RESUMO
Sesquiterpenoids are integral constituents of terpenoid-bearing plants, comprising a diverse and abundant class of natural compounds, among which eudesmane-type sesquiterpenoids have bicyclic structures that feature the fusion of two six-membered carbon rings, thereby attracting considerable attention. They are widespread in nature, with multifaceted biological activities such as anti-inflammatory, anticancer, antimicrobial, antimalarial, and insecticidal activities, thus gaining focus in life science research. The discovery and identification of these active compounds have laid a foundation for unraveling their potential medicinal value. In this review, we comprehensively explore the natural eudesmane-type sesquiterpenoids isolated (totaling 391 compounds) between 2016 and 2022, elucidating their chemical structures, plant distribution patterns, and pertinent biological properties. Accordingly, the study serves not only as a framework for researchers to thoroughly comprehend these compounds but also as a robust reference for future endeavors aimed at exploring the pharmaceutical potential and prospective applications of these molecules.
RESUMO
To explore the sesquiterpenoids in Curcuma longa L. and their activity related to anti-atherosclerosis. The chemical compounds of the rhizomes of C. longa were separated and purified by multiple chromatography techniques. Their structures were established by a variety of spectroscopic experiments. The absolute configurations were determined by comparing experimental and calculated NMR chemical shifts and electronic circular dichroism (ECD) spectra. Their anti-inflammatory effects and inhibitory activity against macrophage-derived foam cell formation were evaluated by lipopolysaccharide (LPS) and oxidized low-density lipoprotein (ox-LDL)-injured RAW264.7 macrophages, respectively. This study resulted in the isolation of 10 bisabolane-type sesquiterpenoids (1-10) from C. longa, including two pairs of new epimers (curbisabolanones A-D, 1-4). Compound 4 significantly inhibited LPS-induced nitric oxide (NO), interleukin-1ß (IL-1ß), interleukin-6 (IL-6), tumor necrosis factor-α (TNF-α), and prostaglandin E2 (PGE2) production in RAW264.7 cells. Furthermore, compound 4 showed inhibitory activity against macrophage-derived foam cell formation, which was represented by markedly reducing ox-LDL-induced intracellular lipid accumulation as well as total cholesterol (TC), free cholesterol (FC), and cholesterol ester (CE) contents in RAW264.7 cells. These findings suggest that bisabolane-type sesquiterpenoids, one of the main types of components in C. longa, have the potential to alleviate the atherosclerosis process by preventing inflammation and inhibiting macrophage foaming.
Assuntos
Aterosclerose , Sesquiterpenos , Sesquiterpenos Monocíclicos/farmacologia , Lipopolissacarídeos/farmacologia , Curcuma/química , Aterosclerose/tratamento farmacológico , Aterosclerose/metabolismo , Sesquiterpenos/química , Células Espumosas/metabolismo , Lipoproteínas LDL/metabolismo , Colesterol/metabolismoRESUMO
This study investigated the chemical components from the florets of Carthamus tinctorius. Five compounds were isolated from C. tinctorius by column chromatography with silica gel and toyopearl HW-40 F, preparative thin-layer chromatography(TLC), and semi-preparative reverse phased high performance liquid chromatography(RP-HPLC). Their structures were identified by mass spectrometry(MS), one-dimension nuclear magnetic resonance(1 D-NMR), two-dimension nuclear magnetic resonance(2 D-NMR), and single-crystal X-ray diffraction as(-)-(2S,3S,5S,7S,10R)-eudesma-4(15)-en-2,3,11-triol(1 a),(+)-(2R,3R,5R,7R,10S)-eudesma-4(15)-en-2,3,11-triol(1 b), rosin(2),(+)-syringaresinol(3), and(E)-1-(4'-hydroxyphenyl)-but-1-en-3-one(4). Compounds 1 a and 1 b are a pair of enantiomeric sesquiterpenoids. Compound 1 a is a new eudesmene and is named(-)-plucheol A. Compound 1 a at 100 µmol·L~(-1) showed significant antioxidant activity against ABTS~(+·) and DPPH·, with the scavenging rates of 30.98%±4.17% and 27.52%±1.24%, respectively, while compound 1 b was inactive. In addition, compounds 1 a and 1 b showed no obvious anti-inflammatory activity.