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1.
Chem Biodivers ; 20(2): e202201111, 2023 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-36546830

RESUMO

Leptosperols C-G (1-5), five new phenylpropanoyl phloroglucinol derivatives were isolated from the leaves of Leptospermum scoparium. Compounds 1-3 are phenylpropanoyl phloroglucinol-sesquiterpene adducts with new carbon skeletons. Their structures with absolute configurations were elucidated by detailed spectroscopic analyses, single-crystal X-ray diffraction, and electronic circular dichroism (ECD) calculation. Compounds 2 and 3 exhibited moderate anti-inflammatory activity in zebrafish acute inflammatory models.


Assuntos
Leptospermum , Floroglucinol , Animais , Leptospermum/química , Estrutura Molecular , Floroglucinol/química , Peixe-Zebra , Cristalografia por Raios X
2.
Fitoterapia ; 163: 105303, 2022 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-36152926

RESUMO

Two novel prenylated acetophenones with new carbon skeletons, acronyrones A and B (1 and 2), and a new analogue, acronyrone C (3), together with two known compounds (4 and 5) were isolated from the leaves of Acronychia pedunculata. Their structures with absolute configurations were identified by interpretation of spectroscopic data, single crystal X-ray diffraction, and electronic circular dichroism (ECD) calculations. Compounds 1 and 2 represent the first example of prenylated acetophenones possessed a C7 (1) and a C6 (2) side chain, forming a 4-isobutylchroman-2-one unit and a 3-(2-methylpropylidene)benzofuran-2(3H)-one moiety with the acetophenone core, respectively. In addition, compound 4 exhibited significant dose-dependent transcriptional activation effect against retinoid X receptor-α (RXRα), and could be regarded as a new type of non-classical RXR ligand.


Assuntos
Rutaceae , Thoracica , Animais , Estrutura Molecular , Rutaceae/química , Acetofenonas/química , Folhas de Planta/química
3.
Chem Biodivers ; 18(6): e2100252, 2021 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-33988294

RESUMO

Leptosparones A-F (1-6), six new dimeric acylphloroglucinol derivatives with unprecedented skeletons, were isolated from Leptospermum scoparium. Compounds 1-3 and 5-6 are phenylpropanoyl-phloroglucinol dimers, while 4 is a phenylpropanoylphloroglucinol-isovalerylphloroglucinol hybrid. Structurally, these compounds represent the first examples of dimeric phloroglucinols with unprecedented C(7')-C(8) linkage between the phloroglucinol core and the acyl side chain. Their structures were elucidated by comprehensive analyses of spectroscopic data, single crystal X-ray diffraction and chemical calculations. In addition, all compounds showed inhibitory effects against α-glucosidase with IC50 values ranging from 39.5 to 186.8 µM.


Assuntos
Inibidores de Glicosídeo Hidrolases/farmacologia , Leptospermum/química , Floroglucinol/farmacologia , alfa-Glucosidases/metabolismo , Cristalografia por Raios X , Relação Dose-Resposta a Droga , Inibidores de Glicosídeo Hidrolases/síntese química , Inibidores de Glicosídeo Hidrolases/química , Humanos , Modelos Moleculares , Estrutura Molecular , Floroglucinol/síntese química , Floroglucinol/química
4.
Org Lett ; 22(5): 1796-1800, 2020 03 06.
Artigo em Inglês | MEDLINE | ID: mdl-32091219

RESUMO

Leptosperols A and B (1 and 2), two cinnamoylphloroglucinol-sesquiterpenoid hybrids featuring unprecedented 1-benzyl-2-(2-phenylethyl) cyclodecane and 2-benzyl-3-phenylethyl decahydronaphthalene backbones, along with their biosynthetic precursor (3), were isolated from Leptospermum scoparium. Compounds 1 and 2 represent the first example of phloroglucinol derivatives biogenetically constructed by a De Mayo reaction. The biomimetic synthesis of leptosperol B (2) was achieved using the proposed biosynthetic pathway. In addition, compounds 1 and 2 showed significant anti-inflammatory effects in zebrafish acute inflammatory models.


Assuntos
Leptospermum/química , Floroglucinol/química , Sesquiterpenos/química , Biomimética , Estrutura Molecular , Floroglucinol/análogos & derivados , Sesquiterpenos/síntese química
5.
Opt Express ; 26(19): 25037-25046, 2018 Sep 17.
Artigo em Inglês | MEDLINE | ID: mdl-30469612

RESUMO

Metallic nanoparticles (NPs) support localized surface plasmon resonances (LSPRs), which enable to concentrate sunlight at the active layer of solar cells. However, full-wave modeling of the plasmonic solar cells faces great challenges in terms of huge computational workload and bad matrix condition. It is tremendously difficult to accurately and efficiently simulate near-field multiple scattering effects from plasmonic NPs embedded into solar cells. In this work, a preconditioned volume integral equation (VIE) is proposed to model plasmonic organic solar cells (OSCs). The diagonal block preconditioner is applied to different material domains of the device structure. As a result, better convergence and higher computing efficiency are achieved. Moreover, the calculation is further accelerated by two-dimensional periodic Green's functions. Using the proposed method, the dependences of optical absorption on the wavelengths and incident angles are investigated. Angular responses of the plasmonic OSCs show the super-Lambertian absorption on the plasmon resonance but near-Lambertian absorption off the plasmon resonance. The volumetric method of moments and explored physical understanding are of great help to investigate the optical responses of OSCs.

6.
Fitoterapia ; 118: 112-117, 2017 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-28300700

RESUMO

Five new koumine-type alkaloids (1-5) along with six known ones were isolated from the roots of Gelsemium elegans. Their structures with absolute configurations were elucidated on the basis of NMR spectroscopy and electronic circular dichroism spectral analyses. The inhibitory effects of compounds 1-11 on the viability of three tumor cell lines (A-649, HepG2, and HuH7) were evaluated by the MTT assay.


Assuntos
Gelsemium/química , Alcaloides Indólicos/química , Linhagem Celular Tumoral , Dicroísmo Circular , Humanos , Alcaloides Indólicos/isolamento & purificação , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Extratos Vegetais/química , Raízes de Plantas/química
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