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Natural Product Research 2015A new type of isoquinoline alkaloid leptopyrine was isolated from the aerial parts of Leptopyrum fumarioides L. (Ranunculaceae) of Mongolian origin. The known alkaloids...
A new type of isoquinoline alkaloid leptopyrine was isolated from the aerial parts of Leptopyrum fumarioides L. (Ranunculaceae) of Mongolian origin. The known alkaloids protopine and thalifoline were isolated for the first time from this the species. All structures were established by physical and spectral analyses.
Topics: Alkaloids; Benzophenanthridines; Berberine Alkaloids; Isoquinolines; Molecular Structure; Plant Components, Aerial; Ranunculaceae
PubMed: 25529023
DOI: 10.1080/14786419.2014.991322 -
Phytochemistry Mar 2014In an attempt to reveal the relationships between alkaloid biosynthesis and phylogeny, we investigated by GC-MS the alkaloid patterns of 22 species and 3 hybrids (from...
In an attempt to reveal the relationships between alkaloid biosynthesis and phylogeny, we investigated by GC-MS the alkaloid patterns of 22 species and 3 hybrids (from 45 locations) from seven main sections of the genus Narcissus (Amaryllidaceae). The results indicate that the first alkaloids to evolve in the genus Narcissus were of the lycorine- and homolycorine-type. The alkaloid pattern of the Nevadensis section supports its recent separation from the Pseudonarcissus section. The plants of Narcissus pallidulus (Ganymedes section) show a predominance of Sceletium-type compounds, which are quite rare in the Amaryllidaceae family. Two successful evolutionary strategies involving alkaloid biosynthesis and leading to an expansion in taxa and occupied area were determined. Firstly, a diversification of alkaloid patterns and a high alkaloid concentration in the organs of the large Narcissus species (in the Pseudonarcissus section) resulted in an improved chemical defence in diverse habitats. Secondly, both plant size and alkaloid biosynthesis were reduced (in the Bulbocodium and Apodanthi sections) relegated to dry pastures and rocky places.
Topics: Alkaloids; Gas Chromatography-Mass Spectrometry; Molecular Structure; Narcissus; Phylogeny; Principal Component Analysis
PubMed: 24461780
DOI: 10.1016/j.phytochem.2013.11.002 -
Journal of Chromatography. A Aug 2002Systems for efficient separation of selected alkaloid groups by high performance liquid chromatography (HPLC), capillary electrophoresis (CE) and capillary... (Review)
Review
High-performance liquid chromatographic, capillary electrophoretic and capillary electrophoretic-electrospray ionisation mass spectrometric analysis of selected alkaloid groups.
Systems for efficient separation of selected alkaloid groups by high performance liquid chromatography (HPLC), capillary electrophoresis (CE) and capillary electrophoresis coupled with electrospray ionisation mass spectrometry (CE-ESI-MS) are described. The optimized HPLC system was applied for the separation of 23 standard indole alkaloids as well as for qualitative and quantitative analyses of crude alkaloid extracts of Rauvolfia serpentina X Rhazya stricta hybrid cell cultures. The developed conditions for CE analysis proved to be efficient for separation of mixtures of standard indole and beta-carboline alkaloids. The described buffer system is also applicable in the combination of CE with electrospray ionisation mass spectrometry. This analytical technique allowed the separation and identification of components of standard indole alkaloid mixture as well as crude extracts of R. serpentina roots, R. serpentina cell suspension cultures and cortex of Aspidosperma quebracho-blanco. The influence of buffer composition and analyte structures on separation is discussed.
Topics: Alkaloids; Chromatography, High Pressure Liquid; Electrophoresis, Capillary; Molecular Structure; Spectrometry, Mass, Electrospray Ionization
PubMed: 12219932
DOI: 10.1016/s0021-9673(02)00037-7 -
The Journal of Organic Chemistry May 2019An asymmetric total synthesis of lycopoclavamine-A (1), a structurally unique fawcettimine-type Lycopodium alkaloid, was achieved via a stereoselective Pauson-Khand...
An asymmetric total synthesis of lycopoclavamine-A (1), a structurally unique fawcettimine-type Lycopodium alkaloid, was achieved via a stereoselective Pauson-Khand reaction and a stereoselective conjugate addition to construct a quaternary carbon center at C-12.
Topics: Alkaloids; Chemistry Techniques, Synthetic; Lycopodium; Stereoisomerism
PubMed: 30919625
DOI: 10.1021/acs.joc.9b00586 -
Nature Chemical Biology Feb 2017Alkaloid-derived pharmaceuticals are commonly semisynthesized from plant-extracted starting materials, which often limits their availability and final price. Recent...
Alkaloid-derived pharmaceuticals are commonly semisynthesized from plant-extracted starting materials, which often limits their availability and final price. Recent advances in synthetic biology have enabled the introduction of complete plant pathways into microbes for the production of plant alkaloids. Microbial production of modified alkaloids has the potential to accelerate the semisynthesis of alkaloid-derived drugs by providing advanced intermediates that are structurally closer to the final pharmaceuticals and could be used as advanced intermediates for the synthesis of novel drugs. Here, we analyze the scientific and engineering challenges that must be overcome to generate microbes to produce modified plant alkaloids that can provide more suitable intermediates to US Food and Drug Administration-approved pharmaceuticals. We highlight modified alkaloids that currently could be produced by leveraging existing alkaloid microbial platforms with minor variations to accelerate the semisynthesis of seven pharmaceuticals on the market.
Topics: Alkaloids; Metabolic Engineering; Pharmaceutical Preparations; Plants
PubMed: 28199297
DOI: 10.1038/nchembio.2308 -
Zeitschrift Fur Naturforschung. C,... 2016GC-MS analysis of alkaloid profiles of five Fumaria species, naturally grown in Bulgaria (F. officinalis, F. thuretii, F. kralikii, F. rostellata and F. schrammii) and...
GC-MS analysis of alkaloid profiles of five Fumaria species, naturally grown in Bulgaria (F. officinalis, F. thuretii, F. kralikii, F. rostellata and F. schrammii) and analysis of acetylcholinesterase inhibitory activity of alkaloid extracts were performed. Fourteen isoquinoline alkaloids were identified, with the principle ones being protopine, cryptopine, sinactine, parfumine, fumariline, fumarophycine, and fumaritine. Protopine contents, defined by HPLC analysis varied between 210.6 ± 8.8 μg/g DW (F. schrammii) and 334.5 ± 7.1 μg/g DW. (F. rostellata). While all of the investigated alkaloid extracts significantly inhibited acetylcholinesterase activity, the F. kralikii demonstrated the highest level of inhibition (IC(50) 0.13 ± 0.01 mg extract/mL).
Topics: Acetylcholinesterase; Alkaloids; Benzophenanthridines; Berberine Alkaloids; Bulgaria; Cholinesterase Inhibitors; Fumaria; Isoquinolines
PubMed: 26756091
DOI: 10.1515/znc-2014-4179 -
Acta Crystallographica. Section C,... Apr 2015Tetrahydroberberine (systematic name: 9,10-dimethoxy-5,8,13,13a-tetrahydro-6H-benzo[g][1,3]benzodioxolo[5,6-a]quinolizine), C20H21NO4, a widely distributed naturally...
Tetrahydroberberine (systematic name: 9,10-dimethoxy-5,8,13,13a-tetrahydro-6H-benzo[g][1,3]benzodioxolo[5,6-a]quinolizine), C20H21NO4, a widely distributed naturally occurring alkaloid, has been crystallized as a racemic mixture about an inversion center. A bent conformation of the molecule is observed, with an angle of 24.72 (5)° between the arene rings at the two ends of the reduced quinolizinium core. The intermolecular hydrogen bonds that play an apparent role in crystal packing are 1,3-benzodioxole -CH2···OCH3 and -OCH3···OCH3 interactions between neighboring molecules.
Topics: Alkaloids; Berberine Alkaloids; Crystallography, X-Ray; Molecular Conformation; Molecular Structure
PubMed: 25836282
DOI: 10.1107/S2053229615004076 -
Chemistry & Biodiversity Jan 2011Seventy alkaloids of galanthamine, lycorine, homolycorine, tazettine, haemanthamine, narciclasine, and tyramine types were detected by GC/MS in 25 Galanthus elwesii and...
Seventy alkaloids of galanthamine, lycorine, homolycorine, tazettine, haemanthamine, narciclasine, and tyramine types were detected by GC/MS in 25 Galanthus elwesii and seven Galanthus nivalis populations, collected from different locations in Bulgaria. Intraspecies diversity in the alkaloid profiles regarding the main alkaloid types (chemotypes) was observed. Tyramine-type protoalkaloids (namely, hordenine and its derivatives) were dominant in 19 populations of G. elwesii. In other populations of G. elwesii, the plants accumulated mainly homolycorine-, lycorine-, and galanthamine-type alkaloids. The alkaloid profiles of G. nivalis were dominated by narciclasine-, galanthamine-, lycorine-, haemanthamine-, or tazettine-type compounds. Geographical distribution of chemotypes indicated a relationship between populations, since adjacent populations often displayed similar alkaloid profiles. The results from year-to-year sampling and transplantation experiments imply genetic determination of alkaloid synthesis in the two studied species of Galanthus.
Topics: Alkaloids; Amaryllidaceae Alkaloids; Galantamine; Galanthus; Gas Chromatography-Mass Spectrometry; Phenanthridines
PubMed: 21259423
DOI: 10.1002/cbdv.200900380 -
Accounts of Chemical Research Oct 2002The vinylogous Mannich reaction is rapidly emerging as an important process for the construction of derivatives of delta-aminocarbonyl compounds. Because the iminium and... (Review)
Review
The vinylogous Mannich reaction is rapidly emerging as an important process for the construction of derivatives of delta-aminocarbonyl compounds. Because the iminium and dienol components employed in this addition may be either acyclic or cyclic, a wide variety of adducts may be quickly assembled. These intermediates may then in turn be converted into a broad array of alkaloids and substituted nitrogen heterocycles. We have developed a number of variations of this reaction and have applied some of them to the concise syntheses of a number of structurally diverse and complex alkaloid natural products. Many of these results are presented in a historical context in this Account.
Topics: Alkaloids; Chemistry, Organic; Furans; Molecular Structure; Organic Chemistry Phenomena
PubMed: 12379142
DOI: 10.1021/ar950230w -
Molecules (Basel, Switzerland) Apr 2023Alkaloids are a material treasure bestowed on humans by nature owing to their numerous biological activities. Orychophragine D, an alkaloid isolated from the seeds of...
Alkaloids are a material treasure bestowed on humans by nature owing to their numerous biological activities. Orychophragine D, an alkaloid isolated from the seeds of was identified as bearing a novel skeleton and proved to have an excellent radioprotective effect. Different from the common alkaloid structure, the main block of orychophragine D is constructed of an oxotriazine and an oxopiperazine, which are connected in parallel by a C-N bond. In this paper, a preparation method for the novel heterocycle skeleton of orychophragine D is proposed for the first time. N-Boc-L-serine was utilized as the original material to complete the preparation with 11 steps in a 13% overall yield. A hydroxyl group was established on the side chain of the skeleton as the reaction site for researchers to conduct further structural modification or derivatization.
Topics: Humans; Alkaloids; Antineoplastic Agents; Binding Sites; Skeleton; Molecular Structure
PubMed: 37175238
DOI: 10.3390/molecules28093829