Three new biflavonoids from the branches and leaves of Cephalotaxus oliveri and their antioxidant activity

Three new biflavonoids, named oliveriflavones A-C (1–3), together with two known flavonoids (quercetin (4) and rutin (5)), were isolated from the endangered plant Cephalotaxus oliveri. The chemical structures of these compounds were elucidated by comprehensive spectroscopic methods including NMR, HRESIMS, IR, UV, and CD spectra. Compounds 1–5 were first isolated from the genus Cephalotaxus. All the compounds were tested for their antioxidant activity. Compounds 4 and 5 showed excellent activity with IC₅₀ values of 0.03 ± 0.06 μM and 0.02 ± 0.10 μM, respectively.     

A new naphthoquinone analogue and antiviral constituents from the root of Rhinacanthus nasutus

Rhinacanthus nasutus (L.) Kurz (Acanthaceae) is known as traditional medicine for the treatment of fungal and herpes virus infections. A new naphthoquinone racemate, rhinacasutone (1) together with seven known compounds, rhinacanthone (2), rhinacanthins C, D, N, Q, and E (3–7), and heliobuphthalmin (8) were isolated from root of R. nasutus. Their structures were determined on the basis of extensive spectroscopic methods, including 1D-, 2D-NMR and MS data. All the isolated compounds were tested for their antiviral activities against PR8, HRV1B, and CVB3-infected vero cells. Compounds 3–6 exhibited significant antiviral activities with the IC₅₀ value ranging from 0.03 to 23.7 μM in all three infections.     

A new abietane diterpenoid glycoside from ajuga ovalifolia var. calantha

A new abietane diterpenoid glycoside, ajugaside B (1), along with three known compounds (2–4), were isolated from the whole plants of Ajuga ovalifolia var. calantha. The structure of the new compound (1) was elucidated by means of spectroscopic analyses (HRESIMS, IR, NMR and ECD). All of the isolated compounds were evaluated for their antitumor activities against MGC803, MCF-7, A549, HT29 and HepG2 cell lines. Compounds 3–4 showed moderate cytotoxicity against all tested cell lines with IC₅₀ values of 1.8–7.3?μM.     

Two new linear acetogenins from the fruits of Goniothalamus gracilipes

Two new linear acetogenins, gracilipin A (1) and methylsaccopetrin A (2) along with seven known compounds, saccopetrin A (3), 7,3′,4′-trimethylquercetin (4), rhamnazin (5), casticin (6), isokanugin (7), melisimplexin (8) and 5-hydroxy-3,7-dimethoxy-3′,4′-methylenedioxyflavone (9) were isolated from the fruits of Goniothalamus gracilipes Bân. Their structures were established by spectral analysis, such as mass spectrometry, 1D-NMR, 2D-NMR and circular dichroism (CD). Compounds 1 and 3 showed cytotoxic activity against KB cell line with IC₅₀ values of 14.6 and 15.3 μM, respectively.     

Study on chemical constituents of an edible mushroom Volvariella volvacea and their antitumor activity in vitro

Abstract

Phytochemical investigation of the fruiting body of Volvariella volvacea led to the isolation of a new furanone, 2(5H)-furanone-4-propionic acid named volvafuranone A (1), together with twelve known compounds (2–13). Compounds 2–7, 9–11 were isolated from this mushroom for the first time. The isolated compounds were assessed for their cytotoxicity against four human tumour lines (SGC-7901, PC-3M, MCF-7, HepG-2), and the results showed that compound 2, 3, 12, 13 have significant cytotoxicity with IC₅₀ values of 5.90?μM (HepG-2), 20.72?μM (HepG-2), 27.98?μM (PC-3M) and 23.15?μM (PC-3M), respectively.     

A new phenolic compound with antioxidant activity from the branches and leaves of Pyrus pashia

The branches and leaves of Pyrus pashia are used to cure abdominal pain and diarrhoea in Chinese folk medicine. A new phenilic compound, 4-O-β-d-glucopyranosylbenzyl-benzoate ester (1), along with 21 known ones (2–22) were isolated from the branches and leaves of this plant. Compounds 2 and 3 displayed remarkable antioxidant activities against 1,1-diphenyl-2-picrylhydrazyl radical (IC₅₀ = 13.26 ± 0.04 μM, 13.28 ± 0.11 μM, respectively), which were at the same grade as positive control rutin. The caffeoyl group in compounds 2 and 3 was supposed to play an important role in the antioxidant activities.     

Two new aromatic polyketides from a deep-sea fungus Penicillium sp. SCSIO 06720

Abstract

Two new compounds, 5-[2-hydroxypropane-1-yl]-2,6-dimethlbenzene-1,3-diol (1) and coniochaetone L (2), together with 19 known compounds (3–21), were isolated from a deep-sea fungus, Penicillium sp. SCSIO 06720. Their structures and absolute configurations were elucidated by detailed NMR, MS spectroscopic analyses, chiral-phase HPLC analysis, and electronic circular dichroism spectra. All the isolated compounds (1–21) were tested for their antibacterial and HIV latency-reversal activities. Among these compounds, compound 16 showed moderate antibacterial activities against Staphylococcus aureus ATCC 29213 and Methicillin-Resistant Staphylococcus Aureus-shh-1 with MIC values of 10.4?±?3.7?μg/mL and 46.9?±?29.7?μg/mL, respectively, which were comparable to that of the positive control ampicillin with MIC values of 0.5?±?0.4?μg/mL and 2.7?±?0.9?μg/mL, respectively.     

Two new polyketides from the fungus Penicillium oxalicum MHZ153

Two new polyketides, penicilloxalones A (1) and B (2), together with 13 known compounds (3–15), were isolated from the ethyl acetate extract of the solid substrate fermentation cultures of the fungus Penicillium oxalicum MHZ153. The structures of the isolates were determined by spectroscopic analysis and comparison of their spectroscopic and physicochemical data with the literature values. Compounds 7 and 11 showed inhibition of nitric oxide production in lipopolysaccharide-stimulated BV-2 microglial cells with IC₅₀ values of 0.9 ± 0.2 μM and 87.9 ± 0.7 μM, respectively.     

Officinalioside,a new lignan glucoside from Borago officinalis L.

A new lignan glucoside, officinalioside (1), was isolated from n-BuOH fraction of the aerial parts of Borago officinalis L., together with four known compounds: actinidioionoside (2), roseoside (3), crotalionoside C (4) and kaempferol 3-O-β-D-galactopyranoside (5). The structure of the new compound was established by means of spectroscopic and chemical analyses. Compounds 1 and 2 showed a moderate DPPH radical scavenging activity (IC₅₀: 52.6 ± 1.70 and 41.3 ± 0.25 μM, respectively) comparable with that of the standard trolox (16.6 ± 2.2 μM) without any significant cytotoxicity towards human cell line A549 (IC₅₀ > 100 μM).     

A new triterpenoid glucoside from Leucas zeylanica

Abstract

A new triterpenoid glucoside, leuctriterpencoside (1), along with two known compounds (2–3) were isolated from Leucas zeylanica. The structure of the new compound was elucidated using comprehensive spectroscopic methods. Compound 1 showed significant inhibitory activity against α-glucosidase (IC₅₀ value of 0.85?±?0.12?μM).     

A new morphinandienone alkaloid from the stems of Fissistigma tungfangense

A new morphinandienone alkaloid, fissistigmine A (1), together with three known alkaloids (2?4), were isolated and identified from the stems of Fissistigma tungfangense. Among them, fissistigmine A (1) represents the first example of a novel naturally occurring morphinandienone alkaloid with a unique cleavage of the C-9?N-17 bond. All isolated compounds were evaluated for their anti-rheumatoid arthritis activities via examining their anti-proliferative effects on synoviocytes in vitro. Compound 1 exhibited inhibitory effect on the proliferation of synoviocytes with an IC₅₀ value of 114.6 ± 2.2 μM.     

Neolignan and phenylpropanoid compounds from the fruits of Illicium simonsii Maxim

One new sesqui-neolignan compound, namely, sesqui-illisimonan A (1), one new neolignan, illisimonan A (2), and one new phenylpropanoid compound, illisimoid A (3) were isolated from the fruits of Illicium simonsii Maxim. The structures and absolute configurations of these compounds were determined by extensive spectroscopic, including NMR, circular dichroism and calculated electronic circular dichroism methods. The antioxidant activities of compounds 1–3 were also evaluated. Vitamin E was selected as the positive control (IC₅₀ = 49.73 ± 0.88 μM). Compounds 1 and 2 exhibited in vitro antioxidant activity with an IC₅₀ value of 55.76 ± 1.30 and 59.36 ± 0.50 μM, respectively. However, the compound 3 didn’t show obvious antioxidant activity.     

Hepatoprotective and neuroprotective tocopherol analogues isolated from the peels of Citrus unshiu Marcovich

Three tocopherol analogues methoxytocopherol (1), α-tocopherol (2) and γ-tocopherol (3) were isolated from the peels of Citrus unshiu Marcovich. The protective effects of the isolated compounds against tert-butyl hydroperoxide-induced hepatotoxicity in human liver-derived HepG2 cells and glutamate-induced oxidative stress in HT22-immortalised hippocampal cells were evaluated. Compounds 1–3 were significantly protective in HepG2 cells with EC₅₀ values of 21.22 ± 2.01, 25.21 ± 2.11 and 25.25 ± 1.21 μM, respectively, and in HT22 cells, compounds 1–3 had EC₅₀ values of 20.62 ± 1.36, 6.44 ± 1.65 and 9.52 ± 1.54 μM, respectively.     

A new cytotoxic biflavonoid from the rhizome of Wikstroemia indica

One new chalcone-flavone biflavonoid, 3′-hydroxydaphnodorin A (1), together with 12 known biflavonoids (2–13), was isolated from the rhizome of Wikstroemia indica. Their structures were established on the basis of extensive spectroscopic methods. Eight isolated compounds 1–3, 6, 7, 9, 12 and 13 were evaluated for their cytotoxic activities against cancer-derived cell lines Hep3B, HepG2 and CNE2, and 1 was found to possess moderate cytotoxicity against HepG2 and CNE2 cell lines, with IC₅₀ values of 65.5 ± 11.4 and 53.6 ± 10.1 μM, respectively.     

A new cytotoxic polycyclic polyprenylated acylphloroglucinol from Garcinia nujiangensis screened by the LC-PDA and LC-MS

Abstract

A new polycyclic polyprenylated acylphloroglucinol (1), nujiangefolin D, together with five known analogues (2–6), were isolated from the fruits of Garcinia nujiangensis. Compound 1 was screened by the LC-MS and LC-PDA. The structure of 1 was elucidated on the basis of extensive spectroscopic techniques including 1?D and 2?D NMR and MS analyses. The compounds isolated were evaluated for their cytotoxic activities against three cancer cell lines, 1 showed moderate cytotoxic activity against Hela, PANC-1, and MDA-MB-231 cell lines with IC₅₀ values of 5.6?±?0.1, 9.1?±?0.2, and 8.3?±?0.2?μM, respectively. The antitumor mechanism was explained via virtual docking of 1 to the main sites in the human serine/threonine-protein kinase mTOR (mTOR) crystal structure (PDB code: 4DRI). Furthermore, 1 may inhibit Hela cell proliferation through mTOR by the western blotting analysis. Taken together, 1 may be a potential mTOR inhibitor used for the treatment of cervical cancer.     

A new abietane diterpenoid from the roots of Tripterygium regelii

A new abietane diterpenoid, tripterregeline A (1), together with six known diterpenoids (2–7), were isolated from the roots of Tripterygium regelii. The structure of 1 was elucidated by extensive spectroscopic methods and the known compounds were identified by comparison with data reported in the literature. All isolated compounds were evaluated for their cytotoxicities against five human cancer cell lines: HL-60, SMMC-7721, A-549, MCF-7 and SW480 in vitro. Compounds 1–7 showed significant inhibitory effects against various human cancer cell lines with IC₅₀ values ranging from 0.58 to 21.06 μM.     

Biological and phytochemical studies on Capparis decidua (Forssk) Edgew from Cholistan desert

Abstract

The present work deals with the biological and phytochemical studies on Capparis decidua (Forssk) Edgew from Cholistan desert of Pakistan. Aerial and floral parts of C. decidua were collected and dried under shade. Powdered materials of each part of C. decidua were extracted with methanol separately, followed by phytochemical studies. Hexane fraction of aerial parts of the C. decidua obtained after solvent-solvent extraction was purified through repeated column chromatography by increasing order of polarity. Four compounds were purified and identified as simiarenol (1), lupeol (2), taraxerol (3) and β-sitosterol (4). Simiarenol and lupeol were isolated for the first time from genus Capparis. The structures of these compounds were established by comparing the spectroscopic data (¹H NMR, ¹³C NMR, IR, UV & Mass spectrometry) reported in literature. The structure of 1 was further confirmed by XRD analysis. Anti-bacterial activities of crude methanolic extracts were determined against 13 bacterial strains (MIC 250-1000?μg/mL). α-Glucosidase and urease inhibitory activities of pure compounds were also determined. Compounds 1, 2 and 4 showed α-glucosidase inhibition with IC₅₀ at 96.12?±?0.12, 65.28?±?0.13 and 128.14?±?0.17?μM, respectively.     

A new triterpenoid saponin and a diterpene glucoside from the seeds of Orychophragmus violaceus

One new triterpenoid saponin orychoside A (1) and one new diterpene glucoside orychoside B (12), together with eleven known compounds, were isolated from the seeds of Orychophragmus violaceus. The structures of the new compounds were elucidated on the basis of spectroscopic analysis. The known compounds were identified by comparison with data reported in the literature. All compounds were tested for their cytotoxic activities against the HepG2 and A549 cell lines in vitro. The new compound 1 exhibited potent cytotoxicity against the two cell lines with IC₅₀ values of 7.13 and 8.77 μM, respectively. Compounds 2, 5, 8 and 9 were found to possess obvious cytotoxicity.