Фитохемикалије из бриофита: структура и биолошке активности

Little attention has been paid to the bryophytes as sources for human diet despite the presence of 23,000 species in the world. Some mosses contain Vitamin B1, tocopherols, prostaglandin-like highly unsaturated fatty acids and phenolic compounds. On the other hand, liverworts contain enantiomeric mono-, sesqui- and diterpenoids similar to those found in vascular plants. Additionally, they possess bibenzyls, bis-bibenzyls and polyketides, many of them showing various bioactivity, such as antimicrobial, antiviral, anti-inf­lam­matory, cytotoxicity against cancer cell lines, muscle relaxing, antioxidant and others. In this paper, the structures of phytochemicals from bryophytes and their biological activities are discussed.На бриофите као изворе за људску исхрану се обраћа мала пажња иако их има преко 23000 врста. Неке маховине садрже витамин Б1, токофероле, простагландинима слична једињења, вишеструко незасићене масне киселине и фенолна једињења. С друге стране, јетрењаче садрже моно-, сескви- и дитерпеноиде енентиомерне онима пронађеним у васкуларним биљкама. Поред њих, оне садрже и бибензиле, бис-бибензиле и поликетиде, од којих многи показују антимикробну, антивирусну, анти-инфламаторну, цитотоксичну на ћелије рака, миорекласантску, антиоксидативну и друге. У овом раду су продискутоване структуре и биолошка активност фитохемикалија из јетрењача.Part of the theme issue honoring Professor Emeritus Slobodan Milosavljevićs 80th birthday

Management of Diabetic Bacterial Foot Infections with Organic Extracts of Liverwort Marchantia debilis from Cameroon

Diabetic bacterial foot infections (DBFIs) are limb-threatening complications in patients with diabetes mellitus, accounting for 50% of diabetes related lower limb amputations in developing countries, representing approximately 20 percent of all diabetes-related hospital admissions with significant healthcare-related costs involved. The widespread problem of bacterial resistance to most commonly used antibiotics places a huge economic burden on the healthcare system, with both increased morbidity and mortality among diabetic patients with foot infections. In this study, the antibacterial activity of organic extracts of the fresh liverwort Marchantia debilis from the North West Region of Cameroon is reported. An exit pool system, where patients presenting with DBFIs consented to be involved in the use of phytomedicines, after long term treatment of ulcers with antibiotics and not yielding significant long term benefit, presented themselves at the Phytobiotechnology Research clinic (PRF). Continuous culture of swabs from foot and toe wounds from 30 infected patients on nutrient agar and MacConkey agars in triplicate as well as Gram stain microscopy, revealed the presence of Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli, Proteus mirabilis and Bacillus species. Light petroleum and methanol extracts of the whole bryophyte plants at 100% concentration were tested. In vitro inhibition of the tested bacterial isolates from the diabetic foot ulcers by M debilis was observed only with the light petroleum extract. No inhibition by the extracts was observed for the Pseudomonas aeruginosa isolate. The light petroleum extract of M debilis was formulated into a petroleum oil based cream named BryoCream (TM). This was administered to 20 of the patients with 90% cure rate in a three week time period. The main nonpolar components were determined by GCMS as lepidozene and beta-barbatene, and by NMR. as stigmasterol and beta-sitosterol. In conclusion, nonpolar extracts from bryophytes from Cameroon could, potentially, be used to treat diabetic bacterial foot infections

Bis-bibenzyls from the Cameroon Liverwort Marchantia debilis

Liverworts are rich sources of terpenoids and aromatic compounds among which bis-bibenzyls are well known for their wide spectrum of biological activities. This is the first report of chemical analysis of the African liverwort Marchantia debilis Goebel. From the methanol extract marchantinquinone-l'-methyl ether was newly isolated together with three known bis-bibenzyls, marchantin C, marchantinquinone and perrottetin E. The presence of bis-bibenzyls with a quinone moiety is noted for the first time in the Marchantia genus

Kaempulchraols IO: new isopimarane diterpenoids from Kaempferia pulchra rhizomes collected in Myanmar and their antiproliferative activity

The isolation of the CHCl3 soluble extract of Kaempferia pulchra rhizomes afforded seven new isopimarane diterpenoids, kaempulchraols I−O, together with one known analogue. The structures of these compounds were elucidated using 1D and 2D NMR and X-ray diffraction analyses. The antiproliferative activity of the isolated compounds was evaluated against a panel of five human cancer cell lines. Kaempulchraol L exhibited weak antiproliferative activity against PANC-1 and PSN-1 cells with IC50 values of 39.9 and 22.6 μM, respectively

Kaempulchraols PT: diterpenoids from the Kaempferia pulchra rhizomes collected in Myanmar

The isolation of the oily fraction obtained from the CHCl3-soluble extract of the rhizomes of Kaempferia pulchra (Zingiberaceae) afforded five new isopimarane diterpenoids, kaempulchraols P−T (1−5), along with two known analogues. The structures were elucidated using spectroscopic techniques, including 2D NMR spectroscopy

Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives

Chemical and biocatalytic synthesis of seven previously undescribed marchantin A ester derivatives has been presented. Chemical synthesis afforded three peresterified bisbibenzyl products (TE1-TE3), while enzymatic method, using lipase, produced regioselective monoester derivatives (ME1-ME4). The antiproliferative activities of all prepared derivatives of marchantin A were tested on MRC-5 healthy human lung fibroblast, A549 human lung cancer, and MDA-MB-231 human breast cancer cell lines. All tested esters were less cytotoxic in comparison to marchantin A, but they also exhibited lower cytotoxicity against healthy cells. Monoesters displayed higher cytotoxic activities than the corresponding peresterified products, presumably due to the presence of free catechol group. Monohexanoyl ester ME3 displayed the same IC50 like marchantin A against MDA-MB-231 cells, but the selectivity was higher. In this way, regioselective enzymatic monoesterification enhanced selectivity of marchantin A. ME3 was also the most active among all derivatives against lung cancer cells A549 with the slightly lower activity and selectivity in comparison to marchantin A.Related to published version: [https://imagine.imgge.bg.ac.rs/handle/123456789/1367]This is the peer reviewed version of the paper: Novaković, M., Simić, S., Koracak, L., Zlatović, M., Ilić-Tomić, T., Asakawa, Y., Nikodinović-Runić, J., & Opsenica, I. (2020). Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives. Fitoterapia, 142.[ https://doi.org/10.1016/j.fitote.2020.104520

Management of Diabetic Bacterial Foot Infections with Organic Extracts of Liverwort Marchantia debilis from Cameroon

Diabetic bacterial foot infections (DBFIs) are limb-threatening complications in patients with diabetes mellitus, accounting for 50% of diabetes related lower limb amputations in developing countries, representing approximately 20 percent of all diabetes-related hospital admissions with significant healthcare-related costs involved. The widespread problem of bacterial resistance to most commonly used antibiotics places a huge economic burden on the healthcare system, with both increased morbidity and mortality among diabetic patients with foot infections. In this study, the antibacterial activity of organic extracts of the fresh liverwort Marchantia debilis from the North West Region of Cameroon is reported. An exit pool system, where patients presenting with DBFIs consented to be involved in the use of phytomedicines, after long term treatment of ulcers with antibiotics and not yielding significant long term benefit, presented themselves at the Phytobiotechnology Research clinic (PRF). Continuous culture of swabs from foot and toe wounds from 30 infected patients on nutrient agar and MacConkey agars in triplicate as well as Gram stain microscopy, revealed the presence of Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli, Proteus mirabilis and Bacillus species. Light petroleum and methanol extracts of the whole bryophyte plants at 100% concentration were tested. In vitro inhibition of the tested bacterial isolates from the diabetic foot ulcers by M debilis was observed only with the light petroleum extract. No inhibition by the extracts was observed for the Pseudomonas aeruginosa isolate. The light petroleum extract of M debilis was formulated into a petroleum oil based cream named BryoCream (TM). This was administered to 20 of the patients with 90% cure rate in a three week time period. The main nonpolar components were determined by GCMS as lepidozene and beta-barbatene, and by NMR. as stigmasterol and beta-sitosterol. In conclusion, nonpolar extracts from bryophytes from Cameroon could, potentially, be used to treat diabetic bacterial foot infections

Micromeria thymifolia Essential Oil Suppresses Quorum-sensing Signaling in Pseudomonas aeruginosa

The chemical composition, antimicrobial and antiquorum sensing activity of the essential oil of Micromeria thymifolia (Scop.) Fritsch were investigated. Limonene, piperitone epoxide and piperitenone epoxide were found as the main constituents using a gas chromatography-mass spectrometry technique. In vitro antimicrobial activity of the oil was tested against six bacterial and seven fungal strains and high antimicrobial potential was noticed. Minimum inhibitory concentration varied from 0.031 mg/mL to 0.5 mg/mL for bacterial and 0.062 mg/mL to 0.5 mg/mL for fungal strains. The antiquorum properties of the essential oil were evaluated on Pseudomonas aeruginosa PAO1. The oil was tested at subMiC concentrations for anti-quorum sensing activity. The analyses on quorum-sensing functions have been carried out by evaluating twitching and swarming of bacterial cultures and the total amount of pyocyanin production produced by P. aeruginosa. This study showed that M thymifolia essential oil exhibited antiquorum sensing activity and may be used as an antipathogenic drug

State- and water repellency-controllable molecular glass of pillar[5]arenes with fluoroalkyl groups by guest vapors

Molecular glasses are low-molecular-weight organic compounds that are stable in the amorphous state at room temperature. Herein, we report a state- and water repellency-controllable molecular glass by n-alkane guest vapors. We observed that a macrocyclic host compound pillar[5]arene with the C₂F₅ fluoroalkyl groups changes from the crystalline to the amorphous state (molecular glass) by heating above its melting point and then cooling to room temperature. The pillar[5]arene molecular glass shows reversible transitions between amorphous and crystalline states by uptake and release of the n-alkane guest vapors, respectively. Furthermore, the n-alkane guest vapor-induced reversible changes in the water contact angle were also observed: water contact angles increased and then reverted back to the original state by the uptake and release of the n-alkane guest vapors, respectively, along with the changes in the chemical structure and roughness on the surface of the molecular glass. The water repellency of the molecular glass could be controlled by tuning the uptake ratio of the n-alkane guest vapor