Ursolic acid from apple pomace and traditional plants: A valuable triterpenoid with functional properties

Cargnin, Simone Tasca; Gnoatto, Simone Cristina Baggio

doi:10.1016/j.foodchem.2016.10.029

Cited by 183 publications

(117 citation statements)

References 78 publications

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“…Different isomeric triterpene acids have been reported in apple . We compared our results with the ones reported in previously published methods by Waldbauer et al and by Grigoras et al The main compounds reported by Waldbauer et al presented molecular weights of 502, 488, and 486 Da, corresponding to cuneataol and pomaceic acid, euscaphic and tormentic acids, and annurcoic and pirolonic acids, respectively.…”

Section: Resultssupporting

confidence: 55%

“…These constituents are considered able to protect the plant from biotic and abiotic stress factors. Furthermore, lupane, oleanane, and ursane triterpenes where shown to display various pharmacological effects, although being deprived of prominent toxicity . Thanks to their bioactivities, among which the anti‐inflammatory ones, triterpenes play a role in the health‐promoting properties of apple fruits …”

Section: Introductionmentioning

confidence: 99%

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Fragmentation of the main triterpene acids of apple by LC‐APCI‐MSⁿ

et al. 2018

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In this paper, we investigated the fragmentation of the main triterpene acids of apple using an liquid chromatography atmospheric pressure chemical ionization mass spectrometry (LC-APCI-MS ) approach and high-resolution mass spectrometry (HR-MS) (Q-TOF). Triterpenes were isolated using semipreparative high-performance liquid chromatography, and chemical structures were elucidated by HR-MS and nuclear magnetic resonance spectroscopy. Finally, compounds were used to study MS behavior in ion trap. Isolated triterpenes present similar structures, bearing carboxyl group linked to C-17 and different substitutions. We observed significant changes in MS spectra, which were useful for further compound identification. The observed fragments allowed the discrimination of different derivatives, namely, pomaceic, annurcoic, euscaphic, pomolic, corosolic, maslinic, betulinic, oleanolic, and ursolic acids. The proposed method allows a rapid identification of triterpene acids, and it could be useful for the analysis of these compounds in apple fruits and in other natural sources.

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Section: Resultssupporting

confidence: 55%

Section: Introductionmentioning

confidence: 99%

Fragmentation of the main triterpene acids of apple by LC‐APCI‐MSⁿ

et al. 2018

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“…Ursolic acid and related triterpene compounds, such as oleanolic acid, betulinic acid, uvaol, and α- and β-amyrin are widespread in many plants [77,78]. The most abundant triterpenoid from noni is ursolic acid, which has been widely investigated because of its hypoglycemic property [61,67,68].…”

Section: Morinda Citrifolia Linn (Noni)mentioning

confidence: 99%

Morinda citrifolia Linn. (Noni) and Its Potential in Obesity-Related Metabolic Dysfunction

et al. 2017

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Cultural and economic shifts in the early 19th century led to the rapid development of companies that made good profits from technologically-produced commodities. In this way, some habits changed in society, such as the overconsumption of processed and micronutrient-poor foods and devices that gave rise to a sedentary lifestyle. These factors influenced host-microbiome interactions which, in turn, mediated the etiopathogenesis of “new-era” disorders and diseases, which are closely related, such as obesity, type 2 diabetes mellitus, non-alcoholic fatty liver disease, hypertension, and inflammatory bowel disease, which are characterized by chronic dysregulation of metabolic and immune processes. These pathological conditions require novel and effective therapeutic approaches. Morinda citrifolia (noni) is well known as a traditional healing plant due to its medicinal properties. Thus, many studies have been conducted to understand its bioactive compounds and their mechanisms of action. However, in obesity and obesity-related metabolic (dysfunction) syndrome, other studies are necessary to better elucidate noni’s mechanisms of action, mainly due to the complexity of the pathophysiology of obesity and its metabolic dysfunction. In this review, we summarize not only the clinical effects, but also important cell signaling pathways in in vivo and in vitro assays of potent bioactive compounds present in the noni plant which have been reported in studies of obesity and obesity-associated metabolic dysfunction.

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“…Ursolic acid (UA), a natural pentacyclic triterpenoid that is derived from berries, leaves, flowers, and fruits of medicinal plants, has been reported to have anti‐oxidation, anti‐inflammatory, anti‐ulcer, antibacterial, anti‐virus, anti‐tumor, anti‐obesity, hypoglycemic, antihypertensive, lipid‐lowering, liver protection, and immune regulation activities, among other (Cargnin & Gnoatto, ; Kim, Kim, Han, & Kim, ; Li, Ren, Luo, & Yang, ; Ma, Ding, Zhang, & Liu, ; Wang et al, ). In vitro studies have shown that UA could reverse liver fibrosis by inhibiting the activation of NOX‐mediated fibrotic signaling networks in HSCs, including the NF‐ k B, PI3 K/Akt, P38MAPK, ERK1/2, JAK2‐STAT3, Hedgehog, and other signaling pathways (He et al, ).…”

Section: Introductionmentioning

confidence: 99%

Ursolic acid ameliorates CCl4‐induced liver fibrosis through the NOXs/ROS pathway

Gan

Zhang

Huang

et al. 2018

Journal Cellular Physiology

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Liver fibrosis is a reversible wound‐healing response that occurs after liver injury. NADPH oxidases (NOXs) and reactive oxygen species (ROS) which are expressed in hepatocytes (HCs), hepatic stellate cells (HSCs), and Kupffer cells (KCs) play an important role in the development of hepatic fibrosis. In in vitro studies, we had shown that ursolic acid (UA) could reverse liver fibrosis by inhibiting the activation of NOX‐mediated fibrotic signaling networks in HSCs. In this study, we verified that UA could alleviate CCl4‐induced liver fibrosis by reducing the expression of NOXs/ROS in HCs, HSCs, KCs. Meanwhile, the phagocytic index α and clearance index K which represent phagocytosis of KCs were unchanged. Together, all our data demonstrated that UA induced the proliferation of HCs, promoted apoptosis in HSCs, and prevented activation of KCs in vivo by reducing the expression of NOXs/ROS in HCs, HSCs, KCs. Besides, UA had no effect on the host defense function.

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Ursolic acid from apple pomace and traditional plants: A valuable triterpenoid with functional properties

Cited by 183 publications

References 78 publications

Fragmentation of the main triterpene acids of apple by LC‐APCI‐MSⁿ

Fragmentation of the main triterpene acids of apple by LC‐APCI‐MSⁿ

Morinda citrifolia Linn. (Noni) and Its Potential in Obesity-Related Metabolic Dysfunction

Ursolic acid ameliorates CCl4‐induced liver fibrosis through the NOXs/ROS pathway

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Ursolic acid from apple pomace and traditional plants: A valuable triterpenoid with functional properties

Cited by 183 publications

References 78 publications

Fragmentation of the main triterpene acids of apple by LC‐APCI‐MSn

Fragmentation of the main triterpene acids of apple by LC‐APCI‐MSn

Morinda citrifolia Linn. (Noni) and Its Potential in Obesity-Related Metabolic Dysfunction

Ursolic acid ameliorates CCl4‐induced liver fibrosis through the NOXs/ROS pathway

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Fragmentation of the main triterpene acids of apple by LC‐APCI‐MSⁿ

Fragmentation of the main triterpene acids of apple by LC‐APCI‐MSⁿ