Showing papers on "Isopimpinellin published in 2020"
TL;DR: UHPLC-ESI-QTOF-MS/MS-Based molecular networking guided isolation and dereplication led to the identification of antibacterial and antifungal agents in V. denticulata, an herbal medicine for the treatment of wound infection that may rich in antibacterial agents.
Abstract: Ventilago denticulata is an herbal medicine for the treatment of wound infection; therefore this plant may rich in antibacterial agents. UHPLC-ESI-QTOF-MS/MS-Based molecular networking guided isolation and dereplication led to the identification of antibacterial and antifungal agents in V. denticulata. Nine antimicrobial agents in V. denticulata were isolated and characterized; they are divided into four groups including (I) flavonoid glycosides, rhamnazin 3-rhamninoside (7), catharticin or rhamnocitrin 3-rhamninoside (8), xanthorhamnin B or rhamnetin 3-rhamninoside (9), kaempferol 3-rhamninoside (10) and flavovilloside or quercetin 3-rhamninoside (11), (II) benzisochromanquinone, ventilatones B (12) and A (15), (III) a naphthopyrone ventilatone C (16) and (IV) a triterpene lupeol (13). Among the isolated compounds, ventilatone C (16) was a new compound. Moreover, kaempferol, chrysoeriol, isopimpinellin, rhamnetin, luteolin, emodin, rhamnocitrin, ventilagodenin A, rhamnazin and mukurozidiol, were tentatively identified as antimicrobial compounds in extracts of V. denticulata by a dereplication method. MS fragmentation of rhamnose-containing compounds gave an oxonium ion, C6H9O3+ at m/z 129, while that of galactose-containing glycosides provided the fragment ion at m/z 163 of C6H11O5+. These fragment ions may be used to confirm the presence of rhamnose or galactose in mass spectrometry-based analysis of natural glycosides or oligosaccharide attached to biomolecules, that is, glycoproteins.
21 citations
TL;DR: By examining midgut‐specific gene expression patterns, it is determined that CYP6AE89 transcripts were highly expressed and furanocoumarin‐inducible, and a maximum‐likelihood tree built with six representative lepidopterans with manually annotated cytochrome P450s shows that CYp6AE 89 may have evolved much faster than the other CYP 6AE proteins, possibly indicative of host selection pressure.
Abstract: The parsnip webworm, Depressaria pastinacella, is restricted to two hostplant genera containing six structurally diverse furanocoumarins. Of these, imperatorin is detoxified by a specialized cytochrome P450, CYP6AB3. A previous whole-larva transcriptome analysis confirmed the presence of nine transcripts that belong to the CYP6AE subfamily. Here, by examining midgut-specific gene expression patterns we determined that CYP6AE89 transcripts were highly expressed and furanocoumarin-inducible. Computer docking and energy-minimization of a CYP6AE89 model with all six furanocoumarins showed that 5-methoxylated bergapten and 8-methoxylated xanthotoxin had the smallest distances from the heme to the proton-donor residue in the catalytic I-helix, and that the 5,8-dimethoxylated isopimpinellin and bergapten had the smallest energy-minimized distance from the heme oxygen to the furan ring double bond. To evaluate this prediction, we expressed the CYP6AE89 protein in an Escherichia coli system, and used it to detect high catalytic activity against the two mono-methoxylated linear furanocoumarins - bergapten and xanthotoxin - and weak activity against isopimpinellin. Thus, CYP6AE89, like CYP6AB3, is probably specialized for detoxifying only a subset of hostplant furanocoumarins. A maximum-likelihood tree built with six representative lepidopterans with manually annotated cytochrome P450s shows that CYP6AE89 may have evolved much faster than the other CYP6AE proteins, possibly indicative of host selection pressure.
19 citations
TL;DR: This review summarizes the anticancer effects of coumarins and their hybrid molecules including the novel pharmaceutical formulations adding further information on the topic for the last ten years and basically focusing on the structure-activity relationship of these compounds in cancer.
Abstract: Coumarins are the secondary metabolites of some plants, fungi, and bacteria. Coumarins and the hybrid molecules of coumarins are the compounds which have been widely studied for their potential anticancer effects. They belong to benzopyrone chemical class, more precisely benzo-α-pyrones, where benzene ring is fused to pyrone ring. In nature, coumarins are found in higher plants like Rutaceae and Umbelliferae and some essential oils like cinnamon bark oil, cassia leaf oil and lavender oil are also rich in coumarins. The six main classes of coumarins are furanocoumarins, dihydrofuranocoumarins, pyrano coumarins, pyrone substituted coumarins, phenylcoumarins and bicoumarins. As well as their wide range of biological activities, coumarins and the hybrid molecules of coumarins are proven to have an important role in anticancer drug development due to the fact that many of its derivatives have shown an anticancer activity on various cell lines. Osthol, imperatorin, esculetin, scopoletin, umbelliprenin, angelicine, bergamottin, limettin, metoxhalen, aurapten and isopimpinellin are some of these coumarins. This review summarizes the anticancer effects of coumarins and their hybrid molecules including the novel pharmaceutical formulations adding further information on the topic for the last ten years and basically focusing on the structureactivity relationship of these compounds in cancer.
15 citations
24 Jul 2020
TL;DR: Active compounds in the tap roots from 16 populations harvested at maturity contained comparable amounts of compounds that are characteristic for Apiaceae, and also occur in vegetables as carrots, parsnip, parsley or celeriac.
Abstract: Background: Conium maculatum is known as highly toxic plant, due to piperidine alkaloids present in the aerial parts. In a first attempt, in various tap root samples, however, alkaloids could not be detected. The present study describes active compounds in the tap roots from 16 populations harvested at maturity. The compounds were extracted with dichloromethane from root pieces of single plants and analyzed by gas chromatography–mass spectrometry. Ten bioactive compounds were evaluated: five furocoumarins, two prenylated coumarins, two aliphatic C17-polyacetylenes and the phenylpropanoid elemicin. A high variability could be observed, the highest concentrations were measured for falcarindiol, xanthotoxin and isopimpinellin, the lowest for elemicin. In sum C. maculatum roots contained comparable amounts of compounds that are characteristic for Apiaceae, and also occur in vegetables as carrots, parsnip, parsley or celeriac.
4 citations
01 Jan 2020
TL;DR: Ethanol seed extract decreased TC, TGs and LDL-C, and increased HDL-C of rats, and also produced significant anti-inflammatory, analgesic, and antipyretic effects.
Abstract: Seeds are classified as stimulatory, carminative, anti-inflammatory and extremely useful for vitiligo and leucoderma. Powdered seeds mixed with honey, that has been heated to remove scum, 10 g daily with warm water for fifteen days are claimed to cure vitiligo. It is also used as an emmenagogue to regulate menstruation, as a diuretic, and for the treatment of leprosy, kidney stones, and urinary tract infections. Since ancient times, a tea made from the fruit of Ammi visnaga (khella, as it is known in the Arab world) has been used as a remedy for renal colic due to kidney stones. In Israel and Morocco, the plant is used for the treatment of diabetes. Natural coumarins (furocoumarins), isopimpinellin, xanthotoxin (8-methoxypsoralen, 8-MOP), imperatorin, bergapten, umbelliprenin, maurin, alloimperatorin, ammirin, ammajin and marmesin, have been isolated from the fruits of A. majus. Khellin, visnagin, and khellol glycoside have been isolated from fruits of A. visnaga. 8-MOP is a purified extract of the root, that has been used in a crude form for centuries in the Middle East in the treatment of various skin diseases, and was first utilized in the treatment of vitiligo in 1948. Ethanol seed extract decreased TC, TGs and LDL-C, and increased HDL-C of rats, and also produced significant anti-inflammatory, analgesic, and antipyretic effects. Both a single oral dose and repeated administration of aqueous extract of A. visnaga significantly lowers blood glucose in normal and diabetic rats. Spontaneous passage of multiple ureteral stones in a patient, possibly as a result of using a khellin preparation was reported from Turkey.
1 citations
30 Nov 2020
TL;DR: Evaluated species could be a good candidate for further studies aimed to find new drugs with photocytotoxic potential, and induced up-regulation of apoptotic signals such as BAX and PARP cleavage and, in the presence of UVA radiation, caused a greater upregulation of p21 protein.
Abstract: Melanoma is the most aggressive form of skin cancer. Photochemotherapy, combining the action of a light source and a chemical photosensitizer, is one of the most interesting current therapeutic approaches. Plants represent a rich source of photoactive compounds, and furanocoumarins are some of the most important naturally occurring phytoconstituents. The aim of this study was to evaluate the photocytotoxic potential of Cachrys libanotis L. (Apiaceae) from Southern Italy. This species belongs to a genus rich in furanocoumarins and widely distributed in Europe. The aerial parts were extracted through both traditional maceration and pressurized cyclic solid-liquid (PCSL) extraction using Naviglio extractor®. Qualitative and quantitative analyses were performed to detect the coumarins content using GC-MS, and the photocytotoxic effects of the extracts were assessed on UVA-irradiated C32 melanoma cells. The apoptotic responses were also evaluated. Furthermore, phenolic content and the in vitro antioxidant potential were also estimated. Xanthotoxin, bergapten and isopimpinellin were identified and quantified. Both extracts affected cell viability in a concentration-dependent manner after irradiation for 1 hour at a dose of 1.08 J/cm2. Sample obtained through PCSL extraction was the most effective, with an IC50 equal to 3.16 μg/mL, a very interesting value if compared with the positive control bergapten. This extract induced up-regulation of apoptotic signals such as BAX and PARP cleavage and, in the presence of UVA radiation, it caused a greater upregulation of p21 protein. Obtained results suggest that investigated species could be a good candidate for further studies aimed to find new drugs with photocytotoxic potential.