Atypical Nitrogen-Containing Flavonoid in the Fruits of Cumin (Cuminum cyminum L.) with Anti-inflammatory Activity

Abstract

The dried seeds of Cuminum cyminum L. have been traditionally used as food and medicine. To explore its chemical composition and anti-inflammatory activity, four new compounds (1−4) along with five known compounds (5−9) were isolated from the seeds in the present study. The chemical structures of the new compounds were identified as follows: 3), and (3,4,5-trihydroxy-6-((5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl)oxy)tetrahydro-2H-pyran-2-yl)methyl 3-(4-isopropylphenyl)-2-methoxypropanoate (4). Compound 2, an atypical nitrogen-containing flavonoid, exhibited the most active inhibitory effect on nitride oxide, with IC 50 of 5.25 μM in the lipopolysaccharide-stimulated RAW264.7 cell assay. Compound 2 was found to suppress the expression levels of inducible nitric oxide synthase and cyclooxygenase-2. Furthermore, it was revealed that both nuclear factor κB and mitogenactivated protein kinase were involved in the anti-inflammatory process of compound 2.

A review on traditional uses, phytochemistry, pharmacology, and clinical research of dietary spice Cuminum cyminum L.

“…Considerable expression of three major mitogens activated protein kinases (MAPKs) namely C‐Jun N‐terminal kinases (JNK), extracellular signal‐regulated kinases (ERKs), and p38 acts as the major signalings involved by cumin polysaccharides to impart their immunostimulant effect and to battle against inflammation, infections, and abnormal cells whereas NF‐κB act as a downstream component of MAPKs signaling pathways. In another study, Kang et al (2019) described the inflammation‐protecting mechanism of flavonoids isolated from cumin seeds and observed that these compounds effectively downregulated the nitric oxide synthase and cyclooxygenase‐2 (COX‐2) enzymes. The enzyme COX‐2 is crucial for prostaglandin release, which exert important function in various inflammation associated disorders, such as paw edema, rheumatoid arthritis, bronchitis, and so forth.…”

“…Cumin oil exhibits significant antimicrobial properties (Belal et al, 2017). Kakarla et al (2017) Seeds and fruits (Kang et al, 2019;Goodarzi et al, 2020) Luteolin-7-O-glucoside (Pubchem CID: 4444241) (Goodarzi et al, 2020) Apigenin (Pubchem CID: 4444100) (Kang et al, 2019;Goodarzi et al, 2020) Apigenin-7-O-glucoside (Pubchem CID: 4444290) (Goodarzi et al, 2020) 6. Allylbenzene Eugenol (Pubchem CID: 13876103)…”

“…The fruits contain estrogenic isoflavonoids, luteolin, and apigenin. The seeds exhibit a good amount of flavonoids (4.15–5.75%), in which luteolin, apigenin, and quercetin are the dominant flavonoids (Kang et al, 2019). Cuminaldehyde is the principal bioactive compound of C. cyminum (Ebada, 2017; Nirmala et al, 2020).…”

“…Due to its strong aroma, the seeds are widely utilized in the perfumery industry in small contents. It is also a rich reservoir of medicinally useful bioactive compounds that are widely used for various healthcare purposes (Belal, Ahmed, & Ali, 2017; Goodarzi et al, 2020; Kang et al, 2019). The plant is particularly well known for its therapeutic potential namely antibacterial, antifungal, antioxidant, antidiabetic, hypolipidemic, immunomodulatory, anti‐osteoporotic, antiinflammatory, anti‐asthmatic, anti‐tussive, anti‐infertility, anticancer, anti‐stress, antipyretic, hypotensive, antiplatelet coagulation, hepatoprotective, analgesic, and so on (Agarwal et al, 2017; Al‐Snafi, 2016).…”

“…Antiinflammatory compounds have the potential to alter the signalings involved in the NO production as well as reduces the pro-inflammatory cytokines. Cumin seeds supposed to exhibit good inflammationprotecting potential Kang et al (2019). isolated many new compounds from cumin seeds and compared their antiinflammatory potential with previously known compounds.…”