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1.
Plant J ; 119(3): 1289-1298, 2024 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-38818938

RESUMEN

The apocarotenoid strigolactones (SLs) facilitate pre-symbiotic communication between arbuscular mycorrhizal (AM) fungi and plants. Related blumenol-C-glucosides (blumenols), have also been associated with symbiosis, but the cues that are involved in the regulation of blumenol accumulation during AM symbiosis remain unclear. In rice, our analyses demonstrated a strict correlation between foliar blumenol abundance and intraradical fungal colonisation. More specifically, rice mutants affected at distinct stages of the interaction revealed that fungal cortex invasion was required for foliar blumenol accumulation. Plant phosphate status and D14L hormone signalling had no effect, contrasting their known role in induction of SLs. This a proportion of the SL biosynthetic enzymes, D27 and D17, are equally required for blumenol production. These results importantly clarify that, while there is a partially shared biosynthetic pathway between SL and blumenols, the dedicated induction of the related apocarotenoids occurs in response to cues acting at distinct stages during the root colonisation process. However, we reveal that neither SLs nor blumenols are essential for fungal invasion of rice roots.


Asunto(s)
Lactonas , Micorrizas , Oryza , Simbiosis , Micorrizas/fisiología , Oryza/microbiología , Oryza/metabolismo , Oryza/genética , Oryza/fisiología , Lactonas/metabolismo , Raíces de Plantas/microbiología , Raíces de Plantas/metabolismo , Reguladores del Crecimiento de las Plantas/metabolismo , Glucósidos/metabolismo , Regulación de la Expresión Génica de las Plantas
2.
Trends Genet ; 37(8): 688-690, 2021 08.
Artículo en Inglés | MEDLINE | ID: mdl-33941397

RESUMEN

Horizontal gene transfer (HGT) is a well-documented evolutionary driving phenomenon in prokaryotes and eukaryotes, but its impact on the plant kingdom has remained elusive. A recent study provides compelling evidences, which support the idea that a plant-derived gene allows for the detoxification of plant defense metabolites in a polyphagous arthropod herbivore.


Asunto(s)
Evolución Molecular , Transferencia de Gen Horizontal/genética , Hemípteros/genética , Plantas/genética , Animales , Insectos/genética , Filogenia
3.
Metab Eng ; 83: 1-11, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38447910

RESUMEN

Flavonoids are a diverse set of natural products with promising bioactivities including anti-inflammatory, anti-cancer, and neuroprotective properties. Previously, the oleaginous host Yarrowia lipolytica has been engineered to produce high titers of the base flavonoid naringenin. Here, we leverage this host along with a set of E. coli bioconversion strains to produce the flavone apigenin and its glycosylated derivative isovitexin, two potential nutraceutical and pharmaceutical candidates. Through downstream strain selection, co-culture optimization, media composition, and mutant isolation, we were able to produce168 mg/L of apigenin, representing a 46% conversion rate of 2-(R/S)-naringenin to apigenin. This apigenin platform was modularly extended to produce isovitexin by addition of a second bioconversion strain. Together, these results demonstrate the promise of microbial production and modular bioconversion to access diversified flavonoids.


Asunto(s)
Apigenina , Escherichia coli , Flavanonas , Ingeniería Metabólica , Yarrowia , Apigenina/metabolismo , Apigenina/biosíntesis , Flavanonas/biosíntesis , Flavanonas/metabolismo , Yarrowia/metabolismo , Yarrowia/genética , Escherichia coli/metabolismo , Escherichia coli/genética , Glucósidos/biosíntesis , Glucósidos/metabolismo
4.
Plant Cell Environ ; 47(8): 3076-3089, 2024 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-38679945

RESUMEN

Flavonoids are usually present in forms of glucosides in plants, which could be catabolized by ß-glucosidase (BGLU) to form their corresponding flavonoid aglycones. In this study, we isolated three abiotic-responsive BGLU genes (MtBGLU17, MtBGLU21 and MtBGLU22) from Medicago truncatula, and found only the recombinant MtBGLU17 protein could catalyse the hydrolysis of flavonoid glycosides. The recombinant MtBGLU17 protein is active towards a variety of flavonoid glucosides, including glucosides of flavones (apigenin and luteolin), flavonols (kaempferol and quercetin), isoflavones (genistein and daidzein) and flavanone (naringenin). In particular, the recombinant MtBGLU17 protein preferentially hydrolyses flavonoid-7-O-glucosides over their corresponding 3-O-glucosides. The content of luteoin-7-O-glucoside was reduced in the MtBGLU17 overexpression plants but increased in the Tnt-1 insertional mutant lines, whereas luteoin content was increased in the MtBGLU17 overexpression plants but reduced in the Tnt-1 insertional mutant lines. Under drought and salt (NaCl) treatment, the MtBGLU17 overexpression lines showed relatively higher DPPH content, and higher CAT and SOD activity than the wild type control. These results indicated that overexpression lines of MtBGLU17 possess higher antioxidant activity and thus confer drought and salt tolerance, implying MtBGLU17 could be potentially used as a candidate gene to improve plant abiotic stress tolerance.


Asunto(s)
Antioxidantes , Sequías , Flavonoides , Medicago truncatula , Proteínas de Plantas , Tolerancia a la Sal , beta-Glucosidasa , Medicago truncatula/genética , Medicago truncatula/enzimología , Medicago truncatula/metabolismo , Medicago truncatula/fisiología , Flavonoides/metabolismo , Antioxidantes/metabolismo , beta-Glucosidasa/metabolismo , beta-Glucosidasa/genética , Tolerancia a la Sal/genética , Proteínas de Plantas/metabolismo , Proteínas de Plantas/genética , Regulación de la Expresión Génica de las Plantas
5.
J Sep Sci ; 47(12): e2400118, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-39031866

RESUMEN

Tubers of Gymnadenia conopsea (L.) R. Br. (Orchidaceae), a traditional medicine and food homologous plant, has a broad application and development prospect in the food and drug industries. Benzylester glucosides, the main effective active components in this plant, are difficult to separate due to their similar structures and high polarity. In this study, linear gradient counter-current chromatography was used to separate benzylester glucosides and derivatives, combined with elution-extrusion mode. The main separation parameters were optimized, including the ratio of mobile phase and sample loading. Finally, seven compounds were successfully separated, including 4-hydroxybenzyl alcohol (1), 4-hydroxybenzaldehyde (2), dactylorhin B (3), loroglossin (4), dactylorhin A (5), 4-(ethoxymethyl) phenol (6), and militarine (7). The structures were analyzed by mass spectrometry and nuclear magnetic resonance spectrometry. According to our findings, the established method was an efficient approach to separate benzylester glucosides and derivatives from tubers of G. conopsea. The established strategy could be applied to purify other similar high-polarity compounds from complex natural products.


Asunto(s)
Distribución en Contracorriente , Glucósidos , Orchidaceae , Tubérculos de la Planta , Tubérculos de la Planta/química , Orchidaceae/química , Glucósidos/aislamiento & purificación , Glucósidos/química , Estructura Molecular , Ésteres/química , Ésteres/aislamiento & purificación
6.
Toxicol Ind Health ; 40(6): 306-311, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38575135

RESUMEN

Rinse-off cosmetic products, primarily shampoos, are frequently implicated in the onset of allergic contact dermatitis (ACD) caused by alkyl glucosides (AGs). AGs are increasingly popular surfactants and known contact allergens. Glucoside-induced ACD was most frequently observed with shampoos and skin-cleansing products in both consumer and occupational settings. Thereby, studies have shown that atopic individuals are the most susceptible to ACD. Also, several investigations have indicated that individuals with sensitive skin might be more prone to skin allergies. This is why the presence of AGs was investigated in shampoos and body cleansers marketed as hypoallergenic or for sensitive skin. For this purpose, the website of Amazon.com was surveyed. Four groups of cosmetics were obtained by using the following keywords: "hypoallergenic shampoo for adults," "sensitive skin shampoo for adults," "hypoallergenic body cleanser for adults," and "sensitive skin body cleanser for adults." The first 30 best-selling cosmetics in each group were investigated for the presence of AGs, by analyzing the product information pages. The results showed that as much as 56.7% of hypoallergenic shampoos contained AGs, as ingredients, whereas the percentage was somewhat lower for other product categories. Even though decyl and lauryl glucoside were nearly ubiquitously used AGs in cosmetics over the past decade, the most commonly present AG in our analysis was coco-glucoside. The results of this study indicated a necessity to include coco-glucoside in the baseline series of patch testing allergens. Industry, regulators, and healthcare providers should be made aware of the frequent presence of AGs in rinse-off cosmetic products marketed as hypoallergenic or for sensitive skin to ensure the safety and well-being of consumers and patients.


Asunto(s)
Cosméticos , Dermatitis Alérgica por Contacto , Glucósidos , Glucósidos/análisis , Humanos , Dermatitis Alérgica por Contacto/etiología , Cosméticos/efectos adversos , Cosméticos/química , Alérgenos/análisis , Preparaciones para el Cabello/efectos adversos , Preparaciones para el Cabello/química , Piel/efectos de los fármacos
7.
Zhongguo Zhong Yao Za Zhi ; 49(5): 1255-1259, 2024 Mar.
Artículo en Zh | MEDLINE | ID: mdl-38621972

RESUMEN

The components with hypoglycemic activity in Plumeria rubra were isolated and purified by various column chromatography techniques and activity tracing methods. The physical and chemical properties of all the purified monomer compounds were characterized and analyzed, and a total of six compounds were isolated and identified, including 6″-acetyl-6-hydroxy-benzyl-benzoate-2-O-ß-D-glucoside(1), 6-acetyl-6-hydroxy-benzyl-benzoate-2-O-ß-D-glucoside-(1→6″)-ß-D-glucoside(2), 2-hydroxy-6-methoxy-benzyl-benzoate-2-O-ß-D-glucoside(3), 6-hydroxy-benzyl-benzoate-2-O-ß-D-glucoside(4), 6-hydroxy-benzyl-benzoate-2-O-ß-D-glucoside-(1→6″)-ß-D-glucoside(5), and 6-hydroxy-benzyl-benzoate-2-O-ß-D-glucoside-(1→6″)-ß-D-xyloside(6). Compounds 1 and 2 were new compounds, and compounds 3-6 were isolated from Plumeria for the first time. The α-glucosidase inhibitory activity of six identified compounds was tested. The results show that compounds 1-6 show certain inhibitory activity with an IC_(50) value ranging from 8.2 to 33.5 µmol·L~(-1).


Asunto(s)
Apocynaceae , Glucósidos , Glucósidos/química , Benzoatos
8.
Zhongguo Zhong Yao Za Zhi ; 49(10): 2754-2765, 2024 May.
Artículo en Zh | MEDLINE | ID: mdl-38812176

RESUMEN

This study deciphered the ameliorating effect and molecular mechanism of the total glucosides of White Paeony Capsules(TGP) in the treatment of mice model with acute lung injury(ALI) via NOD-like receptor thermal protein domain associated protein 3(NLRP3) signaling pathway of the inflammasome. The study established an inflammasome activation model of primed bone marrow-derived macrophages(BMDMs), and its molecular mechanism was investigated by Western blot(WB), immunofluorescence staining, enzyme-linked immunosorbent assay(ELISA), and flow cytometry. C57BL/6J mice were randomly divided into a blank control group, a TGP group, a model group(LPS group), LPS+low-and high-dose TGP groups, LPS+MCC950 group, and LPS+MCC950+TGP group, with eight mice per group. The ALI model was induced in mice. Finally, bronchoalveolar lavage fluid(BALF) and lung tissue were collected. Lung index and lung weight wet-to-dry ratio were determined for each group of mice. The pathological changes in lung tissue were observed through hematoxylin-eosin(HE) staining. The number of neutrophils in the BALF of each group was detected using flow cytometry. The levels of interleukin(IL)-1ß, IL-6, and tumor necrosis factor(TNF)-α in the BALF were determined by ELISA. The expressions of IL-1ß, IL-18, IL-6, and TNF-α in the lung tissue were determined by real-time quantitative PCR(RT-qPCR). This study demonstrated that TGP dramatically blocked the activation of the NLRP3 inflammasome by inhibiting the production of upstream mitochondrial reactive oxygen species(mtROS) and the subsequent oligomerization of apoptosis-associated specks(ASC). Additionally, in the ALI mice model, compared with the blank control group, the model group showed alveolar structure rupture, thic-kening of alveolar septa, and dramatically increased lung index, lung weight wet-to-dry ratio in lung tissue, neutrophil count, and inflammatory factor levels. Compared with the model group, the pathological morphology of lung tissue was significantly ameliorated in the TGP and MCC950 groups, and the lung index and lung weight wet-to-dry ratio were significantly reduced. Neutrophil counts were reduced, and levels of inflammatory factors were significantly downregulated. Notably, compared with the MCC950 group, there was no significant difference in effect in the MCC950+TGP group. Collectively, the study reveals that TGP may ameliorate ALI in mice by inhibiting the activation of NLRP3 inflammasome, providing a safe and effective drug candidate for the prevention or treatment of ALI/ARDS.


Asunto(s)
Lesión Pulmonar Aguda , Medicamentos Herbarios Chinos , Glucósidos , Inflamasomas , Ratones Endogámicos C57BL , Proteína con Dominio Pirina 3 de la Familia NLR , Paeonia , Animales , Lesión Pulmonar Aguda/tratamiento farmacológico , Lesión Pulmonar Aguda/metabolismo , Lesión Pulmonar Aguda/inmunología , Proteína con Dominio Pirina 3 de la Familia NLR/metabolismo , Proteína con Dominio Pirina 3 de la Familia NLR/genética , Glucósidos/farmacología , Glucósidos/química , Ratones , Inflamasomas/metabolismo , Inflamasomas/efectos de los fármacos , Masculino , Paeonia/química , Medicamentos Herbarios Chinos/administración & dosificación , Medicamentos Herbarios Chinos/farmacología , Medicamentos Herbarios Chinos/química , Cápsulas , Pulmón/efectos de los fármacos , Pulmón/inmunología , Pulmón/metabolismo , Humanos , Interleucina-1beta/genética , Interleucina-1beta/inmunología , Interleucina-1beta/metabolismo
9.
BMC Plant Biol ; 23(1): 204, 2023 Apr 19.
Artículo en Inglés | MEDLINE | ID: mdl-37076827

RESUMEN

BACKGROUND: Uridine disphosphate (UDP) glycosyltransferases (UGTs) act upon a huge variety of highly diverse and complex substrates, such as phytohormones and specialized metabolites, to regulate plant growth, development, disease resistance, and environmental interactions. However, a comprehensive investigation of UGT genes in tobacco has not been conducted. RESULTS: In this study, we carried out a genome-wide analysis of family-1 UDP glycosyltransferases in Nicotiana tabacum. We predicted 276 NtUGT genes, which were classified into 18 major phylogenetic subgroups. The NtUGT genes were invariably distributed among all the 24 chromosomes with structural diversity in exon/intron structure, conserved motifs, and cis-acting elements of promoters. Three groups of proteins which involved in flavonoid biosynthesis, plant growth and development, transportation and modification were identified that interact with NtUGT proteins using the PPI analysis. Expression analysis of NtUGT genes in cold stress, drought stress and different flower color using both online RNA-Seq data and the realtime PCR analysis, suggested the distinct role of NtUGT genes in resistance of cold, drought and in flavonoid biosynthesis. The enzymatic activities of seven NtUGT proteins that potentially involved in flavonoid glycosylation were analyzed, and found that all seven exhibited activity on myricetin; six (NtUGT108, NtUGT123, NtUGT141, NtUGT155, NtUGT179, and NtUGT195) showed activity on cyanidin; and three (NtUGT108, NtUGT195, and NtUGT217) were active on the flavonol aglycones kaempferol and quercetin, which catalyzing the substrates (myricetin, cyanidin or flavonol) to form new products. We further investigated the enzymatic products and enzymatic properties of NtUGT108, NtUGT195, and NtUGT217, suggested their diverse enzymatic activity toward flavonol, and NtUGT217 showed the highest catalyzed efficient toward quercetin. Overexpression of NtUGT217 significantly increase the content levels of the quercetin-3-O-glucoside, quercetin-3-O-rutinoside and kaempferol-3-O-rutinoside in transgenic tobacco leaves. CONCLUSION: We identified 276 UGT genes in Nicotiana tabacum. Our study uncovered valuable information about the phylogenetic structure, distribution, genomic characters, expression patterns and enzymatic activity of NtUGT genes in tobacco. We further identified three NtUGT genes involved in flavonoid biosynthesis, and overexpressed NtUGT217 to validate its function in catalyze quercetin. The results provide key candidate NtUGT genes for future breeding of cold and drought resistance and for potential metabolic engineering of flavonoid compounds.


Asunto(s)
Glicosiltransferasas , Nicotiana , Quercetina , Flavonoides/metabolismo , Flavonoles , Glicosiltransferasas/genética , Glicosiltransferasas/metabolismo , Filogenia , Fitomejoramiento , Proteínas de Plantas/genética , Proteínas de Plantas/metabolismo , Quercetina/metabolismo , Estrés Fisiológico/genética , Nicotiana/genética , Nicotiana/metabolismo , Uridina/metabolismo , Uridina Difosfato/metabolismo
10.
Pharmacol Res ; 195: 106842, 2023 09.
Artículo en Inglés | MEDLINE | ID: mdl-37402434

RESUMEN

OBJECTIVE: To evaluate efficacy and safety of total glucosides of paeony in the treatment of 5 types of inflammatory arthritis METHODS: Databases such as Pubmed, Cochran Library, Embase were searched to collect RCTs about TGP in the treatment of inflammatory arthritis. Then, the RCTs were assessed for risk of bias and RCT data were extracted. Finally, RevMan 5.4 was used for the meta-analysis. RESULTS: A total of 63 RCTs were finally included, involving 5293 participants and 5 types of types of inflammatory arthritis: rheumatoid arthritis (RA), ankylosing spondylitis (AS), osteoarthritis (OA), juvenile idiopathic arthritis (JIA), psoriatic arthritis. For AS, TGP may improve AS disease activity score (ASDAS), decrease erythrocyte sedimentation rate (ESR), C-reactive protein (CRP), tumor necrosis factor (TNF)- α and interleukin (IL)- 6; for RA, TGP may improve disease activity of 28 joints (DAS28), decrease ESR, CRP, rheumatoid factor (RF), TNF-α and IL-6; for psoriatic arthritis, TGP may improve psoriasis area and severity index (PASI) and decrease ESR; for OA, TGP may improve visual analogue scale (VAS) and decrease nitric oxide (NO); for JIA, TGP may increase total efficiency rate, decrease ESR, CRP and TNF-α. For safety, RCTs showed that the addition of TGP did not increase adverse events, and may even reduce adverse events. CONCLUSION: TGP may improve symptoms and inflammation levels in patients with inflammatory arthritis. However, due to the low quality and small number of RCTs, large-sample, multi-center clinical trials are still needed for revision or validation.


Asunto(s)
Artritis Psoriásica , Artritis Reumatoide , Paeonia , Humanos , Glucósidos/efectos adversos , Factor de Necrosis Tumoral alfa , Artritis Psoriásica/tratamiento farmacológico , Artritis Reumatoide/tratamiento farmacológico
11.
Mar Drugs ; 21(5)2023 Apr 28.
Artículo en Inglés | MEDLINE | ID: mdl-37233477

RESUMEN

Lung cancer is one of the most lethal malignancies in the world. However, current curative approaches for treating this type of cancer have some weaknesses. Therefore, scientists are attempting to discover new anti-lung cancer agents. Sea cucumber is a marine-derived source for discovering biologically active compounds with anti-lung cancer properties. To explore the anti-lung cancer properties of sea cucumber, we analyzed surveys using VOSviewer software and identified the most frequently used keywords. We then searched the Google Scholar database for compounds with anti-lung cancer properties within that keyword family. Finally, we used AutoDock 4 to identify the compounds with the highest affinity for apoptotic receptors in lung cancer cells. The results showed that triterpene glucosides were the most frequently identified compounds in studies examining the anti-cancer properties of sea cucumbers. Intercedenside C, Scabraside A, and Scabraside B were the three triterpene glycosides with the highest affinity for apoptotic receptors in lung cancer cells. To the best of our knowledge, this is the first time that anti-lung cancer properties of sea cucumber-derived compounds have been examined in in silico conditions. Ultimately, these three components displayed anti-lung cancer properties in in silico conditions and may be used for the manufacture of anti-lung cancer agents in the near future.


Asunto(s)
Antineoplásicos , Neoplasias Pulmonares , Pepinos de Mar , Triterpenos , Animales , Humanos , Neoplasias Pulmonares/tratamiento farmacológico , Antineoplásicos/farmacología , Glicósidos , Triterpenos/farmacología , Triterpenos/uso terapéutico , Bibliometría , Estructura Molecular
12.
Int J Mol Sci ; 24(9)2023 Apr 24.
Artículo en Inglés | MEDLINE | ID: mdl-37175474

RESUMEN

In-depth studies on the interaction of natural compounds with cancer-related G-quadruplex structures have been undertaken only recently, despite their high potential as anticancer agents, especially due to their well-known and various bioactivities. In this frame, aiming at expanding the repertoire of natural compounds able to selectively recognize G-quadruplexes, and particularly focusing on phenanthrenoids, a mini-library including dimeric (1-3) and glucoside (4-5) analogues of 9,10-dihydrophenanthrenes, a related tetrahydropyrene glucoside (6) along with 9,10-dihydrophenanthrene 7 were investigated here by several biophysical techniques and molecular docking. Compounds 3 and 6 emerged as the most selective G-quadruplex ligands within the investigated series. These compounds proved to mainly target the grooves/flanking residues of the hybrid telomeric and parallel oncogenic G-quadruplex models exploiting hydrophobic, hydrogen bond and π-π interactions, without perturbing the main folds of the G-quadruplex structures. Notably, a binding preference was found for both ligands towards the hybrid telomeric G-quadruplex. Moreover, compounds 3 and 6 proved to be active on different human cancer cells in the low micromolar range. Overall, these compounds emerged as useful ligands able to target G-quadruplex structures, which are of interest as promising starting scaffolds for the design of analogues endowed with high and selective anticancer activity.


Asunto(s)
Antineoplásicos , G-Cuádruplex , Neoplasias , Humanos , Simulación del Acoplamiento Molecular , Ligandos , Glucósidos/farmacología , Antineoplásicos/química , Telómero/metabolismo , Neoplasias/tratamiento farmacológico
13.
Int J Mol Sci ; 24(8)2023 Apr 10.
Artículo en Inglés | MEDLINE | ID: mdl-37108149

RESUMEN

Plants and phytophagous arthropods have coevolved in a long battle for survival. Plants respond to phytophagous feeders by producing a battery of antiherbivore chemical defences, while herbivores try to adapt to their hosts by attenuating the toxic effect of the defence compounds. Cyanogenic glucosides are a widespread group of defence chemicals that come from cyanogenic plants. Among the non-cyanogenic ones, the Brassicaceae family has evolved an alternative cyanogenic pathway to produce cyanohydrin as a way to expand defences. When a plant tissue is disrupted by an herbivore attack, cyanogenic substrates are brought into contact with degrading enzymes that cause the release of toxic hydrogen cyanide and derived carbonyl compounds. In this review, we focus our attention on the plant metabolic pathways linked to cyanogenesis to generate cyanide. It also highlights the role of cyanogenesis as a key defence mechanism of plants to fight against herbivore arthropods, and we discuss the potential of cyanogenesis-derived molecules as alternative strategies for pest control.


Asunto(s)
Artrópodos , Herbivoria , Animales , Plantas/metabolismo , Cianuros/metabolismo , Glicósidos/química
14.
Int J Mol Sci ; 24(5)2023 Mar 03.
Artículo en Inglés | MEDLINE | ID: mdl-36902364

RESUMEN

In this study, the black fertile (BSs) and the red unfertile seeds (RSs) of the Greek endemic Paeonia clusii subsp. rhodia (Stearn) Tzanoud were studied for the first time. Nine phenolic derivatives, trans-resveratol, trans-resveratrol-4'-O-ß-d-glucopyranoside, trans-ε-viniferin, trans-gnetin H, luteolin, luteolin 3'-O-ß-d-glucoside, luteolin 3',4'-di-O-ß-d-glucopyranoside, and benzoic acid, along with the monoterpene glycoside paeoniflorin, have been isolated and structurally elucidated. Furthermore, 33 metabolites have been identified from BSs through UHPLC-HRMS, including 6 monoterpene glycosides of the paeoniflorin type with the characteristic cage-like terpenic skeleton found only in plants of the genus Paeonia, 6 gallic acid derivatives, 10 oligostilbene compounds, and 11 flavonoid derivatives. From the RSs, through HS-SPME and GC-MS, 19 metabolites were identified, among which nopinone, myrtanal, and cis-myrtanol have been reported only in peonies' roots and flowers to date. The total phenolic content of both seed extracts (BS and RS) was extremely high (up to 289.97 mg GAE/g) and, moreover, they showed interesting antioxidative activity and anti-tyrosinase properties. The isolated compounds were also biologically evaluated. Especially in the case of trans-gnetin H, the expressed anti-tyrosinase activity was higher than that of kojic acid, which is a well-known whitening agent standard.


Asunto(s)
Antioxidantes , Paeonia , Antioxidantes/química , Paeonia/química , Monofenol Monooxigenasa , Luteolina , Monoterpenos/análisis , Extractos Vegetales/química , Fenoles/análisis , Glicósidos/química , Fitoquímicos/análisis , Semillas/química
15.
Molecules ; 28(18)2023 Sep 14.
Artículo en Inglés | MEDLINE | ID: mdl-37764389

RESUMEN

Four previously undescribed terpenoid glucosides, including one sesquiterpenoid di-glucoside (1), two new iridoid glucosides (2, 3), and a new triterpenoid tri-glucoside (4), were isolated from a 70% ethanol extract of the root of Gentiana macrophylla (Gentianaceae), along with eight known terpenoids. Their structures were determined by spectroscopic techniques, including 1D, 2D NMR, and HRMS (ESI), as well as chemical methods. The absolute configuration of compound 1 was determined by quantum chemical calculation of its theoretical electronic circular dichroism (ECD) spectrum. The sugar moieties of all the new compounds were confirmed to be D-glucose by GC analysis after acid hydrolysis and acetylation. Anti-pulmonary inflammation activity of the iridoids were evaluated on a TNF-α induced inflammation model in A549 cells. Compound 2 could significantly alleviate the release of proinflammatory cytokines IL-1ß and IL-8 and increase the expression of anti-inflammatory cytokine IL-10.


Asunto(s)
Gentiana , Neumonía , Humanos , Terpenos/farmacología , Factor de Necrosis Tumoral alfa , Glucósidos/farmacología , Células A549 , Citocinas , Extractos Vegetales/farmacología
16.
Plant J ; 105(3): 754-770, 2021 02.
Artículo en Inglés | MEDLINE | ID: mdl-33164279

RESUMEN

Manihot esculenta (cassava) is a root crop originating from South America that is a major staple in the tropics, including in marginal environments. This study focused on South American and African germplasm and investigated the genetic architecture of hydrogen cyanide (HCN), a major component of root quality. HCN, representing total cyanogenic glucosides, is a plant defense component against herbivory but is also toxic for human consumption. We genotyped 3354 landraces and modern breeding lines originating from 26 Brazilian states and 1389 individuals were phenotypically characterized across multi-year trials for HCN. All plant material was subjected to high-density genotyping using genotyping by sequencing. We performed genome-wide association mapping to characterize the genetic architecture and gene mapping of HCN. Field experiments revealed strong broad- and narrow-sense trait heritability (0.82 and 0.41, respectively). Two major loci were identified, encoding for an ATPase and a MATE protein, and contributing up to 7 and 30% of the HCN concentration in roots, respectively. We developed diagnostic markers for breeding applications, validated trait architecture consistency in African germplasm and investigated further evidence for the domestication of sweet and bitter cassava. Fine genomic characterization revealed: (i) the major role played by vacuolar transporters in regulating HCN content; (ii) the co-domestication of sweet and bitter cassava major alleles are dependent upon geographical zone; and (iii) the major loci allele for high HCN in M. esculenta Crantz seems to originate from its ancestor, M. esculenta subsp. flabellifolia. Taken together, these findings expand our insights into cyanogenic glucosides in cassava roots and its glycosylated derivatives in plants.


Asunto(s)
Glicósidos/genética , Manihot/genética , África , Alelos , Brasil , Cromosomas de las Plantas , Genética de Población , Estudio de Asociación del Genoma Completo , Glicósidos/metabolismo , Cianuro de Hidrógeno/metabolismo , América Latina , Manihot/metabolismo , Mutación , Filogenia , Fitomejoramiento/métodos , Proteínas de Plantas/genética , Raíces de Plantas/genética , Raíces de Plantas/metabolismo , Polimorfismo de Nucleótido Simple , Gusto
17.
BMC Plant Biol ; 22(1): 405, 2022 Aug 18.
Artículo en Inglés | MEDLINE | ID: mdl-35982415

RESUMEN

BACKGROUND: Flower color patterns play an important role in the evolution and subsequent diversification of flowers by attracting animal pollinators. This interaction can drive the diversity observed in angiosperms today in many plant families such as Liliaceae, Paeoniaceae, and Orchidaceae, and increased their ornamental values. However, the molecular mechanism underlying the differential distribution of anthocyanins within petals remains unclear in Paeonia. RESULTS: In this study, we used an intersectional hybrid between the section Moutan and Paeonia, hereafter named Paeonia 'He Xie', which has purple flowers with dark purple blotches. After Ultra-high performance liquid chromatography-diode array detector (UPLC-DAD) analysis of blotched and non-blotched parts of petals, we found the anthocyanin content in the blotched part was always higher than that in the non-blotched part. Four kinds of anthocyanins, namely cyanidin-3-O-glucoside (Cy3G), cyanidin-3,5-O-glucoside (Cy3G5G), peonidin-3-O-glucoside (Pn3G), and peonidin-3,5-O-glucoside (Pn3G5G) were detected in the blotched parts, while only Cy3G5G and Pn3G5G were detected in the non-blotched parts. This suggests that glucosyltransferases may play a vital role in the four kinds of glucosylated anthocyanins in the blotched parts. Moreover, 2433 differentially expressed genes (DEGs) were obtained from transcriptome analysis of blotched and non-blotched parts, and a key UDP-glycosyltransferase named PhUGT78A22 was identified, which could use Cy3G and Pn3G as substrates to produce Cy3G5G and Pn3G5G, respectively, in vitro. Furthermore, silencing of PhUGT78A22 reduced the content of anthocyanidin 3,5-O-diglucoside in P. 'He Xie'. CONCLUSIONS: A UDP-glycosyltransferase, PhUGT78A22, was identified in P. 'He Xie', and the molecular mechanism underlying differential distribution of anthocyanins within petals was elucidated. This study provides new insights on the biosynthesis of different kinds of anthocyanins within colorful petals, and helps to explain petal blotch formation, which will facilitate the cultivar breeding with respect to increasing ornamental value. Additionally, it provides a reference for understanding the molecular mechanisms responsible for precise regulation of anthocyanin biosynthesis and distribution patterns.


Asunto(s)
Antocianinas , Paeonia , Flores/química , Flores/genética , Glucosa , Glucósidos , Glicosiltransferasas/genética , Paeonia/genética , Fitomejoramiento , Uridina Difosfato/análisis
18.
Planta ; 255(4): 74, 2022 Feb 28.
Artículo en Inglés | MEDLINE | ID: mdl-35226202

RESUMEN

MAIN CONCLUSION: Droughted sorghum had higher concentrations of ROS in both wildtype and dhurrin-lacking mutants. Dhurrin increased in wildtype genotypes with drought. Dhurrin does not appear to mitigate oxidative stress in sorghum. Sorghum bicolor is tolerant of high temperatures and prolonged droughts. During droughts, concentrations of dhurrin, a cyanogenic glucoside, increase posing a risk to livestock of hydrogen cyanide poisoning. Dhurrin can also be recycled without the release of hydrogen cyanide presenting the possibility that it may have functions other than defence. It has been hypothesised that dhurrin may be able to mitigate oxidative stress by scavenging reactive oxygen species (ROS) during biosynthesis and recycling. To test this, we compared the growth and chemical composition of S. bicolor in total cyanide deficient sorghum mutants (tcd1) with wild-type plants that were either well-watered or left unwatered for 2 weeks. Plants from the adult cyanide deficient class of mutant (acdc1) were also included. Foliar dhurrin increased in response to drought in all lines except tcd1 and acdc1, but not in the roots or leaf sheaths. Foliar ROS concentration increased in drought-stressed plants in all genotypes. Phenolic concentrations were also measured but no differences were detected. The total amounts of dhurrin, ROS and phenolics on a whole plant basis were lower in droughted plants due to their smaller biomass, but there were no significant genotypic differences. Up until treatments began at the 3-leaf stage, tcd1 mutants grew more slowly than the other genotypes but after that they had higher relative growth rates, even when droughted. The findings presented here do not support the hypothesis that the increase in dhurrin commonly seen in drought-stressed sorghum plays a role in reducing oxidative stress by scavenging ROS.


Asunto(s)
Sorghum , Cianuro de Hidrógeno , Nitrilos , Estrés Oxidativo , Sorghum/química
19.
J Exp Bot ; 73(8): 2650-2665, 2022 04 18.
Artículo en Inglés | MEDLINE | ID: mdl-35083483

RESUMEN

Cyanogenic glucosides (CNglcs) play an important role in plant defense response; however, the mechanism of regulation of CNglc synthesis by the external environment and endogenous hormones is largely unclear. In this study, we found that jasmonates (JAs) promoted the synthesis of CNglcs by activating the expression of CNglc biosynthesis genes in Lotus japonicus. Several differentially expressed basic helix-loop-helix (bHLH) family genes related to the synthesis of CNglcs were identified by RNA-seq. LjbHLH7 can directly activate the expression of CYP79D3 gene, the first step of CNglc synthesis, by binding to the G-box sequence of its promoter. Transgenic plants overexpressing LjbHLH7 exhibited higher relative CNglc content and enhanced insect resistance compared with the wild type. Furthermore, the transcriptional activity of LjbHLH7 was suppressed by the interaction with the L. japonicus JASMONATE-ZIM DOMAIN protein LjJAZ4. Based on these results, we propose that LjbHLH7 acts as an activator and LjJAZ4 acts as a repressor of JA-induced regulation of CNglc biosynthesis in L. japonicus.


Asunto(s)
Lotus , Factores de Transcripción con Motivo Hélice-Asa-Hélice Básico/genética , Factores de Transcripción con Motivo Hélice-Asa-Hélice Básico/metabolismo , Ciclopentanos/metabolismo , Regulación de la Expresión Génica de las Plantas , Glucósidos/metabolismo , Glicósidos/metabolismo , Lotus/genética , Lotus/metabolismo , Oxilipinas/metabolismo , Plantas Modificadas Genéticamente/genética , Plantas Modificadas Genéticamente/metabolismo
20.
Crit Rev Food Sci Nutr ; : 1-14, 2022 Jul 12.
Artículo en Inglés | MEDLINE | ID: mdl-35821660

RESUMEN

Sesamum indicum is a major and important oilseed crop that is believed to promote human health in many countries, especially in China. Sesame seeds contain two types of lignans: lipid-soluble lignans and water-soluble glucosylated lignans. The major glucosylated lignans are sesaminol glucosides (SGs). So far, four sesaminol isomers and four SGs are identified. During the naturally occurring process of SGs production, sesaminol is generated first from two molecules of E-coniferyl alcohol, and then the sugar is added to the sesaminol one by one, leading to production of SGs. Sesaminol can be prepared from SGs, from sesamolin, and through artificial synthesis. SGs are metabolized in the liver and intestine and are then transported to other tissues. They exhibit several biological activities, most of which are based on their antioxidant and anti-inflammatory activities. In this paper, we present an overview of the current status of research on sesaminol and SGs. We have also discussed their synthesis, preparation, metabolism, and biological activities. It has been suggested that sesaminol and SGs are important biological substances with strong antioxidant properties in vitro and in vivo and are widely used in the food industry, medicine, and cosmetic products. The recovery and utilization of SGs from sesame seed cake after oil processing will generate massive economic benefits.

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