RESUMEN
Ten new B-ring aromatized 6/6/6-tricyclic dearomatized benzocogeijerene-based meroterpenoids with unusual methyl 1,2-shift or demethylation (2-9b), and two new geranylquinol derivatives (1 and 10), together with two known compounds (11 and 12), were isolated from the roots of Arnebia euchroma. Their structures were elucidated by extensive spectroscopic methods, X-ray diffraction crystallography, and ECD calculations. The plausible biosynthetic pathways including the unusual methyl 1,2-shfit and demethylation for B-ring aromatized 6/6/6-tricyclic meroterpenoids were discussed. Compounds 1, 2, 5, 6, 11, and 12 showed significant cardioprotective activities comparable to diltiazem against isoprenaline (ISO)-induced H9C2 cell damage in vitro. Compound 11 probably exerted heart-protective effect on ISO-induced H9C2 cells by modulating the PI3K-AKT-mTOR pathway, reducing excessive autophagy, and decreasing myocardial apoptosis.
RESUMEN
Two new cucurbitane-type triterpenoid saponins, 2,20ß,22ß-trihydroxy-16α,23(R)-epoxycucurbita-1,5,24-triene-3,11-dione 2-O-ß-D-glucopyranoside (1), 2,20ß,22α-trihydroxy-16α,23(S)-epoxycucurbita-1,5,11,24-tetraene-3-one 2-O-ß-D-glucopyranoside (2) were isolated from the fruit of Citrullus colocynthis (L.) Schrad. Their structures were elucidated by mass spectrometry, IR, 1D, and 2D NMR spectroscopy, etc. Besides, both of the compounds showed significant hepatoprotective activities at 10 µM against paracetamol-induced HepG2 cell damage.
RESUMEN
Six new iridoid glycosides were isolated from the ethyl acetate fraction of the whole plants of Hedyotis diffusa Willd. They were identified as E-6-O-p-methoxycinnamoyl-10-O-acetyl scandoside acid methyl ester (1), Z-6-O-p-methoxycinnamoyl-10-O-acetyl scandoside acid methyl ester (2), E-6-O-caffeoyl scandoside methyl ester (3), E-6-O-p-coumaroyl-6'-O-acetyl scandoside methyl ester (4), Z-6-O-p-coumaroyl-6'-O-acetyl scandoside methyl ester (5), and E-6-O-p-coumaroyl-4'-O-acetyl scandoside methyl ester (6). The structures of them were elucidated based on unambiguous spectroscopic data (UV, IR, HRESIMS, and NMR). They were screened for anti-inflammatory effect, antioxidant effect, antitumor effect, and neuroprotective effect and did not show potent activities.
Asunto(s)
Ácidos Cumáricos , Hedyotis , Glicósidos Iridoides , Glicósidos Iridoides/farmacología , Hedyotis/química , Antioxidantes , Espectroscopía de Resonancia Magnética , Ésteres , Glicósidos/farmacologíaRESUMEN
Three new flavonoids including two isoflavanones sophortones A and B (1 and 2), and one chalcone sophortone C (3) were isolated from the roots of Sophora tonkinensis. Their structures were established by UV, IR, HRESIMS, and NMR data. The absolute configurations of 1 and 2 were determined by electronic circular dichroism (ECD) calculations.
RESUMEN
Eight new arnebinol B-based meroterpenoids ((-)-1, 2, 3, (-)-5, and 7-10) with a constrained 6/10/5 tricyclic backbone were isolated from the roots of Arnebia euchroma. The planar and steric structures of these new compounds were unambiguously elucidated by extensive spectroscopic analyses, X-ray diffraction crystallography, and ECD calculations. The predominant relative orientation between H-7 and the Z double bond with a methyl substituent in the rigid 10-membered carbocycle, along with the planar chirality of the Z double bond was analyzed and discussed for the first time. The illustration of the planar chirality derived from the Z double bond should be paid great importance during the structure elucidation on these homologous meroterpenoids. All the isolated meroterpenoids were screened for their cytotoxicities against the HCT-8, PANC-1, HGC-27, HepG2, and PC9 cell lines, and compounds (+)-5 and (-)-5 exhibited the most potent cytotoxicity.
Asunto(s)
Boraginaceae , Boraginaceae/química , Estructura Molecular , Raíces de Plantas/química , Esqueleto , Terpenos/química , Terpenos/farmacologíaRESUMEN
To further reveal the active ingredients of Danshen, we systematically studied its chemical components and obtained two new lithospermic acid derivatives (compounds 1 and 2) together with five known phenylpropionic acids (compounds 3-7) from the dried rhizomes of Salvia miltiorrhiza. The structures of the two new compounds were determined by multiple spectral analyses (UV, IR, HR-ESI-MS, NMR, and ECD). In addition, the absolute configurations were established by chiral analysis and calculated and experimental circular dichroism spectra. Biological research indicated that compound 1 could significantly inhibit the proliferation of isoproterenol (ISO)-treated cardiac fibroblasts (AC16 cells), and MMP9 was found to be the most likely target of compound 1. The protein expression and mRNA levels of MMP9 were increased in ISO-induced AC16 cells, which could be reversed by treatment with compound 1. Furthermore, this treatment could alleviate the migration and activation of ISO-induced cardiac fibroblasts.
Asunto(s)
Salvia miltiorrhiza , Descarboxilación , Metaloproteinasa 9 de la Matriz , Raíces de Plantas/química , Rizoma , Salvia miltiorrhiza/químicaRESUMEN
Neuroinflammation is emerging as a crucial reason of major neurodegenerative diseases in recent years. Increasingly evidences have supported that bioactive natural products from traditional Chinese medicines have efficiency for neuroinflammation. Forsythia suspensa, a typical medicinal herb, showed potential neuroprotective and anti-inflammatory properties in previous pharmacological studies. In our research to obtain neuroprotective and anti-inflammatory natural products, three unprecedented C6-C7'/C6-C16' linked phenylethanoidglycoside dimers (1-3), three new phenylethanoidglycosides (4-6), and six known compounds (7-12) were isolated from the fruits of Forsythia suspensa. Their structures were determined by comprehensive spectroscopic data and comparison to the literature data. All isolated compounds were evaluated their neuroprotective and anti-inflammatory activities. Compounds 1 and 10 exhibited significant neuroprotective activities with the cell viability values of 75.24 ± 8.05% and 93.65 ± 10.17%, respectively, for the serum-deprivation and rotenone induced pheochromocytoma (PC12) cell injury. Meanwhile, compound 1 exhibited excellent anti-inflammatory activity against tumor necrosis factor (TNF)-α expression in LPS induced RAW264.7 cells with the IC50 value of 1.30 µM. This study revealed that the bioactive phenylethanoidglycosides may attenuate neuroinflammation through their neuroprotective and anti-inflammatory activities.
Asunto(s)
Antiinflamatorios/química , Forsythia/química , Glicósidos/química , Fármacos Neuroprotectores/química , Animales , Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/farmacología , Supervivencia Celular/efectos de los fármacos , Forsythia/metabolismo , Frutas/química , Frutas/metabolismo , Glicósidos/aislamiento & purificación , Glicósidos/farmacología , Lipopolisacáridos/farmacología , Macrófagos/citología , Macrófagos/efectos de los fármacos , Macrófagos/metabolismo , Ratones , Conformación Molecular , Fármacos Neuroprotectores/aislamiento & purificación , Fármacos Neuroprotectores/farmacología , Células PC12 , Extractos Vegetales/química , Células RAW 264.7 , Ratas , Factor de Necrosis Tumoral alfa/metabolismoRESUMEN
Five new dimeric phloroglucinol derivatives, agrimones A - E (1-5), were isolated from the whole plant of Agrimonia pilosa. Their structures including absolute configurations were determined by a series of spectroscopic data (UV, IR, HR-ESI-MS, 1D and 2D NMR), complemented with the comparison of the experimental and calculated ECD spectra, and gauge-independent atomic orbital (GIAO) NMR calculations. Notably, compounds 1 and 2 represent a highly oxidized 6/6/6 tricyclic ring skeleton based on the cis-fused paraquinone and chroman. Compounds 1a, 4, and 5 exhibited moderate hepatoprotective activities against APAP-induced HepG2 cell injury at 10 µM.
Asunto(s)
Agrimonia/química , Floroglucinol/farmacología , Sustancias Protectoras/farmacología , Acetaminofén , Supervivencia Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Células Hep G2 , Humanos , Estructura Molecular , Floroglucinol/química , Floroglucinol/aislamiento & purificación , Sustancias Protectoras/química , Sustancias Protectoras/aislamiento & purificación , Relación Estructura-ActividadRESUMEN
Aiming to discover potent anti-proliferative agents from the roots of Sophora flavescens, seven new prenylated flavanones were isolated, along with 16 known compounds. Their structures were elucidated by interpretation of their spectroscopic data (1D and 2D NMR, UV, IR, CD, and HRESIMS) and comparison to literature data. In the in vitro assay, 21 showed anti-proliferative activity against human hepatoma cells (HepG2). Studies of its mechanism revealed that 21 could significantly activate autophagic flux and trigger ROS release in HepG2 cells. Western blot experiments demonstrated that 21 could activate the key signaling protein of autophagy and ROS, while it does not affect the main protein of the apoptosis signaling pathway. These results suggested that 21 mediates its anti-proliferative effects through autophagic cell death, which is apoptosis-independent.
Asunto(s)
Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Flavanonas/química , Raíces de Plantas/química , Sophora/química , Animales , Autofagia/efectos de los fármacos , Células CHO , Cricetinae , Cricetulus , Células Hep G2 , Humanos , Estructura MolecularRESUMEN
One pair of new amides enantiomers (1a and 1b) and two known amides were isolated from the rhizomes of Polygonum cuspidatum. Their structures were established using UV, IR, HRESIMS, and NMR data. Notably, compound 1 possesses unique C-C connection between feruloyltyramine and resveratrol. Their absolute configurations were determined by the ECD method. All compounds were evaluated for their α-glucosidase inhibitory activity and compounds 2 and 3 showed significant inhibitory activity with IC50 values of 2.82 and 13.06 µmol/L, respectively (positive control acarbose, IC50 385 µmol/L).
Asunto(s)
Fallopia japonica , Polygonum , Amidas/farmacología , Estructura Molecular , Extractos Vegetales , RizomaRESUMEN
Three new monocyclic monoterpenoid containing ß-D-apiofuranosyl-(1â2)-O-ß-D-glucopyranosyl moieties, together with three other known monocyclic monoterpenoid O-glycosides, were obtained from the roots of Glycyrrhiza uralensis for the first time. Their structures were determined by UV, IR, HRESIMS, and 1D and 2D NMR data.[Formula: see text].
Asunto(s)
Glycyrrhiza uralensis , Glycyrrhiza , Glicósidos , Estructura Molecular , Monoterpenos , Raíces de PlantasRESUMEN
Eight new geranylquinol derivatives (1-8) were purified from the roots of Arnebia euchroma. Compounds 1-6 possess an unprecedented dearomatic benzocogeijerene skeleton with a rare trans-fused hydronaphthalene moiety. Their structures and absolute configurations were elucidated by HRESIMS, NMR, ECD, and X-ray diffraction. A convenient strategy for rapid determination of the relative configuration of H-1/H-7/Me-16 and the absolute configuration at C-1 for 1-6 was summarized. Compound 2 exhibited cytotoxicity against all the tested cell lines, namely PC9, BGC823, HCT116, HepG2, HeLa, and U87-MG, with IC50 values ranging from 13.7 to 29.3 µM.
Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Boraginaceae/química , Raíces de Plantas/química , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Conformación Molecular , Relación Estructura-ActividadRESUMEN
Two pairs of unusual phthalide analog enantiomers, (+)- and (-)-neophathalides A and B [(+)- and (-)-1 and 2], were isolated from the rhizome of Ligusticum chuanxiong Hort. Notably, neophathalide A presented a novel spiro-[4.5]dec-6-ene skeleton that originated from an aldol condensation process from sedanonic acid. Neophathalide B is an unprecedented 3-substituted phthalide analog that possesses a four-membered lactone ring system. The structures of the compounds were established using UV, IR, HRESIMS, NMR and ECD methods. All of the compounds were evaluated for their hepatoprotective activity against N-acetyl-p-aminophenol-induced HepG2 cell injury. Compounds 1a, 1b, and 2a exhibited moderate hepatoprotective activity compared with the positive control drug bicyclol at a concentration of 10 µM (p < 0.01).
RESUMEN
Ligusticum chuanxiong Hort is a famous health promoting plant cultivated in China, and widely consumed due to its various curative effects. To study the potential bioactive constituents from the rhizome of L. chuanxiong, a chemical investigation was thus performed. In present study, we report the isolation and identification of ten new compounds, including two coumarins (1-2), four lignans (3-6), and four phenols (7-10), along with five known compounds (11-15) from the rhizome of L. chuanxiong. The structures of these compounds were unambiguously established by HR-ESI-MS, UV, IR, CD, NMR spectral data and comparison to reported data. Meanwhile, the anti-inflammation and hepatoprotective activities of all these compounds were evaluated. The results show that compounds 5, 6 and 7 showed excellent inhibition of NO production in LPS-induced RAW 264.7 cells stronger than curcumin, and compounds 5, 7 and 9 exhibited greater hepatoprotective effect than that of bicyclol.
Asunto(s)
Antiinflamatorios/farmacología , Ligusticum/química , Hígado/efectos de los fármacos , Animales , Antiinflamatorios/química , Células Hep G2 , Humanos , Lipopolisacáridos/farmacología , Ratones , Óxido Nítrico/antagonistas & inhibidores , Óxido Nítrico/biosíntesis , Células RAW 264.7 , Análisis Espectral/métodosRESUMEN
Two new isobenzofuranone derivatives, polyphthaliside A (1) and polyphthaliside B (2), and a new isocoumarin derivative, polyisocoumarin (3), were isolated from Polygonum cuspidatum. Their structures were elucidated by detailed spectroscopic analysis and chemical methods. The cytotoxicity activity and PTP1B inhibitory activity of compounds 1-3 were estimated and none of them exhibited activities at a concentration of 10 µM.
Asunto(s)
Fallopia japonica , Polygonum , Glicósidos , Isocumarinas , Estructura Molecular , FenolesRESUMEN
Phytochemical investigation of the rhizome of Ligusticum chuanxiong Hort led to the isolation and identification of three new compounds, chuanxiongoside A, (2E,4E)-8-(6-O-inositolyl)-8-oxo-2,7-dimethyl-octadienoic acid (2), chuanxiongoside C (3). The structures of these compounds were unambiguously established by HR-ESI-MS, UV, IR, CD, NMR spectral data and comparison to reported data. All the isolated compounds (1-3) were investigated for their inhibitory effects on nitric oxide (NO) production in LPS-induced RAW 264.7 cells. All compounds showed excellent inhibition of NO production stronger than curcumin. [Formula: see text].
Asunto(s)
Medicamentos Herbarios Chinos , Ligusticum , Humanos , Inflamación , Estructura Molecular , RizomaRESUMEN
Two new quinochalcone glycosides, hydroxysafflor yellow A-4'-O-ß-D-glucopyranoside (1) and 3'-hydroxyhydroxysafflor yellow A (2), were isolated from the safflower yellow pigments of Carthamus tinctorius. The structures of new compounds were elucidated by a detailed spectroscopic analysis (UV, IR, HR-ESI-MS, 1D and 2D NMR, ECD). The in vitro assay indicated that compound 1 could improve the survived rate of primary mouse cortical neurons on glutamate-induced neurons damage model at a concentration of 10 µM.
Asunto(s)
Carthamus tinctorius , Chalcona , Animales , Chalcona/análogos & derivados , Glicósidos , Ratones , Estructura MolecularRESUMEN
Two new naturally occurring products named salviamine G (1) and 4-methyl-9-(ethoxycarbonyl)-8-naphthoic acid (2) were isolated from the rhizomes of Salvia miltiorrhiza. Their structures were elucidated using spectroscopic data (UV, IR, HRESIMS, 1D and 2D NMR). Compounds 1 and 2 were screened for their inhibitory activity against HSV-1 and influenza A (H3N2) using acyclovir (ACV, IC50 = 0.67 µM) and oseltamivir (IC50 = 2.01 µM) as a positive control. Compound 1 exhibited moderate inhibitory activity against HSV-1 and influenza A (H3N2) with IC50 values of 11.11 and 8.62 µM, respectively.
Asunto(s)
Antivirales , Salvia miltiorrhiza , Salvia , Abietanos , Subtipo H3N2 del Virus de la Influenza A , Estructura Molecular , RizomaRESUMEN
Two new lignans, wikstronoside B (1) and forsysesquinorlignan (2), were isolated from the fruits of Forsythia suspensa, along with two known sesquineolignans, hedyotol A and hedyotol C (3 and 4). The structures of new compounds were established via extensive spectroscopy techniques, including UV, IR, HRESIMS, NMR, and ECD. Compounds 3 and 4 were isolated from this plant for the first time. Their anti-inflammatory effects were evaluated via a detection model with LPS-induced murine macrophage RAW264.7 cells, and compound 3 showed a moderate activity.
Asunto(s)
Forsythia , Lignanos , Animales , Frutas , Ratones , Estructura Molecular , Extractos VegetalesRESUMEN
Two new benzoic acid derivatives, sophophenoside A (1) and sophophenoside B (2), were isolated from Sophora flavescens. Their structures were elucidated by detailed spectroscopic analysis and chemical methods. Compounds 1 and 2 were assayed for their hepatoprotective activity on the cytotoxic effect of D-galactosamine on HL-7702 cells, and compound 1 exhibited a moderate hepatoprotective activity at a concentration of 10 µM.