Isolation and Identification of a Flavone Apigenin from Marine Red Alga Acanthophora spicifera with Antinociceptive and Anti-Inflammatory Activities

Abstract

Physicochemical investigation of the red alga Acanthophora spicifera (Vahl) Borgesen, collected from Al-Shoaiba coast, Red Sea, Saudi Arabia, led to the isolation of a flavone from the algal tissue with acetone. Preparative chromatography on silica gel thin-layer chromatography was used for the separation of the flavone and eluted with the methanol:chloroform:ethyl acetate (1:7:2) solvent system. The physicochemical analyses infrared, mass spectra, and ultraviolet spectra in addition to shift reagents (NaOMe, NaOAc, NaOAc + H3BO3, AlCl3, and AlCl3 + HCl) were used for the identification and elucidation of the structure of the flavone compound (4,5,7-trihydroxy flavonoids). The flavone compound was identified as apigenin bycomparing its physicochemical data with those in the literature. Analgesic and anti-inflammatory activities of apigenin were evaluated. Apigenin showed promising analgesic and anti-inflammatory activities in the hot plate test and writhing test in mice as well as tail-immersion tests and carrageenan-induced paw edema and cotton pellet-induced granuloma formation in rats. It is concluded that apigenin possesses potent analgesic, anti-inflammatory, and antiproliferative activities, which might be due to the inhibition of PGE2 as well as proinflammatory cytokines such as interleukin-1β, interleukin-6, and tumor necrosis factor-α.

Metabolites Unravel Nutraceutical Potential of Edible Seaweeds: An Emerging Source of Functional Food

“…The green seaweed Caulerpa sertularioides (Gmelin) Howe contained gallocatechin, epicatechin, and gallocatechin gallate, while the brown seaweed Eisenia bicyclis (Kjellman) Setchell was found to have the highest content of polyphenols, including epigallocatechin, catechin, epicatechin, epigallocatechin gallate, epicatechin gallate, hesperidin, and morin (Santoso, Yoshie, & Suzuki, 2004). The flavone apigenin with antinociceptive and anti-inflammatory activities has been isolated from Acanthophora spicifera (El Shoubaky, Abdel-Daim, Mansour, & Salem, 2016). Similarly, phlorotannins with high antioxidant activity have been extracted from the brown seaweed Cystoseira trinodis (Forsskål) Agardh as well as from other Fucales species (Ferreres et al, 2012;Sathya, Kanaga, Sankar, & Jeeva, 2013).…”

The Evolution of Flavonoid Biosynthesis: A Bryophyte Perspective

“…Indeed, many metabolite studies on algae report only amounts of "total flavonoids" measured using general assays. Nevertheless, there are some reports detailing specific flavonoid structures in algal preparations, including compounds such as chalcones, flavones, flavonols, isoflavonoids, and proanthocyanidins (Klejdus et al, 2010;Goiris et al, 2014;El Shoubaky et al, 2016;Agregán et al, 2017;Ben Saad et al, 2017). Although the concentrations of flavonoid compounds reported in most examples are extremely low compared with those commonly found in land plants (ng gDW −1 amounts compared with mg gDW −1 ), these reports mean that the presence of a biosynthetic pathway to flavonoids in algae cannot be ruled out.…”

Therapeutic effects of Qian-Yu decoction and its three extracts on carrageenan-induced chronic prostatitis/chronic pelvic pain syndrome in rats

“…Carrageenan is a highly sulfated polygalactan with 15-40% of ester-sulfate content and an average molecular weight well above 100 kDa [27]. Carrageenan has been widely used to induce inflammation in animal models and human cells [28, 29]. Carrageenan triggers inflammatory cascades in which Toll-like receptor 4 (TLR4) and B-cell leukemia/lymphoma 10 (BCL10) are critical [30, 31].…”