RESUMEN
Twelve compounds, comprising of four new ones, 6ß,7α-limondiol (1) and ethyl 19-hydroxyisoobacunoate diosphenol (2), N-benzoyl 3-prenyltyramine (9) and 9-O-methyl integrifoliodiol (12), were isolated from the twigs with leaves of Tetradium trichotomum. The structures were elucidated by analysis of MS, NMR, and single-crystal X-ray diffraction. Compounds 1, 6, 8, 9 and 12 exhibited immunosuppressive activities in vitro against the proliferation of ConA-induced T lymphocytes and LPS-induced B cells.
RESUMEN
Alopecines A-E (1-5), five unusual matrine-type alkaloids featuring with an additional dichlorocyclopropane (1-3) or a di/tri-chloromethyl (4/5) attached on the D ring, were isolated from the seeds of Sophora alopecuroides. Their structures and absolute configurations were elucidated by extensive spectroscopic techniques, and X-ray diffraction analyses or time-dependent density functional theory-based electronic circular dichroism (TDDFT-ECD) calculations. Alkaloid 4 exhibited potent inhibitory effects on the proliferation of ConA-induced T lymphocytes or LPS-induced B cells with IC50 value of 3.98 or 3.74 µM, respectively.
Asunto(s)
Alcaloides/farmacología , Inmunosupresores/farmacología , Extractos Vegetales/farmacología , Sophora/química , Alcaloides/química , Alcaloides/aislamiento & purificación , Animales , Linfocitos B/efectos de los fármacos , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Células Cultivadas , Concanavalina A/antagonistas & inhibidores , Concanavalina A/farmacología , Relación Dosis-Respuesta a Droga , Femenino , Inmunosupresores/química , Inmunosupresores/aislamiento & purificación , Lipopolisacáridos/antagonistas & inhibidores , Lipopolisacáridos/farmacología , Ratones , Ratones Endogámicos BALB C , Conformación Molecular , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Semillas/química , Estereoisomerismo , Relación Estructura-Actividad , Linfocitos T/efectos de los fármacosRESUMEN
Three new mexicanolide-type limonoids, 3-O-propionylproceranolide (1), 6-O-acetylswietenin B (2), and 6-deoxyswietemahonin A (3), together with 15 known limonoids, were isolated from the seeds of Swietenia macrophylla (Meliaceae). The structures of those new compounds were established by extensive analysis of MS, 1D, and 2D NMR spectral data.
Asunto(s)
Medicamentos Herbarios Chinos/aislamiento & purificación , Limoninas/aislamiento & purificación , Meliaceae/química , Medicamentos Herbarios Chinos/química , Limoninas/química , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Semillas/químicaRESUMEN
The first synthesis of dendroflorin has been achieved in 10 steps with an overall yield of 5.5%. The key step in the synthesis features the biphenyl structure is built through Suzuki-Miyaura reaction. In addition, the ortho-localization effect induced by aromatic substituent during the bromination of intermediate 8 is also observed and discussed.
Asunto(s)
Benzoatos/síntesis química , Dendrobium/química , Fluorenos/aislamiento & purificación , Benzoatos/química , Compuestos de Bifenilo/química , Catálisis , Fluorenos/química , Hidroquinonas/química , Estructura MolecularRESUMEN
Two new triterpenoids, termichebuloside A (1), an unusual dimeric triterpenoid saponin, and termichebulolide (2), an oleanolic acid-type lactone, along with 11 known triterpenoids, were isolated from MeOH extract of the barks of Terminalia chebula. The structures of 1 and 2 were elucidated to be arjunglucoside I-(3-O-19',23-O-19')-18,19-seco-19-hydroxyarjunglucoside I (1) and 2α,3ß,23-trihydroxyolean-11,13(18)-dien-28,19ß-olide (2), respectively, on the basis of spectroscopic evidences and biogenetic consideration.
Asunto(s)
Saponinas/aislamiento & purificación , Terminalia/química , Triterpenos/aislamiento & purificación , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Corteza de la Planta/química , Saponinas/química , Estereoisomerismo , Triterpenos/químicaRESUMEN
The EtOAc-soluble portion of the 80â% (v/v) EtOH extract from the twigs of Garcinia esculenta exhibited strong xanthine oxidase inhibition in vitro. Bioassay-guided purification led to the isolation of 1,3,6,7-tetrahydroxyxanthone (3) and griffipavixanthone (8) as the main xanthine oxidase inhibitors, along with six additional compounds (1, 2, 4-7), including two new compounds (1 and 2). This enzyme inhibition was dose dependent with an IC50 value of approximately 1.2 µM for 3 and 6.3 µM for 8. The inhibitory activity of 3 was stronger than the control allopurinol (IC50 value: 5.3 µM). To our knowledge, compound 8 is the first bixanthone that demonstrated potent XO inhibitory activity in vitro. The structures of the new compounds were established by spectroscopic analysis, and the optical properties and absolute stereochemistry of racemic (±) esculentin A (2) were further determined by the calculation of the DP4 probability and analysis of its MTPA ester derivatives.
Asunto(s)
Inhibidores Enzimáticos/farmacología , Garcinia/química , Xantina Oxidasa/antagonistas & inhibidores , Evaluación Preclínica de Medicamentos/métodos , Inhibidores Enzimáticos/química , Concentración 50 Inhibidora , Espectroscopía de Resonancia Magnética , Estructura Molecular , Xantonas/química , Xantonas/aislamiento & purificación , Xantonas/farmacologíaRESUMEN
Laggeric acid (1), a novel 4,5-seco-eudesmane sesquiterpene acid, along with 19 known compounds, was isolated from the MeOH extract of the whole plant of Laggera crispata. The structure of 1 was elucidated to be (4S,5S*,7R*,10R*)-4,5-seco-4,5-dihydroxy-11(13)-eudesmen-12-oic acid on the basis of spectroscopic analysis and a convenient Mosher's method.
Asunto(s)
Medicamentos Herbarios Chinos/aislamiento & purificación , Sesquiterpenos de Eudesmano/aislamiento & purificación , Asteraceae/química , Medicamentos Herbarios Chinos/química , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Sesquiterpenos , Sesquiterpenos de Eudesmano/química , EstereoisomerismoRESUMEN
A pair of new enantiomeric indolopyridoquinazoline-type alkaloids, (+)-1,7S,8R- and (-)-1,7R,8S-trihydroxyrutaecarpine (3a and 3b), and a new limonoid-tyrosamine hybrid, austrosinin (8), along with six known alkaloids and limonoids, were isolated from the stems with leaves of Tetradium austrosinense. Their structures were elucidated on the basis of analysis of MS, NMR, ECD and time-dependent density functional theory-based electronic circular dichroism (TDDFT-ECD) calculations, as well as proposed biosynthetic pathway. An anti-inflammatory bioassay in vitro showed 8 had significant immunosuppressive effect against the production of pro-inflammatory cytokine TNF-α in lipopolysaccharide (LPS)-stimulated RAW264.7 cells.
Asunto(s)
Alcaloides , Limoninas , Rutaceae , Limoninas/farmacología , Limoninas/química , Estructura Molecular , Alcaloides/farmacología , Alcaloides/química , Rutaceae/química , Dicroismo CircularRESUMEN
Aglinin A (1) is a mixture of C(24)-epimeric 20S,24-epoxy-24,25-dihydroxy-3,4-secodammar-4(28)-en-3-oic acid and present in plants of the family Meliaceae. The two epimers of 1 were resolved through an acetonide reaction, and the absolute configurations of two derivatives were deduced by the analysis of their (13)C NMR differences induced by γ-gauche or steric effect. Based on it, the (13)C NMR assignment of 24R-1 and 24S-1 was also established.
Asunto(s)
Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/aislamiento & purificación , Meliaceae/química , Triterpenos/química , Triterpenos/aislamiento & purificación , Medicamentos Herbarios Chinos/farmacología , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Estereoisomerismo , Triterpenos/farmacologíaRESUMEN
Hyperacmotone A, a polycyclic polyprenylated acylphloroglucinol (PPAP) with an unprecedented skeleton, along with five undescribed congeners and eleven reported ones, was isolated from Hypericum acmosepalum. Hyperacmotone A possesses a unique monocyclic ring skeleton based on a cyclopent-4-ene-1,3-dione acylphloroglucinol core. Their structures were elucidated by extensive analysis of HRESIMS, NMR, biogenetic pathway, and quantum-chemical calculations. In addition, hypercohone G exhibited significant protective effects on high-glucose-injured HUVECs.
Asunto(s)
Hypericum , Humanos , Células Endoteliales , GlucosaRESUMEN
Fraxinifolines A-F (1-6), six new B-seco limonoids, together with four known A,D-di-seco ones, were isolated from the twigs with leaves of Tetradium fraxinifolium. Their structures with absolute configurations were elucidated on the basis of analysis of MS, NMR, single-crystal X-ray diffraction and biogenetic pathway. An anti-inflammatory bioassay in vitro showed limonoids 1-3 had significant immunosuppressive effect against the production of pro-inflammatory cytokines (IL-1ß and/or TNF-α) in lipopolysaccharide (LPS)-stimulated RAW264.7 cells.
Asunto(s)
Limoninas , Estructura Molecular , Limoninas/farmacología , Limoninas/química , Antiinflamatorios/farmacología , Citocinas , Factor de Necrosis Tumoral alfa/metabolismoRESUMEN
Two new arylnaphthalene lignan glycosides, named reticulatusides A (1) and B (2), together with eight known compounds were isolated from the 95% EtOH extract of the whole plant of Phyllanthus reticulatus. The structures of the new compounds were elucidated by spectroscopic methods.
Asunto(s)
Medicamentos Herbarios Chinos/aislamiento & purificación , Glicósidos/aislamiento & purificación , Lignanos/aislamiento & purificación , Naftalenos/aislamiento & purificación , Phyllanthus/química , Medicamentos Herbarios Chinos/química , Glicósidos/química , Lignanos/química , Estructura Molecular , Naftalenos/química , Resonancia Magnética Nuclear BiomolecularRESUMEN
OBJECTIVE: To study the chemical constituents of the ethyl acetate extract from Blumea aromatica. METHODS: Column chromatographic techniques were used for the isolation and purification. Spectroscopic techniques were used for the identification of structures. RESULTS: Seven compounds were isolated from the ethyl acetate extract of 80% alcohol extract of the whole plant, and their structures were identified as xanthoxylin(1), dibutyl phthalate(2), luteolin-3',4',7-trimethyl ether(3), rubiadin(4), eriodictyol(5), kaempherol(6), luteolin 7,3'-dimethyl ether(7). CONCLUSION: All the compounds are isolated from this plant for the first time. Among them, compounds 2,4 and 7 are isolated from this genus for the first time.
Asunto(s)
Antraquinonas/aislamiento & purificación , Asteraceae/química , Dibutil Ftalato/aislamiento & purificación , Medicamentos Herbarios Chinos/química , Luteolina/aislamiento & purificación , Acetatos , Antraquinonas/química , Cromatografía Líquida de Alta Presión , Dibutil Ftalato/química , Medicamentos Herbarios Chinos/aislamiento & purificación , Glucósidos/química , Glucósidos/aislamiento & purificación , Quempferoles/química , Quempferoles/aislamiento & purificación , Luteolina/química , Estructura Molecular , Solventes/químicaRESUMEN
Melodicochinines A - D (1-4), four new monoterpene indole alkaloids (MIAs), along with 21 known ones, were isolated from the stems and twigs of Melodinus cochinchinensis. Their structures were elucidated on the basis of extensive spectroscopic analysis. A ubiquitin-rhodamine 110 assay showed that 11-methyloxytabersonine had potential inhibitory effect against ubiquitin-specific protease 7 (USP7).
Asunto(s)
Apocynaceae/química , Extractos Vegetales/química , Alcaloides de Triptamina Secologanina/aislamiento & purificación , China , Cromatografía Líquida de Alta Presión , Espectroscopía de Resonancia Magnética , Rotación Óptica , Extractos Vegetales/aislamiento & purificación , Tallos de la Planta/química , Alcaloides de Triptamina Secologanina/química , Espectrofotometría InfrarrojaRESUMEN
A series of tryptamine derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activity and cytotoxicity in the HepG2.2.15 cell line. The preliminary SAR was discussed. Compounds 2e and 4a showed potent antiviral activity (IC(50)=0.4 and <1 µM, respectively) and low cytotoxicity (CC(50)=40.6 and >25 µM, respectively).
Asunto(s)
Antivirales/química , Antivirales/farmacología , Virus de la Hepatitis B/efectos de los fármacos , Hepatitis B/tratamiento farmacológico , Triptaminas/química , Triptaminas/farmacología , Supervivencia Celular/efectos de los fármacos , ADN Viral/metabolismo , Células Hep G2 , Humanos , Relación Estructura-ActividadRESUMEN
Three new compounds, debilitriol (1), debilignanoside (2), and equisetumine (3), along with nine known compounds, were isolated from the whole plant of Equisetum debile. Their structures were elucidated by spectral and chemical methods.
Asunto(s)
Alcaloides/aislamiento & purificación , Derivados del Benceno/aislamiento & purificación , Medicamentos Herbarios Chinos/aislamiento & purificación , Equisetum/química , Glucósidos/aislamiento & purificación , Lignanos/aislamiento & purificación , Alcaloides/química , Derivados del Benceno/química , Medicamentos Herbarios Chinos/química , Glucósidos/química , Lignanos/química , Estructura Molecular , Resonancia Magnética Nuclear BiomolecularRESUMEN
A new dammarane-type triterpenoid saponin, (20R)-ginsenoside ST(2) (1), along with five known saponins was isolated from the hongshen extract of Shenmai injection. The structure of 1 was elucidated to be (20R)-dammar-23(E)-ene-3ß,6α,12ß,20,25-pentol 6-O-ß-D-glucopyranoside by means of spectroscopic methods.
Asunto(s)
Medicamentos Herbarios Chinos/aislamiento & purificación , Ginsenósidos/aislamiento & purificación , Panax/química , Plantas Medicinales/química , Triterpenos/aislamiento & purificación , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/farmacología , Ginsenósidos/química , Ginsenósidos/farmacología , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Estereoisomerismo , Triterpenos/química , Triterpenos/farmacología , DamaranosRESUMEN
Twenty-one polycyclic polyprenylated acylphloroglucinols, including three new compounds named as hyperichoisins A (3), B (14) and C (21), were isolated from the aerial parts of Hypericum choisianum. The structures of those new compounds were elucidated by analysis of mass, NMR data, and chiroptical properties. A bioassay showed that otogirinin B had significant inhibitory effect on cell proliferation of A549.
Asunto(s)
Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Hypericum/química , Células A549 , Proliferación Celular/efectos de los fármacos , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Espectroscopía de Resonancia Magnética , Estructura Molecular , Floroglucinol/químicaRESUMEN
Uralins A - D, four undescribed polycyclic polyprenylated acylphloroglucinols (PPAPs) featuring an unprecedented fused hexacyclic architecture, a unique monocyclic tetra-seco-tetranor-b-PPAP, an oxidative b-PPAP and a rare norspiroindane-type m-PPAP, respectively, were isolated from the aerial parts of Hypericum uralum, along with ten known PPAPs. Their structures and absolute configurations were elucidated by extensive spectroscopic techniques (MS, NMR, [α]D, CD), conceivable biogenetic pathways and time-dependent density functional theory-based electronic circular dichroism (TDDFT-ECD) calculations. Biological assays showed three b-PPAPs had moderate antioxidative damage activities, while spiroindanes exhibited moderate cytotoxic effects.
Asunto(s)
Hypericum , Dicroismo Circular , Espectroscopía de Resonancia Magnética , Estructura Molecular , Floroglucinol/farmacologíaRESUMEN
Acmoxanthones A-E (1-5), five new lavandulylated xanthones, were isolated from the aerial parts of Hypericum acmosepalum, together with four known xanthones. Their structures with absolute configurations were elucidated on the basis of analysis of MS, NMR and chiroptical properties. A bioassay against high glucose-induced damage on human umbilical vein endothelial cells (HUVECs) showed ananixanthone (6) and osajaxanthone (7) had potential antioxidative damage activity with EC50 values of 10.5 µg/mL and 7.6 µg/mL, respectively, while 3-hydroxy-2,4-dimethoxyxanthone (8) exhibited cytotoxic effect on the damaged cells with IC50 values of 7.1 µg/mL.