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    ORIGINAL ARTICLES
    Tissue culture tools for selenium hyperaccumulator Neptunia amplexicaulis for development in phytoextraction   Collect
    Billy O'Donohue, Jayeni Hiti-Bandaralage, Madeleine Gleeson, Chris O'Brien, Maggie-Anne Harvey, Antony van der Ent, Katherine Pinto Irish, Neena Mitter, Alice Hayward
    Natural Products and Bioprospecting. 2022, 12 (5): 28-28.   DOI: 10.1007/s13659-022-00351-2
    Abstract ( 3761 )   HTML ()     PDF (1609KB) ( 5510 )  
    Neptunia amplexicaulis is an herbaceous legume endemic to the Richmond area in central Queensland, Australia and is one of the strongest known Selenium hyperaccumulators on earth, showing significant potential to be utilised in Se phytoextraction applications. Here a protocol was established for in vitro micropropagation of Se hyperaccumulator N. amplexicaulis using nodal segments from in vitro-germinated seedlings. Shoot multiplication was achieved on Murashige and Skoog (MS) basal media supplemented with various concentrations of 6-Benzylaminopurine (BA) (1.0, 2.0, 3.0 mg L-1) alone or in combination with low levels of Naphthaleneacetic acid (NAA) (0.1, 0.2, 0.3 mg L-1), with 2.0 mg L-1 BA + 0.2 mg L-1 NAA found to be most effective. Elongated shoots were rooted in vitro using NAA, with highest root induction rate of 30% observed at 0.2 mg L-1 NAA. About 95% of the in vitro rooted shoots survived acclimatization. Clonally propagated plantlets were dosed with selenate/selenite solution and assessed for Se tissue concentrations using Inductively Coupled Plasma Atomic Emission Spectroscopy (ICP-AES) and found to retain their ability to hyperaccumulate. The protocol developed for this study has potential to be optimised for generating clonal plants of N. amplexicaulis for use in research and phytoextraction industry applications.
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    New seco-anthraquinone glucoside from the roots of Rumex crispus   Collect
    Yong-Xiang Li, Na Li, Jing-Juan Li, Man Zhang, Hong-Tao Zhu, Dong Wang, Ying-Jun Zhang
    Natural Products and Bioprospecting. 2022, 12 (5): 29-29.   DOI: 10.1007/s13659-022-00350-3
    Abstract ( 3879 )   HTML ()     PDF (1553KB) ( 5744 )  
    A new seco-anthraquinone, crispuside A (1), and three new 3,4-dihydronaphthalen-1(2H)-ones, napthalenones A-C (24), were isolated from the roots of Rumex crispus L., along with 10 known anthraquinones (614) and naphthalenone (5). Their structures were fully determined by extensive spectroscopic analyses, including ECD, and X-ray crystallography in case of compound 5, whose absolute configuration was determined for the first time. The isolates 1, 614 were evaluated for their anti-inflammatory and anti-fungal activity against three skin fungi, e.g., Epidermophyton floccosum, Trichophyton rubrum, and Microsporum gypseum. Most of the isolates showed weak antifungal and anti-inflammatory activity. Only compound 9 exhibited obvious anti-fungal activity against E. floccosum (MIC50 = 2.467 ± 0.03 μM) and M. gypseum ( MIC50 = 4.673 ± 0.077 μM), while the MIC50 values of the positive control terbinafine were 1.287 ± 0.012 and 0.077 ± 0.00258 μM, respectively. The results indicated that simple emodin type anthraquinone is more potential against skin fungi than its oxyglucosyl, C-glucosyl and glycosylated seco analogues.
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    Arctostaphylos uva-ursi L. leaves extract and its modified cysteine preparation for the management of insulin resistance: chemical analysis and bioactivity   Collect
    Ganna Kravchenko, Oksana Krasilnikova, Ain Raal, Matar Mazen, Natalia Chaika, Igor Kireyev, Andriy Grytsyk, Oleh Koshovyi
    Natural Products and Bioprospecting. 2022, 12 (5): 30-30.   DOI: 10.1007/s13659-022-00352-1
    Abstract ( 3862 )   HTML ()     PDF (1925KB) ( 5952 )  
    Bearberry (Arctostaphylos uva-ursi L.) is a perennial plant of the heather family (Ericaceae). The leaves are dominated by arbutin, phenol carbonic acids flavonoids, saponins, etc. It was previously shown that the bearberry leaves extract reduced blood glucose level in healthy animals under glucose overload, so it need to be studied more detail. The aim of the study was to investigate the chemical composition and the effect of dry alcohol extract from bearberry leaves, which enriched with cysteine, on the rats pancreas under experimental dexamethasone-induced insulin resistance (IR). Arctostaphylos uva-ursi L. leaves extract and its modified cysteine preparation were obtained according to the developed method with 50% ethanol solution. Their phytochemical profile, hypoglycaemic and pancreatic protective effect were investigated. Phenologlycoside (arbutin), phenolic carboxylic acid (gallic acid), 5 flavonoids and 4 hydroxycinnamic acids were identified and quantified in the extracts by HPLC. Present data revealed that bearberry leaves alcoholic dry extract enriched with cysteine has a hypoglycaemic and pancreatic protective effect in treated animals under dexamethasone-induced IR model. Treatment improved hyperglycaemia, insulin resistance and beta cell reduction induced by dexamethasone injections.
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    REVIEW
    Mulberry Diels–Alder-type adducts: isolation, structure, bioactivity, and synthesis   Collect
    Si-Yuan Luo, Jun-Yu Zhu, Ming-Feng Zou, Sheng Yin, Gui-Hua Tang
    Natural Products and Bioprospecting. 2022, 12 (5): 31-31.   DOI: 10.1007/s13659-022-00355-y
    Abstract ( 4065 )   HTML ()     PDF (5628KB) ( 6085 )  
    Mulberry Diels–Alder-type adducts (MDAAs) are unique phenolic natural products biosynthetically derived from the intermolecular [4 + 2]-cycloaddition of dienophiles (mainly chalcones) and dehydroprenylphenol dienes, which are exclusively distributed in moraceous plants. A total of 166 MDAAs with diverse skeletons have been isolated and identified since 1980. Structurally, the classic MDAAs characterized by the chalcone-skeleton dienophiles can be divided into eight groups (Types A - H), while others with non-chalcone dienophiles or some variations of classic MDAAs are non-classic MDAAs (Type I). These compounds have attracted significant attention of natural products and synthetic chemists due to their complex architectures, remarkable biological activities, and synthetic challenges. The present review provides a comprehensive summary of the structural properties, bioactivities, and syntheses of MDAAs. Cited references were collected between 1980 and 2021 from the SciFinder, Web of Science, and China National Knowledge Internet (CNKI).
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    ORIGINAL ARTICLE
    Tetra-, penta-, and hexa-nor-lanostane triterpenes from the medicinal fungus Ganoderma australe   Collect
    Lin Zhou, Subiy Akbar, Meng-Xi Wang, He-Ping Chen, Ji-Kai Liu
    Natural Products and Bioprospecting. 2022, 12 (5): 32-32.   DOI: 10.1007/s13659-022-00356-x
    Abstract ( 3736 )   HTML ()     PDF (1395KB) ( 5612 )  
    Chemical investigation on the medicinal fungus Ganoderma australe led to the identification of ten new nor-lanostane triterpenes, namely two hexa-nor ones, ganoaustratetraenones A (1) and B (2), five penta-nor ones, ganoaustraldehydes A–E (37), and three tetra-nor ones ganoaustrenoic acids A–C (810). The chemical structures along with the absolute configurations were determined by extensive spectroscopic analysis of 1D & 2D NMR and HRESIMS data. The postulated biosynthesis pathways of these compounds were proposed. Ganoaustraldehydes A (3) and B (4) showed moderate inhibition against nitric oxide production in RAW264.7 macrophage cells with the respective IC50 values of 32.5, 34.2 μM (the IC50 of positive control pyrrolidine dithiocarbamate was 20.0 μM).
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    REVIEW
    Beauty of the beast: anticholinergic tropane alkaloids in therapeutics   Collect
    Kyu Hwan Shim, Min Ju Kang, Niti Sharma, Seong Soo A.An
    Natural Products and Bioprospecting. 2022, 12 (5): 33-33.   DOI: 10.1007/s13659-022-00357-w
    Abstract ( 3666 )   HTML ()     PDF (1610KB) ( 5893 )  
    Tropane alkaloids (TAs) are among the most valued chemical compounds known since pre-historic times. Poisonous plants from Solanaceae family (Hyoscyamus niger, Datura, Atropa belladonna, Scopolia lurida, Mandragora officinarum, Duboisia) and Erythroxylaceae (Erythroxylum coca) are rich sources of tropane alkaloids. These compounds possess the anticholinergic properties as they could block the neurotransmitter acetylcholine action in the central and peripheral nervous system by binding at either muscarinic and/or nicotinic receptors. Hence, they are of great clinical importance and are used as antiemetics, anesthetics, antispasmodics, bronchodilator and mydriatics. They also serve as the lead compounds to generate more effective drugs. Due to the important pharmacological action they are listed in the WHO list of essential medicines and are available in market with FDA approval. However, being anticholinergic in action, TA medication are under the suspicion of causing dementia and cognitive decline like other medications with anticholinergic action, interestingly which is incorrect. There are published reviews on chemistry, biosynthesis, pharmacology, safety concerns, biotechnological aspects of TAs but the detailed information on anticholinergic mechanism of action, clinical pharmacology, FDA approval and anticholinergic burden is lacking. Hence the present review tries to fill this lacuna by critically summarizing and discussing the above mentioned aspects.
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    ORIGINAL ARTICLES
    Therapeutic roles of plants for 15 hypothesised causal bases of Alzheimer’s disease   Collect
    Sheena E.B.Tyler, Luke D.K.Tyler
    Natural Products and Bioprospecting. 2022, 12 (5): 34-34.   DOI: 10.1007/s13659-022-00354-z
    Abstract ( 4078 )   HTML ()     PDF (2251KB) ( 6409 )  
    Alzheimer’s disease (AD) is progressive and ultimately fatal, with current drugs failing to reverse and cure it. This study aimed to find plant species which may provide therapeutic bioactivities targeted to causal agents proposed to be driving AD. A novel toolkit methodology was employed, whereby clinical symptoms were translated into categories recognized in ethnomedicine. These categories were applied to find plant species with therapeutic effects, mined from ethnomedical surveys. Survey locations were mapped to assess how this data is at risk. Bioactivities were found of therapeutic relevance to 15 hypothesised causal bases for AD. 107 species with an ethnological report of memory improvement demonstrated therapeutic activity for all these 15 causal bases. The majority of the surveys were found to reside within biodiversity hotspots (centres of high biodiversity under threat), with loss of traditional knowledge the most common threat. Our findings suggest that the documented plants provide a large resource of AD therapeutic potential. In demonstrating bioactivities targeted to these causal bases, such plants may have the capacity to reduce or reverse AD, with promise as drug leads to target multiple AD hallmarks. However, there is a need to preserve ethnomedical knowledge, and the habitats on which this knowledge depends.
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    Apatite phosphate doped by cobalt as hight efficient catalyst of multi-component synthesis of therapeutic spiropyrimidine compound   Collect
    Abdallah Rhihil, Youness Aichi, Mohamed Zahouily, Sa?d Sebti, Mohamed El Guendouzi
    Natural Products and Bioprospecting. 2022, 12 (5): 35-35.   DOI: 10.1007/s13659-022-00359-8
    Abstract ( 3483 )   HTML ()     PDF (1320KB) ( 5197 )  
    Spiropyrimidines vanquish a significant situation in the field of heterocyclic chemistry, they are broadly utilized as an antibacterial, an inhibitor of multidrug opposition, or an antiplatelet and antithrombotic drug. Phosphate, the principal Moroccan mineral wealth occupies a vital spot in the economic sector and its valuation is a goal continually looked for. Among the conceivable outcomes of valorization, its utilization in heterogeneous catalysis which thought about an exceptionally encouraging new way. In this context, the focus on the reaction of the synthesis of spiropyrimidine, catalyzed by natural phosphate (NP) and by fluoroapatite (Fap), are used alone or doped by cobalt. These phosphate catalysts were characterized by XRD, IR and SEM, while the synthesized spiropyrimidine was identified by IR, GC–MS and NMR. The obtained yield with fluorapatite doped by cobalt (Co/Fap), at room temperature in ethanol is very high and shows a high impact performance induced by a synergistic effect compared to that of NP alone.
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2022, Volume 12 Issue 5