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1.
Mol Nutr Food Res ; 68(6): e2300583, 2024 Mar.
Article in English | MEDLINE | ID: mdl-38389156

ABSTRACT

SCOPE: Piper excelsum (kawakawa) has a history of therapeutic use by Maori in Aotearoa New Zealand. It is currently widely consumed as a beverage and included as an ingredient in "functional" food product. Leaves contain compounds that are also found in a wide range of other spices, foods, and medicinal plants. This study investigates the human metabolism and excretion of kawakawa leaf chemicals. METHODS AND RESULTS: Six healthy male volunteers in one study (Bioavailability of Kawakawa Tea metabolites in human volunteers [BOKA-T]) and 30 volunteers (15 male and 15 female) in a second study (Impact of acute Kawakawa Tea ingestion on postprandial glucose metabolism in healthy human volunteers [TOAST]) consume a hot water infusion of dried kawakawa leaves (kawakawa tea [KT]). Untargeted Liquid Chromatography-Tandem Mass spectrometry (LC-MS/MS) analyses of urine samples from BOKA-T identified 26 urinary metabolites that are significantly associated with KT consumption, confirmed by the analysis of samples from the independent TOAST study. Seven of the 26 metabolites are also detected in plasma. Thirteen of the 26 urinary compounds are provisionally identified as metabolites of specific compounds in KT, eight metabolites are identified as being derived from specific compounds in KT but without resolution of chemical structure, and five are of unknown origin. CONCLUSIONS: Several kawakawa compounds that are also widely found in other plants are bioavailable and are modified by phase 1 and 2 metabolism.


Subject(s)
Phytochemicals , Piper , Humans , Chromatography, Liquid , Piper/metabolism , Plant Leaves , Tandem Mass Spectrometry , Phytochemicals/metabolism
2.
J Ethnopharmacol ; 308: 116293, 2023 May 23.
Article in English | MEDLINE | ID: mdl-36806346

ABSTRACT

ETHNOPHARMACOLOGICAL RELEVANCE: Piper wallichii (family: Piperaceae), a folk herbal medicine with anti-inflammatory and anti-thrombotic properties, has been traditionally used to treat rheumatic arthralgia, lumbocrural pain, gastrointestinal flatulence, and other intestinal diseases in China, Thailand, and India. However, there is no scientific report on the efficacy and potential mechanisms of Piper wallichii for ulcerative colitis (UC). AIM OF THE STUDY: The study aims to investigate the therapeutic effect and possible molecular mechanisms of the ethanol extract of Piper wallichii (EEPW) on DSS-induced UC in BALB/c mice. MATERIALS AND METHODS: The main components in EEPW were characterized by UPLC-QE-Orbitrap-MS. Subsequently, the anti-inflammatory effect of EEPW in vitro was preliminarily evaluated in RAW264.7 cells stimulated with LPS. UC model mice were triggered by free access to 4% DSS aqueous solution for 12 consecutive days, and simultaneously, EEPW (25, 50, and 100 mg/kg) and tofacitinib (positive control, 30 mg/kg) were orally administrated, respectively. The therapeutic efficacy of EEPW on UC was assessed by body weight, DAI, colon length, and pathological morphology. Besides, we investigated the effects of EEPW on intestinal barrier function, inflammatory factors, and immune systems of UC mice through immunohistochemistry (IHC), flow cytometry, and other techniques. Moreover, the expression of related proteins in the TLR4/NF-κB/COX-2 pathway was analyzed by Western blot. RESULTS: A total of 14 components were identified in the positive and negative modes, including isofutoquinol A (11), hancinone C (12), and futoquinol (14) which characterized by references. In the RAW264.7 cells experiments, the extract significantly suppressed the levels of TNF-α and IL-6. More importantly, EEPW distinctly improved the symptoms of DSS-induced UC mice as reflected by a significant recovery from body weight, colon length, pathological injuries of the colon, and so on. Further research found that EEPW remarkably restored the levels of occludin, promoted proliferation, and inhibited apoptosis in colon to maintain the integrity of intestinal barrier. In addition, the down-regulation of TNF-α and IL-1ß in colon, Th1 and Th17 cells in spleen, as well as the up-regulation of IL-10 in colon and Th2 cells in spleen were distinctly observed in EEPW-treated groups. Furthermore, the protein expression of TLR4, p-IκB-α, p-p65, and COX-2 were significantly inhibited by EEPW. CONCLUSIONS: This study confirmed for the first time that EEPW effectively ameliorated DSS-induced UC in mice, which might be related to improving intestinal barrier function, maintaining the levels of inflammatory factors, and regulating the immune system. In addition, we found that the anti-inflammatory effect of EEPW on UC mice was involved in the TLR4/NF-κB/COX-2 signaling pathway. In conclusion, Piper wallichii can be used as a candidate for the treatment of UC.


Subject(s)
Colitis, Ulcerative , Piper , Mice , Animals , Colitis, Ulcerative/drug therapy , NF-kappa B/metabolism , Toll-Like Receptor 4/metabolism , Cyclooxygenase 2/metabolism , Tumor Necrosis Factor-alpha/metabolism , Piper/metabolism , Signal Transduction , Colon , Anti-Inflammatory Agents/pharmacology , Dextran Sulfate , Disease Models, Animal , Mice, Inbred C57BL
3.
Nutrients ; 14(13)2022 Jun 28.
Article in English | MEDLINE | ID: mdl-35807865

ABSTRACT

The aim of the present study was to examine the effect of green tea extract containing Piper retrofractum fruit (GTP) on dextran-sulfate-sodium (DSS)-induced colitis, the regulatory mechanisms of microRNA (miR)-21, and the nuclear factor-κB (NF-κB) pathway. Different doses of GTP (50, 100, and 200 mg/kg) were administered orally once daily for 14 days, followed by GTP with 3% DSS for 7 days. Compared with the DSS-treated control, GTP administration alleviated clinical symptoms, including the disease activity index (DAI), colon shortening, and the degree of histological damage. Moreover, GTP suppressed miR-21 expression and NF-κB activity in colon tissue of DSS-induced colitis mice. The mRNA levels of inflammatory mediators, such as tumor necrosis factor-alpha (TNF-α), interleukin 6 (IL-6), interleukin-1ß (IL-1ß), inducible nitric oxide synthase (iNOS), and cyclooxygenase-2 (COX-2), were downregulated by GTP. Colonic nitric oxide (NO) and prostaglandin E2 (PGE2) production, and myeloperoxidase (MPO) activity were also lowered by GTP. Taken together, our results revealed that GTP inhibits DSS-induced colonic inflammation by suppressing miR-21 expression and NF-κB activity, suggesting that it may be used as a potential functional material for improving colitis.


Subject(s)
Colitis , MicroRNAs , Piper , Animals , Colitis/chemically induced , Colitis/drug therapy , Colitis/pathology , Dextran Sulfate/adverse effects , Disease Models, Animal , Fruit/metabolism , Guanosine Triphosphate/therapeutic use , Mice , MicroRNAs/genetics , NF-kappa B/metabolism , Piper/metabolism , Tea/adverse effects
4.
Nutrients ; 14(8)2022 Apr 14.
Article in English | MEDLINE | ID: mdl-35458200

ABSTRACT

Background: Piper excelsum (kawakawa) is an endemic shrub of Aotearoa, New Zealand, of cultural and medicinal importance to Maori. Its fruits and leaves are often consumed. These tissues contain several compounds that have been shown to be biologically active and which may underpin its putative health-promoting effects. The current study investigates whether kawakawa tea can modulate postprandial glucose metabolism. Methods: We report a pilot three-arm randomized crossover study to assess the bioavailability of kawakawa tea (BOKA-T) in six male participants with each arm having an acute intervention of kawakawa tea (4 g/250 mL water; 1 g/250 mL water; water) and a follow-up two-arm randomized crossover study to assess the impact of acute kawakawa tea ingestion on postprandial glucose metabolism in healthy human volunteers (TOAST) (4 g/250 mL water; and water; n = 30 (15 male and 15 female)). Participants consumed 250 mL of kawakawa tea or water control within each study prior to consuming a high-glycemic breakfast. Pre- and postprandial plasma glucose and insulin concentrations were measured, and the Matsuda index was calculated to measure insulin sensitivity. Results: In the BOKA-T study, lower plasma glucose (p < 0.01) and insulin (p < 0.01) concentrations at 60 min were observed after consumption of a high-dose kawakawa tea in comparison to low-dose or water. In the TOAST study, only plasma insulin (p = 0.01) was lower at 60 min in the high-dose kawakawa group compared to the control group. Both studies showed a trend towards higher insulin sensitivity in the high-dose kawakawa group compared to water only. Conclusions: Consuming kawakawa tea may modulate postprandial glucose metabolism. Further investigations with a longer-term intervention study are warranted.


Subject(s)
Insulin Resistance , Piper , Blood Glucose/metabolism , Cross-Over Studies , Female , Humans , Insulin , Male , Piper/metabolism , Postprandial Period , Tea , Water
5.
Molecules ; 27(4)2022 Feb 09.
Article in English | MEDLINE | ID: mdl-35208941

ABSTRACT

The Piper species are a recognized botanical source of a broad structural diversity of lignans and its derivatives. For the first time, Piper tectoniifolium Kunth is presented as a promising natural source of the bioactive (-)-grandisin. Phytochemical analyses of extracts from its leaves, branches and inflorescences showed the presence of the target compound in large amounts, with leaf extracts found to contain up to 52.78% in its composition. A new HPLC-DAD-UV method was developed and validated to be selective for the identification of (-)-grandisin being sensitive, linear, precise, exact, robust and with a recovery above 90%. The absolute configuration of the molecule was determined by X-ray diffraction. Despite the identification of several enantiomers in plant extracts, the major isolated substance was characterized to be the (-)-grandisin enantiomer. In vascular reactivity tests, it was shown that the grandisin purified from botanical extracts presented an endothelium-dependent vasorelaxant effect with an IC50 of 9.8 ± 1.22 µM and around 80% relaxation at 30 µM. These results suggest that P. tectoniifolium has the potential to serve as a renewable source of grandisin on a large scale and the potential to serve as template for development of new drugs for vascular diseases with emphasis on disorders related to endothelial disfunction.


Subject(s)
Furans/chemistry , Lignans/chemistry , Piper/chemistry , Plant Extracts/chemistry , Furans/metabolism , Lignans/metabolism , Piper/metabolism
6.
F1000Res ; 11: 1115, 2022.
Article in English | MEDLINE | ID: mdl-37151610

ABSTRACT

Mycoses or fungal infections are a general health problem that often occurs in healthy and immunocompromised people in the community. The development of resistant strains in Fungi and the incidence of azole antibiotic resistance in the Asia Pacific which reached 83% become a critical problem nowadays. To control fungal infections, substances and extracts isolated from natural resources, especially in the form of plants as the main sources of drug molecules today, are needed. Especially from Piperaceae, which have long been used in India, China, and Korea to treat human ailments in traditional medicine. The purpose of this review is to describe the antifungal mechanism action from Piper crocatum and its phytochemical profiling against lanosterol 14a demethylase CYP51. The methods used to search databases from Google Scholar to find the appropriate databases using Preferred Reporting Items for Systematic Reviews and Meta-analyses (PRISMA) Flow Diagram as a clinical information retrieval method. From 1.150.000 results searched by database, there is 73 final results article to review. The review shows that P. crocatum contains flavonoids, tannins, terpenes, saponins, polyphenols, eugenol, alkaloids, quinones, chavibetol acetate, glycosides, triterpenoids or steroids, hydroxychavikol, phenolics, glucosides, isoprenoids, and non-protein amino acids. Its antifungal mechanisms in fungal cells occur due to ergosterol, especially lanosterol 14a demethylase (CYP51) inhibition, which is one of the main target sites for antifungal activity because it functions to maintain the integrity and function of cell membranes in Candida. P. crocatum has an antifungal activity through its phytochemical profiling against fungal by inhibiting the lanosterol 14a demethylase, make damaging cell membranes, fungal growth inhibition, and fungal cell lysis.


Subject(s)
Antifungal Agents , Piper , Humans , Antifungal Agents/pharmacology , Sterol 14-Demethylase/chemistry , Sterol 14-Demethylase/metabolism , Lanosterol/chemistry , Piper/metabolism , Fungal Proteins/chemistry , Fungal Proteins/metabolism , Phytochemicals/pharmacology
7.
Molecules ; 26(11)2021 May 28.
Article in English | MEDLINE | ID: mdl-34071493

ABSTRACT

In this study, the antifungal potential of chemical constituents from Piper pesaresanum and some synthesized derivatives was determined against three phytopathogenic fungi associated with the cocoa crop. The methodology included the phytochemical study on the aerial part of P. pesaresanum, the synthesis of some derivatives and the evaluation of the antifungal activity against the fungi Moniliophthora roreri, Fusarium solani and Phytophthora sp. The chemical study allowed the isolation of three benzoic acid derivatives (1-3), one dihydrochalcone (4) and a mixture of sterols (5-7). Seven derivatives (8-14) were synthesized from the main constituents, of which compounds 9, 10, 12 and 14 are reported for the first time. Benzoic acid derivatives showed strong antifungal activity against M. roreri, of which 11 (3.0 ± 0.8 µM) was the most active compound with an IC50 lower compared with positive control Mancozeb® (4.9 ± 0.4 µM). Dihydrochalcones and acid derivatives were active against F. solani and Phytophthora sp., of which 3 (32.5 ± 3.3 µM) and 4 (26.7 ± 5.3 µM) were the most active compounds, respectively. The preliminary structure-activity relationship allowed us to establish that prenylated chains and the carboxyl group are important in the antifungal activity of benzoic acid derivatives. Likewise, a positive influence of the carbonyl group on the antifungal activity for dihydrochalcones was deduced.


Subject(s)
Antifungal Agents/pharmacology , Cacao/metabolism , Piper/metabolism , Agaricales/metabolism , Benzoic Acid/chemistry , Chalcones/chemistry , Chromatography , Fusarium/metabolism , Inhibitory Concentration 50 , Ions , Magnetic Resonance Spectroscopy , Molecular Structure , Phytochemicals , Phytophthora/metabolism , Structure-Activity Relationship
8.
Arch Microbiol ; 203(7): 4727-4736, 2021 Sep.
Article in English | MEDLINE | ID: mdl-34052872

ABSTRACT

Infectious diseases caused by multidrug-resistant microorganisms has increased in the last years. Piper species have been reported as a natural source of phytochemicals that can help in combating fungal and bacterial infections. This study had as objectives characterize the chemical composition of the essential oil from Piper caldense (EOPC), evaluate its potential antimicrobial activity, and investigate the synergistic effect with Norfloxacin against multidrug-resistant S. aureus overproducing efflux pumps, as well as, verify the EOPC ability to inhibit the Candida albicans filamentation. EOPC was extracted by hydrodistillation, and the chemical constituents were identified by gas chromatography, allowing the identification of 24 compounds (91.9%) classified as hydrocarbon sesquiterpenes (49.6%) and oxygenated sesquiterpenes (39.5%). Antimicrobial tests were performed using a 96-well plate microdilution method against C. albicans ATCC 10231, Escherichia coli ATCC 25922 and Staphylococcus aureus ATCC 25923 standard strains, as well as against multidrug-resistant strains S. aureus SA1199B (overexpressing norA gene), S. aureus K2068 (overexpressing mepA gene) and S. aureus K4100 (overexpressing qacC gene). The oil showed activity against C. albicans ATCC 10231 (≥ 512 µg/mL) and was able to inhibit hyphae formation, an important mechanism of virulence of C. albicans. On the other hand, EOPC was inactive against all bacterial strains tested (≤ 1,024 µg mL). However, when combined with Norfloxacin at subinhibitory concentration EOPC reduced the Norfloxacin and Ethidium bromide MIC values against S. aureus strains SA1199B, K2068 and K4100. These results indicate that EOPC is a source of phytochemicals acting as NorA, MepA and QacC inhibitors.


Subject(s)
Bacterial Proteins , Methicillin-Resistant Staphylococcus aureus , Norfloxacin , Oils, Volatile , Piper , Staphylococcus aureus , Anti-Bacterial Agents/pharmacology , Bacterial Proteins/genetics , Bacterial Proteins/metabolism , Microbial Sensitivity Tests , Multidrug Resistance-Associated Proteins , Norfloxacin/chemistry , Norfloxacin/pharmacology , Oils, Volatile/pharmacology , Piper/chemistry , Piper/metabolism , Staphylococcus aureus/drug effects , Staphylococcus aureus/genetics
9.
Molecules ; 26(6)2021 Mar 10.
Article in English | MEDLINE | ID: mdl-33802144

ABSTRACT

Piper, Capsicum, and Pimenta are the main genera of peppers consumed worldwide. The traditional use of peppers by either ancient civilizations or modern societies has raised interest in their biological applications, including cytotoxic and antiproliferative effects. Cellular responses upon treatment with isolated pepper-derived compounds involve mechanisms of cell death, especially through proapoptotic stimuli in tumorigenic cells. In this review, we highlight naturally occurring secondary metabolites of peppers with cytotoxic effects on cancer cell lines. Available mechanisms of cell death, as well as the development of analogues, are also discussed.


Subject(s)
Antineoplastic Agents, Phytogenic/pharmacology , Capsicum/metabolism , Pimenta/metabolism , Piper/metabolism , Antineoplastic Agents, Phytogenic/chemistry , Apoptosis/drug effects , Capsaicin/chemistry , Capsaicin/pharmacology , Capsicum/chemistry , Capsicum/drug effects , Humans , Pimenta/chemistry , Pimenta/drug effects , Piper/chemistry , Piper/drug effects , Vegetables/chemistry
10.
Z Naturforsch C J Biosci ; 76(5-6): 229-241, 2021 May 26.
Article in English | MEDLINE | ID: mdl-33660490

ABSTRACT

Species of Piperaceae are known by biological properties, including antiparasitic such as leishmanicidal, antimalarial and in the treatment of schistosomiasis. The aim of this work was to evaluate the antileishmania activity, cytotoxic effect, and macrophage activation patterns of the methanol (MeOH), hexane (HEX), dichloromethane (DCM) and ethyl acetate (EtOAc) extract fractions from the leaves of Piper cabralanum C.DC. The MeOH, HEX and DCM fractions inhibited Leishmanina amazonensis promastigote-like forms growth with a half maximal inhibitory concentration (IC50) of 144.54, 59.92, and 64.87 µg/mL, respectively. The EtOAc fraction did not show any relevant activity. The half maximal cytotoxic concentration (CC50) for macrophages were determined as 370.70, 83.99, 113.68 and 607 µg/mL for the MeOH, HEX and DCM fractions, respectively. The macrophage infectivity was concentration-dependent, especially for HEX and DCM. MeOH, HEX and DCM fractions showed activity against L. amazonensis with low cytotoxicity to murine macrophages and lowering infectivity by the parasite. Our results provide support for in vivo studies related to a potential application of P. cabralanum extract and fractions as a promising natural resource in the treatment of leishmaniasis.


Subject(s)
Antiprotozoal Agents/chemistry , Piper/chemistry , Plant Extracts/chemistry , Animals , Antiprotozoal Agents/isolation & purification , Antiprotozoal Agents/pharmacology , Cell Survival/drug effects , Cells, Cultured , Female , Hexanes/chemistry , Leishmania/drug effects , Leishmania/growth & development , Life Cycle Stages/drug effects , Liquid-Liquid Extraction , Macrophages/cytology , Macrophages/drug effects , Macrophages/metabolism , Male , Methylene Chloride/chemistry , Mice , Mice, Inbred BALB C , Nitric Oxide/metabolism , Phagocytosis/drug effects , Piper/metabolism , Plant Extracts/isolation & purification , Plant Extracts/pharmacology , Plant Leaves/chemistry , Plant Leaves/metabolism
11.
J Ethnopharmacol ; 264: 113262, 2021 Jan 10.
Article in English | MEDLINE | ID: mdl-32818574

ABSTRACT

ETHNOPHARMACOLOGICAL RELEVANCE: In the Peruvian Amazon as in the tropical countries of South America, the use of medicinal Piper species (cordoncillos) is common practice, particularly against symptoms of infection by protozoal parasites. However, there is few documented information about the practical aspects of their use and few scientific validation. The starting point of this work was a set of interviews of people living in six rural communities from the Peruvian Amazon (Alto Amazonas Province) about their uses of plants from Piper genus: one community of Amerindian native people (Shawi community) and five communities of mestizos. Infections caused by parasitic protozoa take a huge toll on public health in the Amazonian communities, who partly fight it using traditional remedies. Validation of these traditional practices contributes to public health care efficiency and may help to identify new antiprotozoal compounds. AIMS OF STUDY: To record and validate the use of medicinal Piper species by rural people of Alto Amazonas Province (Peru) and annotate active compounds using a correlation study and a data mining approach. MATERIALS AND METHODS: Rural communities were interviewed about traditional medication against parasite infections with medicinal Piper species. Ethnopharmacological surveys were undertaken in five mestizo villages, namely: Nueva Arica, Shucushuyacu, Parinari, Lagunas and Esperanza, and one Shawi community (Balsapuerto village). All communities belong to the Alto Amazonas Province (Loreto region, Peru). Seventeen Piper species were collected according to their traditional use for the treatment of parasitic diseases, 35 extracts (leaves or leaves and stems) were tested in vitro on P. falciparum (3D7 chloroquine-sensitive strain and W2 chloroquine-resistant strain), Leishmania donovani LV9 strain and Trypanosoma brucei gambiense. Assessments were performed on HUVEC cells and RAW 264.7 macrophages. The annotation of active compounds was realized by metabolomic analysis and molecular networking approach. RESULTS: Nine extracts were active (IC50 ≤ 10 µg/mL) on 3D7 P. falciparum and only one on W2 P. falciparum, six on L. donovani (axenic and intramacrophagic amastigotes) and seven on Trypanosoma brucei gambiense. Only one extract was active on all three parasites (P. lineatum). After metabolomic analyses and annotation of compounds active on Leishmania, P. strigosum and P. pseudoarboreum were considered as potential sources of leishmanicidal compounds. CONCLUSIONS: This ethnopharmacological study and the associated in vitro bioassays corroborated the relevance of use of Piper species in the Amazonian traditional medicine, especially in Peru. A series of Piper species with few previously available phytochemical data have good antiprotozoal activity and could be a starting point for subsequent promising work. Metabolomic approach appears to be a smart, quick but still limited methodology to identify compounds with high probability of biological activity.


Subject(s)
Antiprotozoal Agents/metabolism , Ethnopharmacology/methods , Medicine, Traditional/methods , Metabolomics/methods , Piper/metabolism , Plant Extracts/metabolism , Animals , Antimalarials/isolation & purification , Antimalarials/metabolism , Antimalarials/therapeutic use , Antiprotozoal Agents/isolation & purification , Antiprotozoal Agents/therapeutic use , Female , Human Umbilical Vein Endothelial Cells/drug effects , Human Umbilical Vein Endothelial Cells/metabolism , Humans , Leishmania donovani/drug effects , Leishmania donovani/metabolism , Mesocricetus , Mice , Peru/ethnology , Plant Extracts/isolation & purification , Plant Extracts/therapeutic use , Plasmodium falciparum/drug effects , Plasmodium falciparum/metabolism , RAW 264.7 Cells , Surveys and Questionnaires
12.
Food Chem ; 298: 125067, 2019 Nov 15.
Article in English | MEDLINE | ID: mdl-31260989

ABSTRACT

An ultra-high performance supercritical fluid chromatography-photodiode array detection-mass spectrometry (UHPSFC-MS) method for quality control of Piper longum L. has been developed and optimized. Hexane/isopropanol (70/30, v/v) was determined as the final injection solvent and methanol as the organic modifier. A design-of-experimental (DoE) approach was used to optimize column temperature, back-pressure and the gradient slope simultaneously using Trefoil CEL1 column. The back-pressure, temperature, flow rate were set at 130 bar, 32.5 °C and 1.0 mL/min, respectively. Positive electrospray ionization was used in the single ion monitoring mode. The 12 analytes were analyzed within 8 min using the optimized conditions. The linearities of the standard calibrations were satisfactory with coefficients of determination (R2) > 0.995. The recovery measured varied from 96.34% to 105.00% with relative standard deviation (RSD) ≤ 4.68%. The method was sensitive, reliable and effective, and successfully applied to simultaneous determination of 12 compounds in 28 batches of P. longum.


Subject(s)
Alkaloids/chemistry , Chromatography, Supercritical Fluid/methods , Piper/chemistry , Alkaloids/isolation & purification , Benzodioxoles/chemistry , Benzodioxoles/isolation & purification , Chromatography, High Pressure Liquid , Chromatography, Supercritical Fluid/standards , Fruit/chemistry , Fruit/metabolism , Limit of Detection , Mass Spectrometry , Methanol/chemistry , Piper/metabolism , Piperidines/chemistry , Piperidines/isolation & purification , Polyunsaturated Alkamides/chemistry , Polyunsaturated Alkamides/isolation & purification , Principal Component Analysis , Quality Control , Solvents/chemistry , Temperature
13.
Biotech Histochem ; 94(7): 498-513, 2019 Oct.
Article in English | MEDLINE | ID: mdl-31064227

ABSTRACT

Essential oils are a promising alternative to insecticides. We investigated the LD50 of oils extracted from Piper corcovadensis, P. marginatum, and P. arboreum after 48 h topical contact with Spodoptera frugiperda larvae using morphometry, histochemistry and immunohistochemistry of the midgut and fat body. Chromatography revealed that E-caryophyllene was the principal compound common to the Piper species. The essential oils of P. corcovadensis, P. marginatum and P. arboreum caused deleterious changes in the midgut of S. frugiperda larvae. P. corcovadensis oil produced the lowest LD50 and significant histopathological alterations including elongation of the columnar cells, formation of cytoplasmic protrusions, reduction in carbohydrate, increased apoptotic index and decreased cell proliferation. P. arboreum oil caused histopathological alterations similar to P. corcovadensis, but caused the highest rate of cell proliferation and increased regenerative cells, which indicated rapid regeneration of the epithelium. Our findings demonstrated the insecticidal potential of P. corcovadensis for control of S. frugiperda owing to the significant damage it inflicted on S. frugiperda midgut.


Subject(s)
Fat Body/drug effects , Fat Body/pathology , Oils, Volatile/pharmacology , Piper/metabolism , Animals , Digestive System/metabolism , Digestive System/pathology , Fat Body/metabolism , Insecticides/metabolism , Insecticides/pharmacology , Larva/drug effects , Oils, Volatile/chemistry , Piper/chemistry , Plant Oils/metabolism , Plant Oils/pharmacology , Spodoptera
14.
Magn Reson Chem ; 57(12): 994-1070, 2019 12.
Article in English | MEDLINE | ID: mdl-30779382

ABSTRACT

Alkamides are the major and characteristic chemical compounds of the plants belonging to the Piper genus. These compounds are responsible for the flavor of pepper spices and for its broad use in cuisine across many regions of the world. Humans are in contact every day with these substances, which additionally show a broad variety of pharmacological activities, making them an important research target. A large amount of NMR data for these natural products is dispersed throughout literature. Its organization will help those research groups interested in their identification and structural elucidation. This review summarizes the 1 H and 13 C NMR data of 268 Piper amides in a systematic and orderly way, with a discussion on their biological activities, biosynthetic aspects, and NMR analysis of typical and relevant aspects of this information.


Subject(s)
Amides/analysis , Piper/chemistry , Amides/metabolism , Carbon-13 Magnetic Resonance Spectroscopy , Molecular Structure , Piper/metabolism , Proton Magnetic Resonance Spectroscopy
15.
Braz. j. biol ; 78(1): 117-124, Feb. 2018. tab, graf
Article in English | LILACS | ID: biblio-888838

ABSTRACT

Abstract Piper tuberculatum (Piperaceae) is a species that accumulates especially amides as secondary metabolites and several biological activities was previously reported. In this article, we report a proteomic study of P. tuberculatum. Bidimensional electrophoresis (2D SDS-PAGE) and mass spectrometry (ESI-Q-TOF) were used in this study. Over a hundred spots and various peptides were identified in this species and the putative functions of these peptides related to defense mechanism as biotic and abiotic stress were assigned. The information presented extend the range of molecular information of P. tuberculatum.


Resumo Piper tuberculatum (Piperaceae) é uma espécie que acumula especialmente amidas como metabólitos secundários e diversas atividades biológicas dessa espécie foram relatadas anteriormente. No presente artigo, relatamos um estudo proteômico dessa espécie. Eletroforese bidimensional (2D SDS-PAGE) e espectrometria de massas (ESI-Q-TOF) foram utilizadas nesse estudos. Mais de cem spots e vários peptídeos foram identificados nesta espécie e as funções putativas desses peptídeos relacionadas a mecanismo de defesa como estresse biótico e abiótico foram atribuídos. As informações apresentadas ampliam a gama de informações moleculares dessa espécie.


Subject(s)
Plant Proteins/analysis , Proteome/analysis , Piper/chemistry , Plant Proteins/physiology , Plant Proteins/chemistry , Electrophoresis, Gel, Two-Dimensional , Proteome/physiology , Proteome/chemistry , Spectrometry, Mass, Electrospray Ionization , Piper/physiology , Piper/metabolism , Proteomics
16.
Appl Biochem Biotechnol ; 184(3): 987-1008, 2018 Mar.
Article in English | MEDLINE | ID: mdl-28933036

ABSTRACT

The oomycetes, Phytophthora capsici, cause foot rot disease in black pepper. Piper colubrinum Link, a distant relative of cultivated black pepper, is highly resistant to this destructive pathogen. Identification of resistance (R) genes in P. colubrinum and the study of its expression profile during interaction with the pathogen can help in understanding the resistance mechanism involved. In the present study, 1289 R gene-related transcripts were mined from P. colubrinum transcriptome, clustered, and classified according to the conserved motifs and domains. Transcripts belonging to four major R gene classes were identified in P. colubrinum, but TIR-NBS-LRR-type R genes were absent. The relative expression of 12 selected R genes was studied using two virulent isolates of P. capsici, and these were found to be upregulated in the initial hours of plant pathogen interaction. The R genes studied were expressed even in aseptically maintained tissue-cultured plants and uninoculated greenhouse-grown plants at basal level suggesting that the plants are geared up with the R gene all the time and are under continuous surveillance for the pathogen and basal level of R gene expression do not require a pathogen trigger. ACT, ATUB, and EIF3E were identified as the most stable reference genes that can be used for real-time PCR study. The present study identified promising R genes in P. colubrinum which can be used in developing Phytophthora-resistant black pepper.


Subject(s)
Disease Resistance/physiology , Gene Expression Regulation, Plant , Phytophthora , Piper , Plant Diseases/microbiology , Plant Leaves , Transcriptome , Piper/genetics , Piper/metabolism , Piper/microbiology , Plant Leaves/genetics , Plant Leaves/metabolism , Plant Leaves/microbiology
17.
Curr Med Chem ; 25(37): 4918-4928, 2018.
Article in English | MEDLINE | ID: mdl-28545378

ABSTRACT

Recently many studies showed anticancer activities of piperine, a pungent alkaloid found in black pepper and some other Piper species. We attempted to summarize acquired data that support anticancer potential of this natural agent. Piperine has been reported to possess effective chemopreventive activity. It has been studied to affect via several mechanisms of action, in brief enhancing antioxidant system, increasing level and activity of detoxifying enzymes and suppressing stem cell self-renewal. Moreover, piperine has been found to inhibit proliferation and survival of various cancerous cell lines via modulating cell cycle progression and exhibiting anti-apoptotic activity, respectively. This compound has been shown to modify activity of various enzymes and transcription factors to inhibit invasion, metastasis and angiogenesis. Interestingly, piperine has exhibited antimutagenic activity and also inhibited activity and expression of multidrug resistance transporters such as P-gp and MRP-1. Besides, about all reviewed studies have reported selective cytotoxic activity of piperine on cancerous cells in compared with normal cells. Altogether, the studies completely underline promising candidacy of piperine for further development. The collected preclinical data we provided in this article can be useful in the design of future researches especially clinical trials with piperine.


Subject(s)
Alkaloids/therapeutic use , Anticarcinogenic Agents/therapeutic use , Antineoplastic Agents, Phytogenic/therapeutic use , Benzodioxoles/therapeutic use , Piperidines/therapeutic use , Polyunsaturated Alkamides/therapeutic use , Alkaloids/biosynthesis , Alkaloids/metabolism , Alkaloids/pharmacology , Animals , Anticarcinogenic Agents/pharmacokinetics , Antimutagenic Agents/pharmacology , Antineoplastic Agents, Phytogenic/pharmacokinetics , Antioxidants/pharmacology , Benzodioxoles/metabolism , Benzodioxoles/pharmacology , Biological Availability , Cell Proliferation/drug effects , Cell Survival/drug effects , Drug Evaluation, Preclinical , Drug Resistance, Multiple/drug effects , Drug Resistance, Neoplasm/drug effects , Humans , Inactivation, Metabolic/drug effects , Neoplasm Invasiveness/prevention & control , Neoplasm Metastasis/prevention & control , Neoplasms/blood supply , Neoplasms/drug therapy , Neoplasms/pathology , Neoplasms/prevention & control , Neovascularization, Pathologic/prevention & control , Piper/metabolism , Piperidines/metabolism , Piperidines/pharmacology , Polyunsaturated Alkamides/metabolism , Polyunsaturated Alkamides/pharmacology , Stem Cells/cytology , Stem Cells/drug effects
18.
Braz J Biol ; 78(1): 117-124, 2018 Feb.
Article in English | MEDLINE | ID: mdl-28699966

ABSTRACT

Piper tuberculatum (Piperaceae) is a species that accumulates especially amides as secondary metabolites and several biological activities was previously reported. In this article, we report a proteomic study of P. tuberculatum. Bidimensional electrophoresis (2D SDS-PAGE) and mass spectrometry (ESI-Q-TOF) were used in this study. Over a hundred spots and various peptides were identified in this species and the putative functions of these peptides related to defense mechanism as biotic and abiotic stress were assigned. The information presented extend the range of molecular information of P. tuberculatum.


Subject(s)
Piper/chemistry , Plant Proteins/analysis , Proteome/analysis , Electrophoresis, Gel, Two-Dimensional , Piper/metabolism , Piper/physiology , Plant Proteins/chemistry , Plant Proteins/physiology , Proteome/chemistry , Proteome/physiology , Proteomics , Spectrometry, Mass, Electrospray Ionization
19.
An. acad. bras. ciênc ; 89(2): 1167-1174, Apr.-June 2017. graf
Article in English | LILACS | ID: biblio-886713

ABSTRACT

ABSTRACT Piper hispidinervum C. DC. is popularly known as long-pepper and it owns a commercial value due to the essential oil it produces. Long-pepper oil is rich in safrole and eugenoln components that have insecticidal, fungicidal and bactericidal activity. It has been establish that to medicinal plants light influences not only growth but also essential oil production. The growth, the content of photosynthetic pigments and the essential oil production of Piper hispidinervum at greenhouses with different light conditions was evaluated. The treatments were characterized by cultivation of plants for 180 days under different light conditions, produced by shading greenhouses with 50% and 30% of natural incident irradiance, two colored shading nets red (RN) and blue (BN) both blocking 50% of the incident radiation and one treatment at full-sun (0% of shade). The results showed that the treatments of 50% shade and RN and BN were the ones which stimulated the greater growth. Blue and red light also had the best production of photosynthetic pigments. Essential oil yielded more under full sun therefore this is the most indicated condition to produce seedlings for the chemical and pharmaceutical industry.


Subject(s)
Photosynthesis/physiology , Sunlight , Oils, Volatile/metabolism , Piper/growth & development , Piper/radiation effects , Piper/metabolism , Photosynthesis/radiation effects , Time Factors , Chlorophyll/analysis , Chlorophyll/metabolism , Reproducibility of Results , Plant Leaves/growth & development , Plant Leaves/radiation effects , Plant Leaves/metabolism
20.
An Acad Bras Cienc ; 89(2): 1167-1174, 2017.
Article in English | MEDLINE | ID: mdl-28489190

ABSTRACT

Piper hispidinervum C. DC. is popularly known as long-pepper and it owns a commercial value due to the essential oil it produces. Long-pepper oil is rich in safrole and eugenoln components that have insecticidal, fungicidal and bactericidal activity. It has been establish that to medicinal plants light influences not only growth but also essential oil production. The growth, the content of photosynthetic pigments and the essential oil production of Piper hispidinervum at greenhouses with different light conditions was evaluated. The treatments were characterized by cultivation of plants for 180 days under different light conditions, produced by shading greenhouses with 50% and 30% of natural incident irradiance, two colored shading nets red (RN) and blue (BN) both blocking 50% of the incident radiation and one treatment at full-sun (0% of shade). The results showed that the treatments of 50% shade and RN and BN were the ones which stimulated the greater growth. Blue and red light also had the best production of photosynthetic pigments. Essential oil yielded more under full sun therefore this is the most indicated condition to produce seedlings for the chemical and pharmaceutical industry.


Subject(s)
Oils, Volatile/metabolism , Photosynthesis/physiology , Piper/growth & development , Piper/metabolism , Piper/radiation effects , Sunlight , Chlorophyll/analysis , Chlorophyll/metabolism , Photosynthesis/radiation effects , Plant Leaves/growth & development , Plant Leaves/metabolism , Plant Leaves/radiation effects , Reproducibility of Results , Time Factors
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