Pentacyclic triterpenes and steroids from the stem bark of uchi (Sacoglottis uchi, Humiriaceae)

Abstract

The ethanol extract from stem bark of Sacoglottis uchi Huber (popularly known as "uchi" in the Amazon Region) was submitted to chromatographic fractionation. The dichloromethane fractions provided the pentacyclic triterpene 3-oxo-friedelin (1). The dichloromethane:methanol fractions provided the pentacyclic triterpenes pseudotaraxasterol (2), lupeol (3), α-amyrin (4), betulin (5), and methyl 2β,3β-dihydroxy-urs-12-en-28-oate (6) and a mixture of the steroids sitosterol (7) and stigmasterol (8). Their chemical structures were determined by NMR spectroscopy and comparison with spectroscopic data from the literature. All compounds are described for the first time in this species. KEYWORDS: Humiriaceae, medicinal plants, Amazon Region, triterpenesTriterpenos pentacíclicos e esteróides da casca do uchi (Sacoglottis uchi, Humiriaceae) RESUMO O extrato etanólico da casca do caule de Sacoglottis uchi Huber (conhecida popularmente como "uchi" na Amazônia) foi submetido a fracionamento cromatográfico. As frações eluídas com diclorometano forneceram o triterpeno pentacíclico 3-oxofriedelina (1). As frações em diclorometano:metanol forneceram os triterpenos pentacíclicos pseudotaraxasterol (2), lupeol (3), α-amirina (4), betulina (5) e 2β,3β-di-hidroxi-urs-12-en-28-oato de metila (6), além de uma mistura dos esteróides sitosterol (7) e estigmasterol (8). Suas estruturas químicas foram determinadas por espectroscopia de RMN e comparação com os dados espectroscópicos descritos na literatura. Todas as substâncias isoladas são descritas pela primeira vez nesta espécie.

Betulin, a Newly Characterized Compound in Acacia Auriculiformis Bark, is a Multi-target Protein Kinase Inhibitor

“…A compound was isolated from Acacia auriculiformis stem bark as a white amorphous solid. Its spectral properties ( 1 H and 13 C) are consistent with literature data for betulin (3lup-20(29)-ene-3,28-diol) [25]. Acacia auriculiformis stem bark was found to contain about 0.002% of betulin by dry weight.…”

Phytochemical Characterization of Cannabis sativa L. Roots from Northeastern Brazil

“…[22,24] The 1 H-NMR spectrum (Figure 12) allowed the identification of an apparent doublet at δ H 5. hydrogen atoms of aliphatic groups typical of steroids. [22,24,25,26] The infrared spectrum of compounds 3 and 4 (Figure 13) showed an absorption band at 3432 cm À 1 assigned to the OÀ H stretching vibration. The absorptions in the region from 3000 to 2800 cm À 1 , at 1464 cm À 1 and at 1384 cm À 1 refer to stretching or bending vibrations of CÀ H bonds of aliphatic compounds.…”

Humiria balsamifera extract inhibits nitric oxide and tumor necrosis factor production in LPS-stimulated macrophages

“…Some of the identified compounds have already been described for species from the same family Humiriaceae, such Rodriguésia 72: e00292020. 2021 as bergenin in Sacoglottis gabonensis (Ogan 1971), and hexadecanoic acid, friedelin, betulin and bergenin identified in Endopleura uchi (Marx et al 2002;Abreu et al 2013), being bergenin associated to the anti-inflammatory activitiy of the plant (Nunomura et al 2009). It is important to highlight that it is the first time that tetratetracontane, ß-amyrone, betulin, citronellol, eremophillene, dihydroactinolide and borneol are being reported for this species and also for the genus Humiria.…”