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1.
Chin Herb Med ; 13(1): 98-104, 2021 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-36117764

RESUMEN

Objective: Peptidyl alkaloids, a series of important natural products can be assembled by fungal non-ribosomal peptide synthetases (NRPSs). However, many of the NRPSs associated gene clusters are silent under laboratory conditions, and the traditional chemical separation yields are low. In this study, we aim to discovery and efficiently prepare fungal peptidyl alkaloids assembled by fungal NRPSs. Methods: Bioinformatics analysis of gene cluster containing NRPSs from the genome of Penicillium thymicola, and heterologous expression of the putative gene cluster in Aspergillus nidulans were performed. Isolation, structural identification, and biological evaluation of the product from heterologous expression were carried out. Results: The putative tri-modular NRPS AncA was heterologous-expressed in A. nidulans to give anacine (1) with high yield, which showed moderate and selective cytotoxic activity against A549 cell line. Conclusion: Heterologous expression in A. nidulans is an efficient strategy for mining fungal peptidyl alkaloids.

2.
Org Lett ; 22(9): 3428-3432, 2020 05 01.
Artículo en Inglés | MEDLINE | ID: mdl-32301324

RESUMEN

Commiphoranoids A-E (1-5), five novel sesquiterpenoids, dinorditerpenoids, and heterodimers with unprecedented carbon skeletons, were isolated from Resina Commiphora. The structure of 1 was secured by X-ray crystallography. Compound 4 represents the first example of C38 terpenoids, whereas 5 is a C30 terpenoid formed by two types of sesquiterpenoids. These metabolites possess lipid regulatory activities via activating PPARα and CPT1.


Asunto(s)
Commiphora , Sesquiterpenos , Commiphora/química , Metabolismo de los Lípidos , PPAR alfa , Resinas de Plantas/química , Sesquiterpenos/química , Sesquiterpenos/farmacología , Terpenos/química , Terpenos/farmacología
3.
Molecules ; 24(8)2019 Apr 15.
Artículo en Inglés | MEDLINE | ID: mdl-30991677

RESUMEN

Four new compounds including two new sesquiterpenoid dimers, commiphoroids E (1) and F (2), a new triterpenoid (3), and a new sesquiterpenoid (4), along with three known terpenoids (5-7) were isolated from Resina Commiphora, whose structures were identified by NMR spectra, HRESIMS, and X-ray diffraction analysis. Compounds 1 and 2 both bear an O-bridge ring and feature a plausible [4 + 2] Diels-Alder cycloaddition reaction. Antimycobacterial activities show that all the tested compounds (200 µM) could inhibit the growth of both sensitive and clinically multi-drug resistant (MDR) isolated strains. In addition, cellular toxicity of the isolates against human cancer cells and THP-1 monocyte cells was examined.


Asunto(s)
Antituberculosos , Commiphora/química , Mycobacterium tuberculosis/crecimiento & desarrollo , Resinas de Plantas/química , Terpenos , Antituberculosos/química , Antituberculosos/farmacología , Humanos , Células THP-1 , Terpenos/química , Terpenos/farmacología
4.
Org Lett ; 21(6): 1837-1840, 2019 03 15.
Artículo en Inglés | MEDLINE | ID: mdl-30810324

RESUMEN

Populusone (1), a cembrane-type macrocyclic trinorditerpenoid, was isolated from the exudates of Populus euphratica and shown to have an unprecedented carbon skeleton, The structure was identified using spectroscopic methods and X-ray crystallography. A possible pathway for the biosynthesis of 1 was proposed. Populusone (10 µM) was found to promote proliferation and differentiation of umbilical cord derived mesenchymal stem cells into keratinocyte like cells.


Asunto(s)
Células Madre Mesenquimatosas/fisiología , Populus/fisiología , Cordón Umbilical/fisiología , Diferenciación Celular , Células Madre Mesenquimatosas/química , Estructura Molecular , Populus/química , Cordón Umbilical/química
5.
Org Lett ; 20(8): 2220-2223, 2018 04 20.
Artículo en Inglés | MEDLINE | ID: mdl-29582665

RESUMEN

Two sesquiterpene dimers, commiphoratones A (1) and B (2), were isolated from Resina Commiphora. Their structures were elucidated by spectroscopic, computational, and crystallographic methods. Compounds 1 and 2 represent an unusual pattern of dimerization between two types of sesquiterpenes. Moreover, compound 1 has a saddle shape. The plausible biosynthetic pathway for 1 and 2 is presented. Bioassay showed that 1 and 2 significantly block lipid metabolism in a concentration-dependent manner.

6.
J Org Chem ; 83(5): 2725-2733, 2018 03 02.
Artículo en Inglés | MEDLINE | ID: mdl-29430927

RESUMEN

The new sesquiterpene dimers commiphoroids A-D (1-4) were isolated from Resina Commiphora, and their structures were assigned by spectroscopic methods and X-ray diffraction analysis. Compounds 1 and 2 are stereoisomers of putative [2 + 4]-cycloaddition reactions, and 3 is a trinorsesquiterpene dimer containing a 6/6/5/6/6/6 hexacyclic framework, while 4 possesses a 8-oxabicyclo[3.2.1]oct-6-ene skeletal core. Plausible biosynthetic pathways for 1-4 are proposed. Biochemical studies show that compound 1 promotes ca. 60% expression of keratinocyte-specific markers in adipose-derived stem cells at 10 µM.


Asunto(s)
Tejido Adiposo/citología , Diferenciación Celular/efectos de los fármacos , Commiphora/química , Dimerización , Sesquiterpenos/química , Sesquiterpenos/farmacología , Células Madre/efectos de los fármacos , Proliferación Celular/efectos de los fármacos , Humanos , Células Madre/citología
7.
Fitoterapia ; 125: 135-140, 2018 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-29309828

RESUMEN

Three new diterpenoids, spicatusenes A-C (1-3), and eleven known ones (4-14) were isolated from the aerial parts of Clerodendranthus spicatus. Their structures were identified by spectroscopic methods. The cytotoxic activities of all the compounds against human cancer cells (HL-60, SMMC-7721, A-549, MCF-7, and SW-480) were examined and found that compounds 2, 3, 6, 8, 10, and 13 were active against one or more cancer cell lines. Besides, the renoprotective effects of all the isolates in TGF-ß1-induced rat kidney fibroblasts revealed that compounds 3-7, 9, 13, and 14 were beneficial for renal fibrosis. Finally, a plausible biosynthetic pathway for 1 via a Hantzsch-type reaction was proposed.


Asunto(s)
Diterpenos/química , Lamiaceae/química , Animales , Línea Celular Tumoral , China , Diterpenos/aislamiento & purificación , Fibroblastos/efectos de los fármacos , Humanos , Estructura Molecular , Componentes Aéreos de las Plantas/química , Ratas , Factor de Crecimiento Transformador beta1
8.
Beijing Da Xue Xue Bao Yi Xue Ban ; 38(4): 365-9, 2006 Aug 18.
Artículo en Chino | MEDLINE | ID: mdl-16892139

RESUMEN

OBJECTIVE: To explore the role of anti-alphabeta T cell receptor (TCR) and anti-CD80 monoclonal antibodies (mAbs) combined with donor bone marrow cells (BMCs) infusion in the induction of murine skin allografts tolerance. METHODS: On day 0, 2 x 10(8) BMCs of BALB/c mice were injected into recipient C57BL/6 mice via the tail vein, meanwhile, an intraperitoneal injection of TCRalphabeta mAb (500 microg) was given. On day 2, CD80 mAb was administered intraperitoneally. Skin grafting was performed on day 6. Delayed type hypersensitivity (DTH), mixed lymphocyte reaction (MLR), IL-2 reverse assay of MLR, adoptive transfer assay and chimerism detection were performed at different time points and tolerance mechanisms were investigated. RESULTS: The mean survival time (MST) of BALB/c skin allografts in C57BL/6 recipients that were treated by anti-TCRalphabeta and anti-CD80 mAbs combined with donor BMCs infusion was 70 days. DTH and MLR assay indicated that the tolerant mice displayed significant hyporesponsiveness. The result of IL-2 reverse test showed that clone anergy was probably involved in the formation of tolerance in the tolerant C57BL/6 mice. In vivo and in vitro adoptive transfer assay, suppressive activity in the spleens of tolerant C57BL/6 mice was observed. Chimerism existed in both the thymus and spleen of the tolerant C57BL/6 mice. The chimerism level gradually declined with time. CONCLUSION: Treatment of anti-TCRalphabeta and anti-CD80 mAbs combined with donor BMCs infusion can successfully induce a long-term tolerance in BALB/c mice to C57BL/6 skin graft. Multiple mechanisms, including clone anergy, suppressor cells and chimerism are involved in the tolerance.


Asunto(s)
Anticuerpos Monoclonales/administración & dosificación , Trasplante de Médula Ósea , Antígenos CD8/inmunología , Receptores de Antígenos de Linfocitos T alfa-beta/inmunología , Trasplante de Piel/inmunología , Animales , Anticuerpos Monoclonales/inmunología , Anergia Clonal/inmunología , Femenino , Tolerancia Inmunológica/efectos de los fármacos , Tolerancia Inmunológica/inmunología , Prueba de Cultivo Mixto de Linfocitos , Ratones , Ratones Endogámicos BALB C , Ratones Endogámicos C57BL
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