4,5-Dihydropiperlonguminine

Local Anesthetic Activity from Extracts, Fractions and Pure Compounds from the Roots of Ottonia anisum Spreng. (Piperaceae).[Pubmed:27991959]

An Acad Bras Cienc. 2016 Oct-Dec;88(4):2229-2237.

Piperaceae species can be found worldwide in tropical and subtropical areas and many of them have been used for centuries in traditional folk medicine and in culinary. In Brazil, species of Piperaceae are commonly used in some communities as local anesthetic and analgesic. Countrified communities have known some species of the genus Ottonia as "anestesia" and it is a common habit of chewing leaves and roots of Ottonia species to relief toothache. The purpose of this study is to report our findings on new molecules entities obtained from the roots of Ottonia anisum Spreng, in which local anesthetic activity (sensory blockage) is demonstrated for the first time in vivo guinea pig model. Phytochemical investigation led to the isolation of three amides (pipercallosidine, piperine and valeramide) and in an enriched mixture of seven amides (valeramide, 4,5-Dihydropiperlonguminine, N-isobutil-6-piperonil-2-hexenamide, piperovatine, dihydropipercallosidine, pipercallosidine and pipercallpsine). Our findings demonstrated the anesthetic potential for the methanolic extract from roots, its n-hexane partition and amides from O. anisum and it is in agreement with ethnobotanical survey.

Isobutyl amides--potent compounds for controlling Diatraea saccharalis.[Pubmed:18785219]

Pest Manag Sci. 2009 Jan;65(1):47-51.

BACKGROUND: A dichloromethane-methanol extract of the seeds of Piper tuberculatum Jacq. (Piperaceae) and two isobutyl amides, 4,5-Dihydropiperlonguminine (1) and pellitorine (2), which were isolated by chromatographic methods, were assayed for their lethality against the sugarcane borer Diatraea saccharalis F. (Lepidoptera: Pyralidae). RESULTS: Bioassays were carried out with fourth-instar caterpillars through topical application of test solutions to the dorsal surface of the prothorax, and dose-response correlations were determined. Significant insect mortalities were observed 24, 48 and 72 h after treatment at concentrations of >or= 100 microg insect(-1). The LD(50) and LD(90) values for compound 1 were 92.83 and 176.50 microg insect(-1), and for compound 2 they were 91.19 and 184.56 microg insect(-1). CONCLUSION: According to the LD(50) and LD(90) for compounds 1 and 2, it can be inferred that the values reflect an acute lethal response to both compounds, based on interaction(s) of the toxicants with a primary target or series of targets. Thus, the amides were demonstrated to have potential value in the control of the sugarcane borer.

Toxicity of extracts and isobutyl amides from Piper tuberculatum: potent compounds with potential for the control of the velvetbean caterpillar, Anticarsia gemmatalis.[Pubmed:17323416]

Pest Manag Sci. 2007 Apr;63(4):399-403.

The isobutyl amides pellitorine (compound 1) and 4,5-Dihydropiperlonguminine (compound 2) were extracted from the seeds of Piper tuberculatum Jacq. (Piperaceae) in yields of 6.10 and 4.45% respectively. The acute toxicities to the velvetbean caterpillar, Anticarsia gemmatalis (Hubner) (Lepidoptera: Noctuidae), of extracts of seeds, leaves and stems of P. tuberculatum, and of compounds 1 and 2, were evaluated by means of contact bioassays. The extracts caused 80% mortality when doses higher than 800.00 microg insect(-1) of extract of seeds, leaves and stems were administered to the velvetbean caterpillars. Compounds 1 and 2 showed 100% mortality at doses of 200 and 700 microg insect(-1) respectively. The LD(50) and LD(90) values were respectively 31.3 and 104.5 microg insect(-1) for compound 1, and 122.3 and 381.0 microg insect(-1) for compound 2. The potential value of extracts and amides derived from P. tuberculatum as efficient insecticides against velvetbean caterpillars is discussed.

Analysis of Piperaceae germplasm by HPLC and LCMS: a method for isolating and identifying unsaturated amides from Piper spp extracts.[Pubmed:15769112]

J Agric Food Chem. 2005 Mar 23;53(6):1907-13.

A method for extraction and high performance liquid chromatography-mass spectrometer (HPLC-MS) analysis of the medicinally important genus Piper (Piperaceae) was developed. This allows for a rapid and accurate measure of unsaturated amides, or piperamides, in black pepper, Piper nigrum L., and in wild species from Central America. Reflux extraction provided the highest recovery of piperine (>80%) from leaf and peppercorn material. HPLC analysis using a binary gradient of acetonitrile and water separated the major amide peaks between 5 and 12 min. Atmospheric pressure chemical ionization (APCI)-MS improved the detection limit to 0.2 ng, 10-fold below the 2 ng limit of the HPLC-diode array detector (DAD) based on linear standard curves between 0.1 and 250 microg/mL (R2 = 0.999). The HPLC-MS method identified pellitorine, piperylin, 4,5-Dihydropiperlonguminine, piperlonguminine, 4,5-dihydropiperine, piperine, and pipercide. The biological activity of six Costa Rican Piper species assessed by mosquito larval bioassays correlated well with piperamide content.