Geranyl Flavonoid Derivatives from the Fresh Leaves of Artocarpus communis and Their Anti-inflammatory Activity

Abstract

Breadfruit (Artocarpus communis) is a widely distributed crop in tropical and subtropical regions of the world. It is used in Southeast Asia and India to treat several inflammatory disorders. The aim of this study was to investigate the presence of anti-inflammatory flavonoids in A. communis leaves. Three new geranyl flavonoids, arcommunol C (1), arcommunol D (3), and 5'-geranyl-3,4,2',4'-tetrahydroxychalcone (5), together with four known compounds, prostratol (2), arcommunol E (4), 3'-geranyl-3,4,2',4'-tetrahydroxydihydrochalcone (6), and 3'-geranyl-3,4,2',4'-tetrahydroxychalcone (7), were isolated from the leaves of A. communis. Compound 4 was isolated for the first time from natural sources. The anti-inflammatory activity of the isolated compounds (1-7) was evaluated by determining their inhibitory activity on the production of proinflammatory mediators in lipopolysaccharide (LPS)-activated RAW 264.7 murine macrophage cells. Compounds 2, 3, and 4 suppressed the LPS-induced production of nitric oxide (NO) in RAW 264.7 cells with IC50 values of 8.13 ± 0.17, 18.45 ± 2.15, and 22.74 ± 1.74 µM, respectively. Furthermore, 2 decreased lipopolysaccharide (LPS)-mediated induction of protein expressions of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in RAW 264.7 cells. It was also found that 2 suppressed LPS-induced phosphorylation of JNK and p38 mitogen-activated protein kinase (MAPK) signaling.

Inhibitory effects of phenolic compounds fromArtocarpus styracifoliuson respiratory burst of rat neutrophils

“…A large number of phenolic compounds including flavonoids, stilbenoids, and 2-arylbenzofurons have been isolated from Artocarpus plants and possess a wide range of biological properties such as anti-inflammatory (Hsu et al, 2012;Lin et al, 2011), antiplatelet (Jagtap & Bapat, 2010;Weng et al, 2006), antimycobacterial (Loizzo et al, 2010;Siritapetawee et al, 2012), and antiprotozoal activities (Bourjot et al, 2010). Among these activities, the antioxidant actions of these polyphenols derived from Artocarpus species have been frequently reported in vivo and in vitro (Omar et al, 2011;Sidahmed et al, 2013).…”

Geranylated Flavanones from <i>Paulownia coreana</i> and Their Inhibitory Effects on Nitric Oxide Production

“…[20][21][22] In conclusion, these results indicate that P. coreana is a rich source of geranylated flavanones, which has potential to be used as candidates for the treatment of various inflammatory diseases. However, further investigation is needed to clarify the detailed mechanism of action of these geranylated flavanones.…”

Novel stilbenes fromArtocarpus nanchuanensis

“…Some plants of this genus are used as traditional folk medicines in Indonesia [2], India [3], Cameroon [4], and China [5]. The previous studies on the plants of this genus led a series of isoprenylated flavonoids and stilbenoids [6,7], some of which possessed cytotoxicity [8] and tyrosinase inhibitory effects [9], and antibacterial [10] and antiinflammatory activities [11].…”