Isolation and Identification of Lignans and Other Phenolic Constituents from the Stem Bark of Albizia julibrissin Durazz and Evaluation of Their Nitric Oxide Inhibitory Activity

Abstract

A dibenzylbutane-type lignan (16), along with eight furofuran-type (1–8), five furan-type (9–13), two dibenzylbutane-type (14 and 15), two bibenztetrahydronaphthalene-type lignans (17 and 18), two neolignans (19 and 20), and six phenolic derivatives (21–26) were isolated from an MeOH extract of the stem bark of Albizia julibrissin Durazz. The chemical structures of the obtained compounds were elucidated by nuclear magnetic resonance (NMR) and mass spectrometry (MS) analyses. Of the evaluated compounds, 14 were isolated from A. julibrissin and the Fabaceae family for the first time. Anti-inflammatory effects of the isolated analogs were investigated in terms of the inhibition of the nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated murine RAW264.7 macrophage cells. Ten compounds (10–12, 14, and 17–22) displayed significant dose-dependent inhibitory effects against the NO production, with IC50 values ranging from 5.4 to 19.2 µM. Moreover, eight compounds (1–4, 9, 13, 15, and 16) exhibited moderate inhibitory activities, with IC50 values ranging from 21.0 to 62.5 µM.

Two Lignan Glycosides from Albizia julibrissin Durazz. Noncompetitively Inhibit Serotonin Transporter

“…Compound 1 , white amorphous powder, [α] 24 D : −3.8 °C (MeOH), MS: [M-H] − ion peak at m / z 711.2510 (calculated value for C 33 H 43 O 17 − , 711.2532); CD: -0.69535 at 206 nm; 1 H-NMR δ (300 MHZ, methanol-d4): 6.74 (2H, H-2, H-6), 6.68 (2H, H-2′, H-6′), 4.89 (1H, H-1″), 4.79 (1H, H-7′), 4.73 (1H, H-7), 4.31 (2H, H-9a, 9′a), 4.30 (2H, H-9b, 9′b), 3.22 (1H, H-8′), 3.15 (1H, H-8), 3.88 (6H, s, 3, 5 -OCH 3 ), 3.86 (6H, s, 3′, 5′-OCH 3 ); 13 C-NMR (75 MHZ, methanol-d): 153.0 (C-3, C-5), 148.0 (C-3′, C-5′), 138.2 (C-4), 134.8(C-4′), 134.2 (C-1), 131.7 (C-1′), 104.4 (C-1″), 103.4 (C-2, C-6), 103.1 (C-2′, C-6′), 86.2 (C-7′), 85.8 (C-7), 77.0 (C-5″), 76.4 (C-3″), 74.3 (C-2″), 71.5 (C-9, 9′), 70.3 (C-4″), 61.2 (C-6″), 55.7 (-OCH 3 *2), 56.4 (-OCH 3 *2), 54.3 (C-8′), 53.7 (C-8); IR: 3353 (-OH), 2936 (CH 2 ), 2881 (CH 3 ), 1602 (aromatic C=C), 1511 (aromatic C=C), 1463 (CH 2 ), 1331 (OH), 1227 (C-O-C), 1115 (C-O-C), 1060 (C-O-C), 823 (CH). The spectral features match well with the reported compound, (-)-SAG [ 44 , 45 , 46 ].…”

“…In comparison with the spectral and optical characteristics of known compounds isolated from Albizia julibrissin Durazz. and other herbs, the two compounds were identified to be (-)-syringaresinol-4-O-β-D-apiofuranosyl-(1→2)-β-D-glucopyranoside (SAG) and (-)-syringaresinol-4,4′-bis-O-β-D-glucopyranoside (SBG), which had been reported [ 44 , 45 , 46 , 47 , 48 , 49 ]. The two compounds belong to lignan glycosides and share the same parental structure, (-)-syringaresinol ( Figure 2 ).…”

Secondary Metabolite Composition and Bioactivity of Genus Albizia: A Review

“…A. lebbeck seeds, on the other hand, have been used in traditional medicine to cure piles, diarrhea, and gonorrhea [33]. Albizia julibrissin is a sedative and antidepressant plant native to Asia whose bark extracts have been used in Chinese herbal medicine to treat patients suffering from central nervous system disorders such as depression and anxiety [34]. The bark and flowers of A. julibrissin have been used to heal ulcers and hemorrhoids in traditional Asian medicine.…”

Phenolic Constituents from Platycodon grandiflorum Root and Their Anti-Inflammatory Activity

“…A series of twenty-one compounds, including six lignols (1)(2)(3)(4)(5)(6), four phenolic compounds (7-10), a neolignan (11), three alkyl aryl ether-type lignans (12)(13)(14), two furofurantype lignans (15)(16), three benzofuran-type lignans (17)(18)(19), a tetrahydrofuran-type lignans (20), and a dibenzylbutane-type lignan (21), were isolated from the ethyl acetate-soluble fraction of the methanol extract of the root of P. grandiflorum. Their structures were identified as (+)-(7R,8R)-palmitoyl alatusol D (1), (+)-(7R,8R)-linoleyl alatusol D (2), (+)-(7R,8R)lignoceryl alatusol D (3) [16], (+)-(7R,8R)-alatusol D (4) [17], (−)-(7S,8R)-alatusol D (5) [18], (+)-(7S,8R)-guaiacylglycerol ( 6) [19], 3,3 -dimethoxy [1,1 -biphenyl]-4,4 -diol ( 7) [20], (+)-4hydroxy-3-methoxyphenylglycol (8) [21], vanillin (9), vanillic acid (10 [23], wikstroemol (13) [24], threo-4,7,9,9 -tetrahydroxy-3,3 -dimethoxy-8-O-4 -neolignan ( 14) [25], (+)-lariciresinol ( 15) [26], 3 -demethyl-(+)-lariciresinol ( 16) [27], (−)-dehydrodiconiferyl alcohol (17) [28], hawthornnin G (18) [29], dihydrodehydrodiconiferyl alcohol (19) [30], (+)-neoolivil (20) [31], and (−)-secoisolariciresinol (21) [32], based on the consistency of their analytical data with those from ...…”