Jaboticabin and Related Polyphenols from Jaboticaba (Myrciaria cauliflora) with Anti-inflammatory Activity for Chronic Obstructive Pulmonary Disease

Abstract

Myrciaria cauliflora (jaboticaba) is an edible fruit common in Brazil that has been used for treating respiratory diseases, including chronic tonsillitis and asthma. This study explores the distribution of an anti-inflammatory depside, jaboticabin, in different parts of the jaboticaba plant as well as major polyphenols from the wood of jaboticaba, some with biological activity similar to jaboticabin. The peel of the fruit was found to be the major source of jaboticabin. This is the first phytochemical study of the wood of M. cauliflora. The antioxidant-activity-guided fractionation strategy successfully identified 3,3′-dimethylellagic acid-4-O-sulfate from jaboticaba wood. This ellagic acid derivative, in a manner similar to jaboticabin, showed antiradical activity and inhibited the production of the chemokine interleukin-8 after treating the human small airway epithelial cells with cigarette smoke extract. The human intestinal Caco-2 cell studies demonstrated the jaboticabin transport in vitro. The polyphenols, jaboticabin and 3,3′-dimethyellagic acid-4-O-sulfate, from jaboticaba were both found to exhibit anti-inflammatory activities, thus suggesting the potential use of these compounds or even the fruits themselves for chronic obstructive pulmonary disease.

Plantas medicinais utilizadas no tratamento de doenças respiratórias crônicas: Período de 2010 a 2020

“…Andrographolide (Tan et al, 2015;Tan et al, 2018), elfinidina-3-glucosídeo, cianidina-3-glucosídeo, delfinidina, e cianidina (Flores et al, 2012), Silimarina (Li et al, 2014), kuwanon E, kuwanon G e norartocarpanona (Lim et al, 2013), jaboticabino (Zhao et al, 2019), Silibinina (Park et al, 2016), Bixina (Zhang et al, 2018), Morina (Cai et al, 2018), Eucalipitol (Kennedy-Feitosa et al, 2020, resveratrol oligômeros Suffruticosol A (Ryu et al, 2015), Baicalina (Lixuan et al, 2010) e S-Pentasina (Shih et al, 2011) foram os que apresentaram eficácia no tratamento experimental de doenças respiratórias crônicas.…”

“…Compostos como o Revesratrol e a Bixina inibem o TGF-β (Chen et al, 2016,;Zhang et al, 2018); os polissacarídeos de Astragulus, C. pilosula e D. officinale inibem a produção de citocinas Interleucina -6 e -8 (IL-6 e -8) (Chu et al, 2016;Song et al, 2016) bem como outros metabolitos secundários (Flores et al, 2012;Kim et al, 2017;Zhao et al, 2019); Fortisiasida , Timosaponina A-III e Morina inibem a Interleucina 1β (Cheng et al, 2015;Cai et al, 2018;Park et al, 2018); Platicodina D (Gao et al, 2017), Stemonina (Zhang et al, 2017) e Tuberstemonia N (Jung et al 2015) apresentaram atividade inibitória do fator de necrose tumoral α (TNF-α).…”

“…As investigações de fitoterapias para as DPOC utilizaram diversos modelos de indução, como indução com células pulmonares primarias humanas (1401, 5401 e 904) (Nabissi et al, 2018), células da linhagem A549 (Park et al, 2016;Lee et al, 2018;Lee et al, 2019), injeção de Lipopolissacarídeos (LPS) (Fan et al, 2018;Park et al, 2018;Zioud et al, 2019) contração da traqueia de ratos com KCl (Águila et al, 2015;Khan et al, 2015;Arefani et al, 2018), material particulado 2,5 μm (Chu et al, 2016;Zhang et al, 2017;Zhang et al, 2018), células RAW264.7 (Fan et al, 2018), ovalbumina (Shih et al, 2011) entre outros modelos, sendo comumente associados a um outro tipo de indutor. Mas os mais utilizados foram modelos com fumaça de cigarro, na forma de inalação o de extrato condensado (Zhao et al, 2019;Carvalho et al, 2020;Kennedy-Feitosa et al, 2020). Research, Society and Development, v. 10, n. 8, e29710817179, 2021 (CC BY 4. A partir desses modelos é possível identificar a existência dos mediadores inflamatórios apresentados anteriormente, validando assim o uso dos mesmos como forma de avaliar as terapias fitoterápicas.…”

Protective effect of Alpinetin on rats with chronic obstructive pulmonary disease

“…In recent years, with the in‐depth study of flavonoids, it was found that Alpinetin had antibacterial, antioxidant, anticancer, antithrombotic, hypotensive, hypolipidemic, hypoglycemic, antiemetic, and analgesic effects (Liu et al., 2019; Zhao et al., 2018; Zhao et al., 2018). At the same time, other flavonoids had been found to play a positive role in improving COPD (Bao et al., 2013; Zhao et al., 2019). However, the effect of Alpinetin on COPD is relatively limited.…”

Antioxidant Action andIn VivoAnti-Inflammatory and Antinociceptive Activities ofMyrciaria floribundaFruit Peels: Possible Involvement of Opioidergic System

“…Gallic acid and ellagic acid (and their derivatives) are usually found in fruits and other plant-derived products [55,58] with antioxidant activity, including those from Myrciaria genus [59,60]. Furthermore, some works have reported that these compounds are potent anti-inflammatory, analgesic, and neuroprotective agents [60][61][62].…”