Flavonoid Aglycones from the Leaf and Stem Exudates of Some Geraniaceae Species

Wollenweber, Eckhard; Dörr, Marion; Christ, Matthias

doi:10.1177/1934578x1100600105

Cited by 6 publications

(7 citation statements)

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“…Alkylation of hydroxyl groups leads to changes in the solubility, thereby affecting both the compartmentation and the biological activity of a metabolite (Ibrahim et al ., ; Zubieta et al ., ; Berim et al ., ). While glycosylation increases the water solubility of a compound, which then tends to accumulate in the vacuole, methylation decreases the water solubility and favors excretion of a metabolite from the cell (Marinova et al ., ; Wollenweber et al ., ). Pterostilbene, which bears two methoxyl groups, exhibited higher antifungal activity than the precursor resveratrol which carries two phenolic hydroxyl groups (Alessandro et al ., ; Pezet et al ., ).…”

Section: Introductionmentioning

confidence: 97%

O‐Methyltransferases involved in biphenyl and dibenzofuran biosynthesis

et al. 2015

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SUMMARYBiphenyls and dibenzofurans are the phytoalexins of the Malinae involving apple and pear. Biosynthesis of the defence compounds includes two O-methylation reactions. cDNAs encoding the O-methyltransferase (OMT) enzymes were isolated from rowan (Sorbus aucuparia) cell cultures after treatment with an elicitor preparation from the scab-causing fungus, Venturia inaequalis. The preferred substrate for SaOMT1 was 3,5-dihydroxybiphenyl, supplied by the first pathway-specific enzyme, biphenyl synthase (BIS). 3,5-Dihydroxybiphenyl underwent a single methylation reaction in the presence of S-adenosyl-L-methionine (SAM). The second enzyme, SaOMT2, exhibited its highest affinity for noraucuparin, however the turnover rate was greater with 5-hydroxyferulic acid. Both substrates were only methylated at the meta-positioned hydroxyl group. The substrate specificities of the OMTs and the regiospecificities of their reactions were rationalized by homology modeling and substrate docking. Interaction of the substrates with SAM also took place at a position other than the sulfur group. Expression of SaOMT1, SaOMT2 and SaBIS3 was transiently induced in rowan cell cultures by the addition of the fungal elicitor. While the immediate SaOMT1 products were not detectable in elicitor-treated cell cultures, noraucuparin and noreriobofuran accumulated transiently, followed by increasing levels of the SaOMT2 products aucuparin and eriobofuran. SaOMT1, SaOMT2 and SaBIS3 were N-and C-terminally fused with the super cyan fluorescent protein and a modified yellow fluorescent protein, respectively. All the fluorescent reporter fusions were localized to the cytoplasm of Nicotiana benthamiana leaf epidermis cells. A revised biosynthetic pathway of biphenyls and dibenzofurans in the Malinae is presented.

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Section: Introductionmentioning

confidence: 97%

O‐Methyltransferases involved in biphenyl and dibenzofuran biosynthesis

et al. 2015

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“…2A) leaves are mainly characterized by the presence of two isomers (9,15) of caffeoylquinic acid, one of them identi ed as 3-Ocaffeoylquini acid (chlorogenic acid; 15) and of two abundant isomers of dicaffeoylquinic acid (34,38); also caffeoylquinic acid hexoside was best represented in this species (7). The leaves of A. absinthium, compared to the other species, present higher proportion of the avonols kaempferol-Ohexoside-deoxyhexoside (23), isorhamnetin-O-hexoside-deoxyhexoside (30), eupatolitin-O-deoxyhexoside-O-hexoside (32) and isorhamnetin-3-Oglucoside (36). Moreover, in leaves and, at a lower level, in stems of this species only, we detected high amounts of the dimeric guaianolide absinthin (81), which is described as a speci c marker of A. absinthium and is responsible for the bitterness of absinth [7,14,15].…”

Section: Metabolic Pro Les Of Artemisia Spp Methanolic Extractsmentioning

confidence: 99%

“…Moreover, this species is strongly characterized by the presence of four ferulic acid derivatives, one with a molecular ion of 693.20 m/z (42) and three isomers showing a molecular ion of 735.21 m/z (58, 62, 64,); the resulting neutral loss of 42.01 Da and the higher retention time strongly suggest that the latter could be the acetylated forms of compound 42. With respect to stems, A. alba leaves presented higher levels of one isomer of a dihydroxybenzoic acid hexoside (4) and various avonoids glycosides including quercetin-3-O-rutinoside (22), kaempferol-O-hexoside-deoxyhexoside (23), kaempferol-3-O-rutinoside (29), isorhamnetin-O-hexoside-deoxyhexoside (30) and apigenin-O-hexosidedeoxyhexoside (31). Interestingly, according to literature [18], we detected high levels in the leaves of A. alba of tuberonic acid hexoside (16), which belong to the class of jasmonate glycosylated derivatives, i.e.…”

Section: Metabolic Pro Les Of Artemisia Spp Methanolic Extractsmentioning

confidence: 99%

Bioprospecting of Artemisia genus: from artemisinin to other potentially bioactive compounds

Negri,

Pietrolucci,

Andreatta

et al. 2023

Preprint

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Species from genus Artemisia are widely distributed throughout temperate regions of the northern hemisphere and many cultures have a long-standing traditional use of these plants as herbal remedies, liquors, cosmetics, spices, etc. Nowadays, the discovery of new plant-derived products to be used as food supplements or drugs has been pushed by the exploitation of bioprospection approaches. Often driven by the knowledge derived from the ethnobotanical use of plants, bioprospection explores the existing biodiversity through integration of modern omics techniques with targeted bioactivity assays. In this work we set up a bioprospection plan to investigate the phytochemical diversity and the potential bioactivity of five Artemisiaspecies with recognized ethnobotanical tradition (A. absinthium, A. alba, A. annua, A. verlotiorum and A. vulgaris), growing wild in the natural areas of the Verona province. We characterized the specialized metabolomes of the species (including sesquiterpenoids from the artemisinin biosynthesis pathway) through an LC-MS based untargeted approach and, in order to identify potential bioactive metabolites, we correlated their composition with the in vitro antioxidant activity. We propose as potential bioactive compounds several isomers of caffeoyl and feruloyl quinic acid esters (e.g. dicaffeoylquinic acids, feruloylquinic acids and caffeoylferuloylquinic acids), which strongly characterize the most antioxidant species A. verlotiorum and A. annua. Morevoer, in this study we report for the first time the occurrence of sesquiterpenoids from the artemisinin biosynthesis pathway in the species A. alba.

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“…132 Aglycones of flavonols encountered in geranium are the common quercetin (219), myricetin (218), kaempferol (217), and ayanin (215). 123,133,134 In the majority of situations, their hydroxylated substitutions form heterosidic linkages (Table 7). A number of quercetin, myricetin and kaempferol glycosides were recently identified in geranium using HPLC-PDA-ESI-MS/MS, however the nature of sugars has not been thoroughly elucidated.…”

Section: Phenolic Compound Of Geranium Flavonoids and Derivativesmentioning

confidence: 99%

Traditional Uses, Botany, Phytochemistry, and Pharmacology of Pelargonium graveolens: A Comprehensive Review

2022

TJNPR

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Pelargonium graveolens (PG) is a popular medicinal plant, widely used in Africa for centuries to treat various diseases. Because of its wide exploitation, the therapeutic studies of P. graveolens keep penetrating. This research engulfs a comprehension of all previous studies related to this medicinal herb, where it summaries and evaluates the traditional uses, the botany, the phytochemistry, the pharmacology, and the toxicology of P. graveolens. A literature review was conducted through the classic books of herbs, medicine, PhD papers, and online scientific databases, searching up to January 2022. This review analyzes all literature on the research subject. Our main findings are: (1) more than 290 biochemical components have been identified from P. graveolens, counting terpenoids, flavonoids, steroids, alkaloids and other composites. (2) Terpenoids are the most significant biologically active matter detected in this plant. (3) Extracts and compounds of P. graveolens exert a wide range of pharmacological effects. Study of the plant's toxicological effects has also been restricted as well. P. graveolens has potential in the treatment of numerous ailments, particularly cancers and diabetes. Current investigations confirmed that much traditional uses of P. graveolens has been corroborated by current studies. However, contemporary reports on its pharmacological impacts are not deep enough, and its underlying mechanisms for the cure of tumours and diabetes should be further elucidated.

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Flavonoid Aglycones from the Leaf and Stem Exudates of Some Geraniaceae Species

Cited by 6 publications

References 4 publications

O‐Methyltransferases involved in biphenyl and dibenzofuran biosynthesis

O‐Methyltransferases involved in biphenyl and dibenzofuran biosynthesis

Bioprospecting of Artemisia genus: from artemisinin to other potentially bioactive compounds

Traditional Uses, Botany, Phytochemistry, and Pharmacology of Pelargonium graveolens: A Comprehensive Review

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