RESUMEN
Hyperatins A-D (1-4), four previously undescribed polycyclic polyprenylated acylphloroglucinols, were isolated from Hypericum perforatum L. (St. John's wort). Compound 1 possessed a unique octahydroindeno[1,7a-b]oxirene ring system with a rare 2,7-dioxabicyclo[2.2.1]heptane fragment. Compounds 2-4 had an uncommon decahydrospiro[furan-3,7'-indeno[7,1-bc]furan] ring system. Their structures were established by spectroscopic analyses and X-ray crystallography. Plausible biosynthetic pathways of 1-4 were also proposed. Compounds 1 and 2 exerted promising hypoglycemic activity by inhibiting glycogen synthase kinase 3 expression in liver cells.
Asunto(s)
Antineoplásicos , Hypericum , Hypericum/química , Cristalografía por Rayos X , Hígado , Furanos , Floroglucinol/farmacología , Floroglucinol/química , Estructura MolecularRESUMEN
Three new furano-lactones, asperilactones A-C (1-3), and two known compounds silvaticol (4) and violaceic acid (5) were isolated from an ethanol extract of Aspergillus nidulans, a fungus isolated from the Annelida Whitmania pigra Whitman (Haemopidae). Their structures were elucidated by a combination of spectroscopy, ECD calculations, comparing optical rotation values, and single-crystal X-ray diffraction analyses. Asperilactone A (1) represented the first example of furano-lactone with an unusual 2-thia-6-oxabicyclo[3.3.0]octane ring system. Asperilactones A and B showed weak toxicity against the HL-60 and RKO.
Asunto(s)
Aspergillus nidulans , Lactonas/química , Estructura Molecular , Cristalografía por Rayos X , Análisis EspectralRESUMEN
Twelve new fungal polyketides, koningiopisins I-P (1-8) and trichoketides C-F (9-12), together with six known congeners (13-18), were isolated from Trichoderma koningiopsis, a rhizosphere fungus obtained from the medicinal plant Polygonum paleaceum. Their structures and absolute configurations were established by spectroscopic analysis, single-crystal X-ray diffraction, the modified Mosher's method, chemical derivatization, the octant rule, and 13C NMR and ECD calculations. Compounds 1-5 are tricyclic polyketides possessing an octahydrochromene framework with a 6,8-dioxabicyclo[3.2.1]octane core. Compounds 7 and 8 contain a unique ketone carbonyl group at C-7 and differ from other members of this group of compounds with the ketone carbonyl group at C-1. Compounds 1, 2, and 13 showed inhibitory activity on LPS-induced BV-2 cells on NO production with IC50 values of 14 ± 1, 3.0 ± 0.5, and 8.9 ± 2.7 µM, respectively.
Asunto(s)
Plantas Medicinales , Polygonum , Policétidos , Policétidos/química , Rizosfera , Estructura Molecular , Espectroscopía de Resonancia Magnética , HongosRESUMEN
Four new polyketides named trichodermatides A-D (1-4), along with five known analogues (5-9), were isolated from the fungus Trichoderma sp. XM-3. Their structures were elucidated on the basis of HRESIMS and NMR analyses, and their absolute configurations were determined by ECD comparison, 1H and 13C NMR calculation, DP4+ analysis, modified Mosher's method, and X-ray crystallography. Trichodermaketone D (9) showed mild antibacterial activity against Pseudomonas aeruginosa.
Asunto(s)
Policétidos , Trichoderma , Trichoderma/química , Estructura Molecular , Espectroscopía de Resonancia Magnética , Cristalografía por Rayos XRESUMEN
Talasterone A (1), an unprecedented 6/6/5 tricyclic 13(14 â 8)abeo-8,14-seco-ergostane steroid, together with two known congeners dankasterone B (2) and (14ß,22E)-9,14-dihydroxyergosta-4,7,22-triene-3,6-dione (3), were characterized from Talaromyces adpressus. The structure of 1 with absolute configuration was elucidated based on NMR spectroscopic data and ECD calculation. Compound 2 belongs to a class of unconventional 13(14 â 8)abeo-ergostanes, which have been renewed via the 1,2-migration of C-13-C-14 bond to C-8. In addition, compound 1 represents the first example of ergostane with a tricyclic 13(14 â 8)abeo-8,14-seco-ergostane skeleton. The proposed biosynthetic pathway was established with the support of the coisolation of the known congeners from the producing organism. It is especially noteworthy that compound 1 exhibited potent anti-inflammatory activity with an IC50 value of 8.73 ± 0.66 µM, inhibiting the NF-κB pathway and thus reducing the production of proinflammatory cytokines.
Asunto(s)
Ergosterol , Talaromyces , Ergosterol/análogos & derivados , Ergosterol/farmacología , Estructura Molecular , Esqueleto , Talaromyces/químicaRESUMEN
Hyperformitins A-I (1-9), nine undescribed polycyclic polyprenylated acylphloroglucinols (PPAPs) with double-bond migration, along with four new isomers hyperformitins J-M (10-13), were isolated from Hypericum perforatum. Their structures and absolute configurations were determined by spectroscopic analyses including HRESIMS, IR, UV, NMR, and ECD, as well as optical rotation (OR) calculations. The absolute configurations of previously reported analogues, garsubellins D and C as well as garcinielliptones L and M, were assigned for the first time by NMR spectra and specific rotations analyses assisting with OR calculations. Selected compounds were tested for their immunosuppressive activities against lipopolysaccharide (LPS)-induced B lymphocyte proliferation. Compounds 1, 3, 4, 5, 7, and 11 showed inhibition activities against the proliferation of B lymphocyte with IC50 values ranging from 4.1 to 9.7 µM. Furthermore, the neuroprotective activities of the isolates against corticosterone (CORT)-induced injury in PC12 cells were also tested, and compounds 1, 12, and 13 exhibited neuroprotective effects with cell viabilities of 68.0%, 71.3%, and 68.4%, respectively under the concentration of 10 µM.
Asunto(s)
Antineoplásicos/farmacología , Hypericum/química , Inmunosupresores/farmacología , Fármacos Neuroprotectores/farmacología , Floroglucinol/farmacología , Animales , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Linfocitos B/efectos de los fármacos , 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 , Inmunosupresores/química , Inmunosupresores/aislamiento & purificación , Lipopolisacáridos/antagonistas & inhibidores , Lipopolisacáridos/farmacología , Estructura Molecular , Fármacos Neuroprotectores/química , Fármacos Neuroprotectores/aislamiento & purificación , Células PC12 , Floroglucinol/química , Floroglucinol/aislamiento & purificación , Ratas , Relación Estructura-ActividadRESUMEN
Five new compounds, including a pair of diphenylcyclopentenone enantiomers (±)-phomopsisin A (1), a sesquiterpenoid 15-hydroxylithocarin A (2), a new diketopiperazine alkaloid prenylcyclotryprostatin A (3) and 7-hydroxy-cis-L(-)-3,6-dibenzyl-2,5-dioxopiperazine (6), along with five known compounds were isolated from the fungus Phomopsis asparagi. Their structures were elucidated on the basis of spectroscopic analyses (1D and 2D NMR), theoretical electronic circular dichroism (ECD) calculation, modified Mosher's method, and X-ray crystallography. The racemates of (±)-phomopsisin A showed inhibition on α-glucosidase with IC50 of 30.07 ± 0.75 µM (positive control acarbose, 121 ± 2.7 µM).
Asunto(s)
Alcaloides/farmacología , Inhibidores de Glicósido Hidrolasas/farmacología , Phomopsis/química , Sesquiterpenos/farmacología , Alcaloides/aislamiento & purificación , Inhibidores de Glicósido Hidrolasas/aislamiento & purificación , Simulación del Acoplamiento Molecular , Estructura Molecular , Sesquiterpenos/aislamiento & purificaciónRESUMEN
Flavipesines A and B (1 and 2) and asperchalasines E-H (3-6), two cytochalasans with an unusual ring system and four merocytochalasans possessing a 5/6/11/5/5/6 ring system, were isolated from Aspergillus flavipes, along with three related compounds (7-9). Their structures, including absolute configurations, were determined on the basis of data from HRESIMS, NMR, ECD, molecular modeling, and single-crystal X-ray diffraction. Flavipesines A and B (1 and 2) represent the first examples of cytochalasans possessing a 5/6/7/6 ring system with a C-18-O-C-21 bridge. Compounds 3, 7, and 9 show moderate inhibitory activities against isocitrate dehydrogenase 1 (IDH1). This is the first report on the IDH1 inhibitory activities of cytochalasans.
Asunto(s)
Aspergillus/química , Citocalasinas/química , Simulación por Computador , Evaluación Preclínica de Medicamentos , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/farmacología , Isocitrato Deshidrogenasa/antagonistas & inhibidores , Modelos Moleculares , Simulación del Acoplamiento Molecular , Estructura Molecular , Difracción de Rayos XRESUMEN
Hyperforatins L-U, ten undescribed polycyclic polyprenylated acylphloroglucinols (PPAPs) bearing a terminal double bond, together with a known compound hypericumoxide J, were isolated from the aerial parts of Hypericum perforatum L. Their structures were elucidated by spectroscopic methods, including HRESIMS, IR, UV, and NMR (1H, 13C, DEPT, HSQC, HMBC, 1H-1H COSY, and NOESY experiments). Their absolute configurations were determined by comprehensive analyses of their experimental ECD spectra in conjunction with a modified Mosher's method. Evaluation of their neuroprotective activities highlighted hyperforatin L, which displayed mild activity at a concentration of 10⯵M.
Asunto(s)
Inhibidores de la Colinesterasa/farmacología , Hypericum/química , Fármacos Neuroprotectores/farmacología , Floroglucinol/farmacología , Acetilcolinesterasa/metabolismo , Animales , Supervivencia Celular/efectos de los fármacos , Células Cultivadas , Inhibidores de la Colinesterasa/química , Inhibidores de la Colinesterasa/aislamiento & purificación , Corticosterona , Relación Dosis-Respuesta a Droga , Conformación Molecular , Fármacos Neuroprotectores/química , Fármacos Neuroprotectores/aislamiento & purificación , Células PC12 , Floroglucinol/análogos & derivados , Floroglucinol/química , Ratas , Relación Estructura-ActividadRESUMEN
Fifteen new polycyclic polyprenylated acylphloroglucinols (PPAPs), hyperforatones A-O (1-15), along with 3 structurally related analogues (16-18), were isolated from the stems and leaves of Hypericum perforatum. Their structures and absolute configurations were established by a combination of NMR spectroscopic analyses, experimental and calculated electronic circular dichroism (ECD), modified Mosher's methods, Rh2(OCOCF3)4- and [Mo2(OAc)4]-induced ECD, X-ray crystallography, and the assistance of quantum chemical predictions (QCP) of 13C NMR chemical shifts. Compound 5 was found to be the first PPAP decorated by a rare 2,2,4,4,5-(pentamethyltetrahydrofuran-3-yl)methanol moiety and an oxepane ring. Furthermore, the isolates were screened for their acetylcholinesterase (AChE) and ß-site amyloid precursor protein cleaving enzyme 1 (BACE1) inhibitory activities. Compounds 5, 10, 11, and 15 showed desirable AChE inhibitory activities (IC50 6.9-9.2 µM) and simultaneously inhibited BACE1 (at a concentration of 5 µM) with inhibition rates of 50.3%, 34.3%, 47.2%, and 34.6%, respectively. Interestingly, compound 5 showed the most balanced inhibitory activities against both AChE and BACE1 of all the tested compounds, which means that 5 could serve as the first valuable dual-targeted PPAP for the treatment of Alzheimer's disease. Preliminary molecular docking studies of 5 with BACE1 and AChE were also performed.
Asunto(s)
Inhibidores de la Colinesterasa/química , Inhibidores de la Colinesterasa/farmacología , Hypericum/química , Floroglucinol/química , Floroglucinol/farmacología , Compuestos Policíclicos/química , Prenilación , Acetilcolinesterasa/química , Acetilcolinesterasa/metabolismo , Enfermedad de Alzheimer/tratamiento farmacológico , Secretasas de la Proteína Precursora del Amiloide/antagonistas & inhibidores , Secretasas de la Proteína Precursora del Amiloide/química , Secretasas de la Proteína Precursora del Amiloide/metabolismo , Ácido Aspártico Endopeptidasas/antagonistas & inhibidores , Ácido Aspártico Endopeptidasas/química , Ácido Aspártico Endopeptidasas/metabolismo , Inhibidores de la Colinesterasa/metabolismo , Inhibidores de la Colinesterasa/uso terapéutico , Simulación del Acoplamiento Molecular , Floroglucinol/metabolismo , Floroglucinol/uso terapéutico , Conformación ProteicaRESUMEN
Eight secondary metabolites, including a new polyketide, named asperetide (1) and a new prenylxanthone derivative, called asperanthone (4), and six known compounds, (S)-3-butyl-7-methoxyphthalide (2), ruguloxanthone C (3), tajixanthone hydrate (5), tajixanthone methanoate (6), salimyxin B (7), and ergosterol (8), were isolated and identified from the medicinal plant-derived fungus, Aspergillus sp. TJ23. The new structures and their absolute configurations were elucidated via multiple methods, including 1D- and 2D-NMR, HR-ESI-MS, UV, IR, and the electronic circular dichroism (ECD) calculations. All of the isolates were characterized from the strain for the first time. The inâ vitro bioassay showed that compounds 3-5 and 8 exerted inhibitory activities against five cancer cell lines (B16, MDA-MB-231, 4T1, HepG2, and LLC) with IC50 values ranging from 5.13 to 36.8â µm.
Asunto(s)
Aspergillus/química , Policétidos/química , Xantonas/química , Aspergillus/metabolismo , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Dicroismo Circular , Humanos , Espectroscopía de Resonancia Magnética , Conformación Molecular , Policétidos/aislamiento & purificación , Policétidos/farmacología , Espectrometría de Masa por Ionización de Electrospray , Xantonas/aislamiento & purificación , Xantonas/farmacologíaRESUMEN
Terrusnolides A-D (1-4), four butenolides were isolated from an endophytic Aspergillus from Tripterygium wilfordii. The structures of 1-4 were established by comprehensive spectroscopic analyses and electronic circular dichroism (ECD) calculation. It is interesting that 1 was a butenolide derived by a triple decarboxylation, while 2-4 were the metabolites with 4-benzyl-3-phenyl-5H-furan-2-one motif possessing an isopentene group fused to the benzene ring. In vitro anti-inflammatory effects of these isolates were evaluated in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. 1-4 exhibited excellent inhibitory effects on the production of interleukin-1ß (IL-1ß), tumor necrosis factor-α (TNF-α), and nitric oxide (NO) in LPS-induced macrophages, comparable with the positive control (indomethacin). Those results indicated that, terrusnolides A-D might serve as new potential natural remedies for the treatment of inflammation.
Asunto(s)
4-Butirolactona/análogos & derivados , Antiinflamatorios/farmacología , Aspergillus/química , Tripterygium/microbiología , 4-Butirolactona/aislamiento & purificación , 4-Butirolactona/farmacología , Animales , Antiinflamatorios/aislamiento & purificación , China , Endófitos/química , Interleucina-1beta/metabolismo , Ratones , Estructura Molecular , Óxido Nítrico/metabolismo , Raíces de Plantas/microbiología , Células RAW 264.7 , Factor de Necrosis Tumoral alfa/metabolismoRESUMEN
Three new cleistanthane diterpenoids, phyllanglins A-C (1-3), a new natural product, 4-acetyl-bergenin (4), and three known compounds (5-7) were isolated from the roots of Phyllanthus glaucus. Their structures were elucidated by extensive spectroscopic data analyses and single-crystal X-ray diffraction. Phyllanglins A-C were unusual cleistanthane diterpenoids with phenylacetylene moieties, and a plausible biogenetic pathway was proposed to discuss the origins of them. All of the isolates were evaluated for their anti-inflammatory activities.
Asunto(s)
Acetileno/análogos & derivados , Diterpenos/aislamiento & purificación , Phyllanthus/química , Raíces de Plantas/química , Acetileno/aislamiento & purificación , Animales , Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/farmacología , Cristalografía por Rayos X , Diterpenos/farmacología , Ratones , Estructura Molecular , Células RAW 264.7RESUMEN
To explore the chemical diversity of metabolites from endophytic fungi, the strain Phomopsis sp. TJ507A, isolated from the medicinal plant Phyllanthus glaucus, was investigated. A 2,3- seco-protoilludane-type sesquiterpenoid (1), eight protoilludane-type sesquiterpenoids (2-9), four illudalane-type sesquiterpenoids (10a/10b, 11, and 12), and a botryane-type sesquiterpenoid (13) in addition to seven known sesquiterpenoids (14-20) were identified from the liquid culture of the fungus. Structures of the isolated compounds, including their absolute configurations, were elucidated based on extensive spectroscopic analyses, a modified Mosher analysis, electronic circular dichroism (ECD) calculations, and [Rh2(OCOCF3)4]-induced ECD spectra as well as X-ray crystallographic analyses. Compound 1 represents the first example of a naturally occurring sesquiterpenoid containing the unusual 2,3- seco-protoilludane scaffold. Compounds 1 ( p < 0.001); 2-6, 15, and 18 ( p < 0.01); and 7, 9, and 20 ( p < 0.05) displayed ß-site amyloid precursor protein cleaving enzyme 1 (BACE1) inhibitory activities ranging from 19.4% to 43.8% at the concentration of 40 µM. LY2811376 was used as the positive control with an inhibitory activity of 38.6% ( p < 0.01). Furthermore, none of these compounds showed obvious hepatotoxicity at concentration of 40 µM.
Asunto(s)
Ascomicetos/química , Endófitos/química , Sesquiterpenos/química , Terpenos/química , Línea Celular , Cristalografía por Rayos X , Humanos , Hongos Mitospóricos/química , Sesquiterpenos Policíclicos , Sesquiterpenos/farmacología , Terpenos/farmacologíaRESUMEN
Hyperattenins L (1) and M (2), two new benzoylated polyprenylated phloroglucinol derivatives possessing unusual adamantyl and homoadamantyl core structures, were isolated from the aerial parts of Hypericum attenuatum. Their structures were determined by extensive NMR spectroscopic methods. Compound 1 possesses an unusual tetracyclo[6.3.1.11,10.01,5]tridecane skeleton, representing the second report of natural product with this carbon skeleton. Compound 2 features an unexpected 2,3,13-trioxapentacyclo[7.5.3.17,11.05,16.012,16]octodecane ring system formed by the fusion of 2,3,8-trioxabicyclo[4.3.1]decane moiety to the tricycle[4.3.1.13,8]undecane core. Both compounds were evaluated for their cytotoxic activities against five human cancer cell lines and compound 1 showed excellent inhibitory activities against HL-60, A-549, and MCF-7 cell lines with IC50 values of 3.86, 4.34, and 5.78µM, respectively.
Asunto(s)
Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Hypericum/química , Floroglucinol/análogos & derivados , Floroglucinol/farmacología , Antineoplásicos Fitogénicos/aislamiento & purificación , Línea Celular Tumoral , China , Humanos , Espectroscopía de Resonancia Magnética , Estructura Molecular , Floroglucinol/química , Floroglucinol/aislamiento & purificación , Componentes Aéreos de las Plantas/químicaRESUMEN
Azacoccones A-E (1-5), five new aza-epicoccone derivatives, were isolated from the culture of Aspergillus flavipes. Their structures were determined by extensive NMR spectroscopic analyses and the absolute configuration of 5 was determined by electronic circular dichroism (ECD) calculation. Compounds 1-5 are proposed to be generated via a Pictet-Spengler reaction-based biosynthetic route starting from the precursor flavipin. Pictet-Spengler reaction is rarely found in the fungal kingdom, which indicated the distinctive nature of 1-5. Compounds 3 and 5 exhibit significant free radical scavenging activities with IC50 values of 4.0 and 2.4µg/mL, respectively, which are better than the positive control trolox (4.55µg/mL).
Asunto(s)
Aspergillus/química , Polifenoles/aislamiento & purificación , Dicroismo Circular , Depuradores de Radicales Libres/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Estructura MolecularRESUMEN
An endophytic fungal strain named Trichoderma atroviride was isolated from the bulb of Lycoris radiata. Following cultivation on rice medium, a novel 3-amino-5-hydroxy-5-vinyl-2-cyclopenten-1-one dimer, atrichodermone A (1), a new cyclopentenone derivative, atrichodermone B (2), and a new sesquiterpene, atrichodermone C (3), together with three known cyclopentenone derivatives (4-6) were isolated. Their structures were elucidated by extensive spectroscopic (UV, IR, ECD, HRESIMS, and NMR) data analyses, and absolute configurations of the new compounds were determined by comparing their experimental ECD spectra with structurally similar compounds and computational analyses of their electronic circular dichroism (ECD) spectra. Compounds 1-3 were evaluated for their cytotoxicity against HL60 and U937 cell lines, as well as anti-inflammatory effect against the production of the pro-inflammatory cytokines TNF-α and IL-1ß.
Asunto(s)
Ciclopentanos/química , Sesquiterpenos/química , Trichoderma/química , Animales , Ciclopentanos/aislamiento & purificación , Células HL-60 , Humanos , Interleucina-1beta/metabolismo , Lycoris/microbiología , Ratones , Estructura Molecular , Raíces de Plantas/microbiología , Células RAW 264.7 , Sesquiterpenos/aislamiento & purificación , Factor de Necrosis Tumoral alfa/metabolismo , Células U937RESUMEN
A rare depsipeptide, chaetomiamide A (1), together with two known diketopiperazines (2, 3) were isolated from the cultures of endophytic fungus Chaetomium sp., which was isolated from the root of Cymbidium goeringii. Compound 1 represents a rare skeleton with a 13-membered ring system. It structure was established on the basis of spectroscopic data interpretation. The configuration of 1 was determined by NOESY and Marfey's analysis. These isolates were evaluated for anticancer activity and 3 displayed more potent cytotoxicity than the positive control cisplatin associated with G2/M cell cycle arrest. In addition, 3 induced apoptosis via caspase-3 induction and PARP cleavage, concomitantly with the increase of Bax and decrease of Bcl-2.
Asunto(s)
Apoptosis , Chaetomium/química , Neoplasias del Colon/patología , Depsipéptidos/farmacología , Caspasa 3/metabolismo , Puntos de Control del Ciclo Celular , Línea Celular Tumoral , Neoplasias del Colon/tratamiento farmacológico , Depsipéptidos/aislamiento & purificación , Dicetopiperazinas/aislamiento & purificación , Dicetopiperazinas/farmacología , Humanos , Estructura Molecular , Poli(ADP-Ribosa) Polimerasas/metabolismo , Proteínas Proto-Oncogénicas c-bcl-2/metabolismo , Proteína X Asociada a bcl-2/metabolismoRESUMEN
The new polyprenylated acylphloroglucinol derivatives 1-15 and the known furohyperforin (16) were isolated from the stems and leaves of Hypericum perforatum. Their structures were determined by analyses of NMR and HRESIMS data. Their absolute configurations were elucidated by a combination of electronic circular dichroism (ECD) and Rh2(OCOCF3)4-induced ECD, as well as X-ray diffraction crystallography. The new hyperforatin F (9) contains a unique acetyl functionality at C-1 of the bicyclo[3.3.1]nonane core. Hyperforatins G (10) and H (11) are similarly the first examples of naturally occurring [3.3.1]-type polycyclic prenylated acylphloroglucinols possessing a carbonyl functionality at C-32. The compounds were tested for their acetylcholinesterase (AChE) inhibitory activities and cytotoxic activities against a panel of human tumor cell lines. Compounds 3, 5, 6, 8, and 9 exerted moderate inhibitory activities (IC50 3.98-9.13 µM) against AChE.
Asunto(s)
Acetilcolinesterasa/química , Acetilcolinesterasa/efectos de los fármacos , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Floroglucinol/análogos & derivados , Floroglucinol/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Línea Celular Tumoral , Dicroismo Circular , Humanos , Hypericum , Concentración 50 Inhibidora , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Floroglucinol/química , Floroglucinol/farmacología , Difracción de Rayos XRESUMEN
Two new glycosides, cinnacassides F (1) and G (2), with a rare geranylphenylacetate carbon skeleton, were isolated from the barks of Cinnamomum cassia, along with three known analogues, cinnacassides A (3), B (4) and C (5). The structures of the new compounds were elucidated on the basis of extensive NMR spectroscopic analyses and chemical method. Compounds 1-5 were investigated for their immunomodulatory activities, and compounds 1, 3 and 4 showed differential immunosuppressive activities against murine lymphocytes.