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Chemical Biology & Drug Design Jan 2022In recent years, biological macromolecules have piqued the interest of researchers owing to their vast variety of biological uses. As a result, the marine sponge is a... (Review)
Review
In recent years, biological macromolecules have piqued the interest of researchers owing to their vast variety of biological uses. As a result, the marine sponge is a multicellular heterotrophic parazoan with chemicals for defence against predator assaults, biofouling and microbial diseases. These priceless molecules are known as secondary metabolites, and they are essential for survival in a highly competitive environment. So far, over 5,000 marine natural compounds have been extracted from marine sponges, making them an excellent option for drug formulation. One among them is, aaptamine, a marine alkaloid with a benzo[de][1,6]-napthyridine framework extensively distributed in marine sponges. Due to this reason, aaptamine has been intensively researched for various biological purposes, including cancer and protease inhibition, offering fresh insights into novel treatments. Keeping this in mind, we reviewed the biological significance of the marine sponge alkaloid aaptamine.
Topics: Alkaloids; Animals; Antineoplastic Agents; Antioxidants; Antiviral Agents; Cell Proliferation; HIV-1; Naphthyridines; Porifera
PubMed: 34331335
DOI: 10.1111/cbdd.13932 -
Planta Medica Jan 2022Tuberculosis is the main cause of death from a single infectious agent. Globally, according to the World Health Organization, in 2018, there were an estimated 1.2...
Tuberculosis is the main cause of death from a single infectious agent. Globally, according to the World Health Organization, in 2018, there were an estimated 1.2 million tuberculosis deaths. Moreover, there is a continuous appearance of drug-resistant strains. Thus, development of new antituberculosis medicines should receive high priority. Plant-derived natural products are promising candidates for this purpose. We therefore screened alkaloid extracts obtained from the root and stem barks of the Mexican Apocynaceae species and , as well as the pure alkaloids ibogaine, voacangine, and voacamine, tested for activity against H37Rv and cytotoxicity to mammalian Vero cells using the resazurin microtiter and the MTT assays, respectively. The extracts were analyzed by GC-MS and HPLC-UV. root bark alkaloid extract showed the highest activity against (MIC = 7.8 µg/mL) of the four extracts tested. HPLC suggested that voacangine and voacamine were the major components. The latter was isolated by column chromatography, and its chemical structure was elucidated by H and C NMR, and MS. Unambiguous assignation was performed by HSQC, HMBC, and NOESY experiments. Voacamine is a dimeric bis-indole-type alkaloid and is 15 times more potent than the monomeric ibogan-type alkaloids ibogaine and voacangine (MIC = 15.6, 250.0, and 250.0 µg/mL, respectively). However, all of these compounds showed cytotoxicity to Vero cells, with a poor selectivity index of 1.00, 0.16, and 1.42, respectively. This is the first report of voacamine activity against .
Topics: Alkaloids; Animals; Apocynaceae; Chlorocebus aethiops; Indole Alkaloids; Plant Extracts; Tabernaemontana; Vero Cells
PubMed: 32392600
DOI: 10.1055/a-1157-1732 -
Alternative Therapies in Health and... Jul 2020Having been used for thousands of years to treat gastrointestinal diseases, the natural isoquinoline alkaloid, berberine, has exhibited a wide spectrum of biochemical... (Review)
Review
CONTEXT
Having been used for thousands of years to treat gastrointestinal diseases, the natural isoquinoline alkaloid, berberine, has exhibited a wide spectrum of biochemical and pharmacological effects in studies of recent years.
OBJECTIVE
The review intended to examine the many novel bioactivities of berberine, including antidiabetic, anticancer, neuroprotective, anti-inflammatory, and anti-atherosclerotic actions.
DESIGN
The research team searched the MEDLINE database using PubMed, using different keyword combinations, including berberine AND diabetes, berberine AND cancer, berberine AND (neuron OR brain), berberine AND inflammation, and "berberine AND atherosclerosis to find studies evaluating the various effects exerted berberine.
CONCLUSION
Berberine is a promising multipotent agent to combat diabetes, cancer, Alzheimer's disease, and other diseases.
Topics: Alkaloids; Berberine; Biological Products; Humans
PubMed: 31634873
DOI: No ID Found -
Phytochemistry Nov 2022Thirteen indole alkaloids comprising six vobasine/sarpagine, one vincamine, two voaphylline, two tacaman, one iboga, and one corynantheine alkaloid, were isolated from...
Thirteen indole alkaloids comprising six vobasine/sarpagine, one vincamine, two voaphylline, two tacaman, one iboga, and one corynantheine alkaloid, were isolated from the leaf extract of Tabernaemontana corymbosa (sample from Taiping, Perak, Malaysia). The structures of these alkaloids were determined based on analysis of the spectroscopic data (NMR and MS), and in the case of vincarudine, the absolute configuration was established by ECD and X-ray diffraction analysis. Vobasidine E represents the first vobasine-type alkaloid characterized by a contracted ring C and loss of the ethylidene/ethyl side chain. A possible biogenetic pathway from a perivine precursor, which was also present in the leaf extract, is presented. Differences in the new alkaloid content between the present and previous sample of the same plant (occurring in a different location) are discussed.
Topics: Alkaloids; Antineoplastic Agents, Phytogenic; Drug Screening Assays, Antitumor; Indole Alkaloids; Molecular Structure; Plant Extracts; Tabernaemontana; Vincamine
PubMed: 36007666
DOI: 10.1016/j.phytochem.2022.113384 -
Chemistry & Biodiversity Apr 2024One new fawcettimine-type Lycopodium alkaloid, hupertimine F (1), together with five known (2-6) Lycopodium alkaloids were isolated from Huperzia goebelii. The structure...
One new fawcettimine-type Lycopodium alkaloid, hupertimine F (1), together with five known (2-6) Lycopodium alkaloids were isolated from Huperzia goebelii. The structure of 1 was elucidated by 1D and 2D NMR spectra, HRESIMS, and X-ray diffraction. Structurally, 1 represents the fourth example of Lycopodium alkaloids characterized by a 5/5/5/5/6 pentacyclic ring system with a 1-aza-7-oxabicyclo[2.2.1]heptane moiety. These known compounds 2, 3, 5, and 6 were isolated from H. goebelii for the first time. Compounds 1-6 were evaluated for acetylcholinesterase, butyrylcholinesterase and monoamine oxidase B inhibitory activities in vitro.
Topics: Huperzia; Lycopodium; Butyrylcholinesterase; Acetylcholinesterase; Molecular Structure; Cholinesterase Inhibitors; Alkaloids
PubMed: 38419385
DOI: 10.1002/cbdv.202400209 -
Molecules (Basel, Switzerland) Aug 2022Amaryllidaceae alkaloids (AAs) are a structurally diverse family of alkaloids recognized for their many therapeutic properties, such as antiviral, anti-cholinesterase,...
Amaryllidaceae alkaloids (AAs) are a structurally diverse family of alkaloids recognized for their many therapeutic properties, such as antiviral, anti-cholinesterase, and anticancer properties. Norbelladine and its derivatives, whose biological properties are poorly studied, are key intermediates required for the biosynthesis of all ~650 reported AAs. To gain insight into their therapeutic potential, we synthesized a series of O-methylated norbelladine-type alkaloids and evaluated their cytotoxic effects on two types of cancer cell lines, their antiviral effects against the dengue virus (DENV) and the human immunodeficiency virus 1 (HIV-1), and their anti-Alzheimer’s disease (anti-cholinesterase and -prolyl oligopeptidase) properties. In monocytic leukemia cells, norcraugsodine was highly cytotoxic (CC50 = 27.0 μM), while norbelladine was the most cytotoxic to hepatocarcinoma cells (CC50 = 72.6 μM). HIV-1 infection was impaired only at cytotoxic concentrations of the compounds. The 3,4-dihydroxybenzaldehyde (selectivity index (SI) = 7.2), 3′,4′-O-dimethylnorbelladine (SI = 4.8), 4′-O-methylnorbelladine (SI > 4.9), 3′-O-methylnorbelladine (SI > 4.5), and norcraugsodine (SI = 3.2) reduced the number of DENV-infected cells with EC50 values ranging from 24.1 to 44.9 μM. The O-methylation of norcraugsodine abolished its anti-DENV potential. Norbelladine and its O-methylated forms also displayed butyrylcholinesterase-inhibition properties (IC50 values ranging from 26.1 to 91.6 μM). Altogether, the results provided hints of the structure−activity relationship of norbelladine-type alkaloids, which is important knowledge for the development of new inhibitors of DENV and butyrylcholinesterase.
Topics: Alkaloids; Amaryllidaceae; Amaryllidaceae Alkaloids; Antiviral Agents; Butyrylcholinesterase; Cholinesterase Inhibitors; Humans; Tyramine
PubMed: 36080382
DOI: 10.3390/molecules27175621 -
The Plant Genome Jun 2022The tomato (Solanum spp.) clade of Solanaceae features a unique assortment of cholesterol-derived steroidal alkaloids. However, little quantitative data exists reporting...
The tomato (Solanum spp.) clade of Solanaceae features a unique assortment of cholesterol-derived steroidal alkaloids. However, little quantitative data exists reporting the profile and concentration of these alkaloids across diverse fruit germplasm. To address the lack of knowledge regarding the chemical diversity, concentration, and genetic architecture controlling tomato steroidal alkaloids, we quantitatively profiled and genotyped two tomato populations representing diversity in the red-fruited clade. We grew 107 genetically diverse fresh market, processing, landrace, and wild tomato in multiple environments. Nine steroidal alkaloid groups were quantified using ultra-high performance liquid chromatography tandem mass spectrometry. The diversity panel and a biparental population segregating for high alpha-tomatine were genotyped to identify and validate quantitative trait loci (QTL) associated with steroidal alkaloids. Landraces and wild material exhibited higher alkaloid concentrations and more chemical diversity. Average total content of steroidal alkaloids, often dominated by lycoperoside F/G/esculeoside A, ranged from 1.9 to 23.3 mg 100 g fresh wt. across accessions. Landrace and wild cherry accessions distinctly clustered based on elevated concentrations of early or late-pathway steroidal alkaloids. Significant correlations were observed among alkaloids from the early and late parts of the biosynthetic pathway in a species-dependent manner. A QTL controlling multiple, early steroidal alkaloid pathway intermediates on chromosome 3 was identified by genome-wide association studies (GWAS) and validated in a backcross population. Overall, tomato steroidal alkaloids are diverse in the red-fruited clade and their biosynthesis is regulated in a coordinated manner.
Topics: Alkaloids; Fruit; Genome-Wide Association Study; Solanum lycopersicum; Quantitative Trait Loci
PubMed: 35184399
DOI: 10.1002/tpg2.20192 -
Current Pharmaceutical Design 2021Cancer is a serious and growing global health issue worldwide. In the cancerous cells, the normal cell cycle has been disrupted via a series of irreversible changes.... (Review)
Review
BACKGROUND
Cancer is a serious and growing global health issue worldwide. In the cancerous cells, the normal cell cycle has been disrupted via a series of irreversible changes. Recently, the investigations on herbal medicine and clarifying the phytochemicals potential in treat cancer has been increased. The combination of phytochemicals with conventional cancer treatment approaches can improve outcomes via advancing cell death, restraining cell proliferation and invasion, sensitizing cancerous cells, and promoting the immune system. Therefore, phytochemicals can be introduced as relevant complementary medicaments in cancer therapy. Peganum harmala L. (Zygophyllaceae) as a valuable medicinal herb, possesses various alkaloid ingredient.
OBJECTIVE
Pointing to the importance of new avenues for cancer management and P. harmala convincing effect in this field, this review strived to collect a frame to epitome possible scopes to develop novel medicines in cancer treatment.
METHODS
Keywords "Peganum harmala" and cancer, or chemotherapy, or anti-neoplasm were searched through the "Scopus" database up to 29th of February 2020. Papers linking to agriculture, chemistry, environmental, and genetics sciences were omitted and, papers centered on cancer were selected.
RESULTS AND DISCUSSION
In the current study, 42 related papers to cancer treatment and 22 papers on alkaloid bioactive components are collected from 72 papers. The β-carboline alkaloids derived from P. harmala, especially harmine, demonstrate notable anticancer properties by targeting apoptosis, autophagy, abnormal cell proliferation, angiogenesis, metastasis, and cytotoxicity. Based on the collected information, P. harmala holds significant anticancer activity. Considering the mechanism of the various anticancer drugs and their acting similarity to P. harmala, the alkaloids derived from this herb, particularly harmine, can introduce as a novel anticancer medicine solely or in adjuvant cancer therapy.
Topics: Alkaloids; Biomarkers; Peganum; Plant Extracts; Seeds
PubMed: 33238864
DOI: 10.2174/1381612826666201125103941 -
Scientific Reports May 2022This study evaluated the morphological changes caused by fractions and subfractions, obtained from barks of Aspidosperna nitidum, against L. (L.) amazonensis...
This study evaluated the morphological changes caused by fractions and subfractions, obtained from barks of Aspidosperna nitidum, against L. (L.) amazonensis promastigotes. The ethanolic extract (EE) obtained through the maceration of trunk barks was subjected to an acid-base partition, resulting the neutral (FN) and the alkaloid (FA) fractions, and fractionation under reflux, yielded hexane (FrHEX), dichloromethane (FrDCL), ethyl acetate (FrACoET), and methanol (FrMEOH) fractions. The FA was fractionated and three subfractions (SF5-6, SF8, and SF9) were obtained and analyzed by HPLC-DAD and H NMR. The antipromastigote activity of all samples was evaluated by MTT, after that, scanning electron microscopy (SEM) and transmission electron microscopy (TEM) for the active fractions were performed. Chromatographic analyzes suggest the presence of alkaloids in EE, FN, FA, and FrDCL. The fractionation of FA led to the isolation of the indole alkaloid dihydrocorynantheol (SF8 fractions). The SF5-6, dihydrocorynantheol and SF-9 samples were active against promastigotes, while FrDCL was moderately active. The SEM analysis revealed cell rounding and changes in the flagellum of the parasites. In the TEM analysis, the treated promastigotes showed changes in flagellar pocket and kinetoplast, and presence of lipid inclusions. These results suggest that alkaloids isolated from A. nitidum are promising as leishmanicidal.
Topics: Alkaloids; Antiprotozoal Agents; Aspidosperma; Indole Alkaloids; Leishmania; Plant Extracts
PubMed: 35606396
DOI: 10.1038/s41598-022-12396-x -
Current Opinion in Plant Biology Aug 2023Plants synthesize tens of thousands of bioactive nitrogen-containing compounds called alkaloids, including some clinically important drugs in modern medicine. The... (Review)
Review
Plants synthesize tens of thousands of bioactive nitrogen-containing compounds called alkaloids, including some clinically important drugs in modern medicine. The discovery of new alkaloid structures and their metabolism in plants have provided ways to access these rich sources of bioactivities including new-to-nature compounds relevant to therapeutic and industrial applications. This review discusses recent advances in alkaloid biosynthesis discovery, including complete pathway elucidations. Additionally, the latest developments in the production of new and established plant alkaloids based on either biosynthesis or semisynthesis are discussed.
Topics: Biosynthetic Pathways; Drug Repositioning; Alkaloids; Plants
PubMed: 37182414
DOI: 10.1016/j.pbi.2023.102379