Bis-benzylisoquinoline alkaloids from Abuta pahni

Fournet, Alain; Cavé, A.; Duté, Pascale; Weber, Jean Frederic; Bruneton, J.

doi:10.1016/s0031-9422(00)81784-7

Cited by 17 publications

(2 citation statements)

References 6 publications

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“…Those assertions were further supported based on consideration of the biogenic source, UV–vis spectroscopic data, their reported DNA binding activities, and MS/MS data for the two metabolites. , LC-MS data obtained from testing the M. dauricum extract supported the presence of two active compounds based on the appearance of [M + H] + ions exhibiting m / z values of 611.50 and 625.42, which were preliminarily identified as daurisoline ( 17 ) and dauricine ( 18 ), respectively (Scheme ). Likewise, those assignments were buttressed by evidence derived from considerations of the biogenic source, UV–vis spectroscopic data, their reported DNA binding activities, and MS/MS data for the two metabolites. , The preliminary structure assignments of 15 – 18 were subsequently confirmed based on comparisons of their 1 H NMR spectroscopic data, specific rotation values, and MS features with reported data. ,− The DNA-binding activities of purified 15 – 18 were subsequently confirmed using the LLAMAS method (Figure S7, Supporting Information).…”

Section: Resultsmentioning

confidence: 90%

An Integrated Strategy for the Detection, Dereplication, and Identification of DNA-Binding Biomolecules from Complex Natural Product Mixtures

et al. 2020

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A fundamental factor in natural product drug discovery programs is the necessity to identify the active component(s) from complex chemical mixtures. Whereas this has traditionally been accomplished using bioassay-guided fractionation, we questioned whether alternative techniques could supplement and, in some cases, even supplant this approach. We speculated that a combination of ligand-fishing methods and modern analytical tools (e.g., LC-MS and online natural product databases) offered a route to enhance natural product drug discovery. Herein, a candidate solution referred to as the lickety-split ligand-affinity-based molecular angling system (LLAMAS) is described. This approach utilizes an ultrafiltration-based LC-PDA-MS/MS-guided DNAbinding assay in combination with the (i) Global Natural Products Social Molecular Networking, (ii) Dictionary of Natural Products, and (iii) SciFinder platforms to identify DNA binders in complex chemical mixtures. LLAMAS was initially vetted in tests using known small-molecule DNA binders and then optimized to a 96-well plate-based format. A set of 332 plant samples used in traditional Chinese medicine was screened for DNA-binding activity with LLAMAS, resulting in the identification of seven DNAbinding molecules, including berberine (12), palmatine (13), coptisine (14), fangchinoline (15), tetrandrine (16), daurisoline (17), and dauricine (18). These results demonstrate that LLAMAS is an effective natural product discovery platform for the efficient identification and dereplication of DNA-binding molecules from complex mixtures.N atural products are an important source of therapeutic drug leads due to the incredible diversity of their structures and bioactivities. 1−3 Many of the success stories to emerge from natural product drug development are legendary: the discovery of the antibiotic penicillin in 1928, 4 the identification and subsequent clinical approval of the anticancer drug Taxol (paclitaxel) in 1992, 5 the development of the antimalarial drug artemisinin (a discovery that was acknowledged by the 2015 Nobel Prize in Physiology or Medicine), 6 and more. 7 These milestones in drug discovery established natural products as an unparalleled resource for identifying therapeutically useful compounds to combat a wide range of diseases.Strikingly, a majority of these and other iconic natural products that are used as medicines 1,8,9 were discovered using the well-established, yet powerful technique known as bioassay-guided purification. 10,11 This approach relies on subjecting mixtures of compounds (e.g., extracts and fractions) to iterative steps of fractionation and biological testing with the

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Section: Resultsmentioning

confidence: 90%

An Integrated Strategy for the Detection, Dereplication, and Identification of DNA-Binding Biomolecules from Complex Natural Product Mixtures

et al. 2020

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“…[2] Various alkaloids and different pharmacological activities of these plants have been reported. Hydrocolloids, [3] Cissampeloflavone, [4] A tropone-isoquinoline alkaloid, pareitropone, [5] Bisbenzylisoquinoline alkaloids, cissamperine with tumor inhibitor activity, [6] trandrine, [7] tropoloisoquinoline alkaloids such as pareirubrine A and B with antileukemic activity [8] have been isolated from C. pareira Var. hirsuta. Plant extracts were tested for Antipyretic activity, [9] Chemomodulatory influence of Hirsuta on Gastric cancer and antioxidant system in experimental animal, [10] anti-inflammatory activity, [9] Immunomodulatory activity, [10] antifertility activity, antinociceptive, antiarthritic activity, antibacterial activity, [11] antimalarial activity, [12] diuretic activity, [13] hypoglycemic activity [14] and anticonvulsant activity.…”

Section: Introductionmentioning

confidence: 99%

Pharmacognostical and Phytochemical Evaluation of Leaves of Cissampelos pareira

Gupta¹,

Pandey

Shah³

et al. 2011

Pharmacognosy Journal

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In ethanomedicinal practices the the tradicinal healers use the roots of Cissampelos pareira in the treatment of various ailments related to urinary problems, skin infections,in tumor inhibitor activity,antibacterial, antimalarial, diuretic activity and anticonvulsant activity etc. Macro-and microscopical characters, behaviour of drug on treatment with different chemical reagents, fluorescence analysis, extractive values, ash values and preliminary phytochemical tests were carried out to study the distinctive features of the drugs. Such parameters provide basis for standardisation/characterisation of genuine drug. A serious limitation encountered in the use and research of traditional medicine is the lack of standardisation and quality control of raw material forming the drug. the ultimate objective of the pharmcognostic investigation is identification of the genuine crude drug and determining the extent of adulteration/substitution, if any. Advancement in recent years in pharmacognosy, phytochemistry and physicochemical techniques can be of immense value in removing this major shortcoming of traditional medicine. These techniques can be utilised for correct botanical identification of plants. The details of organoleptic, macro-and microscopic characters, various evaluative parameters, fluorescence analysis, results of preliminary phytochemical analysis established in the present study will facilitate in identifying the g drug from any substitute or spurious samples and will also be useful in preparation of monographs on these plants.

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Concise and Modular Chemoenzymatic Total Synthesis of Bisbenzylisoquinoline Alkaloids

Wang,

Zhao,

et al. 2024

Angewandte Chemie

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The bisbenzylisoquinoline alkaloids (bisBIAs) have attracted tremendous attention from the synthetic community due to their diverse and intriguing biological activities. Herein, we report the convergent and modular chemoenzymatic syntheses of eight bisBIAs bearing various substitutes and linkages in 5‐7 steps. The gram‐scale synthesis of various well‐designed enantiopure benzylisoquinoline monomers was accomplished via an enzymatic stereoselective Pictet–Spengler reaction, followed by regioselective enzymatic methylation or chemical functionalizations in a sequential one‐pot process. A modified intermolecular copper‐mediated Ullmann coupling enabled the concise and efficient total synthesis of five different linear bisBIAs with either head‐to‐tail or tail‐to‐tail linkage. A biomimetic oxidative phenol dimerization selectively formed the sterically hindered, electron‐rich diaryl ether bond, and subsequent intramolecular Suzuki–Miyaura domino reaction or Ullmann coupling facilitated the first enantioselective total synthesis of three macrocyclic bisBIAs, including ent‐isogranjine, tetrandrine and O‐methylrepandine. This study highlights the great potential of chemoenzymatic strategies in the total synthesis of diverse bisBIAs and paves the way to further explore the biological functions of these natural products.

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Bis-benzylisoquinoline alkaloids from Abuta pahni

Cited by 17 publications

References 6 publications

An Integrated Strategy for the Detection, Dereplication, and Identification of DNA-Binding Biomolecules from Complex Natural Product Mixtures

An Integrated Strategy for the Detection, Dereplication, and Identification of DNA-Binding Biomolecules from Complex Natural Product Mixtures

Pharmacognostical and Phytochemical Evaluation of Leaves of Cissampelos pareira

Concise and Modular Chemoenzymatic Total Synthesis of Bisbenzylisoquinoline Alkaloids

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