Browse
Submit Data
Databases
API
Help

Dataset Information

20 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

New amide alkaloids from Piper longum fruits

ABSTRACT: Three new amide alkaloids piperlongumamides A-C (1–3), together with 12 known ones (4–15), were isolated from the fruits of Piper longum. The structures of the new isolates were determined using spectroscopic data analyses. Cytotoxic activity of these amides against HL-60 (human leukemia), A-549 (human lung cancer), MCF-7 (human breast cancer), SMMC-7721 (human liver cancer) and SW480 (human rectal cancer) cell lines were evaluated. Piperchabamide B (11) exhibited weak inhibitory activity against HL-60 (IC50 = 21.32 μM ), A-549 (IC50 = 23.82 μM ) and MCF-7 (IC50 = 16.58 μM ) cell lines.

Electronic Supplementary Material

Supplementary material is available for this article at 10.1007/s13659-013-0073-0 and is accessible for authorized users.

SUBMITTER: Yang J

PROVIDER: S-EPMC4131601 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Multidrug resistance-selective antiproliferative activity of Piper amide alkaloids and synthetic analogues.

Project description:Twenty-five amide alkaloids (1-25) from Piper boehmeriifolium and 10 synthetic amide alkaloid derivatives (39-48) were evaluated for antiproliferative activity against eight human tumor cell lines, including chemosensitive and multidrug-resistant (MDR) cell lines. The results suggested tumor type-selectivity. 1-[7-(3,4,5-Trimethoxyphenyl)heptanoyl]piperidine (46) exhibited the best inhibitory activity (IC50=4.94 ?M) against the P-glycoprotein (P-gp)-overexpressing KBvin MDR sub-line, while it and all other tested compounds, except 9, were inactive (IC50 >40 ?M) against MDA-MB-231 and SK-BR-3. Structure-activity relationships (SARs) indicated that (i) 3,4,5-trimethoxy phenyl substitution is critical for selectivity against KBvin, (ii) the 4-methoxy group in this pattern is crucial for antiproliferative activity, (iii) double bonds in the side chain are not needed for activity, and (iv), in arylalkenylacyl amide alkaloids, replacement of an isobutylamino group with pyrrolidin-1-yl or piperidin-1-yl significantly improved activity. Further study on Piper amides is warranted, particularly whether side chain length affects the ability to overcome the MDR cancer phenotype.

| S-EPMC4366620 | biostudies-literature

New Amides and Phenylpropanoid Glucosides from the Fruits of Piper retrofractum.

Project description:Two new amides (E)-N-cinnamoyl-2-methoxypiperidine (1) and (R)-1-(2-oxopyrrolidin-3-yl)-5,6-dihydropyridin-2(1H)-one (2), four new amide glucosides, retrofractosides A-D (3-6), and two new phenylpropanoid glucosides, retrofractosides E (7) and F (8), together with 24 known compounds (9-32) were isolated from the fruits of Piper retrofractum. The chemical structures of these new compounds were elucidated based on extensive spectroscopic analysis. All of these isolates (1-32) were evaluated for inhibitory activity against mouse platelet aggregation induced by the peptide AYPGKF-NH2. (E)-N-(Tetrahydro-2H-pyran-2-yl)cinnamamide (9) showed a weak inhibitory effect, with an inhibition ratio of 52.0% at a concentration of 150 ?M.

| S-EPMC6538700 | biostudies-literature

Piper longum

Project description:Piper longum Transcriptome or Gene expression

| PRJNA592814 | ENA

Piper longum

Project description:Piper longum overview

| PRJNA1005383 | ENA

Molecular docking analysis of COX-2 with compounds from Piper longum.

Project description:Piper longum (Indian long pepper) is known for its use as an anti inflammatory agent in Indian Ayurvedic System of medicine. Therefore, it is of interest to document the molecular docking analysis of compounds from Piper longum with COX-2 using the Autodock Vina PyRx tool. Molecular docking results show that asarinine, sesamine, fargesin, and piperlonguminine have optimal binding energy of 10, 10, -9.5 and 9.4 Kcal/mol, respectively for further consideration.

| S-EPMC8819790 | biostudies-literature

Piper longum cultivar:Viswam

Project description:Piper longum cultivar:Viswam Genome sequencing and assembly

| PRJNA1005045 | ENA

Amides, Isoquinoline Alkaloids and Dipeptides from the Aerial Parts of Piper mullesua.

Project description:One undescribed amide, pipermullesine A, two undescribed isoquinoline alkaloids, pipermullesines B and C, and six undescribed dipeptides, pipermullamides A-F, along with 28 known compounds, were isolated from the aerial parts of Piper mullesua. The structures of the undescribed compounds were elucidated based on the analysis of 1D and 2D NMR and MS data. Furthermore, the structures of pipermullesines A-C were confirmed by single crystal X-ray diffraction analysis. All isolates were evaluated for inhibitory activity against platelet aggregation induced by thrombin (IIa) or platelet-activating factor (PAF). (-)-Mangochinine, pellitorine, and (2E,4E)-N-isobutyl-2,4-dodecadienamide showed weak inhibitory activity against rabbit platelet aggregation induced by PAF, with IC50 values of 470.3 µg/mL, 614.9 µg/mL, and 579.7 µg/mL, respectively.

| S-EPMC6224811 | biostudies-literature

Tissue-specific variations of piperine in ten populations of Piper longum L.: bioactivities and toxicological profile.

Project description:P. longum L., one of the most significant species of the genus Piperaceae, is most frequently employed in Indian-Ayurvedic and other traditional medicinal-systems for treating a variety of illnesses. The alkaloid piperine, is the key phytoconstituent of the plant, primarily responsible for its' pharmacological-impacts. The aim of the study is to analyse the intra-specific variation in piperine content among different chemotypes (PL1 to PL 30) and identify high piperine yielding chemotype (elite-chemotype) collected from 10 different geographical regions of West Bengal by validated HPTLC chromatography method. The study also focused on the pharmacological-screening to better understand the antioxidant activity of the methanol extracts of P. longum by DPPH and ABTS radical-scavenging activity and genotoxic activity by Allium cepa root tip assay. It was found that the P. longum fruit chemotypes contain high amount piperine (highest 16.362 mg/g in chemotype PL9) than the stem and leaf chemotypes. Both DPPH and ABTS antioxidant assays revealed that P. longum showed moderate radical-scavenging activity and the highest activity was found in PL9 (fruit) chemotype with IC50 values of 124.2 ±0.97 and 104 ±0.78 µg/ml respectively. The A. cepa root tip assay showed no such significant genotoxic-effect and change in mitotic-index. The quick, reproducible, and validated HPTLC approach offers a useful tool for determining quantitative variations of piperine among P. longum chemotypes from different geographical-regions and also according to the different tissues and choose elite genotypes with high piperine production for continued propagation and commercialization for the pharmaceutical sector. Additionally, the plant's in-vitro antioxidant property and lack of genotoxicity directly supports its' widespread and long history of use as a medicinal and culinary plant.

| S-EPMC10904381 | biostudies-literature

Epigenetic Modifiers Affect the Bioactive Compounds Secreted by an Endophyte of the Tropical Plant Piper longum.

Project description:Seven endophytic fungi were isolated from the tropical medicinal plant Piper longum L. After preliminary screening, Phomopsis heveicola was selected for the epigenetic activation treatments. The antibacterial, antifungal, and antioxidant potentials of crude extracts obtained from the treatments (with and without epigenetic modifiers) were analyzed in vitro. The extracts inhibited growth of the human pathogens Pseudomonas aeruginosa, Shigella sonnei, Streptococcus pyogenes, and Salmonella typhi, as well as the phytopathogens Puccinia recondita, Rhizoctonia solani, Phytophthora infestans, and Botrytis cinerea. Furthermore, DPPH-scavenging activity was higher in valproic acid treated extracts. Volatile chemicals with known biological activities (measured with GC-MS/MS), were released in the valproic acid treatment. The antimicrobial potentials of the extracts were confirmed using MRM/MS analysis. The experiments revealed a new promising endophytic fungus, P. heveicola, to be utilized in biological plant protection and in biomedical applications.

| S-EPMC7793533 | biostudies-literature

Temporal dynamics of endophytic bacterial and fungal communities during spike development in <i>Piper longum</i> L.

Project description:The female spikes (fruits) of Piper longum are widely used in Ayurvedic, Siddha and Unani medicine systems to treat respiratory and digestive disorders. The spikes are rich in piperine, a pharmacologically active amide alkaloid and a potent bioavailability enhancer, which accumulates to the highest level during the dark-green stage of spike development. Plant-associated microbiota influence the plant's fitness, response, and production of economically important metabolites. Considering the economic importance of piperine and other spike-derived alkaloids, understanding microbial community dynamics during spike development would be key to bioprospecting for economically important metabolites. In the present study, the structural diversity of microbial communities associated with early (SI), mid (SII), and late (SIII) stages of spike development in P. longum has been analysed by Illumina-based amplicon sequencing of 16S rRNA gene and ITS region. Results revealed that spike development significantly drives the diversity and abundance of spike-associated microbiota, especially bacterial communities. Cyanobacteria and Ascomycota constituted the most abundant bacterial and fungal phyla, respectively, across all stages of spike development. Interestingly, Halomonas, Kushneria and Haererehalobacter were found to be exclusively associated with SIII (corresponding to economically important) stage of spike development. Sphingomonas, Mortierella, Cladosporium and Vishniacozyma constituted the core microbiome of the spike. Besides, PICRUSt analysis revealed that amino acid metabolism was the most dominant metabolic function attributed to spike-associated bacterial communities. To the best of our knowledge, this is the first study to investigate the endomicrobiome dynamics during spike development in a medicinal plant species.Supplementary informationThe online version contains supplementary material available at 10.1007/s12298-023-01352-2.

| S-EPMC10564784 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data