Bioactive A-Type Proanthocyanidins from Cinnamomum cassia

• Published in: Journal of natural products (Washington, D.C.) Vol. 74; no. 9; pp. 1833 - 1841
• Main Authors: Killday, K. Brian, Davey, Matthew H, Glinski, Jan A, Duan, Penggao, Veluri, Ravikanth, Proni, Gloria, Daugherty, F. Joseph, Tempesta, Michael S
• Format: Journal Article
• Language: English
• Published: Northbrook, IL American Chemical Society and American Society of Pharmacognosy 23-09-2011; American Society of Pharmacognosy
• Subjects: Biological and medical sciences; Cinnamomum aromaticum - chemistry; Cyclooxygenase 2 Inhibitors - chemistry; Cyclooxygenase 2 Inhibitors - isolation & purification; Cyclooxygenase 2 Inhibitors - pharmacology; General pharmacology; Medical sciences; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Plant Bark - chemistry; Proanthocyanidins - chemistry; Proanthocyanidins - isolation & purification; Proanthocyanidins - pharmacology; Asia; China; Trimer; Catechin; Pharmacognosy; Bark; Oligomer; Flavonoid; Biological activity; Medicinal plant; Cinnamomum cassia; Polyphenol; Folk medicine; Dicotyledones; Tetramer; Angiospermae; Plant origin; Isolation; Active ingredient; Spermatophyta; Proanthocyanidin; Lauraceae; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np1007944

Two trimeric proanthocyanidins, cinnamtannin B-1 (1) and cinnamtannin D-1 (2), have been isolated from the bark of Cinnamomum cassia along with the known tetramer parameritannin A-1 (3) and a previously unreported tetramer, named cassiatannin A (4). The structures of 1–4 were elucidated on the basis of 1D and 2D NMR, MS, and CD analyses and compared to the reported data. Proanthocyanidins (1–4) possess significant in vitro inhibitory activity against cyclooxygenase-2 (COX-2) at micromolar concentrations.