Biological evaluation of secondary metabolites from the roots of Myrica adenophora.
Bioassay-guided fractionation of the roots of Myrica adenophora led to isolation of 24 known compounds and hitherto unknown compounds, including three A-type proanthocyanidins [adenodimerins A-C], two esters of sucrose [myricadenins A and B ], and the phenolic glycoside 6'-O-galloyl orbicularin. Spectroscopic analyses were used to determine their structures. Adenodimerin A, myricananin C, and myricetin showed strong 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activities, with SC50 values of 7.9, 16.3, and 15.9 μM, respectively. Adenodimerin A, myricanone, myricananin C, (-)-myricanol, myricanol 11-O-β-D-glucopyranoside, and myricetin showed stronger 2,2'-azino-bis-3-ethylbenzthiazoline-6-sulphonic acid (ABTS) radical scavenging activities than the positive control, with SC50 values of 7.5, 19.6, 12.0, 22.3, 19.6, and 15.6 μM, respectively. 5-Deoxymyricanone, porson, 12-hydroxymyricanone (-)-myricanol, and (+)-galeon exhibited anti-tubercular activity against Mycobacterium tuberculosis H37Rv in vitro and MICs values of 25.8, 40.0, 35.8, 30.0, and 15.0 μg/mL, respectively. Myricadenin A, myricanone, myricananin C, and (-)-myricanol exhibited anti-inflammatory activities in the iNOS assay with EC50 values of 18.1, 1.00, 13.0, and 7.5 μM, respectively.
Biological Activities of Triterpenoids and Phenolic Compounds from Myrica cerifera Bark
Seven triterpenoids, 1 – 7, two diarylheptanoids, 8 and 9, four phenolic compounds, 10 – 13, and three other compounds, 14 – 16, were isolated from the hexane and MeOH extracts of the bark of Myrica cerifera L. (Myricaceae). Among these compounds, betulin (1), ursolic acid (3), and myricanol (8) exhibited cytotoxic activities against HL60 (leukemia), A549 (lung), and SK‐BR‐3 (breast) human cancer cell lines (IC50 3.1 – 24.2 μm). Compound 8 induced apoptotic cell death in HL60 cells (IC50 5.3 μm) upon evaluation of the apoptosis‐inducing activity by flow cytometric analysis and by Hoechst 33342 staining method. Western blot analysis on HL60 cells revealed that 8 activated caspases‐3, ‐8, and ‐9 suggesting that 8 induced apoptosis via both mitochondrial and death receptor pathways in HL60. Upon evaluation of the melanogenesis‐inhibitory activity in B16 melanoma cells induced with α‐melanocyte‐stimulating hormone (α‐MSH), erythrodiol (7), 4‐hydroxy‐2‐methoxyphenyl β‐d‐glucopyranoside (13), and butyl quinate (15) exhibited inhibitory effects (65.4 – 86.0% melanin content) with no, or almost no, toxicity to the cells (85.9 – 107.4% cell viability) at 100 μm concentration. In addition, 8, myricanone (9), myricitrin (10), protocatechuic acid (11), and gallic acid (12) revealed potent DPPH radical‐scavenging activities (IC50 6.9 – 20.5 μm).
Oligosaccharide esters from the roots of Polygala arillata.
Two new sucrose esters, arillatoses A (1) and B (2), and four new trisaccharide esters, arillatoses C-F (3-6), were isolated from the roots of Polygala arillata, together with four known sucrose esters, glomeratose E (7) and sibiricoses A(1) (8), A(5) (9), and A(6) (10). The structures of the new compounds were elucidated on the basis of chemical and spectroscopic evidence.