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1.
Microsc Res Tech ; 2024 Mar 31.
Artigo em Inglês | MEDLINE | ID: mdl-38556928

RESUMO

This article describes detailed and novel data on the anatomy and histochemistry of leaves, stems, and roots of Camonea umbellata (L.) A.R.Simões & Staples in different environments for the identification of characters with taxonomical value and of ecological importance, with provision of light and scanning electron microscopy images. To analyze the characters, we collected samples of the vegetative organs of three individuals in each of three populations, which were in a grazing area, an urban environment, and a biological reserve. The main diagnostic anatomical markers for the identification of C. umbellata include amphistomatic leaves, tetracytic and brachyparatetracytic stomata, peltate trichomes, long simple trichomes, epidermis with striated cuticle ornamentation, mesophyll with acute borders, presence of druses, secretory channels, angular collenchyma, fibrous pericycle in the stem, intraxylary phloem in the vegetative organs, oil bodies throughout the midrib, petiole, stem and root, and epicuticular waxes of the crust and coiled rodlet types. Since the characters above did not show variation in the environments evaluated, we consider these characters taxonomically useful for the identification of C. umbellata. RESEARCH HIGHLIGHTS: The anatomy of the aerial vegetative organs of Camonnea umbellata retains common Convolvulaceae characters. The sinuosity of the epidermal cell walls and the density of trichomes in the epidermis of the petiole were visually variable characters among the analyzed individuals. Amphistomatic leaves, tetracytic and brachyparatetracytic stomata, peltate trichomes, epidermis with striated cuticle ornamentation, dorsiventral mesophyll with border acute, presence of druses, secretory structures, angular collenchyma, fibrous pericycle in the stem, intraxillary phloem, presence of oil bodies in all organs, and epicuticular waxes of the crust type and coiled rods were considered important anatomical markers for the recognition and correct identification of Camonea umbellata.

2.
J Nat Med ; 2024 Mar 08.
Artigo em Inglês | MEDLINE | ID: mdl-38457082

RESUMO

Ipomoea muricata (L.) Jacq. seeds (Convolvulaceae) are used as a traditional laxative and carminative medicine. Muricatins XIV (1), XV (2), XVI (3), and XVII (4), were isolated from I. muricata seeds as four new resin glycosides, along with seven known compounds, three of which were isolated for the first time as natural products; their structures were determined using MS and NMR spectroscopy. Compounds 1-4 are macrolactones (jalapins); the sugar moieties of 1, 2, and 4 are partially acylated with 2S-methylbutyric acid, while that of 3 is esterified with 2S-methylbutyric and 2S-methyl-3S-hydroxybutyric acids. In addition, the antiviral activities of the seven compounds obtained in this study, together with five known compounds obtained in our previous study into resin glycosides from I. muricata seeds, were evaluated against herpes simplex virus type 1 (HSV-1); their cytotoxicities against HL-60 human promyelocytic leukemia cells were also investigated. All examined jalapins exhibited similar or slightly weaker anti-HSV-1 activities than acyclovir, the positive control; however, the glycosidic acid of 4 was inactive, while its methyl ester was weakly active. On the other hand, cytotoxicity testing against HL-60 cells showed similar results to those observed during anti-HSV-1 activity testing, with the exception that one jalapin was less active.

3.
AoB Plants ; 16(2): plae001, 2024 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-38352178

RESUMO

Argyreia versicolor and Argyreia mekongensis are extremely rare plant species. The former had not been seen for nearly 100 years until two individuals were found in Thailand in 2018, and only a handful of populations are known for the latter. The aims of this study were to examine the breeding systems of A. versicolor and A. mekongensis using pollination experiments and to determine their potential pollinators via floral observations. Our controlled pollination experiments uncovered the self-incompatibility of both species. Pollinator censuses indicated that females of two carpenter bee species, Xylocopa aestuans and Xylocopa latipes, were the predominant floral visitors for both Argyreia species. Our observations confirmed a harmonious match between the floral shape of both Argyreia species and the body sizes of these pollinators, ensuring effective pollen transfer and validating their role as putative pollinators. In line with the high frequency of pollinator visits observed, our controlled pollination experiments found no evidence of pollen limitation under field conditions. The findings of this study hold significance for the conservation of these endangered species, yet the situation is dire for A. versicolor, with one of the two individuals under study recently lost. Hence, it is crucial to intensify monitoring efforts for the species, aiming to identify additional individuals for potential inclusion in an ex-situ conservation program. Simultaneously, safeguarding the habitat of these plant species and their pollinators will be critical.

4.
Carbohydr Res ; 536: 109048, 2024 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-38310808

RESUMO

Resin glycosides are commonly found in plants belonging to the Convolvulaceae family. Ipomoea lacunosa L. (Convolvulaceae) is an herbaceous vine native to the United States. The resin glycosides of this plant have not been studied in detail. In this study, the components of the crude resin glycoside fraction extracted from the seeds of I. lacunosa are characterized. Alkaline hydrolysis of the crude resin glycoside fraction obtained from methanolic extract of the seeds yielded three organic acids, namely, 2S-methylbutyric, (E)-2-methylbut-2-enoic, and 2R-methyl-3R-hydroxybutyric acids, and a glycosidic acid fraction. Acidic hydrolysis of the glycosidic acid fraction yielded hydroxyl fatty acid components, including 7S-hydroxydecanoic, 11S-hydroxytetradecanoic, 11S-hydroxyhexadecanoic, 3S,11S-dihydroxytetradecanoic, 3S,11S-dihydroxyhexadecanoic, and 3S,12S-dihydroxyhexadecanoic acids, as well as monosaccharide components, including d-glucose, d-quinovose, d-fucose, and l-rhamnose. Trimethylsilyldiazomethane-hexane treatment of the glycosidic acid fraction further yielded eleven previously undescribed glycosidic acid methyl esters and two known glycosidic acid methyl esters. The structures of the obtained compounds were characterized using various spectral techniques. Four of the undescribed compounds were hexaglycosides, five were heptaglycosides, and two were octaglycosides. The aglycone of these compounds was either methyl 11S-hydroxytetradecanoate, methyl 3S,11S-dihydroxytetradecanoate, or methyl 3S,11S-dihydroxyhexadecanoate. Among the undescribed compounds identified, eight contained novel glycans, and three were rare bisdesmosides with sugar linkages at the C-3 and C-11 positions of methyl 3S,11S-dihydroxytetradecanoate.


Assuntos
Convolvulaceae , Ipomoea , Glicosídeos/química , Convolvulaceae/química , Sementes/química , Resinas Vegetais/análise , Resinas Vegetais/química , Estrutura Molecular
5.
Carbohydr Res ; 535: 108993, 2024 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-38048746

RESUMO

Biological effects attributed to resin glycosides, including cytotoxicity against cancer cells and antibacterial, multidrug resistance-modulating, and antiviral activities have been documented. Penta-glycosides composed of calysolic acid A or calyhedic acid A, which are glycosidic acid components of the crude resin glycoside fraction of Calystegia hederacea, have not yet been isolated from this plant. In this study, eight new resin glycosides, termed calyhedins XVI (1)-XXIII (8), were isolated from the rhizomes of C. hederacea. Compounds 1-8 are penta- or hexa-glycosides with macrolactone structures, and their sugar moieties are partially acylated by five organic acids, including 2S-methylbutyric, (E)-2-methylbut-2-enoic, and 2R-methyl-3R-hydroxybutyric acids. Compounds 1-5 are the first identified macrocyclic resin glycosides with five monosaccharides obtained from this plant, and 2 and 4 are the first to be characterized as containing calyhedic acid A as the glycosidic acid component. Compounds 1-8 were of the four following macrolactone types: one with a 22-membered ring (5), another with a 23-membered ring (6-8), the third with a 27-membered ring (1, 3), and the fourth with a 28-membered ring (2, 4). Compounds 2-8 exhibited cytotoxic activity against HL-60 human promyelocytic leukemia cells comparable to that of the positive control, cisplatin.


Assuntos
Calystegia , Humanos , Calystegia/química , Glicosídeos/química , Rizoma , Resinas Vegetais/química , Estrutura Molecular
6.
Phytochemistry ; 217: 113922, 2024 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-37972675

RESUMO

The jalap roots, Operculina hamiltonii D.F. Austin & Staples (Convolvulaceae), are extensively commercialized as a depurative and laxative remedy in traditional medicine of the north and northeast regions of Brazil. The purification by recycling HPLC and structure elucidation of three new acyl sugars or resin glycosides are described here from a commercial product made of powdered roots. Three macrocyclic structures of a tetrasaccharide of (11S)-hydroxyhexadecanoic acid, operculinic acid C (1), the undescribed hamiltonins II and III (3 and 4), in addition to the known batatinoside III (5), presented a diastereoisomeric relationship as one residue of n-dodecanoic acid esterified the oligosaccharide core on a different position in each compound. Furthermore, hamiltonin IV (6) was characterized as an ester-type homodimer of acylated operculinic acid C with the same substitution pattern identified in hamiltonins II (3) and III (4) for each of the dimer subunits. All the isolated resin glycosides did not display any intrinsic cytotoxicity (IC50 > 25 µM). However, a combination of the individual isolated compounds 3-6 (1-50 µM) demonstrated an enhancement of cytotoxic effects with sublethal doses of vinblastine and podophyllotoxin (0.003 µM) in multidrug-resistant breast carcinoma epithelial cells (MCF-7/Vin).


Assuntos
Convolvulaceae , Neoplasias , Humanos , Células MCF-7 , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Convolvulaceae/química , Glicosídeos/farmacologia , Glicosídeos/química , Resinas Vegetais/química , Oligossacarídeos/química , Oligossacarídeos/farmacologia
7.
Plants (Basel) ; 12(14)2023 Jul 18.
Artigo em Inglês | MEDLINE | ID: mdl-37514293

RESUMO

Alkaliweed (Cressa truxillensis) is a native perennial plant of the western USA and in California, they are found primarily in saline and alkaline soils. Lately, it has been observed in Central Valley pistachio, olive, and almond orchards as a problematic species. Very little information is available on the effect of environmental factors on germination, shade tolerance, and the response of this species to herbicides. Therefore, studies were conducted to assess the effect of environmental factors (water potential, salinity, and pH) on seed germination, the influence of shade (30% shade 70% shade, and no shade) on aboveground growth, and the response of alkaliweed to common registered post-emergent herbicides. Results showed that the seeds were moderately tolerant to drought but highly adapted to salinity and pH as germination occurred up to an electrical conductivity level of 20 dS m-1 and pH range of 5 to 9. Both shade levels reduced aboveground growth and formation of reproductive structures. None of the postemergence herbicides provided adequate control of the plants. Therefore, an integrated management plan needs to be developed for alkaliweed control in Central Valley orchards.

8.
Plants (Basel) ; 12(12)2023 Jun 09.
Artigo em Inglês | MEDLINE | ID: mdl-37375882

RESUMO

Serra dos Carajás harbors a unique open plant community in Amazonia, known as canga vegetation, with several endemic species coexisting with the potential threat of large-scale iron ore mining. In this sense, Convolvulaceae occur in a wide variety of canga geoenvironments with multiple flower visitors, but the scarcity of data on its pollen morphology prevents the correct association between Convolvulaceae species with floral visitors, as well as the precise identification of their habitats throughout the Quaternary. Therefore, this study aims to contribute to the taxonomic knowledge and refinement of the identification of insect-plant networks of endangered plants, including Ipomoea cavalcantei. Pollen grains were examined by light and scanning electron microscopy (LM and SEM, respectively), and the morphological parameters obtained were statistically analyzed using principal component analysis. Therefore, all species were differentiated based on aperture types and exine ornamentation. The set of morphological characters indicated that echinae morphology, easily identified under LM, was effective for the identification of Ipomoea species. This work represents the first robust pollen database for a precise identification at the species level of Convolvulaceae from southeastern Amazonian cangas.

9.
J Nat Med ; 77(4): 774-791, 2023 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-37358722

RESUMO

Calystegia hederacea Wall. (Convolvulaceae) is a perennial herbaceous vine that grows widely in India and East Asia. All parts of this plant are used to treat various disorders such as menoxenia and gonorrhea. Four new resin glycosides, calyhedins XI (1)-XIV (4), were isolated from the rhizomes of C. hederacea. A new glycoside, calyhedin XV (5), was isolated from its leaves and stems. Alkaline hydrolysis of 1 and 2 furnished a new glycosidic acid, calyhedic acid G (1a), from 1 and a new acid, calyhedic acid H (2a), from 2 along with 2S-methylbutyric acid and 2R-methyl-3R-hydroxybutyric (2R,3R-nilic) acid. The structures of 1-5, 1a, and 2a were determined using MS and NMR spectral analyses. Compounds 1a and 2a had the same sugar moiety, ß-D-glucopyranosyl-(1 → 6)-O-ß-D-glucopyranosyl-(1 → 6)-O-ß-D-glucopyranosyl-(1 → 3)-[O-ß-D-glucopyranosyl-(1 → 3)-O-α-L-rhamnopyranosyl-(1 → 2)]-O-ß-D-glucopyranosyl-(1 → 2)-ß-D-fucopyranose, while their aglycones were 11S-dihydroxyhexadecanoic acid and 12S-dihydroxyhexadecanoic acid, respectively. These compounds are the first glycosidic acids, with fucose as the monosaccharide component obtained from the resin glycosides of C. hederacea. Compounds 1-5, comprising either 1a or 2a, were heptaglycosides with macrolactone structures, and their sugar moieties were partially acylated with 5 mol of organic acids comprising 2S-methylbutyric, (E)-2-methylbut-2-enoic, and 2R,3R-nilic acids. Compounds 1 and 5 had 22-membered rings, while 2-4 had 28-membered rings. In addition, 1 and 5 exhibited cytotoxic activity against HL-60 human promyelocytic leukemia cells, comparable to that of the positive control cisplatin.


Assuntos
Calystegia , Convolvulaceae , Humanos , Calystegia/química , Glicosídeos/farmacologia , Glicosídeos/química , Convolvulaceae/química , Plantas , Resinas Vegetais/química , Açúcares
10.
Phytochemistry ; 211: 113689, 2023 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-37121293

RESUMO

Scarlet morning glory, Ipomoea hederifolia L. (Convolvulaceae), is an ornamental vine native to the Americas with oxytocic, cytotoxic, antipsychotic, anti-inflammatory, antioxidant, and antimicrobial properties. A chemical study of the glycosidic acids from the resin glycosides contained in the aerial parts was carried out, through their isolation as peracetylated derivatives, by recycling preparative liquid chromatography. Structure elucidation was performed by HR-MS in accordance with NMR. Four peracetylated derivatives of glycosidic acids, named hederifolic acids A-D, were identified as heptaglycosides and hexaglycosides linked to 3S,12S-dihydroxyheptadecanoic acid or 12 S-hydroxyheptadecanoic acid. Consequently, hederifolic acids B and D were found to be dehydroxylated homologs at C-3 of the fatty acid aglycones of hederifolic acids A and C, respectively.


Assuntos
Ipomoea , Ipomoea/química , Estrutura Molecular , Glicosídeos/química , Extratos Vegetais/química , Ácidos Graxos/química , Resinas Vegetais/química
11.
Nat Prod Res ; 37(24): 4251-4255, 2023.
Artigo em Inglês | MEDLINE | ID: mdl-36775581

RESUMO

Antidiabetic activity of methanolic extract, petroleum ether, ethyl acetate and n-butanol fractions of Ipomoea cairica (L.) Sweet leaves was performed in-vitro using α-glucosidase and α-amylase inhibition methods. Phytochemical study of the ethyl acetate fraction which possessed the highest antidiabetic activity led to isolation of five flavonoids for the first time from this plant, including two rare flavonoid sulphates, ombuin-3-sulphate [1] and rhamnetin-3-sulphate [2] and three flavonoid glycosides, kaempferol 7-O-α-L-rhamnopyranoside [3], kaempferol 3,7-di-O-α-L-rhamnopyranoside [4] and quercetin 3-O-α-L-arabinopyranoside [5]. The 1H and 13C NMR of 1 and 13C NMR of 2, were reported here for the first time. Compounds [1-4] showed a concentration-dependent in-vitro inhibitory activity against α-glucosidase and α-amylase. Furthermore, in-silico study predicted that compounds (1-5) showed good interactions with α-glucosidase, α-amylase, and protein tyrosine phosphatase 1b.


Assuntos
Flavonoides , Ipomoea , Flavonoides/química , Hipoglicemiantes/farmacologia , Hipoglicemiantes/análise , Quempferóis/farmacologia , Quempferóis/análise , Ipomoea/química , alfa-Glucosidases , Glicosídeos/química , Folhas de Planta/química , Extratos Vegetais/química , Sulfatos , alfa-Amilases/análise
12.
Curr Opin Plant Biol ; 73: 102348, 2023 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-36842412

RESUMO

Acylsugars constitute a diverse class of secondary metabolites found in many flowering plant families. Comprising sugar cores and acyl groups connected by ester and/or ether linkages, acylsugar structures vary considerably at all taxonomic levels - from populations of the same species to across species of the same family and across flowering plants, with some species producing hundreds of acylsugars in a single organ. Acylsugars have been most well-studied in the Solanaceae family, but structurally analogous compounds have also been reported in the Convolvulaceae, Martyniaceae, Geraniaceae, Rubiaceae, Rosaceae and Caryophyllaceae families. Focusing on Solanaceae and Convolvulaceae acylsugars, this review highlights their structural diversity, the potential biosynthetic mechanisms that produce this diversity, and its functional significance. Finally, we also discuss the possibility that some of this diversity is merely "noise", arising out of enzyme promiscuity and/or non-adaptive evolutionary mechanisms.


Assuntos
Magnoliopsida , Açúcares , Açúcares/metabolismo , Magnoliopsida/metabolismo , Evolução Biológica
13.
Nat Prod Res ; 37(8): 1328-1337, 2023 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-34814779

RESUMO

Four new resin glycosides with macrolactone structures (jalapins), namely, calyhedins VII (1)-X (4), were isolated from the rhizomes of Calystegia hederacea Wall. (Convolvulaceae). The structures of 1-4 were determined based on spectroscopic data. They were classified into three ring types: a 27-membered ring (1), a 22-membered ring (2, 3), and a 23-membered ring (4). Their sugar moieties were partially acylated using five organic acids, including (E)-2-methylbut-2-enoic acid, 2S-methylbutyric acid, and 2 R-methyl-3R-hydroxybutyric acid. Compound 4 was the first genuine resin glycoside with calyhedic acid F as the glycosidic acid component. Additionally, the cytotoxic activities of 1, 2, and 4 towards HL-60 human promyelocytic leukaemia cells were evaluated. All compounds demonstrated almost the same activity as the positive control, cisplatin.


Assuntos
Calystegia , Glicosídeos Cardíacos , Convolvulaceae , Humanos , Calystegia/química , Glicosídeos/farmacologia , Glicosídeos/química , Rizoma , Convolvulaceae/química , Resinas Vegetais/química , Estrutura Molecular
14.
Environ Entomol ; 52(1): 98-107, 2023 02 17.
Artigo em Inglês | MEDLINE | ID: mdl-36585828

RESUMO

Bactericera cockerelli (Sulc) (Hemiptera: Triozidae) is a vector of 'Candidatus Liberibacter solanacearum' (Lso), the pathogen that causes potato zebra chip. Zebra chip incidence varies regionally, perhaps because of geographic differences in species of noncrop hosts available to the vector and in susceptibility of those hosts to Lso. Native and introduced species of Lycium (Solanales: Solanaceae) are important noncrop hosts of B. cockerelli in some regions of North America. Susceptibility of native Lycium species to Lso is uncertain. We investigated the use of two native species of Lycium by B. cockerelli in South Texas and tested whether they are susceptible to Lso. Bactericera cockerelli adults and nymphs were collected frequently from L. berlandieri Dunal and L. carolinianum Walter. Greenhouse assays confirmed that B. cockerelli develops on both species and showed that Lso infects L. carolinianum. Molecular gut content analysis provided evidence that B. cockerelli adults disperse between potato and Lycium. These results demonstrate that L. berlandieri and L. carolinianum are likely noncrop sources of potato-colonizing B. cockerelli in South Texas and that L. carolinianum is a potential source of Lso-infected psyllids. We also routinely collected the congeneric psyllid, Bactericera dorsalis (Crawford), from both Lycium species. These records are the first for this psyllid in Texas. Bactericera dorsalis completed development on both native Lycium species, albeit with high rates of mortality on L. berlandieri. B. dorsalis acquired and transmitted Lso on L. carolinianum under greenhouse conditions but did not transmit Lso to potato. These results document a previously unknown vector of Lso.


Assuntos
Hemípteros , Lycium , Rhizobiaceae , Solanum tuberosum , Animais , Solanales , Texas , Doenças das Plantas
15.
J Nat Med ; 77(2): 284-297, 2023 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-36527581

RESUMO

The alkaline hydrolysis of the crude resin glycoside fraction from the leaves and stems of the plant Calystegia japonica Choisy (Convolvulaceae) yielded organic acid and glycosidic acid fractions. The organic acid fraction was esterified with p-bromophenacyl bromide to obtain p-bromophenacyl 2R-methyl-3R-hydroxybutyrate (1) and p-bromophenacyl (E)-2-methylbut-2-enoate (2). By treating the glycosidic acid fraction with trimethylsilyldiazomethane-hexane, seven new methyl esters of glycosidic acids, namely calyjaponic acid A methyl ester (3) calyjaponic acid B methyl ester (5), calyjaponic acid C methyl ester (6), calyjaponic acid D methyl ester (7), calyjaponic acid E methyl ester (8), calyjaponic acid F methyl ester (9), and calyjaponic acid G methyl ester (10), were isolated along with one known ester (4). Their structures were characterized based on spectroscopic and chemical analyses. Compounds 3-8 had the same sugar moiety, α-L-rhamnopyranosyl-(1 → 2)-O-ß-D-glucopyranosyl-(1 → 2)-[O-α-L-rhamnopyranosyl-(1 → 6)]-O-ß-D-glucopyranose, and the aglycones of 3-8 were methyl 3S,11S-dihydroxyhexadecanoate, methyl 3S,12S-dihydroxyhexadecanoate, methyl 11S-hydroxyhexadecanoate, methyl 11S-hydroxypentadecanoate, methyl 3S,11S-dihydroxypentadecanoate, and methyl 3S,12S-dihydroxypentadecanoate, respectively. Compounds 9 and 10 were derivatives of 3 and 4, respectively, in which the C-6 of the second glucosyl residue was methylated. Compounds 6-8 contained methyl esters of unusual odd-carbon fatty acids as aglycones. The cytotoxicity of the crude resin glycoside fraction and 3 against HL-60 human promyelocytic leukemia cells was evaluated further; both were either weakly active or inactive compared to the positive control, cisplatin.


Assuntos
Calystegia , Convolvulaceae , Humanos , Glicosídeos/química , Calystegia/química , Convolvulaceae/química , Ácidos , Resinas Vegetais/química , Folhas de Planta/química , Ésteres/análise
16.
Bioinformation ; 19(12): 1173-1178, 2023.
Artigo em Inglês | MEDLINE | ID: mdl-38250531

RESUMO

Evolvulus alsinoides is a medicinal plant in the Convolvulaceae family. Traditionally, it is used for different ailments in India and in several other countries. It has a variety of pharmacological qualities, including those that aid wound healing, hepato-protection, cardio-protection, anti-diabetic action, asthma, and epilepsy, memory and learning, and neuroprotection. The whole plant is utilized in Ayurvedic medicine to treat neurological disorders, including amnesia, and it is called the brain tonic by them. Therefore, the use of GC-MS in phytochemical research and chemotaxonomic investigations of medicinal plants containing physiologically active components is critical. Hence, the various secondary metabolites from the methanolic extract of E. alsinoides were analyzed using GC-MS technique. The methanolic extract of E. alsinoides yielded ten compounds. All ten compounds showed the highest number of hits. Those with the highest concentration were chosen to identify the qualitative compound. All compounds are non-toxic. Molecules with specific properties are capable of modulating a variety of proteins, including some enzymes. Thus, these molecules are potential hit-to-lead molecules in preclinical studies.

17.
Molecules ; 27(23)2022 Nov 23.
Artigo em Inglês | MEDLINE | ID: mdl-36500257

RESUMO

Resin glycoside is a type of secondary metabolite isolated commonly from the Convolvulaceae family. It consists of oligosaccharides conjugated to organic acids with a larger percentage having a macrocyclic structure. The resin glycosides reported in this review is classified mostly based on the number of sugar units constructing the structure, which is correlated to the biological properties of the compounds. According to preliminary reviews, the protocols to isolate the compounds are not straightforward and require a special technique. Additionally, the structural determination of the isolated compounds needs to minimize the structure for the elucidation to become easier. Even though resin glycosides have a complicated structural skeleton, several total syntheses of the compounds have been reported in articles published from 2010 to date. This review is an update on the prior studies of the resin glycosides reported in 2010 and 2017. The review includes the classification, isolation techniques, structural determination, biological properties, and total synthesis of the resin glycosides.


Assuntos
Convolvulaceae , Convolvulaceae/química , Glicosídeos/química , Resinas Vegetais/química , Oligossacarídeos/química , Estrutura Molecular
18.
Front Plant Sci ; 13: 1001402, 2022.
Artigo em Inglês | MEDLINE | ID: mdl-36212355

RESUMO

Solanales, an order of flowering plants, contains the most economically important vegetables among all plant orders. To date, many Solanales genomes have been sequenced. However, the evolutionary processes of polyploidization events in Solanales and the impact of polyploidy on species diversity remain poorly understood. We compared two representative Solanales genomes (Solanum lycopersicum L. and Ipomoea triloba L.) and the Vitis vinifera L. genome and confirmed two independent polyploidization events. Solanaceae common hexaploidization (SCH) and Convolvulaceae common hexaploidization (CCH) occurred ∼43-49 and ∼40-46 million years ago (Mya), respectively. Moreover, we identified homologous genes related to polyploidization and speciation and constructed multiple genomic alignments with V. vinifera genome, providing a genomic homology framework for future Solanales research. Notably, the three polyploidization-produced subgenomes in both S. lycopersicum and I. triloba showed significant genomic fractionation bias, suggesting the allohexaploid nature of the SCH and CCH events. However, we found that the higher genomic fractionation bias of polyploidization-produced subgenomes in Solanaceae was likely responsible for their more abundant species diversity than that in Convolvulaceae. Furthermore, through genomic fractionation and chromosomal structural variation comparisons, we revealed the allohexaploid natures of SCH and CCH, both of which were formed by two-step duplications. In addition, we found that the second step of two paleohexaploidization events promoted the expansion and diversity of ß-amylase (BMY) genes in Solanales. These current efforts provide a solid foundation for future genomic and functional exploration of Solanales.

19.
Phytochemistry ; 203: 113409, 2022 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-36049525

RESUMO

Vitamin A deficiency (VAD) in Low and Medium Income countries remains a major health concern. Ipomoea batatas, orange sweet potato (OSP), is one of the biofortification solutions being implemented by the World Health Organisation (WHO) to combat VAD. However, high provitamin A (ß-carotene) content has been associated with a reduction in dry matter, reducing calorific value and having adverse effects on consumer traits. Both starch and carotenoid formation are located in amyloplasts and could potentially compete for the same precursors. Hence, five different sweet potato storage root phenotypes were characterized through spatial metabolomics and proteomics at the sub-plastidal level. The metabolite data suggested an indirect correlation of starch and carotenoids through the TCA cycle and pentose phosphate pathway. Furthermore, a change in lipid composition was observed to accommodate the storage of carotenoids in the hydrophilic environment of the amyloplast. The data suggests an alteration of cellular ultra-structures and perturbation of metabolism in high ß-carotene producing sweet potato roots. This corroborates with previous gene expression analysis through biochemical analysis of sweet potato root tissue.


Assuntos
Ipomoea batatas , Carbono/metabolismo , Carotenoides/metabolismo , Ipomoea batatas/química , Lipídeos , Fenótipo , Raízes de Plantas/química , Plastídeos/metabolismo , Provitaminas/análise , Amido/metabolismo , beta Caroteno/análise , beta Caroteno/metabolismo
20.
Nat Prod Res ; : 1-10, 2022 Sep 23.
Artigo em Inglês | MEDLINE | ID: mdl-36148550

RESUMO

Two new resin glycosides, muricatins XII (1) and XIII (2), were isolated from the crude resin glycoside fraction of the seeds of Ipomoea muricata (L.) Jacq. (Convolvulaceae), along with three known ones, muricatins V (3), VI (4), and IX (5). Compounds 1 and 2 contained new glycosidic acids, muricatic acids E (1a) and F (2a), respectively. The structures of these compounds were determined using data obtained from spectroscopy measurements and chemical evidence. The results suggested that 1 and 2 have macrolactone structures (jalapins). Furthermore, the cytotoxic activity of the crude resin glycoside fraction and 3-5 against HL-60 human promyelocytic leukaemia cells was evaluated. All tested samples demonstrated cytotoxic activities.

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