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1.
BMC Genomics ; 24(1): 571, 2023 Sep 26.
Article in English | MEDLINE | ID: mdl-37752438

ABSTRACT

BACKGROUND: Malvaceae is an economically important plant family of 4,225 species in nine subfamilies. Phylogenetic relationships among the nine subfamilies have always been controversial, especially for Brownlowioideae, whose phylogenetic position remains largely unknown due to the lack of samples in previous analysis datasets. To greatly clarify the phylogenetic relationship of Malvaceae, we newly sequenced and assembled the plastome of Diplodiscus trichospermus taxonomically located in Brownlowioideae, and downloaded the allied genomes from public database to build a dataset covering all subfamily members of Malvaceae. RESULTS: The annotation results showed that the plastome of Diplodiscus trichospermus has a typical quadripartite structure, comprising 112 unique genes, namely 78 protein-coding genes, 30 tRNA genes and 4 rRNA genes. The total length was 158,570 bp with 37.2% GC content. Based on the maximum likelihood method and Bayesian inference, a robust phylogenetic backbone of Malvaceae was reconstructed. The topology showed that Malvaceae was divided distinctly into two major branches which were previously recognized as Byttneriina and Malvadendrina. In the Malvadendrina clade, Malvoideae and Bombacoideae formed, as always, a close sister clade named as Malvatheca. Subfamily Helicteroideae occupied the most basal position and was followed by Sterculioideae which was sister to the alliance of Malvatheca, Brownlowioideae, Dombeyoideae, and Tilioideae. Brownlowioideae together with the clade comprising Dombeyoideae and Tilioideae formed a sister clade to Malvatheca. In addition, one specific conservation SSR and three specific palindrome sequences were observed in Brownlowioideae. CONCLUSIONS: In this study, the phylogenetic framework of subfamilies in Malvaceae has been resolved clearly based on plastomes, which may contribute to a better understanding of the classification and plastome evolution for Malvaceae.


Subject(s)
Genome, Chloroplast , Malvaceae , Phylogeny , Malvaceae/genetics , Bayes Theorem , Base Sequence
2.
Mol Phylogenet Evol ; 182: 107687, 2023 05.
Article in English | MEDLINE | ID: mdl-36581141

ABSTRACT

Dispersals have been shown to be critical to the evolution of the long isolated but megadiverse flora of Madagascar and the surrounding islands of the western Indian Ocean, but we are just beginning to understand the directionality of these dispersals. With more than half of its species occurring in the western Indian Ocean region (WIOR), the paleotropical subfamily Dombeyoideae provides a particularly useful case study through which to better understand the biogeography of the WIOR, and yet its biogeography is poorly understood. Here we sampled six molecular markers from all 20 genera in the Dombeyoideae to reconstruct the most complete phylogeny to date for the subfamily. From this, divergence times, calibrated with three fossils (two dombeyoid, one malvoid), and ancestral range estimations were hypothesized. Biogeographic stochastic mapping (BSM) analyses on the maximum clade credibility tree were completed and compared to BSM analyses on 1,000 trees randomly sampled from the posterior distribution of trees resulting from the dating analysis. We found the Dombeyoideae crown node diverged ca. 53 million years ago out of a broad ancestral range involving all three major areas of its distribution: Madagascar, Africa, and Asia. The majority of diversification and dispersals in the subfamily occurred within the last ca. 10 million years, mostly from the Pliocene onwards. There were roughly five dispersals from Madagascar to Africa (and only one in reverse), at least six from Madagascar to surrounding islands of the WIOR (Mascarenes and Comoros), and one dispersal from Madagascar to Asia (and ca. 1 in reverse). Other long-distance dispersals included one from Africa to St. Helena and one from Africa to Australasia, both from within the most widespread clade, the Cheirolaena & allies clade, and one dispersal from Asia to Africa. Critically, the Dombeyoideae provide strong evidence for considering the island of Madagascar as a source for the colonization of continents, as well as the surrounding islands of the WIOR. Furthermore, narrow sympatry was a key process in the evolution of the subfamily, particularly in Madagascar and the Mascarenes.


Subject(s)
Malvaceae , Phylogeny , Madagascar , Phylogeography , Africa
3.
Virol J ; 20(1): 17, 2023 01 30.
Article in English | MEDLINE | ID: mdl-36710353

ABSTRACT

Leaves of hollyhock (Alcea rosea) exhibiting vein chlorosis and yellow mosaic symptoms were collected at public sites in Lausanne and Nyon, two cities of western Switzerland. Diagnostic methods untangled in samples from both sites the mixed infections of a novel isometric virus, tentatively named "Alcea yellow mosaic virus" (AYMV) with the carlavirus Gaillardia latent virus. A new potyvirus was also identified in samples from Nyon. A combination of Illumina, Nanopore and Sanger sequencing was necessary to assemble the full-length genome of AYMV, revealing an exceptionally high cytidine content and other features typically associated with members of the genus Tymovirus. The host range of AYMV was found to be restricted to mallows, including ornamentals as well as economically important plants. Phylogenetic analyses further showed that AYMV belongs to a Tymovirus subclade that also gathers the other mallow-infecting members. The virus was readily transmitted by sap inoculation, and the weevil species Aspidapion radiolus was evidenced as a vector. Transmission assays using another weevil or other insect species did not succeed, and seed transmission was not observed.


Subject(s)
Coinfection , Malvaceae , Mosaic Viruses , Tymovirus , Weevils , Animals , Tymovirus/genetics , Phylogeny , Plant Diseases
4.
J Nat Prod ; 86(2): 276-289, 2023 02 24.
Article in English | MEDLINE | ID: mdl-36746775

ABSTRACT

Sixteen new quinoline alkaloids (1a-7, 8a, 9, 10, 13-15, 17, and 21) and 10 known analogs (8b, 11, 12, 16, 18-20, and 22-24), along with three known cyclopeptide alkaloids (25-27), were isolated from the roots of Waltheria indica. The structures of the new compounds were elucidated by detailed NMR and circular dichroism with computational support and mass spectrometry data interpretation. Anti-inflammatory potential of isolates was evaluated based on inhibition of lipopolysaccharide (LPS)-induced nitric oxide (NO) production and tumor necrosis factor-alpha (TNF-α)-induced nuclear factor kappa B (NF-κB) activity with cell culture models. In the absence of cell growth inhibition, compounds 6, 8a, 9-11, 13, 21, and 24 reduced TNF-α-induced NF-κB activity with IC50 values ranging from 7.1 to 12.1 µM, comparable to the positive control (BAY 11-7082, IC50 = 9.7 µM). Compounds 6, 8a, 8b, and 11 showed significant NO-inhibitory activity with IC50 values ranging from 11.0 to 12.8 µM, being more active than the positive control (l-NMMA, IC50 = 22.7 µM). Structure-activity relationships indicated that NO inhibitory activity was significantly affected by C-8 substitution. Inhibition of LPS-induced nitric oxide synthase (iNOS) by 8b [(5S)-waltherione M, IC50 11.7 ± 0.8 µM] correlated with inhibition of iNOS mRNA expression. The biological potential of W. indica metabolites supports the traditional use of this plant for the treatment of inflammatory-related disorders.


Subject(s)
Alkaloids , Malvaceae , Quinolines , NF-kappa B/metabolism , Tumor Necrosis Factor-alpha/metabolism , Lipopolysaccharides/pharmacology , Alkaloids/pharmacology , Anti-Inflammatory Agents/pharmacology , Malvaceae/chemistry , Nitric Oxide Synthase Type II/metabolism , Nitric Oxide
5.
Lett Appl Microbiol ; 76(3)2023 Mar 01.
Article in English | MEDLINE | ID: mdl-36881723

ABSTRACT

The present work aimed to produce a cupuassu juice (Theobroma grandiflorum) fermented by the probiotic bacterium Lactiplantibacillus plantarum Lp62 and to analyze its antioxidant potential, antimicrobial activity, and resistance to biological barriers. The fermented beverage showed an increase in the content of phenolics, flavonoids, and antioxidant potential. The culture showed antagonistic activity against pathogens, but this result was not observed when the juice was tested. The probiotic strain remained viable under refrigeration, even in an acidified environment, and survived simulated gastrointestinal transit in vitro. L. plantarum Lp62 showed 30% adherence to HT-29 intestinal cells and proved to be safe in terms of antibiotic resistance and production of virulence factors. Fermentation increased the functional characteristics of cupuassu juice. This drink proved to be a good vehicle for the delivery of the probiotic bacteria L. plantarum Lp62.


Subject(s)
Fruit and Vegetable Juices , Lactobacillaceae , Malvaceae , Probiotics , Humans , Drug Resistance, Bacterial , Fermentation , Fruit and Vegetable Juices/analysis , Fruit and Vegetable Juices/microbiology , HT29 Cells , Lactobacillaceae/drug effects , Lactobacillaceae/metabolism
6.
Pestic Biochem Physiol ; 196: 105587, 2023 Nov.
Article in English | MEDLINE | ID: mdl-37945224

ABSTRACT

Systemic pesticide exposure through nectar is a growing global concern linked to loss of insect diversity, especially pollinators. The insecticide sulfoxaflor and the fungicide tebuconazole are currently widely used systemic pesticides which are toxic to certain pollinators. However, their metabolisms in floral or extrafloral nectar under different application methods have not yet been well studied. Hibiscus rosa-sinensis was exposed to sulfoxaflor and tebuconazole via soil drenching and foliar spraying. Sulfoxaflor, tebuconazole, and their main metabolites in floral and extrafloral nectar, soil, and leaves were identified and quantified using liquid chromatography coupled with triple quadrupole mass spectrometry (LC-QqQ MS). The chemical compositions of unexposed and contaminated H. rosa-sinensis floral nectar or extrafloral nectar were compared using regular biochemical methods. The activities of two pesticide detoxifying enzymes, glutathione-s-transferase and nitrile hydratase, in H. rosa-sinensis nectar were examined using LC-MS and spectrophotometry. The floral nectar proteome of H. rosa-sinensis was analysed using high-resolution orbitrap-based MS/MS analysis to screen for sulfoxaflor and tebuconazole detoxifying enzymes. H. rosa-sinensis can absorb sulfoxaflor and tebuconazole through its roots or leaf surfaces and secrete them into floral nectar and extrafloral nectar. Both sulfoxaflor and tebuconazole and their major metabolites were present at higher concentrations in extrafloral nectar than in floral nectar. X11719474 was the dominant metabolite of sulfoxaflor in the nectars we studied. Compared with soil application, more sulfoxaflor and tebuconazole remained in their original forms in floral nectar and extrafloral nectar after foliar application. Sulfoxaflor and tebuconazole exposure did not modify the chemical composition of floral or extrafloral nectar. No active components, including proteins in the nectar, were detected to be able to detoxify sulfoxaflor.


Subject(s)
Hibiscus , Malvaceae , Pesticides , Rosa , Plant Nectar/chemistry , Plant Nectar/metabolism , Hibiscus/metabolism , Malvaceae/metabolism , Tandem Mass Spectrometry , Soil
7.
Int J Mol Sci ; 25(1)2023 Dec 28.
Article in English | MEDLINE | ID: mdl-38203576

ABSTRACT

Hibiscus syriacus belongs to the Malvaceae family, and is a plant with medicinal, edible, and greening values. MADS-box transcription factor is a large family of regulatory factors involved in a variety of biological processes in plants. Here, we performed a genome-wide characterization of MADS-box proteins in H. syriacus and investigated gene structure, phylogenetics, cis-acting elements, three-dimensional structure, gene expression, and protein interaction to identify candidate MADS-box genes that mediate petal developmental regulation in H. syriacus. A total of 163 candidate MADS-box genes were found and classified into type I (Mα, Mß, and Mγ) and type II (MIKC and Mδ). Analysis of cis-acting elements in the promoter region showed that most elements were correlated to plant hormones. The analysis of nine HsMADS expressions of two different H. syriacus cultivars showed that they were differentially expressed between two type flowers. The analysis of protein interaction networks also indicated that MADS proteins played a crucial role in floral organ identification, inflorescence and fruit development, and flowering time. This research is the first to analyze the MADS-box family of H. syriacus and provides an important reference for further study of the biological functions of the MADS-box, especially in flower organ development.


Subject(s)
Hibiscus , Malvaceae , Hibiscus/genetics , Flowers/genetics , Inflorescence , Plant Growth Regulators
8.
Pak J Pharm Sci ; 36(2): 467-476, 2023 Mar.
Article in English | MEDLINE | ID: mdl-37530154

ABSTRACT

High levels of reactive oxygen species (ROS) in the body and diabetes are key factors for the development of hypercholesteremia and related neuropathic pains. Current study aimed to compare the antioxidant, antidiabetic and analgesic activities of aqueous methanolic extracts of C. viminalis L. and A. rosea L. leaves. HPLC method was used for phenolic content evaluation. Antioxidant capacity was determined by DPPH and analgesic activity was performed via acetic acid induced writhing reflex test. Whereas the antidiabetic activity was performed on Alloxan induced diabetes model. HPLC analysis indicated the presence of phenols in both extracts. Based on DPPH radical scavenging activity, C. viminalis and A.rosea L. both leaves extracts showed strong scavenging activity (IC50, 11.96±0.64lg/mL) and (IC50, 10.11±0.74lg/mL) respectively. Antidiabetic effect of C. viminalis L and A. rosea L. were also significant (p<0.05). Further biochemical analysis showed both leaves extracts significantly (P<0.05) reduces glucose, Low density lipid (LDL), triglycerides (TG), total cholesterol (TC) and urea while high density lipid (HDL) were improved. In writhing reflex test both extracts exhibited significant (P<0.01) analgesic activity which was comparable to Aspirin. In conclusion both C. viminalis L. and A. rosea L. leaves extracts displayed significant antioxidant, analgesic and antidiabetic activity.


Subject(s)
Antioxidants , Malvaceae , Antioxidants/chemistry , Hypoglycemic Agents/chemistry , Plant Extracts/chemistry , Analgesics/pharmacology , Lipids/analysis , Plant Leaves/chemistry
9.
BMC Plant Biol ; 22(1): 113, 2022 Mar 12.
Article in English | MEDLINE | ID: mdl-35279080

ABSTRACT

BACKGROUND: Many seed plants produce winged diaspores that use wind to disperse their seeds. The morphology of these diaspores is directly related to the seed dispersal potential. The majority of winged diaspores have flat wings and only seeds; however, some angiosperms, such as Firmiana produce winged fruit with a different morphology, whose seed dispersal mechanisms are not yet fully understood. In this study, we observed the fruit development of F. simplex and determined the morphological characteristics of mature fruit and their effects on the flight performance of the fruit. RESULTS: We found that the pericarp of F. simplex dehisced early and continued to unfold and expand during fruit development until ripening, finally formed a spoon-shaped wing with multiple alternate seeds on each edge. The wing caused mature fruit to spin stably during descent to provide a low terminal velocity, which was correlated with the wing loading and the distribution of seeds on the pericarp. When the curvature distribution of the pericarp surface substantially changed, the aerodynamic characteristics of fruit during descent altered, resulting in the inability of the fruit to spin. CONCLUSIONS: Our results suggest that the curved shape and alternate seed distribution are necessary for the winged diaspore of F. simplex to stabilize spinning during wind dispersal. These unique morphological characteristics are related to the early cracking of fruits during development, which may be an adaptation for the wind dispersal of seeds.


Subject(s)
Fruit/anatomy & histology , Fruit/growth & development , Malvaceae/anatomy & histology , Malvaceae/growth & development , Seed Dispersal , Seeds/anatomy & histology , Seeds/growth & development , China , Phenotype , Wind
10.
BMC Plant Biol ; 22(1): 86, 2022 Feb 25.
Article in English | MEDLINE | ID: mdl-35216551

ABSTRACT

BACKGROUND: Helicteres angustifolia has long been used in Chinese traditional medicine. It has multiple pharmacological benefits, including anti-inflammatory, anti-viral and anti-tumor effects. Its main active chemicals include betulinic acid, oleanolic acid, helicteric acid, helicterilic acid, and other triterpenoid saponins. It is worth noting that some acylated triterpenoids, such as helicteric acid and helicterilic acid, are characteristic components of Helicteres and are relatively rare among other plants. However, reliance on natural plants as the only sources of these is not enough to meet the market requirement. Therefore, the engineering of its metabolic pathway is of high research value for enhancing the production of secondary metabolites. Unfortunately, there are few studies on the biosynthetic pathways of triterpenoids in H. angustifolia, hindering its further investigation. RESULTS: Here, the RNAs of different groups treated by metabolic stimulation were sequenced with an Illumina high-throughput sequencing platform, resulting in 121 gigabases of data. A total of 424,824 unigenes were obtained after the trimming and assembly of the raw data, and 22,430 unigenes were determined to be differentially expressed. In addition, three oxidosqualene cyclases (OSCs) and four Cytochrome P450 (CYP450s) were screened, of which one OSC (HaOSC1) and one CYP450 (HaCYPi3) achieved functional verification, suggesting that they could catalyze the production of lupeol and oleanolic acid, respectively. CONCLUSION: In general, the transcriptomic data of H. angustifolia was first reported and analyzed to study functional genes. Three OSCs, four CYP450s and three acyltransferases were screened out as candidate genes to perform further functional verification, which demonstrated that HaOSC1 and HaCYPi3 encode for lupeol synthase and ß-amyrin oxidase, which produce corresponding products of lupeol and oleanolic acid, respectively. Their successful identification revealed pivotal steps in the biosynthesis of acylated triterpenoids precursors, which laid a foundation for further study on acylated triterpenoids. Overall, these results shed light on the regulation of acylated triterpenoids biosynthesis.


Subject(s)
Malvaceae/genetics , Malvaceae/metabolism , Plant Proteins/metabolism , Triterpenes/metabolism , Acetates/pharmacology , Acylation , Cyclopentanes/pharmacology , Cytochrome P-450 Enzyme System/genetics , Cytochrome P-450 Enzyme System/metabolism , Gene Expression Profiling , Gene Expression Regulation, Plant/drug effects , Intramolecular Transferases/genetics , Intramolecular Transferases/metabolism , Malvaceae/drug effects , Oxylipins/pharmacology , Phylogeny , Plant Proteins/genetics , Plants, Medicinal/genetics , Plants, Medicinal/metabolism , Real-Time Polymerase Chain Reaction , Salicylic Acid/pharmacology , Triterpenes/chemistry
11.
Planta ; 257(1): 3, 2022 Nov 24.
Article in English | MEDLINE | ID: mdl-36418498

ABSTRACT

MAIN CONCLUSIONS: Transmitting tissue cells of Luehea divaricata present a thick middle lamella and prominent convex lens-shaped thickenings of the cell wall that act as reservoir of energy for pollen tube growth. Luehea Milld. is a Neotropical genus with 18 species. This paper reports the study of the structure and the ultrastructure of the stigma and the style of Luehea divaricata Milld. using bright-field microscope and transmission electron microscope. Multiseriate papillae are observed in the stigma. The papillae cells are large with a content that stains intensively and the sub-stigmatic tissue resembles the style's transmitting tissue. L. divaricata has a closed style with an epidermis that presents raised stomata and multicellular trichomes. Numerous organelles and a large nucleus are present in the dense cytoplasm of the transmitting tissue cells. A relevant feature is that the cells of this tissue in the species studied present a very thick middle lamella with two zones of different electron density in the angle of contact between cells, and convex lens-shaped thickenings of the cell wall are prominent mainly also in these angles of contact. The growth of the pollen tube is initiated on the stigmatic papillae surface and continues growing in the middle lamella of the sub-stigmatic tissue and the transmitting tissue, mainly at the contact angle between cells. The present work is the first contribution to the knowledge of structure and ultrastructure of the stigma and style in the genus Luehea, as well as to the subfamily Grewioideae (Malvaceae).


Subject(s)
Malvaceae , Cell Nucleus , Cytoplasm , Pollen Tube , Staining and Labeling
12.
Genetica ; 150(6): 395-405, 2022 Dec.
Article in English | MEDLINE | ID: mdl-36322294

ABSTRACT

Firmiana is a small genus within the subfamily Sterculioideae of the Malvaceae. There are nine Firmiana species distributed in South and South-west China, most of which are endangered. Due to the shortage of plastid genomes data, the phylogenetic relationships and the evolutionary history of this genus remain unclear. Therefore, the complete chloroplast genomes of F. calcarean and F. hainanensis were sequenced using high-throughput sequencing and then compared with the chloroplast genomes of other reported Firmiana species. The genome size of F. calcarean and F. hainanensis is 161,263 and 160,031 bp long, respectively, containing a total of 131 genes (including 85 protein coding genes, 37 tRNAs, 8 rRNAs, and one pseudogene). Comparative analysis revealed that the genome structure, GC content, gene content and order, as well as the RNA editing sites within the chloroplast genomes of F. calcarean and F. hainanensis were similar to previously reported Firmiana species. ML phylogenetic analysis revealed that F. danxiaensis, F. hainanensis, F. calcarean, F. simplex, and F. major form a sister group to F. colorata, F. pulcherrima, and F. kwangsiensis. The SSRs, long repeats, and 21 highly divergent regions (Pi > 0.01) identified in this study might provide potential DNA markers for further population genetics and phylogenetic studies of Firmiana. Our findings can help design new species-specific molecular markers and the general framework to further explore the evolutionary history of Firmiana and to address their conservation challenges.


Subject(s)
Genome, Chloroplast , Malvaceae , Phylogeny , Chloroplasts/genetics , Microsatellite Repeats , Malvaceae/genetics
13.
Arch Virol ; 167(9): 1889-1892, 2022 Sep.
Article in English | MEDLINE | ID: mdl-35660981

ABSTRACT

A new virus, named Mutum virus, related to members of the family Tymoviridae, was isolated from mosquitoes (Mansonia spp.) in clone C6/36 cells, and its complete genome was sequenced. Its genome is 6494 nt in size with an organization resembling that of tymovirids. The isolated virus is phylogenetically related to two viruses isolated from Culex spp. mosquitoes: Ek Balam virus, reported in Mexico, and Culex-originated Tymoviridae-like virus, isolated in China. The results of this study suggest that this virus is a new member of the family Tymoviridae.


Subject(s)
Culex , Culicidae , Malvaceae , Tymoviridae , Animals , Brazil , Genome, Viral , Phylogeny , Tymoviridae/genetics
14.
Mol Biol Rep ; 49(6): 5635-5644, 2022 Jun.
Article in English | MEDLINE | ID: mdl-35598198

ABSTRACT

BACKGROUND: Hollyhock (Alcea rosea) is an ornamental plant belonging to the Malvaceae family and has a remarkable aesthetic and medicinal value. A number of distinct infectious entity including fungi, nematode, bacteria and most importantly both single and double stranded DNA and RNA viruses are reported from infected hollyhock plant. Begomoviruses, the well reputed member of the family Geminiviridae infected the hollyhock recently with a new hollyhock vein yellowing virus and in the present study it infected the hollyhock plant with Cotton leaf curl Multan virus (CLCuMV) which cause the disease of leaf curling. METHODS AND RESULTS: The symptomatic leaves of the hollyhock plants were collected based on the characteristic symptoms of leaf curling, puckering as well as vein thickening. DNA was extracted by using the recommended 2× CTAB protocol and PCR technique was optimized for the detection of begomovirus followed by sequencing. The data of disease incidence of infection location wise was collected based on the positive results of PCR amplification. Virus free whitefly collected from cotton field and feed on infected hollyhock plant in cage for few days then used for the transmission study of begomovirus on healthy hollyhock plants. Results of PCR amplification indicated that the primers Av/Ac core, Begomo 01/02, and CLCV 01/02 showed the bands of 579 bp, 2.8 kb and 1.1 kb respectively. The betasatellite was amplified by using beta01/02 and CLCuMuBF11/R33, which showed the band of 1400 bp and 481 bp. Disease incidence and Transmission study confirmed the begomovirus in hollyhock plants at molecular level. The sequence obtained with Av/Ac core primers showed the 99% identity with Cotton leaf curl Multan virus-Rajasthan strain and betasatellite primers showed 98% identity with Cotton leaf curl Multan betasatellite. CONCLUSION: Hollyhock plants infected by CLCuMV and associated betasatellite has been reported as a possible source of virus inoculum from Pakistan. These findings extend the range of Begomoviruses and betasatellites known to infect A. rosea and highlight this hollyhock species as an important reservoir of agriculturally important Begomoviruses and betasatellites.


Subject(s)
Begomovirus , Malvaceae , Begomovirus/genetics , Pakistan , Phylogeny , Plant Diseases/genetics , Prevalence
15.
J Nat Prod ; 85(7): 1872-1879, 2022 07 22.
Article in English | MEDLINE | ID: mdl-35771599

ABSTRACT

The first asymmetric synthesis of microgrewiapine C, a piperidine alkaloid isolated from Microcos paniculata, is reported. This synthesis prompted correction of the 1H and 13C NMR data for the natural sample of the alkaloid, which was achieved by reanalysis of the original spectra. The corrected data for the natural product were found to be identical to those of the synthetic sample prepared herein, thus confirming the structural and relative configurational assignment of microgrewiapine C. Although comparison of specific rotation values indicates that the (1R,2S,3S,6S) absolute configuration should be assigned to the alkaloid, consideration of potential common biosynthetic origins of microgrewiapine C and congeners suggests that further phytochemical investigations are warranted.


Subject(s)
Alkaloids , Malvaceae , Alkaloids/chemistry , Malvaceae/chemistry , Molecular Structure , Piperidines/chemistry , Stereoisomerism
16.
J Nat Prod ; 85(2): 375-383, 2022 02 25.
Article in English | MEDLINE | ID: mdl-35171609

ABSTRACT

Eight new 2,6-disubstituted piperidin-3-ol alkaloids (1-8), featuring a C10 unsaturated alkyl side chain, together with three previously reported analogues (9-11) were isolated from the leaves of medicinal plant Microcos paniculata. Their structures and absolute configurations were elucidated unambiguously by means of 1D and 2D NMR spectroscopic data analysis, modified Mosher's method, Snatzke's method, and quantum chemical electronic circular dichroism (ECD) calculations, as well as single-crystal X-ray crystallography. The isolates were evaluated for their antiangiogenic effects on human umbilical vein endothelial cells (HUVECs). Compound 2 displayed an inhibitory effect on tube formation of HUVECs in a concentration-dependent manner.


Subject(s)
Alkaloids , Malvaceae , Alkaloids/chemistry , Circular Dichroism , Endothelial Cells , Humans , Molecular Structure , Piperidines/chemistry , Piperidines/pharmacology , Plant Leaves/chemistry
17.
Nucleic Acids Res ; 48(D1): D1076-D1084, 2020 01 08.
Article in English | MEDLINE | ID: mdl-31665439

ABSTRACT

Malvaceae is a family of flowering plants containing many economically important plant species including cotton, cacao and durian. Recently, the genomes of several Malvaceae species have been decoded, and many omics data were generated for individual species. However, no integrative database of multiple species, enabling users to jointly compare and analyse relevant data, is available for Malvaceae. Thus, we developed a user-friendly database named MaGenDB (http://magen.whu.edu.cn) as a functional genomics hub for the plant community. We collected the genomes of 13 Malvaceae species, and comprehensively annotated genes from different perspectives including functional RNA/protein element, gene ontology, KEGG orthology, and gene family. We processed 374 sets of diverse omics data with the ENCODE pipelines and integrated them into a customised genome browser, and designed multiple dynamic charts to present gene/RNA/protein-level knowledge such as dynamic expression profiles and functional elements. We also implemented a smart search system for efficiently mining genes. In addition, we constructed a functional comparison system to help comparative analysis between genes on multiple features in one species or across closely related species. This database and associated tools will allow users to quickly retrieve large-scale functional information for biological discovery.


Subject(s)
Computational Biology/methods , Databases, Genetic , Genome, Plant , Genomics , Malvaceae/genetics , Genomics/methods , High-Throughput Nucleotide Sequencing , Malvaceae/classification , Molecular Sequence Annotation , Software , User-Computer Interface , Web Browser
18.
Drug Chem Toxicol ; 45(4): 1504-1521, 2022 Jul.
Article in English | MEDLINE | ID: mdl-33252270

ABSTRACT

Pachira aquatica is a species used for medicinal and food purposes and has numerous phytochemicals that may have systemic toxic effects and damage to genetic material. This study aimed to evaluate acute and short-term oral toxicity, as well as genotoxic and clastogenic effects of oil extracted from P. aquatica (PASO) seeds in rats and Drosophila melanogaster. The results obtained with biochemical and hematological analyses did not show significant changes in any evaluated parameters when compared with reference values for the species used in the study. Data from the histopathological analysis corroborated results found in this study. These findings indicate low acute and short-term toxicity following oral PASO exposure in rats under the experimental conditions tested. Tests performed in rats showed that PASO did not present significant genotoxic or clastogenic effects on the cells analyzed with the three doses tested. Treatment with PASO in the offspring of HB crossing, which showed high cytochrome P450 levels, did not exhibit genotoxic activity, as demonstrated by the SMART test. These results suggest that products from the hepatic oil metabolism did not show genotoxicity under the conditions tested. Together, the results indicate that, under the experimental conditions tested, PASO is safe for repeated intake. As PASO exhibited low potential to cause harmful effects on living organisms, our study encourages further research aimed at assessing its pharmacological activity, since it is a widely consumed plant.


Subject(s)
Bombacaceae , Malvaceae , Animals , Drosophila melanogaster , Mutagens/chemistry , Plant Extracts/pharmacology , Rats , Seeds , Toxicity Tests, Acute
19.
Chem Biodivers ; 19(12): e202200322, 2022 Dec.
Article in English | MEDLINE | ID: mdl-36269048

ABSTRACT

Preparations of Helicteres sacarolha (Malvaceae) leaves and roots are used in the form of decoction, infusion or maceration, to treat gastrointestinal disturbances, among others. Studies supporting some of its ethnomedicinal uses are still incipient. The present study aimed to investigate it potential effect on chronic ulcer, ulcerative colitis and possible prokinetic activities as part of its mechanism of action. The powdered leaves of Helicteres sacarolha (HEHs) was prepared by maceration in 70 % hydroethanolic solution. Its qualitative phytochemical constituents were investigated by direct flow injection analysis coupled to atmospheric pressure chemical ionization ion trap tandem mass spectrometry (FIA-APCI-IT-MSn ). The gastric ulcer healing effect was evaluated in acetic acid induced chronic ulcer in mice and the lesions were evaluated, including analysis of blood plasma cytokine levels. The prokinetic properties (gastric emptying and intestinal transit) were carried out in mice. Potential anti-ulcerative colitis activity was evaluated in rats using 2,4,6-trinitrobenzenesulfonic acid (5 % TNBS) -induced colitis. All animal experiments were carried out at the doses of 20, 50 and 250 mg/kg (p.o.). Eight compounds were putatively identified, specifically lariciresinol, and its derivatives, kaempferol derivatives and Tricin-O-Glc. The extract promoted increased gastric ulcer healing at all doses tested. Modulation of the cytokines involved inhibition of some key pro-inflammatory cytokines with maximum effect on IL-1ß (70 %, 50 mg/kg, p<0.05), TNF-α (79 %, 20 mg/kg, p<0.01), and in the anti-inflammatory cytokines, namely IL-10 (57 %, 50 mg/kg, p<0.05) and IL-17 (79 %, only at 50 mg/kg, p<0.05). Histological findings demonstrated a mitigated inflammatory activity, and tissues undergoing regeneration. HEHs treatment caused delayed gastric emptying, and increased intestinal transit, but had no effect in the experimentally induced ulcerative colitis. We report for the first time putatively the presence of Lariciresinol and tricin derivatives from the hydroethanolic leaves extract of H. sacarolha. Its possible mechanism of actions of gastric ulcer healing involves cytokines modulation, mitigation of inflammatory response and tissue regeneration and provoked opposing effect in the gastrointestinal system. The present study demonstrates the therapeutic potential of H. sacarolha leaves used in Brazilian ethnomedicine in the treatment of chronic gastric ulcer.


Subject(s)
Anti-Ulcer Agents , Malvaceae , Stomach Ulcer , Rats , Mice , Animals , Stomach Ulcer/chemically induced , Stomach Ulcer/drug therapy , Stomach Ulcer/pathology , Cytokines , Plant Extracts/pharmacology , Plant Extracts/therapeutic use , Plant Extracts/chemistry , Phytotherapy/methods , Rats, Wistar , Anti-Ulcer Agents/pharmacology , Anti-Ulcer Agents/therapeutic use , Anti-Ulcer Agents/chemistry , Malvaceae/chemistry
20.
Molecules ; 27(10)2022 May 10.
Article in English | MEDLINE | ID: mdl-35630547

ABSTRACT

After being harvested, cacao beans are usually subjected to very complex processes in order to improve their chemical and physical characteristics, like tastefulness with chocolate characteristic flavors. The traditional process consists of three major processing stages: fermentation, drying, and roasting, while most of the fermentation is carried out by an on-farm in-box process. In Taiwan, we have two major cocoa beans, the red and the yellow. We proposed that the major factor affecting the variation in tastes and colors in the finished cocoa might be the difference between cultivars. To uncover this, we examined the effect of the three major processes including fermentation, drying and roasting on these two cocoa beans. Results indicated that the two cultivars really behaved differently (despite before or after processing with fermentation, drying, and roasting) with respect to the patterns of fatty acids (palmitic, stearic, oleic, and arachidonic); triacylglycerols:1,2,3-trioleoyl-glycerol (OOO); 1-stearoyl-2,3-oleoyl-glycerol (SOO); 1-stearoyl-sn-2-oleoyl-3-arachidoyl- glycerol (SOA); 1,3-distearyol-sn-2-oleoyl-glycerol (SOS); organic acids (citric, tartaric, acetic, and malic); soluble sugars (glucose and fructose); amino acids; total phenolics; total flavonoids; and volatiles. Our findings suggest that to choose specific processing conditions for each specific cocoa genotype is the crucial point of processing cocoa with consistent taste and color.


Subject(s)
Cacao , Malvaceae , Cacao/chemistry , Fermentation , Glycerol/metabolism , Taiwan
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