Constituintes químicos isolados dos galhos e cascas de amapazeiro (Parahancornia amapa, Apocynaceae)

Abstract

RESUMOParahancornia amapa (Apocynaceae) é típica da região amazônica e conhecida popularmente como amapazeiro e muito utilizada na medicina popular da região Amazônica. O objetivo desse trabalho foi o estudo fitoquímico dos galhos e cascas dessa espécie. Do extrato diclorometânico dos galhos foram isolados o β-sitosterol, estigmasterol, além de triterpenóides pentacíclicos, α-amirina, β-amirina, lupeol e friedelina. Do extrato metanólico das cascas foi isolado o alcaloide indólico isositsiriquina. As estruturas desses compostos foram identificadas por análise dos espectros de massa de alta resolução, Ressonância Magnética Nuclear de 1 H e 13 C e comparações com dados da literatura. Esse é o primeiro relato de isolamento de alcaloide neste gênero. PALAVRAS-CHAVE: Triterpenos, alcaloide, esteroides. Chemical constituents isolated from twigs and barks of amapazeiro (Parahancornia amapa, Apocynaceae)ABSTRACT Parahancornia amapa (Apocynaceae) is typical of the Amazon region and popularly known as amapazeiro and widely used in folk medicine in the Amazon region. The objective of this work was to study the phytochemical composition of twigs and barks of this species. From the dichloromethane extract of twigs were isolated β-sitosterol, stigmasterol, and pentacyclic triterpenoids α-amyrin, β-amyrin, lupeol and friedelin. From the methanol extract of barks was isolated indole alkaloid isositsiriquina. The structures of these compounds were identified by analysis of the mass spectra high-resolution, 1 H and 13 C NMR and comparisons with literature data. This is the first report of isolation of alkaloid in this genus.

Phytochemical Characterization of Cannabis sativa L. Roots from Northeastern Brazil

“…Signals between δ H 2.00 and 1.20 ppm indicate chemical shifts of aliphatic hydrogens from epifriedelanol and friedelan-3-one. [21,22] The infrared spectroscopy data of compounds 1 and 2 (Figure 10) corroborate with the results obtained by 1 H and 13 C-NMR analysis, since the spectrum showed an absorption band at 3478 cm À 1 , which is associated with stretching vibration of the OÀ H bond of compound 1; and an absorption band at 1712 cm À 1 , which refers to the stretching vibration of the C=O bond of compound 2. The absorption bands in the region from 3000 to 2800 cm À 1 , at 1454 cm À 1 and at 1388 cm À 1 correspond to stretching or bending vibrations of CÀ H bonds of aliphatic compounds.…”

“…Multiplet signals between δ H 2.41 and 2.23 ppm are characteristic of three α‐carbonyl hydrogens of the molecule. Signals between δ H 2.00 and 1.20 ppm indicate chemical shifts of aliphatic hydrogens from epifriedelanol and friedelan‐3‐one [21,22] …”

<i>Ximenia americana</i>: Chemical and Spectral Studies of Extracts of Seeds. Analysis of Trimethylsilyl Derivatives by Gas Chromatography and Mass Spectrometry

“…The 1 H NMR spectrum revealed the presence of various methyl groups, one of which (one singlet at 1.80 ppm) bonded to sp 2 carbon; the spectrum also showed signs as broad triplet at 5.72 (1H), broad singlet and 5.51 (1H) and two broad singlet at 4.96 (1H) and 4.78 (1H) due to hydrogens mutually coupled. The first two were attributed to olefinic hydrogens and consistent with the presence of triterpenes of oleanane/ursano types [23], while the last two were correlated to vinyl hydrogens in terminal double bond, characteristic of triterpene lupane type [24]. In turn, the 13 [25]; the spectrum also showed signs at δ C 78,44 (due to oxygenated sp 3 carbon C-3) and 19,12 correlated to methyl carbon C-30 in lupane triterpenoids [24].…”

Aprovechamiento de las semillas del Dipteryx odorata (Aublet.) Willd. (Shihuahuaco) como producto alimenticio

“…El plomo se presenta como un elemento no apto para De los gajos y corteza de la especie Parahancornia amapa (amapazeiro) y Apocynaceae, Henrique extrajo diclorometánico, β-sitosterol, estigmasterol, além de triterpenóides pentacíclicos, α-amirina, β-amirina, lupeol e friedelina. Del extracto metanólico de la corteza aisló el alcaloide indólico isositsiriquina (9).…”