Your browser doesn't support javascript.
loading
Mostrar: 20 | 50 | 100
Resultados 1 - 20 de 32
Filtrar
Más filtros










Base de datos
Intervalo de año de publicación
1.
J Agric Food Chem ; 2024 Apr 11.
Artículo en Inglés | MEDLINE | ID: mdl-38602386

RESUMEN

The genus Salix L. is traditionally used in folk medicine to alleviate pain caused by various kinds of inflammation. In the present study, 10 undescribed salicin derivatives along with 5 known congeners were isolated from the barks of Salix tetrasperma, and their structures were elucidated by spectroscopic analyses, single-crystal X-ray diffraction, electronic circular dichroism (ECD) calculations, and chemical conversions. Compounds 4-6 significantly inhibited NO production in lipopolysaccharide (LPS)-induced RAW 264.7 macrophages, and the most active 4 obviously suppressed the production of IL-1ß and IL-6 and decreased iNOS and COX-2 expression in a dose-dependent manner. Further Western blotting analysis revealed that the anti-inflammatory mechanism of 4 is possibly mediated through the MAPK and NF-κB signaling pathways.

2.
Phytochemistry ; 220: 113993, 2024 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-38266954

RESUMEN

Nine previously unreported various types of monoterpenoid indole alkaloids, together with seven known analogues were isolated from the stem barks of Alstonia scholaris through a silica gel free methodology. The structures of 1-9 were elucidated by spectroscopic data analysis, electronic circular dichroism calculations, and single-crystal X-ray diffraction. Compound 1 is a modified echitamine-type alkaloid with a novel 6/5/5/7/6/6 hetero hexacyclic bridged ring system, and 8 and 9 exist as a zwitterion and trifluoroacetate salt, respectively. The anti-Toxoplasma activity of all isolates on infected Vero cells were evaluated, which revealed that compound 14 at 0.24 µM displayed potent activity. This study expanded the structural diversity of alkaloids of A. scholaris, and presented their potential application in anti-Toxoplasma drug development.


Asunto(s)
Alstonia , Alcaloides de Triptamina Secologanina , Toxoplasma , Animales , Chlorocebus aethiops , Alcaloides de Triptamina Secologanina/farmacología , Alcaloides de Triptamina Secologanina/química , Estructura Molecular , Alstonia/química , Células Vero , Alcaloides Indólicos
3.
J Nat Prod ; 86(10): 2315-2325, 2023 10 27.
Artículo en Inglés | MEDLINE | ID: mdl-37728995

RESUMEN

Eleven densely functionalized new dihydro-ß-agarofuran sesquiterpenoid derivatives, named maytenoids A-K (1-11), as well as one known analog, were isolated and characterized from Maytenus austroyunnanensis. Their structures were assigned based on analysis of spectroscopic data and X-ray crystallography. Compounds 1-9 are macrocyclic sesquiterpene pyridine alkaloids generated by the respective acylation of the hydroxy groups at C-3 and C-13 of dihydro-ß-agarofuran sesquiterpenoids via diverse pyridine dicarboxylic acids. Compounds 1, 2, 5-10, and 12 exhibited significant inhibitory effects on NO production at 10 µM in lipopolysaccharide (LPS)-stimulated BV2 cells.


Asunto(s)
Alcaloides , Maytenus , Sesquiterpenos , Maytenus/química , Estructura Molecular , Alcaloides/farmacología , Alcaloides/química , Sesquiterpenos/farmacología , Sesquiterpenos/química , Piridinas/química
4.
Phytochemistry ; 213: 113745, 2023 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-37277012

RESUMEN

Nine undescribed diterpenoids, euphlactenoids A-I (1-9), including four ingol-type diterpenoids (1-4) with a 5/3/11/3-tetracyclic framework and five ent-pimarane-type diterpenoids (5-9), together with thirteen known diterpenoids (10-22), were identified from the leaves and stems of Euphorbia lactea Haw. The structures and absolute configurations of compounds 1-9 were unequivocally elucidated on the basis of spectroscopic analysis, ECD calculations and single crystal X-ray diffraction. Compounds 3 and 16 showed anti-HIV-1 effects with IC50 values of 1.17 µM (SI = 16.54) and 13.10 µM (SI = 1.93), respectively.


Asunto(s)
Diterpenos , Euphorbia , VIH-1 , Euphorbia/química , Estructura Molecular , Diterpenos/farmacología , Diterpenos/química , Abietanos
5.
J Nat Prod ; 86(6): 1606-1614, 2023 06 23.
Artículo en Inglés | MEDLINE | ID: mdl-37307145

RESUMEN

Chemical investigation of the twigs of Cleistanthus sumatranus (Phyllanthaceae) led to the isolation of 10 undescribed lignans, sumatranins A-J (1-10). Compounds 1-4 are unprecedented furopyran lignans characterized by a unique 2,3,3a,9a-tetrahydro-4H-furo[2,3-b]chromene heterotricyclic framework. Compounds 9 and 10 are rare 9'-nor-dibenzylbutane lignans. Structures were established based on analyses of spectroscopic data, X-ray crystallographic data, and experimental ECD spectra. Immunosuppressive assays revealed compounds 3 and 9 displayed moderate inhibitory effects with good selectivity indexes against LPS-induced B lymphocyte proliferation.


Asunto(s)
Lignanos , Malpighiales , Lignanos/farmacología , Lignanos/química , Estructura Molecular
6.
J Nat Prod ; 86(5): 1345-1359, 2023 05 26.
Artículo en Inglés | MEDLINE | ID: mdl-37159431

RESUMEN

Laeviganoids A-T (1-20), 20 new ent-clerodane-type diterpenoids featuring a 2-furanone (1-3) or a furan (4-20) ring, as well as six analogues (21-26), were isolated from the roots of Croton laevigatus. Their structures were determined by spectroscopic data analysis, experimental electronic circular dichroism measurements, and X-ray crystallographic studies. Compounds 4-6, 16, 21-24, and 26 could influence the anti-inflammatory protumoral phenotype of macrophages. Among these compounds, 21 and 26 are the most potent, as evidenced by consistently downregulating the classic anti-inflammatory cytokine IL-10 and upregulating the classic pro-inflammatory cytokine TNF-α on the secretion level in RAW 264.7 cells.


Asunto(s)
Croton , Diterpenos de Tipo Clerodano , Diterpenos , Animales , Ratones , Diterpenos de Tipo Clerodano/farmacología , Diterpenos de Tipo Clerodano/química , Croton/química , Estructura Molecular , Diterpenos/farmacología , Diterpenos/química , Antiinflamatorios/farmacología , Células RAW 264.7
7.
Org Biomol Chem ; 20(45): 9000-9009, 2022 11 23.
Artículo en Inglés | MEDLINE | ID: mdl-36330968

RESUMEN

Seventeen new cephalotane-type diterpenoids, fortalides A-Q (1-17), along with five known analogues, were isolated from the seeds of Cephalotaxus fortunei var. alpina. Their structures were determined by extensive spectroscopic methods, as well as electronic circular dichroism (ECD) and X-ray crystallographic data analyses. Some isolates exhibited unusual structural features that were first found in cephalotane-type diterpenoids, such as the occurrence of the 7-oxabicyclo[4.1.1]octane moiety in 14 and 15 and the cis-arrangement of 3-OH and Me-19 in 9. Besides, the antiplasmodial activity of these compounds was evaluated in this study.


Asunto(s)
Cephalotaxus , Diterpenos , Cephalotaxus/química , Estructura Molecular , Diterpenos/farmacología , Diterpenos/química , Dicroismo Circular , Cristalografía por Rayos X
8.
J Nat Prod ; 85(8): 2090-2099, 2022 08 26.
Artículo en Inglés | MEDLINE | ID: mdl-35957573

RESUMEN

Spicatulides A-G (1-7), seven new phenolic-monoterpenoid hybrid molecules, along with two known compounds, 8 and 9, were isolated and identified from Chloranthus spicatus. Compound 1 represents an unprecedented skeleton featuring an aryl-fused 2-oxabicyclo[4.3.1]decane moiety, and compound 2 is the first example of a denudaquinol-normonoterpenoid adduct. Their structures with absolute configurations were elucidated on the basis of spectroscopic data analyses and TDDFT-ECD calculations. Compounds 3, 5, 6, and 9 exhibited the activity of reducing lipogenesis in HepG2 cells in a dose-dependent manner.


Asunto(s)
Monoterpenos , Semillas , Estructura Molecular
9.
Phytochemistry ; 198: 113142, 2022 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-35231502

RESUMEN

A chemical investigation on the aerial parts of Euphorbia neriifolia led to the identification of thirteen undescribed diterpenoids, phorneroids A-M, including ent-abietane (A-D), ent-kaurane (E-G), ent-atisane (H-K), and ent-isopimarane (L and M) types, together with three known compounds. Phorneroid A represents the first example of 8-spiro-fused 9,10-seco-ent-abietane diterpenoid lactone featuring a unique 6/5/6/5 spirocyclic framework. Biological assays showed that some of the compounds displayed moderate cytotoxicity against two human tumor cell lines, A549 and HL-60.


Asunto(s)
Diterpenos de Tipo Kaurano , Diterpenos , Euphorbia , Línea Celular Tumoral , Diterpenos/química , Diterpenos/farmacología , Diterpenos de Tipo Kaurano/química , Euphorbia/química , Estructura Molecular
10.
J Nat Prod ; 83(6): 1751-1765, 2020 06 26.
Artículo en Inglés | MEDLINE | ID: mdl-32468815

RESUMEN

Eighteen new limonoids, including eight methyl angolensates (1-8) and 10 cipadesins (9-18), were isolated from the leaves of Cipadessa baccifera. Their structures were characterized by means of spectroscopic data analyses, single-crystal X-ray diffraction, and quantum chemistry computational methods. The C-6 configurations in those compounds possessing a C-6 hydroxy group were all assigned as S regardless of the magnitude of J5,6, and the C-2' configuration in those bearing a 2-methylbutyryl residue was defined by single-crystal X-ray diffraction and NMR data. Compounds 1, 5, 6, 7, 11, and 12 showed moderate antimalarial activities with IC50 values ranging from 12 to 28 µM.


Asunto(s)
Limoninas/química , Meliaceae/química , Animales , Antimaláricos/farmacología , Antineoplásicos Fitogénicos/química , Limoninas/farmacología , Espectroscopía de Resonancia Magnética , Conformación Molecular , Estructura Molecular , Hojas de la Planta/química , Plasmodium falciparum/efectos de los fármacos , Espectrometría de Masa por Ionización de Electrospray , Difracción de Rayos X
11.
Org Lett ; 21(17): 7065-7068, 2019 09 06.
Artículo en Inglés | MEDLINE | ID: mdl-31411483

RESUMEN

The suadimins A-C (1-3) from Melodinus suaveolens are the first example of monoterpenoid quinoline alkaloid dimers featuring an unprecedented carbon skeleton. Their structures and absolute configurations were established on the basis of extensive spectroscopic analyses, electric circular dichroism (ECD), and X-ray crystallography. Suadimin A showed significant antimycobacterial activity in vitro with an MIC90 of 6.76 µM against the H37Rv strain of M. tuberculosis.


Asunto(s)
Antibacterianos/farmacología , Apocynaceae/química , Mycobacterium tuberculosis/efectos de los fármacos , Quinolinas/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Cristalografía por Rayos X , Pruebas de Sensibilidad Microbiana , Modelos Moleculares , Conformación Molecular , Quinolinas/química , Quinolinas/aislamiento & purificación , Estereoisomerismo
12.
J Nat Prod ; 82(6): 1565-1575, 2019 06 28.
Artículo en Inglés | MEDLINE | ID: mdl-31184894

RESUMEN

Seventeen new 17- nor-cephalotane-type diterpenoids, fortalpinoids A-Q (1-17), were isolated from the seeds of Cephalotaxus fortunei var. alpine. Compound 12 represents the first 17- nor-cephalotane-type diterpenoid featuring an 8-oxabicyclo[3.2.1]oct-2-ene moiety. The absolute configuration of fortunolide A (18) was determined for the first time, and the structure of cephinoid Q was revised to 14- epi-cephafortoid A (24) by X-ray crystallographic data analysis. Some of the compounds showed significant cytotoxicity against A549 and HL-60 cells, and the structure-activity relationship of this compound class is discussed.


Asunto(s)
Antineoplásicos Fitogénicos/química , Cephalotaxus/química , Hojas de la Planta/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Línea Celular Tumoral , Diterpenos/química , Ensayos de Selección de Medicamentos Antitumorales , Células HL-60 , Humanos , Estructura Molecular
13.
J Nat Prod ; 82(6): 1550-1557, 2019 06 28.
Artículo en Inglés | MEDLINE | ID: mdl-31117522

RESUMEN

Chemical investigation of an EtOH extract of the twigs and leaves of Croton damayeshu afforded 10 new tigliane diterpenoids, crodamoids A-J (1-10), along with five known compounds. Their structures were elucidated by physical data analysis. Compounds 8, 9, and 15 displayed cytotoxic effects against two human tumor cell lines, A549 and HL-60 (IC50: 0.9-2.4 µM).


Asunto(s)
Antineoplásicos Fitogénicos/química , Croton/química , Diterpenos/química , Forboles/toxicidad , Hojas de la Planta/química , Antineoplásicos Fitogénicos/farmacología , Línea Celular Tumoral , Croton/toxicidad , Diterpenos/aislamiento & purificación , Diterpenos/farmacología , Diterpenos/toxicidad , Células HL-60 , Humanos , Espectroscopía de Resonancia Magnética , Estructura Molecular , Forboles/química
14.
J Org Chem ; 84(9): 5195-5202, 2019 05 03.
Artículo en Inglés | MEDLINE | ID: mdl-30892044

RESUMEN

Capitulactones A-C, three unprecedented 9-norlignans featuring a unique 3,5-dihydrofuro[2,3- d]oxepin-7(2 H)-one scaffold, were isolated from the roots of Curculigo capitulata. Their structures with absolute configurations were unambiguously established by a combination of spectroscopic data, ECD analysis, and total synthesis. Biomimetic total syntheses of three pairs of the corresponding enantiomers were achieved in 9-10 steps with overall yields of 14.8, 12.7, and 10.3%, respectively. Notably, the unique scaffold of the common western hemisphere of the molecules was constructed by using the oxidation-reduction strategy from benzodihydrofuran.


Asunto(s)
Curculigo/química , Lignanos/química , Lignanos/síntesis química , Técnicas de Química Sintética , Modelos Moleculares , Conformación Molecular , Oxidación-Reducción , Estereoisomerismo
15.
Org Lett ; 21(6): 1904-1907, 2019 03 15.
Artículo en Inglés | MEDLINE | ID: mdl-30835483

RESUMEN

Urceoloids A (1) and B (2), two C19 steroids with a rearranged new carbon skeleton by featuring a very unique spiro[4.4]nona-3,6,8-triene system, and a biosynthetically related known steroid (3) were isolated from Urceola quintaretii. Their structures were completely established by a combined method. A plausible biosynthetic pathway for the new carbon skeleton represented by compounds 1 and 2 was proposed. Compounds 2 and 3 showed immunosuppressive activities.


Asunto(s)
Apocynaceae/química , Carbono/química , Esteroides/química , Vías Biosintéticas , Estructura Molecular
16.
Org Lett ; 21(5): 1471-1474, 2019 03 01.
Artículo en Inglés | MEDLINE | ID: mdl-30758208

RESUMEN

Four indole alkaloids, alstonlarsines A-D (1-4), were isolated from Alstonia scholaris and structurally characterized. Compound 1 possesses a new carbon skeleton with a cage-shaped 9-azatricyclo[4.3.1.03,8]decane motif, and compounds 2-4 feature a rare carbon skeleton that was found in nature for the first time. Plausible biosynthetic routes for 1-4 are proposed. Compound 1 showed DRAK2 inhibitory activity with an IC50 value of 11.65 ± 0.63 µΜ.

17.
Org Lett ; 19(3): 734-737, 2017 02 03.
Artículo en Inglés | MEDLINE | ID: mdl-28124917

RESUMEN

Three dimeric sesquiterpenoids (1-3), fortunoid A (1) possessing a new carbon skeleton of rearranged lindenane dimer and fortunoids B (2) and C (3) representing the first example of the dimers of a lindenane and a eudesmane sesquiterpene, were isolated from Chloranthus fortunei. Their structures with absolute configurations were established by spectroscopic data and electric circular dichroism analysis. Their biosynthetic origins were also proposed. Compounds 1 and 2 showed moderate antimalarial activities.

18.
J Nat Prod ; 80(1): 96-107, 2017 01 27.
Artículo en Inglés | MEDLINE | ID: mdl-27997206

RESUMEN

Inspired by the discovery of the antimalarial drug artemisinin from a traditional Chinese medicine (TCM), a natural product library of 44 lindenane-type sesquiterpenoids was assessed for activities against the Dd2 chloroquine-resistant strain of the malaria parasite Plasmodium falciparum. These compounds were mainly isolated from plants of the Chloranthus genus, many species of which are named "Sikuaiwa" in TCM and have long been used to treat malaria. The compounds consisted of 41 sesquiterpenoid dimers and three monomers, including the 12 new dimers 1-12 isolated from Chloranthus fortunei. The results showed that 16 dimers exhibited potent antiplasmodial activities (<100 nM); in particular, compounds 1, 14, and 19 exhibited low nanomolar activities with IC50 values ranging from 1 to 7 nM, which is comparable to the potency of artemisinin, and selectivity index values toward mammalian cells greater than 500. A comprehensive structure-activity relationship study indicated that three functional groups are essential and two motifs can be modified.


Asunto(s)
Antimaláricos/aislamiento & purificación , Antimaláricos/farmacología , Artemisininas/química , Cloroquina/farmacología , Magnoliopsida/química , Plantas Medicinales/química , Plasmodium falciparum/efectos de los fármacos , Animales , Antimaláricos/química , Cloroquina/química , Concentración 50 Inhibidora , Estructura Molecular , Relación Estructura-Actividad
19.
Org Lett ; 18(12): 2894-7, 2016 06 17.
Artículo en Inglés | MEDLINE | ID: mdl-27228486

RESUMEN

Three new ring B-seco limonoids, ciliatonoids A-C (1-3), were isolated from Toona ciliate and structurally characterized by spectroscopic data, X-ray crystallography, and electronic circular dichroism analysis. Ciliatonoids A and B feature an unprecedented limonoid architecture, while ciliatonoid C belongs to a rare class of limonoids. Biological evaluation showed that compound 3 exhibited modest activities against the tested tumor cell lines.


Asunto(s)
Antineoplásicos Fitogénicos/química , Limoninas/química , Meliaceae/química , Extractos Vegetales/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Dicroismo Circular , Cristalografía por Rayos X , Humanos , Limoninas/aislamiento & purificación , Limoninas/farmacología , Espectroscopía de Resonancia Magnética/métodos , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología
20.
J Nat Prod ; 79(5): 1365-72, 2016 05 27.
Artículo en Inglés | MEDLINE | ID: mdl-27142786

RESUMEN

Nine new conjugates of sesquiterpenoids and acylphloroglucinols, named eucarobustols A-I (1-9), as well as 11 known analogues were isolated from the leaves of Eucalyptus robusta. The sesquiterpenoid motifs furnishing the new conjugates included four structural types of aristolane (1 and 2), guaiane (3), eudesmane (4), and aromadendrane (5-9) moieties. Compounds 1 and 2 were found to represent the first examples of conjugates of aristolane and acylphloroglucinol units. In turn, compound 3 features a new coupling model of guaiane and acylphloroglucinol via the C-4-C-7' bond. Compounds 1, 7, and 9 showed inhibitory activities against protein tyrosine phosphatase 1B (PTP1B) with IC50 values of 1.3, 1.8, and 1.6 µM, respectively.


Asunto(s)
Medicamentos Herbarios Chinos/aislamiento & purificación , Eucalyptus/química , Sesquiterpenos de Eudesmano/aislamiento & purificación , Sesquiterpenos de Guayano/aislamiento & purificación , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/farmacología , Concentración 50 Inhibidora , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Hojas de la Planta/química , Proteína Tirosina Fosfatasa no Receptora Tipo 1/antagonistas & inhibidores , Sesquiterpenos , Sesquiterpenos de Eudesmano/química , Sesquiterpenos de Eudesmano/farmacología , Sesquiterpenos de Guayano/química , Sesquiterpenos de Guayano/farmacología
SELECCIÓN DE REFERENCIAS
DETALLE DE LA BÚSQUEDA
...