Artonin E: A Short Review of its Chemistry, Sources, Anti-Cancer Activities and Other Pharmacological Properties

Abstract

Among the prenylated flavonoids is a group known as artonins. To date, 24 of such compounds (artonins A-Y) have been recorded. 6 Pharmacological properties of artonins include anti-plasmodial, anticancer and antibacterial activities. In this article, the chemistry, sources, anti-cancer and other medicinal properties of artonin E from Artocarpus species are reviewed for the first time. A brief account on other artonins is included. Some prospects and future research on artonin E and other artonins are suggested. Chemistry of Artonin EArtonin E or 5'-hydroxymorusin from Artocarpus species (Moraceae) is a prenylated flavonoid with a molecular formula of C25H24O7 and molecular weight of 436.5 g/mol. 6,7 The molecular structure of artonin E has three aromatic rings (A-C) with three OH groups at C2', C4' and C5' of ring B, and one OH group at C5 of ring A (Figure 1). There are two prenyl units, one isoprenoid substituent at C3 of oxygenated ring C and one forming a dimethylpyrane ring D at C7 and C8. The presence of a double bond between C2 and C3, and a carbonyl group at C4 are essential for the bioactivities of artonin E. Morusin has a similar molecular structure as artonin E except that it lacks the OH group at C5'. For this reason, artonin E is sometimes called 5'-hydroxymorusin. 6 The structure of artonin E is a 3-isoprenyl 2',4',5'-trioxygenated flavone. 5,7 Other compounds with the same structural type are artoindonesianins L and U. Prenylated flavonoids also include 3isoprenyl 2',4'-dioxygenated flavones such as artocarpin 8 and morusin. 9Sources of Artonin E Artonin E was first isolated from the bark Artocarpus altilis (syn. A. communis) 10 (Figure 2). Subsequently, artonin E was reported in other Artocarpus species that include A. chama, A. elasticus, A. gomezianus, A. kemando, A. lanceifolius, A. lowii, A. nobilis, A. rigida, A. rigidus (syn. A. rotunda), A. scortechnii and A. teysmannii (Table 1). Plant part most reported are the root and bark, with no reports on the leaf.

Natural Prenylflavones from the Stem Bark of Artocarpus altilis: Promising Anticancer Agents for Oral Squamous Cell Carcinoma Targeting the Akt/mTOR/STAT-3 Signaling Pathway

“…Artonin E, also known as 5′-hydroxymorusin, possesses a flavonoid skeleton linked to a lipophilic prenyl side chain. Initially detected in the bark of AA, this molecule has been widely explored for its varied pharmacological activities, encompassing antibacterial, anticancer, antiestrogenic, anti-FAT10, antimalarial, antinephritis, antioxidant, and antiplasmodial activities . The anticancer effects of Artonin E have been explored across diverse cancer cell types, including breast (MCF-7, MDA-MB-231), , colon (LoVo, HCT116), , gastric cancers (AGS), leukemia (P-388), lung (H460, H23, H292, A549), , and ovarian (SKOV3, 1A9). , These studies highlight the potential of artonin E in inducing apoptosis, anoikis, and cell-cycle arrest and inhibiting proliferation, invasion, migration, and overcoming resistance to the tumor necrosis factor-related apoptosis-inducing ligand (TRAIL). – The underlying mechanisms involve activation and suppression of proapoptotic and antiapoptotic proteins, respectively.…”

“…Artonin E, also known as 5′-hydroxymorusin, possesses a flavonoid skeleton linked to a lipophilic prenyl side chain. Initially detected in the bark of AA, this molecule has been widely explored for its varied pharmacological activities, encompassing antibacterial, 33 anticancer, 34 antiestrogenic, 35 anti-FAT10, 36 antimalarial, 37 antinephritis, 35 antioxidant, 35 and antiplasmodial activities. 38 The anticancer effects of Artonin E have been explored across diverse cancer cell types, including breast (MCF-7, MDA-MB-231), 39 , 40 colon (LoVo, HCT116), 41 , 42 gastric cancers (AGS), 43 leukemia (P-388), 44 lung (H460, H23, H292, A549), 45 , 46 and ovarian (SKOV3, 1A9).…”