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At least 127 records · Page 7Linked to original sources
PubMed2005

Nigramides A-S, dimeric amide alkaloids from the roots of Piper nigrum.

[structure: see text] Fifteen novel dimeric amide alkaloids possessing a cyclohexene ring, nigramides A-O (1-15), as well as four novel dimeric amide alkaloids possessing a cyclobutane ring, nigramides P-S (17-20), have been isolated from the roots of Piper nigrum. Their structures were elucidated on the basis of their spectroscopic data. The biosynthestic hypothesis of nigramides A-O (1-15) was proposed by an intermolecular Diels-Alder reaction from the corresponding monomeric amides. On the basis of this biosynthetic hypothesis, the first study of the thermal and Lewis acid mediated Diels-Alder reactions of piperine in different organic solvents and under solventless conditions is also described.

Alkaloids↗
PubMed2004

New amide alkaloids from the roots of Piper nigrum.

Seven new amide alkaloids, named N-isobutyl-4-hexanoyl-4-hydroxypyrrolidin-1-one (1), (+/-)-erythro-1-(1-oxo-4,5-dihydroxy-2E-decaenyl)piperidine (2), (+/-)-threo-1-(1- oxo-4,5-dihydroxy-2E-decaenyl)piperidine (3), (+/-)-threo-N-isobutyl-4,5-dihydroxy-2E-octaenamide (4), 1-(1,6-dioxo-2E,4E-decadienyl)piperidine (5), 1-[1-oxo-3(3,4-methylenedioxy-5-methoxyphenyl)-2Z-propenyl]piperidine (6), and 1-[1-oxo-5(3,4-methylenedioxyphenyl)-2Z,4E-pentadienyl]pyrrolidine (7), were isolated from the roots of Piper nigrum, together with 32 known amides. Their structures were elucidated on the basis of spectroscopic analysis and chemical evidence.

Alkaloids↗
PubMed2004

Benzoic acid derivatives from Piper species and their fungitoxic activity against Cladosporium cladosporioides and C. sphaerospermum.

Piper crassinervium, P. aduncum, P. hostmannianum, and P. gaudichaudianum contain the new benzoic acid derivatives crassinervic acid (1), aduncumene (8), hostmaniane (18), and gaudichaudianic acid (20), respectively, as major secondary metabolites. Additionally, 19 known compounds such as benzoic acids, chromenes, and flavonoids were isolated and identified. The antifungal activity of these compounds was evaluated by bioautographic TLC assay against Cladosporium cladosporioides and C. sphaerospermum.

Antifungal Agents↗
PubMed2004

A DNA-damaging oxoaporphine alkaloid from Piper caninum.

Bioassay-guided fractionation of an active organic extract of Piper caninum, using a sensitive yeast assay to monitor putative double-strand DNA-damaging activity, resulted in the isolation of the 4,5-dioxoaporphine alkaloid cepharadione A (1). Compound 1 exhibited potent inhibitory activity in a yeast cytotoxicity assay with IC(50) values of 50.2 nM toward RS321NpRAD52 grown on glucose versus 293 nM toward the same yeast strain grown on galactose.

Alkaloids↗
PubMed2004

Antimycobacterial compounds from Piper sanctum.

Bioassay-guided chromatographic separation of the antimycobacterial extract of the leaves of Piper sanctum afforded 14 new compounds, identified as 2-oxo-12-(3',4'-methylenedioxyphenyl)dodecane (1), 2-oxo-14-(3',4'-methylenedioxyphenyl)tetradecane (2), 2-oxo-16-(3',4'-methylenedioxyphenyl)hexadecane (3), 2-oxo-18-(3',4'-methylenedioxyphenyl)octadecane (4), 2-oxo-14-(3',4'-methylenedioxyphenyl)-trans-13-tetradecene (5), 2-oxo-16-(3',4'-methylenedioxyphenyl)-trans-15-hexadecene (6), 2-oxo-18-(3',4'-methylenedioxyphenyl)-trans-17-octadecene (7), 2-oxo-16-phenyl-trans-3-hexadecene (8), methyl [6-(10-phenyldecanyl)tetrahydropyran-2-yl]acetate (9), methyl 2-(6-tridecyltetrahydro-2H-pyran-2-yl)acetate (10), methyl 2-(5-tetradecyltetrahydro-2-furanyl)acetate (11), 2-oxo-14-(3',4'-methylenedioxyphenyl)-trans-3-tetradecene (12), 2-oxo-16-(3',4'-methylenedioxyphenyl)-trans-3-hexadecene (13), and 2-oxo-16-phenyl-3-hexadecane (14). In addition, p-eugenol (15), methyleugenol (16), Z-piperolide (17), demethoxyyangonin (18), 5,6-dehydro-7,8-dihydromethysticin (19), cepharanone B (20), piperolactam A (21), cepharadione B (22), N-trans-feruloyltyramine (23), and N-trans-(p-coumaroyl)tyramine (24) were obtained from the anti-TBC stem extract of the plant. GC-MS and HPLC analyses of the essential oils of the leaves and stem revealed that safrol (25) was the major component of the oils. Compounds 2, 3, 6, 18-21, and 24 inhibited the growth of Mycobacterium tuberculosis when tested by the MABA assay, with MIC values ranging from 4 to 64 microg/mL.

Alkanes↗
PubMed2005

Potent CYP3A4 inhibitory constituents of Piper cubeba.

The EtOAc-soluble fraction of the water extract of Piper cubeba, having shown potent inhibitory activity on the metabolism mediated by CYP3A4, was subjected to activity-guided isolation to yield two new lignans, (8R,8'R)-4-hydroxycubebinone (1) and (8R,8'R,9'S)-5-methoxyclusin (2), and two new sesquiterpenes, (5 alpha,8 alpha)-2-oxo-1(10),3,7(11)-guaiatrien-12,8-olide (3) and (1 alpha,2 beta,5 alpha,8 alpha 10 alpha)-1,10-epoxy-2-hydroxy-3,7(11)-guaiadien-12,8-olide (4), along with 16 known compounds (5-20). The structures of the isolated compounds were elucidated on the basis of spectroscopic and chemical analyses. The isolated compounds were tested for their inhibitory activity on the metabolism mediated by CYP3A4 or CYP2D6 using [N-methyl-(14)C]erythromycin or [O-methyl-(14)C]dextromethorphan as a substrate, respectively. The compounds (8R,8'R,9'S)-5-methoxyclusin (2), (-)-clusin (10), (-)-yatein (13), ethoxyclusin (15), and (-)-dihydroclusin (17), having one methylenedioxyphenyl moiety in their structures, showed very potent and selective inhibitory activity against CYP3A4 with IC(50) values (0.44-1.0 microM) identical to that of the positive control, ketoconazole (IC(50), 0.72 microM).

Cytochrome P-450 CYP2D6 Inhibitors↗
PubMed2005

Synthesis of arieianal, a prenylated benzoic acid from Piper arieianum.

Arieianal (1) is a complex prenylated benzoic acid that was isolated from Piper arieianum. It has been synthesized through a convergent sequence that joins a functionalized diterpenoid chain to a protected aromatic core. Key steps include use of a copper enolate for selective displacement of an allylic bromide in the presence of an allylic acetate and a stereoselective Horner-Wadsworth-Emmons condensation to afford the desired E olefin of the isoprenoid side chain. After the diterpenoid chain was joined to the aromatic ring, use of sodium metal in hot sBuOH allowed selective cleavage of two benzyl ether protecting groups, and a sequence of oxidations gave the target compound. This synthesis confirms the structure assigned to the natural product and establishes a route that may be used to prepare more active analogues.

Benzoates↗
PubMed2006

Anti-inflammatory neolignans from Piper kadsura.

Two new neolignans, piperkadsin A (1) and piperkadsin B (2), as well as 11 known neolignans, three known alkaloids, the highly oxygenated compound (+)-crotepoxide, and stigmasterol were isolated from the stems of Piper kadsura. The anti-inflammatory activities of these compounds were evaluated. Compounds 1, 2, futoquinol (3), piperlactam S (4), and N-p-coumaroyl tyramine (5) showed potent inhibition of PMA-induced ROS production in human polymorphonuclear neutrophils with IC(50) values 4.3 +/-1.0, 12.2 +/- 3.2, 13.1 +/- 5.3, 7.0 +/- 1.9, and 8.4 +/- 1.3 microM, respectively.

Anti-Inflammatory Agents, Non-Steroidal↗
PubMed2003

Synergistic effects of three Piper amides on generalist and specialist herbivores.

The tropical rainforest shrub Piper cenocladum, which is normally defended against herbivores by a mutualistic ant, contains three amides that have various defensive functions. While the ants are effective primarily against specialist herbivores, we hypothesized that these secondary compounds would be effective against a wider range of insects, thus providing a broad array of defenses against herbivores. We also tested whether a mixture of amides would be more effective against herbivores than individual amides. Diets spiked with amides were offered to five herbivores: a naïve generalist caterpillar (Spodoptera frugiperda), two caterpillar species that are monophagous on P. cenocladum (Eois spp.), leaf-cutting ants (Atta cephalotes), and an omnivorous ant (Paraponera clavata). Amides had negative effects on all insects, whether they were naïve, experienced, generalized, or specialized feeders. For Spodoptera, amide mixtures caused decreased pupal weights and survivorship and increased development times. Eois pupal weights, larval mass gain, and development times were affected by additions of individual amides, but increased parasitism and lower survivorship were caused only by the amide mixture. Amide mixtures also deterred feeding by the two ant species, and crude plant extracts were strongly deterrent to P. clavata. The mixture of all three amides had the most dramatic deterrent and toxic effects across experiments, with the effects usually surpassing expected additive responses, indicating that these compounds can act synergistically against a wide array of herbivores.

Amides↗
PubMed2005

Expeditious synthesis of bioactive allylphenol constituents of the genus Piper through a metal-free photoallylation procedure.

Nine bioactive allylphenol (anisole) derivatives (e.g. eugenol, safrole and asaricin) present in several plants of the genus Piper have been synthesized in medium to high yield via aryl cation intermediates. This expeditious metal-free procedure involves the irradiation of the corresponding chlorophenols or chloroanisoles in a polar solvent (MeCN or, better, TFE or aqueous acetonitrile) in the presence of allyltrimethylsilane. Estragole has also been synthesized starting from the corresponding fluoroderivative and diazonium salt, though in a lower yield.

Metals↗
PubMed2002

Larvicidal effects of mineral turpentine, low aromatic white spirits, aqueous extracts of Cassia alata, and aqueous extracts, ethanolic extracts and essential oil of betel leaf (Piper betle) on Chrysomya megacephala.

BACKGROUND: Many methods have been employed, with variable success, in the treatment of cutaneous myiasis caused by Chrysomya species. AIMS: Experiment 1: to assess the larvicidal effect of mineral turpentine (MT) and the main ingredient of MT, low aromatic white spirits (LAWS), on Chrysomya megacephala larvae in vitro. Experiment 2: to assess the larvicidal effects of aqueous extracts of winged senna (Cassia alata), and aqueous extracts, ethanolic extracts and essential oil of betel leaf (Piper betle). METHODS: In experiment 1, two samples of LAWS were obtained from two industrialists (samples 1 and 2). Adult flies of C. megacephala were bred in the insectory of the Department of Parasitology, Faculty of Medicine, University of Colombo. Petri dishes were prepared with pads of cotton wool. These cotton pads were soaked separately in MT, LAWS samples 1 and 2, and normal saline as a control. Ten larvae were placed in each Petri dish. The activity of the larvae was observed and recorded half-hourly. MT and the two samples of LAWS were analyzed by chromatography. In experiment 2, volatile essential oil of betel was prepared using a standard steam distillation process. An ethanolic extract of betel was obtained after boiling the crushed leaf with water, and mixing the stock with ethanol. Betel oil dilutions of 1-4% were prepared using 1% Tween 80 (v/v aq) as a solvent, with 0.05 g/100 mL sodium lauryl sulphate (as stabilizer) and 0.01 g/100 mL methyl paraben (as a preservative). Cotton wool swabs soaked in 1, 2, 3 and 4% essential oil of betel in 1% Tween 80 (v/v aq) prepared as above, 1, 2, 3 and 4% ethanolic extract of betel, 50 and 25% aqueous extract of C. alata, and 50 and 25% aqueous extract of betel were placed in separate Petri dishes. Ten larvae were placed in each Petri dish. 1% Tween 80 solvent with the stabilizer and the preservative, but without betel essential oil, was used as a negative control and MT was used as a positive control. Larval motility was assessed as before. RESULTS: MT and the two LAWS samples killed the larvae in vitro within 4 h. Chromatography showed more unidentified constituents in MT than in pure LAWS, indicating additional substances in MT. The 4 and 3% preparations of the essential oil of betel were effective in killing 100% of the larvae of Chrysomya within 3 h 30 min. The 2% extract of betel essential oil killed 96.7% of larvae in 4 h. Ethanolic and aqueous extracts of betel, the aqueous extract of C. alata, normal saline and the Tween 80 solvent were not larvicidal. CONCLUSIONS: MT and LAWS, the main ingredient of MT, were effective in killing Chrysomya larvae. Essential oil obtained from betel leaves also showed a dose-dependent larvicidal effect on Chrysomya larvae. This natural product may be effective in the treatment of wound myiasis.

Animals↗
PubMed2002

Chabamide, a novel piperine dimer from stems of Piper chaba.

A novel piperine dimer, named chabamide, was isolated from stems of Piper chaba Hunter and its structure was elucidated on the basis of spectroscopic evidence. Chabamide showed antimalarial activity with an IC(50) value of 2.7 microg/ml and antituberculosis activity with the minimum inhibitory concentration (MIC) of 12.5 microg/ml.

Alkaloids↗
PubMed2002

Cytotoxic amides from Piper sintenense.

A new alkaloid, pipersintenamide ( 1), together with fourteen known compounds, have been isolated from the whole plant of Piper sintenense. The structures of these compounds were elucidated by spectroscopic analysis. Pipersintenamide, sintenpyridone, sarmentine, and 1-(3,4-methylenedioxyphenyl)-1 E-dodecene at 20 microg/ml exhibited effective cytotoxicities (cell survival < 15 %) against CCRF-CEM, HL-60, PC-3, and HA22T cell lines.

Alkenes↗
PubMed2004

A new aristolactam alkaloid and anti-platelet aggregation constituents from Piper taiwanense.

A new alkaloid, piperolactam E, and fourteen known compounds have been isolated from the stem of Piper taiwanense. Bioassay-guided fractionation of the methanolic extract led to the isolation, from the chloroform-soluble part, of 4-allylcatechol, eugenol, trans-caffeic aldehyde, 2-hydroxy-1-methoxy-4 H-dibenzo[ de,g]quinoline-4,5-(6 H)-dione, piperolactam B, piperolactam C, and piperolactam E as the active principles of anti-platelet aggregation in vitro. The derived 1,2-diacetoxy-4-allyl-benzene and eugenol acetate exhibit stronger anti-platelet aggregation activities induced by arachidonic acid than 4-allylcatechol and eugenol, respectively.

Alkaloids↗
PubMed2004

Piperlonguminine from Piper longum with inhibitory effects on alpha-melanocyte-stimulating hormone-induced melanogenesis in melanoma B16 cells.

Skin hyperpigmentations such as melasma, freckles and senile lentigines can be subjectively treated by depigmenting agents. In our ongoing study to find melanogenesis inhibitors from natural sources, Piper longum L (fruits, Piperaceae) was discovered to have an inhibitory effect on alpha-melanocyte-stimulating hormone (alpha-MSH)-induced melanogenesis in melanoma B16 cells. Piperlonguminine has been identified as the melanogenesis inhibitor from P. longum by activity-guided extraction and isolation. The compound showed dose-dependent inhibitory effects with 85.1 +/- 4.9% inhibition at 25 microM, 62.1 +/- 6.1% at 12.5 microM, 36.4 +/- 4.6% at 6.3 microM and 18.4 +/- 5.1% at 3.1 microM on alpha-MSH-induced melanogenesis, showing an IC50 value of 9.6 microM. As a positive control, kojic acid exhibited an IC50 value of 44.6 microM on the melanogenesis. As to the mode of action, piperlonguminine showed an inhibitory effect on alpha-MSH-induced tyrosinase synthesis, documented by Western immunoblot analysis. However, piperlonguminine did not show an inhibitory effect on tyrosinase activity or a direct depigmenting effect of melanin.

Animals↗
PubMed2005

New cytotoxic cyclobutanoid amides, a new furanoid lignan and anti-platelet aggregation constituents from Piper arborescens.

Three new cyclobutanoid amides with trans-trans-trans configurations, piperarborenine C, piperarborenine D and piperarborenine E, and a new furanoid lignan, (+)-arborone, together with twelve known compounds, were isolated from the stems of Piper arborescens. The structures of these new compounds were determined by means of spectral analyses. Piperarborenine C, (+)-diayangambin, piplartine, piperolactam B, piperolactam C, aristolactam BIII, goniothalactam, and methyl trans-3,4,5-trimethoxycinnamate possessed anti-platelet aggregation activity in vitro. Among them, piplartine showed the most potent anti-platelet aggregation activity induced by collagen and showed an IC50 value of 21.5 microM. Piperarborenines A - E, piperarborenine, aristololactam BIII and goniothalactam showed significant cytotoxic activity (IC50 values < 4 microg/mL) against P-388, HT-29 and A549 cell lines in vitro.

Animals↗
PubMed2006

Mechanism-based inhibition of human liver microsomal cytochrome P450 2D6 (CYP2D6) by alkamides of Piper nigrum.

Nineteen alkamides isolated from Piper nigrum L. were tested for their mechanism-based inhibition on human liver microsomal dextromethorphan O-demethylation activity, a prototype marker for cytochrome P450 2D6 (CYP2D6). All compounds increased their inhibitory activity with increasing preincubation time. Among them, 15 and 17 showed more than 50 % decrease of the CYP2D6 residual activity after 20 min preincubation. Further investigations on 15 and 17 showed that the characteristic time- and concentration-dependent inhibition, which required a catalytic step with NADPH, was not protected by nucleophiles, and was decreased by the presence of a competitive inhibitor. The kinetic parameters for inactivation (kinact and KI) were 0.028 min-1 and 0.23 microM for 15 and 0.064 min-1 and 0.71 microM for 17, respectively, which were stronger than the known mechanism-based inhibitor, paroxetine (a positive control). Thus, 15 and 17 are potent mechanism-based inhibitors of CYP2D6.

Amides↗