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1.
Fitoterapia ; 158: 105160, 2022 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-35182695

RESUMO

Isogeopyxins A-C (1-3), three new diterpenoids with ent-kaurane, ent-pimarane, and ent-abietane scaffolds, respectively, along with six known ent-kauranoids, were isolated from the fermentation culture of Geopyxis sp. XY93 inhabiting the leaves of Isodon parvifolia. Their structures were elucidated by interpretation of spectroscopic data, and single crystal X-ray diffraction. It marks the first time that ent-kauranoids, characteristic metabolites of Isodon species, have been isolated from an associated endophytic fungus.


Assuntos
Antineoplásicos Fitogênicos , Ascomicetos , Diterpenos do Tipo Caurano , Diterpenos , Isodon , Antineoplásicos Fitogênicos/química , Ensaios de Seleção de Medicamentos Antitumorais , Isodon/química , Estrutura Molecular
2.
Chin J Nat Med ; 17(12): 970-981, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31882053

RESUMO

Nineteen preschisanartane-type schinortriterpenoids (SNTs), among which eleven ones were previously undescribed, were isolated from two Schisandra species, S. sphaerandra and S. rubriflora. Their structures were determined using 1D and 2D NMR spectroscopic analyses, NMR data comparison, quantum chemical calculation of NMR parameters, electronic circular dichroism (ECD), X-ray single crystal diffraction, and chemical derivation. Furthermore, structural re-examination of a few previously reported preschisanartane-type SNTs led to the structural revision of preschisanartanin J. Besides, it is suggested that the reported structures of arisanlactone D and schilancidilactone W should be re-checked. Finally, a few isolated SNTs were found to possess neurite outgrowth-promoting activities, and protective activities against neural injuries.


Assuntos
Schisandra/química , Triterpenos/química , Triterpenos/isolamento & purificação , China , Dicroísmo Circular , Cristalografia por Raios X , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Componentes Aéreos da Planta/química
3.
J Nat Prod ; 80(7): 2026-2036, 2017 07 28.
Artigo em Inglês | MEDLINE | ID: mdl-28654256

RESUMO

Fourteen new diterpenoids (1-14) based on four skeletal types and two known analogues (15 and 16) were isolated from the aerial parts of Isodon scoparius. Compound 2 is the first ent-kaurane diterpenoid featuring a 1,11-ether bridge, and the structures of these new compounds were established mainly by NMR and MS methods. The absolute configurations of 1 and 5 and the relative configuration of 3 were determined using single-crystal X-ray diffraction. The absolute configuration of 14 was determined by comparison of the experimental and calculated electronic circular dichroism spectra. Compounds 1, 4, and 15 were active against five human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW-480), and they also inhibited NO production in LPS-stimulated RAW264.7 cells, with IC50 values of 1.0, 3.1, and 1.8 µM, respectively.


Assuntos
Antineoplásicos Fitogênicos , Diterpenos do Tipo Caurano , Isodon/química , Componentes Aéreos da Planta/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Cristalografia por Raios X , Diterpenos do Tipo Caurano/química , Diterpenos do Tipo Caurano/isolamento & purificação , Diterpenos do Tipo Caurano/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Células HL-60 , Humanos , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Estrutura Molecular , Óxido Nítrico/biossíntese , Ressonância Magnética Nuclear Biomolecular
4.
Molecules ; 22(2)2017 Feb 17.
Artigo em Inglês | MEDLINE | ID: mdl-28218684

RESUMO

Four new ent-abietane diterpenoids, along with four known ones were isolated from the aerial parts of Isodon serra, a traditional Chinese folk medicine. The new diterpenoids were named as serrin K (1), xerophilusin XVII (2), and enanderianins Q and R (3 and 4), while the known ones were identified as rubescansin J (5), (3α,14ß)-3,18-[(1-methylethane-1,1-diyl)dioxy]-ent-abieta-7,15(17)-diene-14,16-diol (6), xerophilusin XIV (7), and enanderianin P (8), respectively. Their structures were elucidated by extensive spectroscopic analysis and comparison with the literature. Compound 1 showed remarkable inhibitory activity towards NO production in LPS-stimulated RAW264.7 cells (IC50 = 1.8 µM) and weak cytotoxicity towards five human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7, SW480).


Assuntos
Abietanos/química , Abietanos/isolamento & purificação , Isodon/química , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Abietanos/farmacologia , Animais , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular , Linhagem Celular Tumoral , Humanos , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Espectroscopia de Ressonância Magnética , Camundongos , Modelos Moleculares , Conformação Molecular , Estrutura Molecular , Óxido Nítrico/biossíntese , Componentes Aéreos da Planta/química , Extratos Vegetais/farmacologia
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