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https://www.readbyqxmd.com/read/27864138/sarniensine-a-mesembrine-type-alkaloid-isolated-from-nerine-sarniensis-an-indigenous-south-african-amaryllidaceae-with-larvicidal-and-adulticidal-activities-against-aedes-aegypti
#1
Marco Masi, Alet E van der Westhuyzen, Nurhayat Tabanca, Marco Evidente, Alessio Cimmino, Ivan R Green, Ulrich R Bernier, James J Becnel, Jeffrey R Bloomquist, Willem A L van Otterlo, Antonio Evidente
A new mesembrine-type alkaloid, named sarniensine, was isolated together with tazettine, lycorine, the main alkaloid, and 3-epimacronine from Nerine sarniensis, with the last two produced for the first time by this plant. This Amaryllidaceae, which is indigenous of South Africa, was investigated for its alkaloid content, because the organic extract of its bulbs showed strong larvicidal activity with an LC50 value of 0.008μgμL(-1) against first instar Aedes aegypti larvae and with an LD50 value 4.6μg/mosquito against adult female Ae...
November 15, 2016: Fitoterapia
https://www.readbyqxmd.com/read/27847203/lycorine-induces-cell-death-in-mm-by-suppressing-janus-kinase-signal-transducer-and-activator-of-transcription-via-inducing-the-expression-of-socs1
#2
Zhouxiang Jin, Shujuan Zhou, Yu Zhang, Haige Ye, Songfu Jiang, Kang Yu, Yongyong Ma
Despite the use of novel anti-myeloma agents,nearly all patients will eventually relapse or become refractory to drug treatment. New and more effective drugs for multiple myeloma (MM) are urgently needed. The JAK-STAT signaling pathway is important in the proliferation of myeloma cells.Lycorine,a natural alkaloid extracted from amaryllidaceae, has shown anti-tumor effects against a variety of solid tumors. However, its effects on MM remain unclear.In this study,we found that lycorine inhibited cellular viability and induced cell death in MM cell lines and primary myeloma cells which were derived from our four MM patients...
November 12, 2016: Biomedicine & Pharmacotherapy, Biomédecine & Pharmacothérapie
https://www.readbyqxmd.com/read/27801807/alkaloids-with-activity-against-the-zika-virus-vector-aedes-aegypti-l-crinsarnine-and-sarniensinol-two-new-crinine-and-mesembrine-type-alkaloids-isolated-from-the-south-african-plant-nerine-sarniensis
#3
Marco Masi, Antonio Cala, Nurhayat Tabanca, Alessio Cimmino, Ivan R Green, Jeffrey R Bloomquist, Willem A L van Otterlo, Francisco A Macias, Antonio Evidente
Two new Amaryllidaceae alkaloids, belonging to the mesembrine- and crinine-types, named crinsarnine (1) and sarniensinol (2), were isolated from the dried bulbs of Nerine sarniensis together with bowdensine (3), sarniensine (4), hippadine (5) and 1-O-acetyl-lycorine (6). Crinsarnine (1) and sarniensinol (2) were characterized using spectroscopic and chiroptical methods as (1S,2S,4aR,10bS)-2,7-dimethoxy-1,2,3,4,4a,6-hexahydro-5,11b-ethano[1,3]dioxolo-[4,5-j]phenanthridin-1-yl acetate and (6-(3aR,4Z,6S,7aS)-6-methoxy-1-methyl-2,3,3a,6,7,7a-hexa-hydro-1H-indol-3a-yl)benzo[d][1,3]dioxol-5-yl)methanol, respectively...
October 27, 2016: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/27693680/cadmium-stress-tolerance-in-wheat-seedlings-induced-by-ascorbic-acid-was-mediated-by-no-signaling-pathways
#4
Zhaofeng Wang, Qien Li, Weiguo Wu, Jie Guo, Yingli Yang
Ascorbic acid (AsA) and nitric oxide (NO) are well known and widespread antioxidants and gaseous molecules that regulate plant tolerance to several stresses. However, the relationship between them in plant response to stress, especially heavy stress, is largely unclear. This study demonstrated that both AsA and NO could enhance the tolerance of wheat seedlings to cadmium stress evidenced by root length change, which resulted from their roles in maintaining the balance in reactive oxygen species (ROS) and reducing the absorption of Cd...
September 29, 2016: Ecotoxicology and Environmental Safety
https://www.readbyqxmd.com/read/27509914/lycorine-protects-cartilage-through-suppressing-the-expression-of-matrix-metalloprotenases-in-rat-chondrocytes-and-in-a-mouse-osteoarthritis-model
#5
Shuai Chen, Xiang-Qian Fang, Jian-Feng Zhang, Yan Ma, Xiao-Zhen Tang, Zhi-Jie Zhou, Ji-Ying Wang, An Qin, Shun-Wu Fan
Extracellular matrix (ECM) degrading enzymes, including matrix metalloproteinases (MMPs), are critical for cartilage destruction in the progression of osteoarthritis (OA). Thus, identifying novel drugs, which suppress the synthesis of MMPs may facilitate the treatment of OA. The cytotoxicity of lycorine was determined using a CCK8 assay. The effects of lycorine on IL‑1β‑induced upregulation of MMPs and activation of mitogen‑activated protein kinase pathways were detected by western blot analysis and reverse transcription‑quantitative polymerase chain reaction...
October 2016: Molecular Medicine Reports
https://www.readbyqxmd.com/read/27320892/-antitumor-activity-of-lycorine-in-renal-cell-carcinoma-achn-cell-line-and-its-mechanism
#6
Yi-Qiang Huang, Yi-Ming Zhang, Zhong Jin, Xie-Zhao Li, Chong-Shan Wang, Kai Xu, Peng Huang, Chun-Xiao Liu
OBJECTIVE: To investigate the antitumor effect of lycorine on renal cell carcinoma ACHN cells and explore the possible mechanism. METHODS: We used flow cytometry to examine the effect of lycorine on ACHN cell cycle and apoptosis. The cell proliferation, migration and invasion were assessed with MTS assay, wound healing assay, and Transwell assay, respectively. Colony forming assay was performed, and the mRNA and protein levels of Bax, Bcl-2, survivin, caspase-3, cyclin D1 and CDK4 were measured with qRT-PCR and Western blotting...
June 2016: Nan Fang Yi Ke da Xue Xue Bao, Journal of Southern Medical University
https://www.readbyqxmd.com/read/27076115/oxidative-dearomatization-of-4-5-6-7-tetrahydro-1h-indoles-obtained-by-metal-and-solvent-free-thermal-5-endo-dig-cyclization-the-route-to-erythrina-and-lycorine-alkaloids
#7
Ivan A Andreev, Nina K Ratmanova, Anton M Novoselov, Dmitry S Belov, Irina F Seregina, Alexander V Kurkin
A facile one-pot approach based on a thermally induced metal- and solvent-free 5-endo-dig cyclization reaction of the amino propargylic alcohols in combination with Dess-Martin periodinane-promoted oxidative dearomatization of 4,5,6,7-tetrahydroindole intermediates provides an efficient and robust access to 5,6-dihydro-1H-indol-2(4H)ones. Green, relatively mild and operationally simple characteristics of the synthetic sequence are the major advantages, which greatly amplify the developed methodology. The utility of obtained indolones as unified key precursors is demonstrated by the application of these products to the formal total syntheses of a whole pleiad of Erythrina- and Lycorine-type alkaloids, namely (±)-erysotramidine, (±)-erysotrine, (±)-erythravine, (±)-γ-lycorane, and abnormal erythrinanes (±)-coccoline and (±)-coccuvinine...
May 17, 2016: Chemistry: a European Journal
https://www.readbyqxmd.com/read/26969844/synthesis-of-amaryllidaceae-constituents-and-unnatural-derivatives
#8
REVIEW
Mukund Ghavre, Jordan Froese, Milan Pour, Tomas Hudlicky
This update covers the syntheses of Amaryllidaceae alkaloids since the publication of the last major review in 2008. A short summary of past syntheses and their step count is provided for the major constituents; pancratistatin, 7-deoxypancratistatin, narciclasine, lycoricidine, lycorine, and for other natural constituents, as well as for unnatural derivatives. Discussion of biological activities is provided for unnatural derivatives. Future prospects and further developments in this area are covered at the end of the review...
May 4, 2016: Angewandte Chemie
https://www.readbyqxmd.com/read/26941773/cyp96t1-of-narcissus-sp-aff-pseudonarcissus-catalyzes-formation-of-the-para-para-c-c-phenol-couple-in-the-amaryllidaceae-alkaloids
#9
Matthew B Kilgore, Megan M Augustin, Gregory D May, John A Crow, Toni M Kutchan
The Amaryllidaceae alkaloids are a family of amino acid derived alkaloids with many biological activities; examples include haemanthamine, haemanthidine, galanthamine, lycorine, and maritidine. Central to the biosynthesis of the majority of these alkaloids is a C-C phenol-coupling reaction that can have para-para', para-ortho', or ortho-para' regiospecificity. Through comparative transcriptomics of Narcissus sp. aff. pseudonarcissus, Galanthus sp., and Galanthus elwesii we have identified a para-para' C-C phenol coupling cytochrome P450, CYP96T1, capable of forming the products (10bR,4aS)-noroxomaritidine and (10bS,4aR)-noroxomaritidine from 4'-O-methylnorbelladine...
2016: Frontiers in Plant Science
https://www.readbyqxmd.com/read/26790307/-study-on-effect-of-lycorine-in-inducing-apoptosis-of-pulmonary-carcinoma-cell-a549
#10
Wei Zhang, En-hai Cui
To explore the effect of lycorine in inducing apoptosis of pulmonary carcinoma cell A549 and its mechanism. In the study, pulmonary carcinoma cell A549 were taken as the experimental subject and processed with different concentrations of lycorine (0, 0.5, 1.0, 2.0, 4.0 and 8.0 μmol x L(-1)). The MTT method was used to observe the cell proliferation. The apoptosis rate of A549 cells was determined by Annexin FITC/PI double staining. The microplate reader was used to detect the activities of Bcl-2, Bax and p53...
August 2015: Zhongguo Zhong Yao za Zhi, Zhongguo Zhongyao Zazhi, China Journal of Chinese Materia Medica
https://www.readbyqxmd.com/read/26714198/design-synthesis-and-structural-optimization-of-lycorine-derived-phenanthridine-derivatives-as-wnt-%C3%AE-catenin-signaling-pathway-agonists
#11
Duo-Zhi Chen, Chen-Xu Jing, Jie-Yun Cai, Ji-Bo Wu, Sheng Wang, Jun-Lin Yin, Xiao-Nian Li, Lin Li, Xiao-Jiang Hao
Lycorine is a benzylphenethylamine-type alkaloid member of the Amaryllidaceae family. A lycorine derivative, HLY78, was previously identified as a new Wnt/β-catenin signaling pathway agonist that targets the DAX domain of axin. Herein, the structural optimization of HLY78 and analyses of the structure-activity relationships of lycorine-derived phenanthridine derivatives as agonists of the Wnt/β-catenin signaling pathway are presented. This research suggests that triazole groups are important pharmacophores for Wnt activation; triazole groups at C-8 and C-9 of phenanthridine compounds markedly enhanced Wnt activation...
January 22, 2016: Journal of Natural Products
https://www.readbyqxmd.com/read/26596952/a-conserved-inhibitory-mechanism-of-a-lycorine-derivative-against-enterovirus-and-hepatitis-c-virus
#12
Yu Guo, Yaxin Wang, Lin Cao, Peng Wang, Jie Qing, Qizhen Zheng, Luqing Shang, Zheng Yin, Yuna Sun
Enterovirus 71 (EV71) (Picornaviridae family) and hepatitis C virus (HCV) (Flaviviridae family) are the causative agents of human hand, foot, and mouth disease (HFMD) and hepatitis C, resulting in a severe pandemic involving millions of infections in the Asia-Pacific region and worldwide. The great impact of EV71 and HCV on public health highlights the need to further our understanding of the biology of these two viruses and develop effective therapeutic antivirals. Here, we evaluated a total of 32 lycorine derivatives and demonstrated that 1-acetyllycorine suppressed the proliferation of multiple strains of EV71 in various cells...
February 2016: Antimicrobial Agents and Chemotherapy
https://www.readbyqxmd.com/read/26577925/apoptosis-inducing-effects-of-amaryllidaceae-alkaloids
#13
REVIEW
Jerald J Nair, Johannes van Staden, Jaume Bastida
The Amaryllidaceae occupies a privileged status amongst medicinal plants in having delivered the Alzheimer's drug galanthamine to the clinical market. Following its resounding success, there have been several positive indicators for the emergence of an anticancer drug from the family due to the potent antiproliferative activities manifested by several of its alkaloid constituents. Of these, the phenanthridones such as pancratistatin hold most promise as potential chemotherapeutics having succumbed to various phases of clinical trials...
2016: Current Medicinal Chemistry
https://www.readbyqxmd.com/read/26526413/gibberellin-like-effects-of-kar1-on-dormancy-release-of-avena-fatua-caryopses-include-participation-of-non-enzymatic-antioxidants-and-cell-cycle-activation-in-embryos
#14
Danuta Cembrowska-Lech, Jan Kępczyński
The induction of dormancy release and germination of Avena fatua caryopses by KAR 1 involves ABA degradation to phaseic acid. Both, KAR 1 and GA 3 , control the AsA-GSH cycle, DNA replication and accumulation of β-tubulin in embryos before caryopses germination. Avena fatua caryopses cannot germinate in darkness at 20 °C because of dormancy, but karrikinolide-1 (KAR1), a compound in plant-derived smoke, and gibberellic acid (GA3) induced an almost complete germination. The radicle protrusion through the coleorhiza was preceded by increased water uptake, rupture of coat, increased embryo size and coleorhiza length as well as coleorhiza protrusion through covering structures...
February 2016: Planta
https://www.readbyqxmd.com/read/26443922/design-synthesis-and-structure-activity-relationship-optimization-of-lycorine-derivatives-for-hcv-inhibition
#15
Duozhi Chen, Jieyun Cai, Junjun Cheng, Chenxu Jing, Junlin Yin, Jiandong Jiang, Zonggen Peng, Xiaojiang Hao
Lycorine is reported to be a multifunctional compound. We previously showed that lycorine is an HCV inhibitor with strong activity. Further research on the antivirus mechanism indicated that lycorine does not affect the enzymes that are indispensable to HCV replication but suppresses the expression of Hsc70 in the host cell to limit HCV replication. However, due to the cytotoxicity and apoptosis induction of lycorine, lycorine is unsafe to be a anti-HCV agent for clinical application. As a result of increasing interest, its structure was optimized for the first time and a novel series of lycorine derivatives was synthesized, all of which lost their cytotoxicity to different degrees...
2015: Scientific Reports
https://www.readbyqxmd.com/read/26265570/hptlc-and-gc-ms-study-of-amaryllidaceae-alkaloids-of-two-narcissus-species
#16
Eman Shawky, Amina H Abou-Donia, Fikria A Darwish, Soad M Toaima, Sarah S Takla, Natalia B Pigni, Jaume Bastida
In this article, we report on the alkaloid profile and dynamic of alkaloid content and diversity in two Narcissus plants at different stages of development. The alkaloid profile of the two Narcissus species was investigated by GC/MS and HPTLC. Fifty eight Amaryllidaceae alkaloids were detected, and 25 of them were identified in the different organs of N. tazetta and N. papyraceus. The alkaloid 3-O-methyl-9-O-demethylmaritidine is tentatively identified here for the first time from the Amaryllidaceae family, and four alkaloids (tazettamide, sternbergine, 1-O-acetyllycorine, 2,11-didehydro-2-dehydroxylycorine) are tentatively identified for the first time in the genus Narcissus...
August 2015: Chemistry & Biodiversity
https://www.readbyqxmd.com/read/26238331/lycorine-suppresses-rankl-induced-osteoclastogenesis-in-vitro-and-prevents-ovariectomy-induced-osteoporosis-and-titanium-particle-induced-osteolysis-in-vivo
#17
Shuai Chen, Gu Jin, Kang-Mao Huang, Jian-Jun Ma, Qiang Wang, Yan Ma, Xiao-Zhen Tang, Zhi-Jie Zhou, Zhi-Jun Hu, Ji-Ying Wang, An Qin, Shun-Wu Fan
Osteoclasts play an important role in diseases involving bone loss. In this study, we assessed the effect of a plant-derived natural alkaloid (lycorine, or LY) on osteoclastogenesis in vitro and in vivo. Our in vitro study showed that receptor activator of nuclear factor-κB ligand (RANKL)-induced osteoclastogenesis could be inhibited by LY; this effect was due to inhibition of mitogen-activated protein kinase (MAPK) signalling via MAP kinase kinases (MKKs). The MAPK agonist anisomycin could partially rescue the inhibitory effect of LY...
August 4, 2015: Scientific Reports
https://www.readbyqxmd.com/read/26156166/-application-of-coagulant-in-the-analysis-of-lycorine-and-galanthamine-in-processed-foods
#18
Jun Sugiura, Shoichiro Noguchi, Masahiro Nakajima
Analytical method by HPLC and LC-MS/MS for determining lycorine and galanthamine in processed food was newly developed. In this method, coagulant which has never been used in food analysis was applied on cleanup process. With coagulant approach, removal of interfering substances on determination for analytes was easily achieved. The method using HPLC showed recovery of 95.4-102.9% on both analytes with repeatability of less than 2.9% and reproducibility of less than 2.9%. The method using LC-MS/MS showed recovery of 97...
2015: Shokuhin Eiseigaku Zasshi. Journal of the Food Hygienic Society of Japan
https://www.readbyqxmd.com/read/26099943/asymmetric-catalytic-cascade-reactions-for-constructing-diverse-scaffolds-and-complex-molecules
#19
Yao Wang, Hong Lu, Peng-Fei Xu
With the increasing concerns about chemical pollution and sustainability of resources, among the significant challenges facing synthetic chemists are the development and application of elegant and efficient methods that enable the concise synthesis of natural products, drugs, and related compounds in a step-, atom- and redox-economic manner. One of the most effective ways to reach this goal is to implement reaction cascades that allow multiple bond-forming events to occur in a single vessel. This Account documents our progress on the rational design and strategic application of asymmetric catalytic cascade reactions in constructing diverse scaffolds and synthesizing complex chiral molecules...
July 21, 2015: Accounts of Chemical Research
https://www.readbyqxmd.com/read/25921398/lycorine-derived-phenanthridine-downregulators-of-host-hsc70-as-potential-hepatitis-c-virus-inhibitors
#20
Duozhi Chen, Jieyun Cai, Junlin Yin, Jiandong Jiang, Chenxu Jing, Yanping Zhu, Junjun Cheng, Yingtong Di, Yu Zhang, Mingming Cao, Shunlin Li, Zonggen Peng, Xiaojiang Hao
BACKGROUND: A new series of potential phenanthridine hepatitis C virus (HCV) inhibitors which work by suppressing Hsc70 expression in the host cell was designed and synthesized from lycorine. RESULTS: Thirty-one new potential phenanthridine HCV inhibitors were synthesized and five of these compounds exhibited good anti-HCV activity and these inhibitors probably inhibit HCV by downregulating the host Hsc70 expression. Structure-activity analysis of these compounds revealed that the double bond between C-11 and C-12 and the substituents at C-8 and C-9 are important for their activity against HCV...
2015: Future Medicinal Chemistry
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