RÉSUMÉ
Many herbal species in the genus Ligustrum have been shown to contain compounds with anti-cancer biological activity. This study aimed to isolate some compounds from the leaves of Ligustrum robustum (Roxb.) Blume (L. robustum) and evaluate their effects against liver cancer cells. As a result, seven previously reported compounds (1-7) were isolated, including four lignans (1-4) and three phenolic derivatives (5-7). The structures of these compounds were determined using spectroscopic methods and comparison with reported data. All isolates were assessed for their inhibitory effects on HepG2 liver cancer cells. Screening results revealed that two compounds, isocubein (3) and 4-(2-acetoxyethyl)phenol (7), exhibited strong inhibitory activity against cell proliferation, with IC50 values of 3.1±0.9 and 4.5±14 µM, respectively. Further analyses demonstrated that both compounds could suppress the formation and development of 3D tumorspheres in terms of quantity and size. Additionally, isocubein (3) and 4-(2-acetoxyethyl)phenol (7) exhibited the ability to inhibit the migration of HepG2 cells. This study represents the first report on the inhibitory activity against HepG2 liver cancer cells of extracts and isolated compounds from L. robustum, providing valuable information for future research aiming to develop products for liver cancer treatment.
RÉSUMÉ
Vietnamese ginseng (Panax vietnamensis Ha and Grushv., Araliaceae) is indigenous in the central highlands of Vietnam and the southernmost distribution in the Panax genus. Like other ginseng, Vietnamese ginseng is well known has been used as a tonic and for management of certain diseases in the traditional medicine. Nevertheless, it is noteworthy that in respect to the long history in use and systematic studied on Korean ginseng (P. ginseng), American ginseng (P. quinquefolius), Japanese ginseng (P. japonicus), and Chinese ginseng (P. notoginseng), the up-to-date published database on Vietnamese ginseng is relatively much less extensive. In our ongoing research on the promising Vietnamese medicinal plants, the present phytochemical investigation of the ethanol extract of the leaves of Panax vietnamensis led to the isolation of three compounds (1-3), including a new indole alkaloid N-glycoside (1) and two known compounds. Their structures were elucidated based on extensive physiochemical and chemical methods, especially the interpretation of NMR and MS spectra. The absolute configuration of 1 was determined based on the comparison of its experimental and theoretical ECD spectra along with NMR calculation. Compound 1 is naturally isolated N-glycoside, which is rarely found in natural products. The isolated compounds showed weak or no inhibitory activity against acetylcholinesterase enzyme (AChE).
Sujet(s)
Glucosides , Panax , Acetylcholinesterase , Glucosides/composition chimique , Panax/composition chimique , Feuilles de plante/composition chimique , VietnamRÉSUMÉ
(±)-Patulinervones A (1) and B (2), two diastereomers of spiro-lignans sharing an unprecedented dimethyl-spiro[furan-2,2'-furo[2,3-b]furan] 5/5/5 tricyclic moiety were isolated from the leaves of Melicope patulinervia (Merr. & Chun) C.C. Huang. Their structures were established by extensive spectroscopic data and electronic circular dichroism (ECD) analyses. The racemates (±)-1 and 2 and their enantiomers exhibited α-glucosidase inhibitory effect with IC50 values range of 10.08 ± 1.24 - 25.58 ± 1.97 µM.
RÉSUMÉ
Six new oligomeric neolignans including two trimeric neolignans (1 and 2) and four dimeric neolignans (3-6) were isolated from the leaves of Magnolia officinalis var. biloba. Their structures were determined based on HR-ESIMS and NMR data, as well as electronic circular dichroism (ECD) calculations. Compound 1 is formed from two obovatol moieties directly linked to an aromatic ring of the remaining obovatol moiety, which is an unprecedented type of linkage between monomers. All isolates were assessed for their inhibitory effects on NO production in LPS-stimulated RAW 264.7 macrophage cells. Compounds 1 and 3 showed significantly inhibitory activities with IC50 values of 6.04 and 3.26 µmol·L-1, respectively.
Sujet(s)
Lignanes , Magnolia , Animaux , Lignanes/pharmacologie , Magnolia/composition chimique , Souris , Structure moléculaire , Composés phytochimiques/pharmacologie , Extraits de plantes/pharmacologie , Feuilles de plante/composition chimique , Cellules RAW 264.7RÉSUMÉ
Four new lignans, patulinones A-D (1-4) and three new acetophenone derivatives, patulinones E-G (5-7) were isolated from the leaves of Melicope patulinervia. Their structures were elucidated on the basis of the interpretation of HR-ESIMS, NMR, CD data. All the isolated compounds were evaluated for α-glucosidase inhibitory activity. Of the isolates, compound 4 was found to exhibit the strongest inhibition against α-glucosidase with IC50 value of 6.02 ± 0.46 µM.
Sujet(s)
Acétophénones/pharmacologie , Inhibiteurs des glycoside hydrolases/pharmacologie , Lignanes/pharmacologie , Rutaceae/composition chimique , Acétophénones/isolement et purification , Chine , Inhibiteurs des glycoside hydrolases/isolement et purification , Lignanes/isolement et purification , Structure moléculaire , Composés phytochimiques/isolement et purification , Composés phytochimiques/pharmacologie , Feuilles de plante/composition chimiqueRÉSUMÉ
(±)-Patulignans A-C (1-3), three unique pairs of lignan enantiomers were isolated from the leaves of Melicope patulinervia. Patulignan A (1) possesses an unprecedented dimethyloxonane moiety in nature, meanwhile patulignans B (2) and C (3) are epimers carrying a novel dimethyl-1,6-dioxaspiro[4.5]decane skeleton. Their structures were established by spectroscopy methods and electronic circular dichroism (ECD) calculations. Compounds 1-3 showed significant inhibitory activity against α-glucosidase.
Sujet(s)
RutaceaeRÉSUMÉ
Six new obovatol trimeric neolignans, houpulignans A-F (1-6) were isolated from the leaves of Magnolia officinalis var. biloba. Their structures were determined on the basis of the interpretation of HRESIMS, NMR data, and electronic circular dichroism (ECD) calculations. Compounds 1 and 2 are the first examples of neolignans derived from three units of obovatol bearing a rare 1,4-benzodioxepane moiety. Compound 3 possesses a benzodihydropyran ring, meanwhile three units of obovatol in 4-6 are connected by an alkyl chain. Compounds 1-3 inhibited NO production in LPS-stimulated RAW264.7 cells with IC50 values of 8.01, 20.21, and 4.05 µM, respectively.
Sujet(s)
Dérivés du biphényle/composition chimique , Dérivés du biphényle/pharmacologie , Lignanes/composition chimique , Lignanes/pharmacologie , Magnolia/composition chimique , Monoxyde d'azote/antagonistes et inhibiteurs , Éthers phényliques/composition chimique , Éthers phényliques/pharmacologie , Animaux , Macrophages/effets des médicaments et des substances chimiques , Macrophages/métabolisme , Souris , Monoxyde d'azote/métabolisme , Extraits de plantes/composition chimique , Extraits de plantes/pharmacologie , Feuilles de plante/composition chimique , Cellules RAW 264.7RÉSUMÉ
(±)-Melipatulinones A-C (1-3), three unique enantiomeric pairs of lignan-phloroglucinol hybrids along with the biogenetically related compound melipatulignan A (4), were isolated from the leaves of Melicope patulinervia. Melipatulinones A (1) and B (2) share a novel spiro[hydrobenzofuran-2,3'-furan] 5/5/6 tricyclic ring system, while melipatulinone C (3) features an unprecedented spiro[cyclopenta[b]hydrofuran-2,3'-furan] 5/5/5 tricyclic framework. Their structures were determined by spectroscopic methods, electronic circular dichroism (ECD) calculations, and X-ray diffraction. Compounds 1-3 exhibited a pancreatic lipase inhibitory effect.
Sujet(s)
Antienzymes/pharmacologie , Lignanes/pharmacologie , Triacylglycerol lipase/antagonistes et inhibiteurs , Rutaceae/composition chimique , Antienzymes/composition chimique , Antienzymes/isolement et purification , Lignanes/composition chimique , Lignanes/isolement et purification , Triacylglycerol lipase/métabolisme , Conformation moléculaire , Pancréas/enzymologie , Feuilles de plante/composition chimique , StéréoisomérieRÉSUMÉ
A new phloroglucinol derivative, named eucalyptin B (1), along with five related known compounds (2 - 6), was isolated from the fruits of Eucalyptus globulus. Their structures were elucidated by means of 1D- and 2D-NMR spectroscopy, with the absolute configuration of 1 determined by electronic circular dichroism (ECD) calculations. All isolated compounds (1 - 6) were evaluated for their cytotoxic activities against lung (A549), breast (4T1), and skin (B16F10) cancer cell lines. On the basis of cell viability assay, the cytotoxic activity of eucalyptin B (1) was further confirmed by apoptosis assay. Additionally, after treatment with eucalyptin B (1), the apoptosis factor proteins (Bcl2 and Bax) and caspase-3 levels in A549 cells were also determined by Western-blot analysis. By cytotoxic assay, eucalyptin B (1) exhibited potent cytotoxicity against A549 cells with an IC50 value of 1.51 µm and induced concentration dependent apoptosis of up to 49%. Additionally, eucalyptin B (1) inhibited 5-fold and increased 10-folds in the level of Bcl2 and Bax, respectively. Furthermore, the 11-fold increase in the level of caspase-3 confirmed eucalyptin B (1) activated caspase dependent apoptosis pathway. In conclusion, the isolated compound eucalyptin B (1) has promising cytotoxic activity in tumor cells, especially in A549.
Sujet(s)
Antinéoplasiques d'origine végétale/pharmacologie , Eucalyptus/composition chimique , Fruit/composition chimique , Phloroglucinol/pharmacologie , Antinéoplasiques d'origine végétale/composition chimique , Antinéoplasiques d'origine végétale/isolement et purification , Apoptose/effets des médicaments et des substances chimiques , Prolifération cellulaire/effets des médicaments et des substances chimiques , Relation dose-effet des médicaments , Tests de criblage d'agents antitumoraux , Humains , Phloroglucinol/composition chimique , Phloroglucinol/isolement et purification , Relation structure-activité , Cellules cancéreuses en cultureRÉSUMÉ
This study investigated the effects of meteorological conditions and spatial variations on the toxicity of polycyclic aromatic hydrocarbons (PAHs) in airborne PM(10) in Ulsan, the largest industrial city in Korea. Daily PM(10) samples were collected on quartz microfiber filters using high volume samplers located in a downtown area, a residential area and an industrial area of Ulsan during spring and summer sampling periods. Sixteen individual PAHs were extracted into a mixture solution of dichloromethane and n-hexane (1:1, v/v) in an ultrasonic bath and were analyzed using a high performance liquid chromatography system with an ultra-violet detector (HPLC-UVD). The average total PAH concentrations from the three representative sampling sites of Ulsan ranged from 16.15 to 57.12 ng/m(3) in spring and from 11.11 to 34.56 ng/m(3) in summer. The toxicity equivalent concentrations (TEQs) of the PAHs in PM(10) of Ulsan ranged from 1.82 to 13.1 ng/m(3), with an average level of 4.17 ng/m(3). The highest TEQs were found in the downtown area, which had an average value of 6.30 ng/m(3) in spring and 5.52 ng/m(3) in summer. BaP and DahA were identified as the major carcinogenic PAHs that contributed to 34.8 and 59.4% of the total carcinogenic potency of PAHs in PM(10) in Ulsan. The identified TEQs were highly correlated (r(2) = 0.73-0.90, p<0.01) with the total PAH concentrations for each area. The TEQs showed a significant correlation (p < 0.01) with the concentration of air pollutants, including PM(10), PM(2.5) and NO(2).