A New Monoterpenoid and a New Flavonoid Glycoside from the Peels of Clausena lansium

Abstract

One new monoterpenoid, nerol oxide-8-carboxylic acid (1), and one new flavonoid glycoside, claulansoside A (2), together with six known compounds, clausenamide (3), quercetin (4), isorhamnetin (5), dihydromyric (6), 2'',3''-dihydroxyanisolactone (7) and (E,E)-8-(7-hydroxy-3,7-dimethylocta-2,5dienyloxy)psoralen (8), have been isolated from the peels of Clausena lansium (Lour.) Skeels. Their structures were determined using a combination of 1D, and 2D NMR (HMQC, HMBC, COSY and NOESY) techniques, and HR-ESI-MS analyses. Compounds 1 and 7 exhibited antibacterial activity against Staphylococcus aureus with the diameter of inhibition zones of 11.5 mm and 14.2 mm. Compounds 3 and 6 showed α-glucosidase inhibitory activity in vitro.

Fruit Peels: Food Waste as a Valuable Source of Bioactive Natural Products for Drug Discovery

“…Dihydromyric (24) and 2",3"-dihydroxyanisolactone (25) (Figure 3) were reported from the peels of Clausena lansium and coumarin 24 illustrated α-glucosidase effects while compound 25 illustrated antibacterial effects towards Staphylococcus aureus [37]. The peels of Clausena lansium produced clauslactone V (26), clauslactoneW (27), clausenalansimin B (28), anisolactone (29) and wampetin (30) and all compounds demonstrated better α-glucosidase effects (IC 50 : 0.12 to 0.72 mM) than standard acarbose (IC 50 : 1.55 mM) [38].…”

“…The peels of Clausena lansium produced clauslactone V (26), clauslactoneW (27), clausenalansimin B (28), anisolactone (29) and wampetin (30) and all compounds demonstrated better α-glucosidase effects (IC 50 : 0.12 to 0.72 mM) than standard acarbose (IC 50 : 1.55 mM) [38]. Dihydromyric (24) and 2′′,3′′-dihydroxyanisolactone (25) (Figure 3) were reported from the peels of Clausena lansium and coumarin 24 illustrated α-glucosidase effects while compound 25 illustrated antibacterial effects towards Staphylococcus aureus [37]. The peels of Clausena lansium produced clauslactone V (26), clauslactoneW (27), clausenalansimin B (28), anisolactone (29) and wampetin (30) and all compounds demonstrated better α-glucosidase effects (IC50: 0.12 to 0.72 mM) than standard acarbose (IC50: 1.55 mM) [38].…”

“…Eleutheroside B (32) and phlorin (33) are produced by the peels of C. grandis [34] and scorazanone (34) was reported from peels of Goniothalamus scortechinii [41]. 3′,5′-Di-C-β-glucopyranosylphloretin (35) was produced by the peels of Fortunella japonica [42] while arbutin (36) and malaxinic acid (37) were reported from Pyrus pyrifolia (Asian pear) [43].…”

“…On the other hand, alkaloid 57 demonstrated moderate antibacterial potential towards Staphylococcus aureus [58]. Another alkaloid, clausenamide (63), was isolated from peels of Clausena lansium and illustrated α-glucosidase effects [37]. Piperine (53) was isolated form the Punica granatum fruit peel and inhibited cathepsin D protease with IC 50 : 12.0 µg/mL [56].…”

“…On the other hand, alkaloid 57 demonstrated moderate antibacterial potential towards Staphylococcus aureus [58]. Another alkaloid, clausenamide (63), was isolated from peels of Clausena lansium and illustrated α-glucosidase effects [37].…”