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IVES 9 IVES Conference Series 9 OIV 9 OIV 2024 9 Short communications - Safety and health 9 Unveiling the bioactive potential of aglianco grape pomace: oleanolic acid as a promising natural product

Unveiling the bioactive potential of aglianco grape pomace: oleanolic acid as a promising natural product

Abstract

The winemaking industry generates a substantial amount of byproducts, including grape pomace, which is often discarded as waste. However, this seemingly useless material holds a wealth of bioactive compounds with potential health benefits. Recognizing the value of circular economy principles, this study delves into the comprehensive chemical analysis of aglianco grape pomace, aiming to transform this byproduct into a valuable resource. To unravel the chemical composition of aglianco grape pomace, a multifaceted approach was employed, combining chromatographic techniques (column chromatography, uv-vis hplc) with spectrometric methods (hrms, lc-ms/ms) and spectroscopic analysis (nmr). Fresh aglianico pomace (2000 g) was lyophilized (418 g) and then extracted with h2o:etoh (2:8) at room temperature to preserve the bioactive compounds. The extract was concentrated and partitioned with n-hexane (fraction a), ethyl acetate (fraction b), and n-butanol (fraction c). Fraction b, particularly intriguing due to its potential for containing a wider range of bioactive compounds, was subjected to further purification using a flash chromatography system equipped with an 80 g silica combiflash column. A gradient elution process was employed, utilizing the following solvent mixtures: dichloromethane:etoac 1:1 (200 ml; fraction 1), 100% etoac (200 ml; fraction 2), etoac:meoh 9:1 (200 ml; fraction 3), and etoac:meoh 7:3 (400 ml; fraction 4). This approach aimed to separate the various bioactive components within the etoac extract based on their differing polarities. Fraction 1, the focus of our investigation, turned out to be composed entirely of a triterpenoid compound. Its chemical identification was achieved through extensive mono and bidimensional 700 mhz nmr analysis (¹³c nmr, cosy, tocsy, roesy, hsqc, and hmbc) without further purification. The compound was identified as oleanolic acid, a triterpenoid with remarkable abundance in aglianco grape pomace (0.45 mg/g of pomace). Intrigued by the abundance of oleanolic acid, we investigated its potential as a natural product. To achieve this, we assessed its impact on mitochondrial activity and glucose uptake in c2c12 myoblasts using established in vitro assays. Its ability to enhance mitochondrial activity and stimulate glucose uptake in c2c12 myoblasts is noteworthy. The identification of oleanolic acid as a major bioactive component of aglianco grape pomace underscores the importance of untargeted chemical analysis in revealing the full spectrum of potential health-promoting compounds present in natural sources. The observed effects of oleanolic acid on mitochondrial activity and glucose uptake warrant further investigation into its potential as an antidiabetic agent, particularly given its reported efficacy in animal models. This study provides a comprehensive chemical analysis of aglianco grape pomace, revealing a rich profile of bioactive compounds, including oleanolic acid, a triterpenoid with promising antidiabetic potential. The observed biological effects of oleanolic acid support further research into its potential applications in metabolic health, particularly in the management of diabetes. Moreover, this study highlights the value of grape pomace as a valuable source of bioactive compounds, promoting circular economy practices by upcycling waste into potential therapeutic agents.

Svelando il potenziale bioattivo delle vinacce d’uva aglianico: l’acido oleanolico come promettente prodotto naturale

L’industria vinicola genera una notevole quantità di sottoprodotti, tra cui le vinacce d’uva, spesso scartata come rifiuto. Tuttavia, questo materiale apparentemente inutile possiede una ricchezza di composti bioattivi con potenziali benefici per la salute. Riconoscendo il valore dei principi dell’economia circolare, questo studio si concentra sull’analisi chimica completa della vinacce d’uva aglianico, con l’obiettivo di trasformare questo sottoprodotto in una risorsa preziosa. Per svelare la composizione chimica vinacce d’uva aglianico, è stato impiegato un approccio multidisciplinare, che combina tecniche cromatografiche (cromatografia su colonna, hplc uv-vis) con metodi spettrometrici (hrms, lc-ms/ms) e analisi spettroscopica (nmr). La vinacce d’uva aglianico fresca (2000 g) è stata liofilizzata (418 g) e successivamente estratta con h2o:etoh (2:8) a temperatura ambiente per preservare i composti bioattivi. L’estratto è stato concentrato e frazionato con n-esano (frazione a), acetato di etile (frazione b) e n-butanolo (frazione c). La frazione b, particolarmente interessante per la sua potenziale capacità di contenere una gamma più ampia di composti bioattivi, è stata ulteriormente purificata utilizzando un sistema di cromatografia flash dotato di una colonna combiflash da 80 g di silice. E stato impiegato un processo di eluizione a gradiente, utilizzando le seguenti miscele di solventi: diclorometano:etoac 1:1 (200 ml; frazione 1), 100% etoac (200 ml; frazione 2), etoac:meoh 9:1 (200 ml; frazione 3) e etoac:meoh 7:3 (400 ml; frazione 4). Questo approccio mirava a separare i vari componenti bioattivi all’interno dell’estratto di etoac in base alle loro diverse polarità. La frazione 1, al centro della nostra indagine, è risultata essere composta interamente da un composto triterpenico. La sua identificazione chimica è stata ottenuta mediante un’ampia analisi nmr mono e bidimensionale a 700 mhz (¹³c nmr, cosy, tocsy, roesy, hsqc e hmbc) senza ulteriore purificazione. Il composto è stato identificato come acido oleanolico, un triterpenoide con notevole abbondanza nella vinacce d’uva aglianico (0,45 mg/g di vinacce). Intrigati dall’abbondanza di acido oleanolico, abbiamo indagato sul suo potenziale come prodotto naturale. Per raggiungere questo obiettivo, abbiamo valutato il suo impatto sull’attività mitocondriale e sull’assorbimento del glucosio nei mioblasti c2c12 utilizzando test in vitro consolidati. E degna di nota la sua capacità di aumentare l’attività mitocondriale e stimolare l’assorbimento del glucosio nei mioblasti c2c12. L’identificazione dell’acido oleanolico come principale componente bioattivo della vinacce d’uva aglianico sottolinea l’importanza dell’analisi chimica non mirata nel rivelare l’intero spettro di potenziali composti che promuovono la salute presenti in fonti naturali. Gli effetti osservati dell’acido oleanolico sull’attività mitocondriale e sull’assorbimento del glucosio giustificano ulteriori indagini sul suo potenziale come agente antidiabetico, soprattutto data la sua efficacia riportata nei modelli animali. Questo studio fornisce un’analisi chimica completa della vinacce d’uva aglianico, rivelando un ricco profilo di composti bioattivi, tra cui l’acido oleanolico, un triterpenoide con promettente potenziale antidiabetico. Gli effetti biologici osservati dell’acido oleanolico supportano ulteriori ricerche sulle sue potenziali applicazioni nella salute metabolica, in particolare nella gestione del diabete. Inoltre, questo studio sottolinea il valore della sansa d’uva come preziosa fonte di composti bioattivi, promuovendo pratiche di economia circolare attraverso il riutilizzo dei rifiuti in potenziali agenti terapeutici.

Revelando el potencial bioactivo del orujo de uva aglianco: el ácido oleanólico como un producto natural prometedor

La industria vitivinícola genera una cantidad sustancial de subproductos, incluido el orujo de uva, que a menudo se desecha como residuo. Sin embargo, este material aparentemente inútil posee una riqueza de compuestos bioactivos con potenciales beneficios para la salud. Reconociendo el valor de los principios de la economía circular, este estudio se adentra en el análisis químico completo del orujo de uva aglianco, con el objetivo de transformar este subproducto en un recurso valioso. Para desentrañar la composición química del orujo de uva aglianco, se empleó un enfoque multidisciplinario, que combina técnicas cromatográficas (cromatografía de columna, hplc uv-vis) con métodos espectrométricos (hrms, lc-ms/ms) y análisis espectroscópico (nmr). El orujo de uva aglianco fresco (2000 g) se liofilizó (418 g) y luego se extrajo con h2o:etoh (2:8) a temperatura ambiente para preservar los compuestos bioactivos. El extracto se concentró y se dividió con n-hexano (fracción a), acetato de etilo (fracción b) y n-butanol (fracción c). La fracción b, particularmente intrigante debido a su potencial para contener una gama más amplia de compuestos bioactivos, se sometió a una purificación adicional utilizando un sistema de cromatografía flash equipado con una columna combiflash de sílice de 80 g. Se empleó un proceso de elución con gradiente, utilizando las siguientes mezclas de solventes: diclorometano:etoac 1:1 (200 ml; fracción 1), 100% etoac (200 ml; fracción 2), etoac:meoh 9:1 (200 ml; fracción 3) y etoac:meoh 7:3 (400 ml; fracción 4). Este enfoque tenía como objetivo separar los diversos componentes bioactivos dentro del extracto de etoac en función de sus diferentes polaridades. La fracción 1, el centro de nuestra investigación, resultó estar compuesta enteramente por un compuesto triterpenoide. Su identificación química se logró mediante un extenso análisis de nmr mono y bidimensional de 700 mhz (¹³c nmr, cosy, tocsy, roesy, hsqc y hmbc) sin purificación adicional. El compuesto se identificó como ácido oleanólico, un triterpenoide con notable abundancia en el orujo de uva aglianco (0,45 mg/g de orujo). Intrigados por la abundancia de ácido oleanólico, investigamos su potencial como producto natural. Para lograr esto, evaluamos su impacto en la actividad mitocondrial y la captación de glucosa en mioblastos c2c12 utilizando ensayos in vitro establecidos. Cabe destacar su capacidad para mejorar la actividad mitocondrial y estimular la captación de glucosa en los mioblastos c2c12. La identificación del ácido oleanólico como un componente bioactivo principal del orujo de uva aglianco subraya la importancia del análisis químico no dirigido para revelar el espectro completo de compuestos potenciales promotores de la salud presentes en fuentes naturales. Los efectos observados del ácido oleanólico sobre la actividad mitocondrial y la captación de glucosa justifican una mayor investigación sobre su potencial como agente antidiabético, especialmente dada su eficacia descrita en modelos animales. Este estudio proporciona un análisis químico completo del orujo de uva aglianco, revelando un rico perfil de compuestos bioactivos, incluido el ácido oleanólico, un triterpenoide con un prometedor potencial antidiabético. Los efectos biológicos observados del ácido oleanólico respaldan la investigación adicional sobre sus posibles aplicaciones en la salud metabólica, particularmente en el control de la diabetes. Además, este estudio destaca el valor del orujo de uva como una fuente valiosa de compuestos bioactivos, promoviendo prácticas de economía circular mediante el reciclaje de residuos en potenciales agentes terapéuticos.

Publication date: November 18, 2024

Issue: OIV 2024

Type: Article

Authors

Francesco Errichiello¹, Angelita Gambuti¹, Luigi Moio¹, Martino Forino¹

¹ Wine and Vine Science Section, Department of Agriculture, University of Naples Federico II, Viale Italia, Angolo Perrottelli, Avellino, Italy

Contact the author*

Tags

IVES Conference Series | OIV | OIV 2024

Citation

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