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1.
Chem Biol Interact ; 348: 109635, 2021 Oct 01.
Artigo em Inglês | MEDLINE | ID: mdl-34506763

RESUMO

Aflatoxin B1 (AFB1) is a mycotoxin highly toxic and carcinogenic to humans due to its potential to induce oxidative stress. The Beta-caryophyllene (BCP) have been highlighted for its broad spectrum of pharmacological effects. The present study aimed to investigate the beneficial effects of BCP against the susceptibility of hepatic and renal tissues to AFB1 toxicity, in biochemical parameters to assess organ function, tissue oxidation, and the immunocontent of oxidative and inflammatory proteins. Male Wistar rats was exposed to AFB1 (250 µg/kg, i.g.) and/or BCP (100 mg/kg, i.p.) for 14 successive days. It was found that exposure to AFB1 did not change the measured renal toxicity parameters. Also, AFB1 increased liver injury biomarkers (gamma glutamyl transferase and alkaline phosphatase) and reduced levels of non-enzymatic antioxidant defenses (ascorbic acid and non-protein thiol), however did not cause changes in the lipid peroxidation levels. Moreover, AFB1 interfered in oxidative pathway regulated by Kelch-like ECH-associated protein (Keap1)/nuclear factor (erythroid-derived 2)-like 2 (Nrf2), overacting Glutathione-S-Transferase (GST) activity. Lastly, a main effect of AFB1 on the total interleukin 1 beta (IL-1ß) was observed. Remarkably, the associated treatment of AFB1 + BCP improved altered liver parameters. In addition, BCP and AFB1 + BCP groups showed an increase in the levels of inhibitor of nuclear factor kappa-B kinase subunit beta (IKKß). Thus, these results indicated that BCP has potential protective effect against AFB1 induced hepatotoxicity.


Assuntos
Aflatoxina B1/toxicidade , Citoproteção/efeitos dos fármacos , Fígado/efeitos dos fármacos , Sesquiterpenos/farmacologia , Animais , Antioxidantes/metabolismo , Glutationa/metabolismo , Proteína 1 Associada a ECH Semelhante a Kelch/metabolismo , Peroxidação de Lipídeos/efeitos dos fármacos , Fígado/citologia , Fígado/metabolismo , Masculino , Fator 2 Relacionado a NF-E2/metabolismo , Estresse Oxidativo/efeitos dos fármacos , Ratos , Ratos Wistar
2.
Integr Cancer Ther ; 20: 15347354211035450, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34490824

RESUMO

Doxorubicin (Dox) induces senescence in numerous cancer cell types, but these senescent cancer cells relapse again if they are not eliminated. On this principle, we investigated the apoptotic effect of thymoquinone (TQ), the active ingredient of Nigella sativa seeds and costunolide (COS), the active ingredient of Costus speciosus, on the senescent colon (Sen-HCT116) and senescent breast (Sen-MCF7) cancer cell lines in reference to their corresponding proliferative cells to rapidly eliminate the senescent cancer cells. The senescence markers of Sen-HCT116 and Sen-MCF7 were determined by a significant decrease in bromodeoxyuridine (BrdU) incorporation and significant increases in SA-ß-gal, p53, and p21 levels. Then proliferative, Sen-HCT116, and Sen-MCF7 cells were subjected to either TQ (50 µM) or COS (30 µM), the Bcl2-associated X protein (Bax), B-cell lymphoma 2 (Bcl2), caspase 3 mRNA expression and its activity were established. Results revealed that TQ significantly increased the Bax/Bcl2 ratio in HCT116 + Dox5 + TQ, MCF7 + TQ, and MCF7 + Dox5 + TQ compared with their corresponding controls. COS significantly increased the Bax/Bcl2 ratio in HCT116 + Dox5 + TQ and MCF7 + Dox5 + TQ compared with their related controls. Also, TQ and COS were significantly increased caspase 3 activity and cell proliferation of Sen-HCT116 and Sen-MCF7. The data revealed a higher sensitivity of senescent cells to TQ or COS than their corresponding proliferative cells.


Assuntos
Apoptose , Recidiva Local de Neoplasia , Benzoquinonas , Colo , Doxorrubicina/farmacologia , Humanos , Sesquiterpenos
3.
Chin J Nat Med ; 19(9): 693-699, 2021 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-34561081

RESUMO

A chemical investigation on the fermentation products of Sanghuangporus sanghuang led to the isolation and identification of fourteen secondary metabolites (1-14) including eight sesquiterpenoids (1-8) and six polyphenols (9-14). Compounds 1-3 were sesquiterpenes with new structures which were elucidated based on NMR spectroscopy, high resolution mass spectrometry (HRMS) and electronic circular dichroism (ECD) data. All the isolates were tested for their stimulation effects on glucose uptake in insulin-resistant HepG2 cells, and cellular antioxidant activity. Compounds 9-12 were subjected to molecular docking experiment to primarily evaluate their anti-coronavirus (SARS-CoV-2) activity. As a result, compounds 9-12 were found to increase the glucose uptake of insulin-resistant HepG2 cells by 18.1%, 62.7%, 33.7% and 21.4% at the dose of 50 µmol·L-1, respectively. Compounds 9-12 also showed good cellular antioxidant activities with CAA50 values of 12.23, 23.11, 5.31 and 16.04 µmol·L-1, respectively. Molecular docking between COVID-19 Mpro and compounds 9-12 indicated potential SARS-CoV-2 inhibitory activity of these four compounds. This work provides new insights for the potential role of the medicinal mushroom S. sanghuang as drugs and functional foods.


Assuntos
Agaricales , COVID-19 , Polifenóis , Sesquiterpenos , Antioxidantes/farmacologia , Basidiomycota , COVID-19/tratamento farmacológico , Glucose , Humanos , Simulação de Acoplamento Molecular , Polifenóis/farmacologia , SARS-CoV-2 , Sesquiterpenos/farmacologia
4.
BMC Genomics ; 22(1): 647, 2021 Sep 07.
Artigo em Inglês | MEDLINE | ID: mdl-34493201

RESUMO

BACKGROUND: Agarwood, generated from the Aquilaria sinensis, has high economic and medicinal value. Although its genome has been sequenced, the ploidy of A. sinensis paleopolyploid remains unclear. Moreover, the expression changes of genes associated with agarwood formation were not analyzed either. RESULTS: In the present work, we reanalyzed the genome of A. sinensis and found that it experienced a recent tetraploidization event ~ 63-71 million years ago (Mya). The results also demonstrated that the A. sinensis genome had suffered extensive gene deletion or relocation after the tetraploidization event, and exhibited accelerated evolutionary rates. At the same time, an alignment of homologous genes related to different events of polyploidization and speciation were generated as well, which provides an important comparative genomics resource for Thymelaeaceae and related families. Interestingly, the expression changes of genes related to sesquiterpene synthesis in wounded stems of A. sinensis were also observed. Further analysis demonstrated that polyploidization promotes the functional differentiation of the key genes in the sesquiterpene synthesis pathway. CONCLUSIONS: By reanalyzing its genome, we found that the tetraploidization event shaped the A. sinensis genome and contributed to the ability of sesquiterpenes synthesis. We hope that these results will facilitate our understanding of the evolution of A. sinensis and the function of genes involved in agarwood formation.


Assuntos
Sesquiterpenos , Thymelaeaceae , Vias Biossintéticas , Genes de Plantas , Humanos , Thymelaeaceae/genética
5.
Zhongguo Zhong Yao Za Zhi ; 46(16): 4145-4149, 2021 Aug.
Artigo em Chinês | MEDLINE | ID: mdl-34467726

RESUMO

With repeated silica gel, octadecyl silica(ODS), and Sephadex LH-20 column chromatography, normal-phase and reverse-phase high performance liquid chromatography(HPLC), etc., a pair of new enantiomers and 5 known compounds were separated from the 95% ethanol extract of Chloranthus multistachys. These compounds were identified by the nuclear magnetic resonance spectroscopy(including 1 D-NMR and 2 D-NMR), single-crystal X-ray diffraction, circular dichroism(CD) spectroscopy, mass spectrometry(MS), and some other methods as(1R,4R,5R,8S,10R)-chloraeudolide H(1 a),(1S,4S,5S,8R,10S)-chloraeudolide H(1 b), hydroxyisogermafurenolide(2), 4α-hydroxy-5α,8ß(H)-eudesm-7(11)-en-8,12-olide(3), chloraniolide A(4), chlorantene D(5), 4α,8ß-dihydroxy-5α(H)-eudesm-7(11)-en-8,12-olide(6). Compounds 1 a and 1 b are a pair of new eudesmane-type sesquiterpene enantiomers, and compounds 2-4 were isolated from C. multistachys for the first time.


Assuntos
Sesquiterpenos , Cromatografia Líquida de Alta Pressão , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular , Estereoisomerismo
6.
Zhongguo Zhong Yao Za Zhi ; 46(15): 3789-3796, 2021 Aug.
Artigo em Chinês | MEDLINE | ID: mdl-34472251

RESUMO

The genus Chloranthus has 13 species and 5 varieties in China, which can be found in the southwest and northeast regions. Phytochemical studies on Chloranthus plants have reported a large amount of terpenoids, such as diterpenoids, sesquiterpenoids, and sesquiterpenoid dimers. Their anti-inflammation, anti-tumor, antifungal, antivirus, and neuroprotection activities have been confirmed by previous pharmacological research. Herein, research on the chemical constituents from Chloranthus plants and their biological activities over the five years was summarized to provide scientific basis for the further development and utilization of Chloranthus plants.


Assuntos
Diterpenos , Sesquiterpenos , Compostos Fitoquímicos/farmacologia , Plantas , Sesquiterpenos/farmacologia , Terpenos
7.
Zhongguo Zhong Yao Za Zhi ; 46(15): 3797-3805, 2021 Aug.
Artigo em Chinês | MEDLINE | ID: mdl-34472252

RESUMO

Terpenes are the largest group of natural products and contain the widest assortment of structural types. Terpene cyclization is also the most complex reaction found in nature. For a long time, terpenoids with diverse structures have attracted natural product chemists to explore their biosynthesis mechanism. Such a large number of terpene skeletons are catalyzed by enzymes called terpene synthase. Sesquiterpene synthase is a kind of terpene synthase, which can catalyze the cyclization of linear precursor farnesyl pyrophosphate(FPP) to sesquiterpene skeletons. Sesquiterpene synthase cyclize a single precursor FPP into many sesquiterpene skeletons. With the continuous discovery of sesquiterpene synthase, the cyclization mechanism of sesquiterpene synthase has been studied deeply. In recent years, with the development and improvement of isotope labeling of substrate FPP and structural analysis of sesquiterpene synthase, the structure and cyclization mechanism of sesquiterpene synthase have been studied more systematically and accurately. In this review, we reviewed the progress of the research methods on the mechanism of sesquiterpene cyclization by substrate isotope labeling and protein structure, as well as the summary and prospect of sesquiterpene synthase research.


Assuntos
Sesquiterpenos , Ciclização , Terpenos
8.
Phytochemistry ; 191: 112901, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-34388663

RESUMO

Nerolidol (3,7,11-trimethyl-1,6,10-dodecatrien-3-ol), a sesquiterpene alcohol present in aromatic essential oils of numerous plants, has been reported to possess anticancer activity. The potential therapeutic effect of nerolidol on uterine fibroids (UF), the most common benign tumor of the uterus worldwide, is unknown. In this study, we examined the anti-UF potential of nerolidol in ELT3 cells, a rat leiomyoma cell line widely used as an in vitro model, to identify the potential therapeutic agents for UF. We observed that treatment with cis- or trans-nerolidol inhibited cell proliferation in a dose-dependent manner and induced cell cycle arrest in the G1 phase, which was accompanied by reduction in Akt phosphorylation and downregulation of cyclin D1, cyclin-dependent kinase 4 (CDK4), and CDK6 protein expression. The proliferation-inhibiting activity of nerolidol correlated with the generation of intracellular reactive oxygen species (ROS), which was suppressed by N-acetyl-l-cysteine, a ROS inhibitor. Nerolidol treatment also increased the percentage of cells for which tail moment could be calculated using an alkaline comet assay, and induced p-γH2AXser139 expression, which indicated induction of DNA damage. We also observed downregulation of ATM and its phosphorylation after nerolidol treatment; furthermore, treatment with KU-55933, an ATM kinase inhibitor, mimicked the inhibitory effects of nerolidol treatment on cell proliferation and Akt phosphorylation. In conclusion, nerolidol displayed anti-UF activity in a leiomyoma cell model via ROS-induced DNA damage and G1 phase cell cycle arrest by inhibiting the expression and activation of the ATM/Akt pathway. Our data suggests that nerolidol is a potential therapeutic agent for UF.


Assuntos
Leiomioma , Sesquiterpenos , Apoptose , Linhagem Celular Tumoral , Proliferação de Células , Dano ao DNA , Regulação para Baixo , Proteínas Proto-Oncogênicas c-akt/metabolismo , Espécies Reativas de Oxigênio/metabolismo , Sesquiterpenos/farmacologia
9.
Phytochemistry ; 191: 112924, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-34428668

RESUMO

Fifteen undescribed dimeric sesquiterpenoids, linderanoids A-O along with one known lindenane-type sesquiterpenoid dimer, lindenaneolide F, were isolated and identified from the roots of Lindera aggregata. Their structures and absolute configurations were elucidated using spectroscopy and electronic circular dichroism (ECD) analysis. All the isolated compounds were screened for transforming growth factor (TGF)-ß inhibitory activity, and the results showed that linderanoid E significantly inhibited the TGF- ß induced smad2 phosphorylation at a concentration of 25 µM.


Assuntos
Lindera , Sesquiterpenos , Raízes de Plantas , Sesquiterpenos/farmacologia
10.
Molecules ; 26(15)2021 Jul 23.
Artigo em Inglês | MEDLINE | ID: mdl-34361609

RESUMO

The use of copaiba oil has been reported since the 16th century in Amazon traditional medicine, especially as an anti-inflammatory ingredient and for wound healing. The use of copaiba oil continues today, and it is sold in various parts of the world, including the United States. Copaiba oil contains mainly sesquiterpenes, bioactive compounds that are popular for their positive effect on human health. As part of our ongoing research endeavors to identify the chemical constituents of broadly consumed herbal supplements or their adulterants, copaiba oil was investigated. In this regard, copaiba oil was subjected to repeated silica gel column chromatography to purify the compounds. As a result, one new and seven known sesquiterpenes/sesquiterpenoids were isolated and identified from the copaiba oil. The new compound was elucidated as (E)-2,6,10-trimethyldodec-8-en-2-ol. Structure elucidation was achieved by 1D- and 2D NMR and GC/Q-ToF mass spectral data analyses. The isolated chemical constituents in this study could be used as chemical markers to evaluate the safety or quality of copaiba oil.


Assuntos
Anti-Inflamatórios/química , Fabaceae/química , Óleos Voláteis/química , Óleos Vegetais/química , Sesquiterpenos/análise , Humanos , Medicina Tradicional
11.
Molecules ; 26(15)2021 Jul 28.
Artigo em Inglês | MEDLINE | ID: mdl-34361712

RESUMO

The genus Maytenus is a member of the Celastraceae family, of which several species have long been used in traditional medicine. Between 1976 and 2021, nearly 270 new compounds have been isolated and elucidated from the genus Maytenus. Among these, maytansine and its homologues are extremely rare in nature. Owing to its unique skeleton and remarkable bioactivities, maytansine has attracted many synthetic endeavors in order to construct its core structure. In this paper, the current status of the past 45 years of research on Maytenus, with respect to its chemical and biological activities are discussed. The chemical research includes its structural classification into triterpenoids, sesquiterpenes and alkaloids, along with several chemical synthesis methods of maytansine or maytansine fragments. The biological activity research includes activities, such as anti-tumor, anti-bacterial and anti-inflammatory activities, as well as HIV inhibition, which can provide a theoretical basis for the better development and utilization of the Maytenus.


Assuntos
Alcaloides/química , Maitansina/análogos & derivados , Maytenus/química , Compostos Fitoquímicos/química , Sesquiterpenos/química , Triterpenos/química , Alcaloides/classificação , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Fármacos Anti-HIV/química , Fármacos Anti-HIV/isolamento & purificação , Fármacos Anti-HIV/farmacologia , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Humanos , Maitansina/isolamento & purificação , Maitansina/farmacologia , Maytenus/metabolismo , Estrutura Molecular , Compostos Fitoquímicos/classificação , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Plantas Medicinais , Sesquiterpenos/classificação , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Relação Estrutura-Atividade , Triterpenos/classificação , Triterpenos/isolamento & purificação , Triterpenos/farmacologia
12.
Biofouling ; 37(7): 791-807, 2021 08.
Artigo em Inglês | MEDLINE | ID: mdl-34455871

RESUMO

Antibacterial screenings are most commonly targeted at planktonic bacteria but less effort is dedicated to the exploration of agents acting on biofilms. Here, a natural compounds library was screened against Staphylococcus aureus using a 384-well plate platform to identify compounds preventing biofilm formation. Five structurally diverse hits were selected for follow-up studies: honokiol, tschimganidin, ferutinin, oridonin and deoxyshikonin. The compounds were evaluated against different bacterial species for their capacity to prevent and disrupt biofilms. The development of resistance and cytotoxicity were also investigated. Ferutinin displayed the best antibacterial activity, with a minimum inhibitory, bactericidal and biofilm preventive concentration of 25 µM against S. aureus. It efficiently disrupted pre-formed biofilms (over 5-log reduction of viable cells) and reduced biofilm formation on a catheter in the presence of neutrophils. This work provides new information on the antibacterial activity of five natural compounds and identified ferutinin as a promising candidate against S. aureus biofilms.


Assuntos
Infecções Estafilocócicas , Staphylococcus aureus , Antibacterianos/farmacologia , Benzoatos , Biofilmes , Compostos Bicíclicos com Pontes , Cicloeptanos , Humanos , Testes de Sensibilidade Microbiana , Sesquiterpenos
13.
Molecules ; 26(16)2021 Aug 09.
Artigo em Inglês | MEDLINE | ID: mdl-34443397

RESUMO

A total of nine sesquiterpenoid lactones together with phenolic compounds and other terpenes were identified from the crude methanol extract of Elephantopus mollis Kunth. Compounds were isolated using different chromatographic techniques and their structures were determined by NMR and IR spectroscopy as well as mass spectrometry. The structures of some detected compounds were assigned based on LC-ToF-ESI-MS screening of main fractions/subfractions from flash chromatography and comparison with isolated analogues as standards. The findings revealed not only the in-source loss of water as the base peak in hirsutinolides but also the in-source loss of corresponding alcohol when the oxygen at position 1 is alkylated. The present study also draws up a complement of data with respect to hirsutinolide-like sesquiterpene lactones whose LC-MS characteristics are not available in the literature. The chemophenetic significance is also discussed. Some of the isolated compounds were reported for the first time to be found in the species, the genus as well as the plant family. The medium-polar fractions of the crude extract, also containing the larger amount of sesquiterpenoid lactones, exhibited activity both against a cancer cell line and bacterial strains. Isolated lactones were also active against the cancer cell line, while the chlorogenic derivatives also valuable in Elephantopus genus showed potent radical scavenging activity. This is the first report of cytotoxic and antibacterial activities of our samples against the tested strains and cell line. The present study follows the ongoing research project dealing with the characterization of taxa with antibacterial and antiparasitic activities from Cameroonian pharmacopeia.


Assuntos
Asteraceae/química , Proliferação de Células/efeitos dos fármacos , Extratos Vegetais/química , Sesquiterpenos/química , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Cromatografia Líquida , Humanos , Espectrometria de Massas , Neoplasias/tratamento farmacológico , Extratos Vegetais/farmacologia , Sesquiterpenos/isolamento & purificação
14.
Bioresour Technol ; 341: 125739, 2021 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-34418846

RESUMO

ß-Farnesene can replace petroleum products as specialty fuel to solve the global fuel energy crisis, but its production by Escherichia coli (E.coli) using glucose and isopropyl ß-D-1-thiogalactopyranoside (IPTG) is costly. Hence, we developed a new strategy to produce ß-farnesene by engineered E.coli strain F13 with bifunctional utilization of whey powder. The utilization of whey powder as a substrate ensured the growth of the strain F13, while whey powder could also replace IPTG to induce the production of ß-farnesene. In shake flasks, ß-farnesene production reached 2.41 g/L by the bifunctional utilization of whey powder as a substrate and inducer, 65.1% higher than that with IPTG and glucose. In the 7 L bioreactor, ß-farnesene production reached 4.74 g/L using whey powder, which was 197% of that in shake flasks. Therefore, this new strategy might be an attractive route to broaden the applications of whey powder and achieve the economical production of ß-farnesene.


Assuntos
Escherichia coli , Sesquiterpenos , Pós , Soro do Leite
15.
Cell Prolif ; 54(9): e13107, 2021 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-34346124

RESUMO

OBJECTIVES: In recent years, cellular senescence has attracted a lot of interest in researchers due to its involvement in non-alcoholic fatty liver disease (NAFLD). However, the mechanism of cellular senescence is not clear. The purpose of this study was to investigate the effect of curcumol on hepatocyte senescence in NAFLD and the molecular mechanisms implicated. MATERIALS AND METHODS: LVG Golden Syrian hamsters, C57BL/6J mice and human hepatocyte cell line LO2 were used. Cellular senescence was assessed by analyses of senescence marker SA-ß-gal, p16 and p21, H3K9me3, γ-H2AX and telomerase activity. RESULTS: The results showed that curcumol could inhibit hepatocyte senescence in both in vivo and in vitro NAFLD models, and the mechanism might be related to its regulation of ferritinophagy and subsequent alleviation of iron overload. Moreover, overexpression of nuclear receptor coactivator 4 (NCOA4) weakened the effect of curcumol on ferritinophagy-mediated iron overload and cellular senescence. Furthermore, we demonstrated that curcumol reduced the expression of NCOA4 by Yes-associated protein (YAP). In addition, depression of YAP could impair the effect of curcumol on iron overload and cellular senescence. CONCLUSION: Our results clarified the mechanism of curcumol inhibition of hepatocyte senescence through YAP/NCOA4 regulation of ferritinophagy in NAFLD. These findings provided a promising option of curcumol to regulate cellular senescence by target YAP/NCOA4 for the treatment of NAFLD.


Assuntos
Proteínas Adaptadoras de Transdução de Sinal/metabolismo , Autofagia/efeitos dos fármacos , Senescência Celular/efeitos dos fármacos , Ferritinas/metabolismo , Hepatócitos/efeitos dos fármacos , Hepatopatia Gordurosa não Alcoólica/tratamento farmacológico , Coativadores de Receptor Nuclear/metabolismo , Sesquiterpenos/farmacologia , Animais , Linhagem Celular , Hepatócitos/metabolismo , Humanos , Ferro/metabolismo , Masculino , Mesocricetus , Camundongos , Camundongos Endogâmicos C57BL , Hepatopatia Gordurosa não Alcoólica/metabolismo
16.
Chem Pharm Bull (Tokyo) ; 69(8): 802-805, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34334525

RESUMO

A new rearranged nitrogenous bisabolone-type sesquiterpene, halichonic acid B (1), was isolated from a marine sponge Axinyssa sp. together with halichonic acid (2) and (6R,7S)-7-amino-7,8-dihydro-α-bisabolene (3). The structure of 1 was determined by extensive NMR and MS analyses, revealing an unprecedented carbon framework, and its absolute configuration was elucidated by time-dependent density-functional theory (TDDFT)-based electronic circular dichroism (ECD) spectrum calculation. We propose that 1 and 2 may be biosynthesized in the same pathway, involving the reaction between farnesyl pyrophosphate and glycine, followed by cyclization.


Assuntos
Poríferos/química , Sesquiterpenos/química , Animais , Dicroísmo Circular , Teoria da Densidade Funcional , Conformação Molecular , Sesquiterpenos/isolamento & purificação , Fatores de Tempo
17.
J Nat Prod ; 84(8): 2385-2389, 2021 08 27.
Artigo em Inglês | MEDLINE | ID: mdl-34351742

RESUMO

The ongoing COVID-19 global pandemic caused by SARS-CoV-2 inspires the development of effective inhibitors to block the SARS-CoV-2 spike-ACE2 interaction. A chemical investigation on the fruiting bodies of Phellinus pini led to the isolation of five aromatic cadinane sesquiterpenoids including four new ones, named piniterpenoids A-D (1-4), as well as three known lignans. Their structures were determined by extensive spectroscopic analysis including HRMS and 1D and 2D NMR. All of the aromatic cadinane sesquiterpenoids inhibited the SARS-CoV-2 spike-ACE2 interaction, with IC50 values ranging from 64.5 to 99.1 µM. A molecular docking study showed the disruption of the interaction of compound 1 via hydrogen interactions with Arg403, Asp405, and Arg408 of SARS-CoV-2 RBD and Arg393 and His34 residues of ACE2. These results suggested that aromatic cadinane sesquiterpenoids might be useful in developing agents for COVID-19.


Assuntos
Enzima de Conversão de Angiotensina 2/antagonistas & inibidores , Antivirais/química , Antivirais/farmacologia , Carpóforos/química , Phellinus/química , Sesquiterpenos Policíclicos/química , Sesquiterpenos Policíclicos/farmacologia , SARS-CoV-2/efeitos dos fármacos , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Glicoproteína da Espícula de Coronavírus/antagonistas & inibidores , Humanos , Ligação de Hidrogênio/efeitos dos fármacos , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Simulação de Acoplamento Molecular
18.
Molecules ; 26(15)2021 Jul 29.
Artigo em Inglês | MEDLINE | ID: mdl-34361731

RESUMO

Strigolactones (SLs) are a class of sesquiterpenoid plant hormones that play a role in the response of plants to various biotic and abiotic stresses. When released into the rhizosphere, they are perceived by both beneficial symbiotic mycorrhizal fungi and parasitic plants. Due to their multiple roles, SLs are potentially interesting agricultural targets. Indeed, the use of SLs as agrochemicals can favor sustainable agriculture via multiple mechanisms, including shaping root architecture, promoting ideal branching, stimulating nutrient assimilation, controlling parasitic weeds, mitigating drought and enhancing mycorrhization. Moreover, over the last few years, a number of studies have shed light onto the effects exerted by SLs on human cells and on their possible applications in medicine. For example, SLs have been demonstrated to play a key role in the control of pathways related to apoptosis and inflammation. The elucidation of the molecular mechanisms behind their action has inspired further investigations into their effects on human cells and their possible uses as anti-cancer and antimicrobial agents.


Assuntos
Antineoplásicos/farmacologia , Compostos Heterocíclicos com 3 Anéis/farmacologia , Lactonas/farmacologia , Micorrizas/metabolismo , Reguladores de Crescimento de Plantas/farmacologia , Plantas/metabolismo , Sesquiterpenos/farmacologia , Adaptação Fisiológica , Agricultura/métodos , Agroquímicos/isolamento & purificação , Agroquímicos/metabolismo , Agroquímicos/farmacologia , Antibacterianos/biossíntese , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Antineoplásicos/isolamento & purificação , Antineoplásicos/metabolismo , Apoptose/efeitos dos fármacos , Compostos Heterocíclicos com 3 Anéis/isolamento & purificação , Compostos Heterocíclicos com 3 Anéis/metabolismo , Humanos , Inflamação/prevenção & controle , Lactonas/isolamento & purificação , Lactonas/metabolismo , Micorrizas/química , Neoplasias/tratamento farmacológico , Patentes como Assunto , Reguladores de Crescimento de Plantas/biossíntese , Reguladores de Crescimento de Plantas/isolamento & purificação , Plantas/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/metabolismo , Estresse Fisiológico , Controle de Plantas Daninhas/métodos
19.
Biomolecules ; 11(7)2021 07 18.
Artigo em Inglês | MEDLINE | ID: mdl-34356677

RESUMO

In continuing our investigation on the chemical diversity of Algerian plants, we examined Centaurea omphalotricha, whose chemical composition has been poorly studied. The present work was aimed at characterizing the secondary metabolite pattern of the CHCl3 extract of the aerial parts of this plant that displayed antiproliferative properties in a preliminary screening on HeLa cell line. The chemical analysis led us to characterize the bioactive oxygenated terpenoid fraction which includes, within major known metabolites, two new minor sesquiterpene lactones, centaurolide-A (1) and centaurolide-B (2). The structures of two compounds exhibiting the 12,8-guaianolide skeleton were determined by spectroscopic methods as well as by chemical correlation with inuviscolide (3), a well-known bioactive guaianolide isolated from Dittrichia (=Inula) viscosa. Centaurolides A and B represent the first report of 8,12-guaianolide skeleton in Centaurea genus. The effect of new compounds 1 and 2 and inuviscolide (3) on HeLa cell has also been evaluated.


Assuntos
Centaurea/química , Lactonas/química , Sesquiterpenos de Guaiano/química , Argélia , Sobrevivência Celular/efeitos dos fármacos , Centaurea/metabolismo , Células HeLa , Humanos , Lactonas/farmacologia , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Extratos Vegetais/química , Metabolismo Secundário , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos de Guaiano/farmacologia
20.
J Chem Ecol ; 47(8-9): 740-746, 2021 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-34347235

RESUMO

Aphids are destructive pests, and alarm pheromones play a key role in their chemical ecology. Here, we conducted a detailed analysis of terpenoids in the vetch aphid, Megoura viciae, and its host plant Pisum sativum using gas chromatography/mass spectrometry. Four major components, (-)-ß-pinene (49.74%), (E)-ß-farnesene (32.64%), (-)-α-pinene (9.42%) and ( +)-limonene (5.24%), along with trace amounts of ( +)-sabinene, camphene and α-terpineol) (3.14%) were found in the aphid. In contrast, few terpenoids were found in the host plant, consisting mainly of squalene (66.13%) and its analog 2,3-epoxysqualene (31.59%). Quantitative analysis of the four major terpenes in different developmental stages of the aphid showed that amounts of the monoterpenes increased with increasing stage, while the sesquiterpene amount peaked in the 3rd instar. (-)-ß-Pinene was the most abundant terpene at all developmental stages. Behavioral assays using a three-compartment olfactometer revealed that the repellency of single compounds varied in a concentration-dependent manner, but two mixtures [(-)-α-pinene: (-)-ß-pinene: (E)-ß-farnesene: ( +)-limonene = 1:44.4:6.5:2.2 or 1:18.4:1.3:0.8], were repellent at all concentrations tested. Our results suggest that (-)-α-pinene and (-)-ß-pinene are the major active components of the alarm pheromone of M. viciae, but that mixtures play a key role in the alarm response. Our study contributes to the understanding of the chemical ecology of aphids and may help design new control strategies against this aphid pest.


Assuntos
Afídeos/fisiologia , Ervilhas/química , Feromônios/química , Terpenos/química , Animais , Afídeos/química , Afídeos/crescimento & desenvolvimento , Comportamento Animal/efeitos dos fármacos , Monoterpenos Bicíclicos/isolamento & purificação , Monoterpenos Bicíclicos/farmacologia , Cromatografia Gasosa-Espectrometria de Massas , Controle de Insetos/métodos , Estágios do Ciclo de Vida , Ervilhas/metabolismo , Ervilhas/parasitologia , Feromônios/análise , Feromônios/farmacologia , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Terpenos/análise , Terpenos/farmacologia
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