However, only weak neuroprotective activities were observed for 1, 4, 7, 8, and 9.     

Microbial deglycosylation and ketonization of ginsenosides Rg1 and Rb1 by Fusarium oxysporum

Two major ginsenosides, ginsenoside-Rg₁ (1) and ginsenoside-Rb₁ (2), were transformed by the fungus Fusarium oxysporum f. sp. Lycopersici (Z-001). 1 was converted into five metabolites, ginsenoside-F₁ (3), 6α,12β-dihydroxydammar-3-one-20(S)-O-β-d-glucopyranoside (4), 3a-oxa-3a-homo-6α,12β-dihydroxydammar-3-one-20(S)-O-β-d-glucopyranoside (5), 20(S)-protopanaxatriol (6), and 3-oxo-20(S)-protopanaxatriol (7). 2 was converted into four metabolites, ginsenoside-Rd (8), ginsenoside-F₂ (9), compound K (10), and 12β-hydroxydammar-3-one-20(S)-O-β-d-glucopyranoside (11). The structures of these metabolites were determined by the analysis of extensive spectroscopic data. Among them, 4 and 5 were two new compounds. Deglycosylation and ketonization at C-3 were recognized as the characteristic reactions of this strain.     

Phytochemical investigation of Tiarella polyphylla

Seven flavonoids (1–7), two triterpenoids (8 and 9) and four steroids (10, 11, 12 and 13) were isolated from the whole plant of Tiarella polyphylla. Based on the physicochemical and spectroscopic analyses, their structures were identified as myricetin (1), astragalin (2), afzelin (3), quercitrin (4), myricitin (5), nicotiflorin (6), isoquercitrin (7), tiarellic acid (8), 3β-hydroxy-20(29)lupen-27-oic acid (9), β-sitosterol-3-O-β-D-glucoside (10), stigmasterol-3-O-β-D-glucoside (11), β-sitosterol (12) and ergosterol endoperoxide (13). All 13 compounds, with the exception of tiarellic acid were isolated for the first time from T. polyphylla. In the anti-complementary assay, the steroids (12 and 13) exhibited potent activities; whereas, the flavonoids (1 to 7) showed weak or no activities, but even the triterpenoids (8 and 9) and steroidal saponins (10 and 11) evoked hemolysis.     

Note: A New Flavone from Hypericum Wightianum

A new flavone, wightianin (1), along with five known compounds, n-triacontanol (2), betulinic acid (3), oleanolic acid (4), 3,4-O-isopropylidene-shikimic acid (5), and isoquercitrin (6), were isolated from the whole plants of Hypericum wightianum Wall ex Wight et Arn. Their structures were elucidated on the basis of spectral data, including 2D NMR techniques.     

Caragasinin C: a new oligostilbene from the roots of Caragana sinica

A new oligostilbene, caragasinin C (1), and seven known compounds, betulinic acid (2), 4-hydroxybenzaldehyde (3), (?)-medicarpin (4), wistin (5), (2E,4S)-4-hydroxy-2-nonenoic acid (6), pallidol (7), and (+)-α-viniferin (8), were isolated from the roots of Caragana sinica. The structure of caragasinin C was established on the basis of spectroscopic techniques, including HRESIMS, 1D and 2D-NMR.