Hsiang-Ruei Liao

Triterpenoids from the Roots of Rhaphiolepis indica var. tashiroi and Their Anti-Inflammatory Activity

Two new triterpenoids, 2α,3β-dihydroxyolean-11,13(18)-dien-19β,28-olide (1) and 3β,5β-dihydroxyglutinol (2), together with eight known compounds (3–10) were isolated from the roots of Rhaphiolepis indica var. tashiroi (Rosaceae). The structures of 1–10 were determined by spectroscopic techniques. Among these isolates, 2α,3β-dihydroxyolean-13(18)-en-28-oic acid (9) exhibited inhibitory effect on N-formyl-methionyl-leucyl-phenylalanine (fMLP)-induced superoxide production, with an IC50 value of 16.50 μM.

Limonoids from the Seeds of Swietenia macrophylla and Their Anti-Inflammatory Activities.

A new limonoid, swietemacrophin (1), was isolated from the seeds of Swietenia macrophylla, together with five known compounds 2–6. The structure of 1 was determined through extensive 1D/2D-NMR and mass-spectrometric analyses. Swietemacrophin (1), humilinolide F (2), 3,6-O,O-diacetylswietenolide (3), 3-O-tigloylswietenolide (4), and swietemahonin E (5) exhibited inhibition (IC50 values ≤ 45.44 μM) of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine (fMLP). Compounds 1, 4, 5, and swietenine (6) showed potent inhibition with IC50 values ≤ 36.32 μM, against lipopolysaccharide (LPS)-induced nitric oxide (NO) generation.

Inverted-T lip reduction for lower lip repair in Van der Woude syndrome: a review and comparison of aesthetic results

Elimination of cosmetic deformity of lower lip pits and lower lip protrusion is the most common indication for lower lip repair in Van der Woude syndrome. 34 patients with lower lip pits that were operated on between 1982 and 2006 were reviewed. Surgical correction was performed with one of three different techniques: simple excision, vertical wedge resection, or inverted-T lip reduction. The aesthetic results were evaluated by two groups of raters. One group consisted of 10 medical professionals, and the other 10 lay people. A rating scheme was utilized, with a score of 3 for good, 2 for fair, and 1 for poor results. The final results were compared based on the mean score for each patient and inter-rater reliability was assessed using a weighted kappa coefficient. There was a fair agreement on the ratings between raters within groups. Inverted-T lip reduction received the best aesthetic result score from both groups of evaluators, with a mean score of 2.38±0.30 in the professional group, and 2.43±0.29 in the lay group. The results conclude that inverted-T lip reduction is a simple, safe and effective technique that achieves a better aesthetic result in lower lip repair of Van der Woude syndrome.

The anti-inflammatory effect of 2-(4-hydroxy-3-prop-2-enyl-phenyl)-4-prop-2-enyl-phenol by targeting Lyn kinase in human neutrophils.

The undesirable respiratory burst in neutrophils can lead to inflammation and tissue damage. This study investigates the effect and the underlying mechanism of 2-(4-hydroxy-3-prop-2-enyl-phenyl)-4-prop-2-enyl-phenol (honokiol), a lignan extracted from the stem bark of Magnolia officinalis Rehd. et Wils (Magnoliaceae), on N-formyl-L-methionyl-L-leucyl-L-phenylalanine (fMLP)-induced respiratory burst in human neutrophils. Signaling pathways regulated by honokiol which modulate fMLP-induced respiratory burst and cathepsin G release were evaluated by phosphorylation of Src family kinase induced by fMLP, Src family kinases activities and by immunoblotting analysis of the downstream targets of Src kinase. Briefly, honokiol inhibited fMLP-induced superoxide anion production (IC50 = 9.80 ± 0.21 μM, n = 4), cathepsin G release (IC50 = 14.23 ± 1.43 μM, n = 4) and migration (IC50 = 5.69 ± 1.51 μM, n = 4) in a concentration dependent manner. Further, honokiol specifically suppresses fMLP-induced Lyn (a member of the Src kinase family) phosphorylation, by inhibiting Lyn kinase activity. Consequently, honokiol attenuated the downstream targets of Lyn kinase, such as Tec translocation from the cytosol to the inner leaflet of the plasma membrane, phosphorylation of AKT, P38, PLCγ2, protein kinase C and membrane localization of p47(phox). On the other hand, fMLP-induced phosphorylation of Hck, Fgr kinase activity (other members of Src kinase), downstream phosphorylation of Vav1 and extracellular signal-regulated kinase remained unaffected. In addition, honokiol neither inhibited NADPH oxidase activity nor increased cyclic AMP levels. Honokiol is not a competitive or allosteric antagonist of fMLP. In conclusion, honokiol specifically modulates fMLP-mediated neutrophil activation by inhibiting Lyn activation which subsequently interferes with the activation of PLCγ2, AKT, p38, protein kinase C, and p47(phox).

Beilschamide, a New Amide, and Cytotoxic Constituents of Beilschmiedia erythrophloia

A new amide, beilschamide (1), has been isolated from the stem of Beilschmiedia erythrophloia, together with seven known compounds, N-trans-feruloyltyramine (2), N-trans-feruloyloctopamine (3), vanillin (4), α-tocopheryl quinone (5), β-sitostenone (6), β-sitosterol (7), and 6α-hydroxystigmast-4-en-3-one (8). The structure of the new compound 1 was determined through spectroscopic and MS analyses. N-trans-Feruloyloctopamine (3) and beilschamide (1) exhibited cytotoxic effects with IC50 values of 10.3 and 21.2 μg/mL, respectively, against CCRF-CEM cell line.

5-Hydroxy-7-methoxyflavone inhibits N-formyl-L-methionyl-L-leucyl-L-phenylalanine-induced superoxide anion production by specific modulate membrane localization of Tec with a PI3K independent mechanism in human neutrophils.

Respiratory burst mediates crucial bactericidal mechanism in neutrophils. However, undesirable respiratory burst leads to pathological inflammation and tissue damage. This study investigates the effect and the underlying mechanism of 5-hydroxy-7-methoxyflavone (MCL-1), a lignan extracted from the leaves of Muntingia calabura L. (Tiliaceae), on N-formyl-L-methionyl-L-leucyl-L-phenylalanine (fMLP)-induced respiratory burst and cathepsin G release in human neutrophils. Signaling pathways regulated by MCL-1 to oppose fMLP-induced respiratory burst were evaluated by membrane localization of Tec induced by fMLP and by immunoblotting analysis of downstream phosphorylation targets of Tec. Briefly, MCL-1 specific inhibited fMLP-induced superoxide anion production in a concentration-dependent (IC(50)=0.16±0.01 μM) and Tec kinase-dependent manner, however, MCL-1 did not affect fMLP-induced cathepsin G release. Further, MCL-1 suppressed fMLP-induced Tec translocation from the cytosol to the inner leaflet of the plasma membrane, and subsequently activation of phospholipase Cγ2 (PLCγ2). Moreover, MCL-1 attenuated PLCγ2 activity and intracellular calcium concentration notably through extracellular calcium influx. Consequently, fMLP-induced phosphorylation of protein kinase C (PKC) and membrane localization of p47(phox) were decreased by MCL-1 in a Tec-dependent manner, while the phosphorylation of extracellular signal-regulated kinase (ERK), p38, AKT and Src tyrosine kinase family remained unaffected. In addition, MCL-1 neither inhibited NADPH oxidase activity nor increased cyclicAMP levels. MCL-1 specific opposes fMLP-mediated respiratory burst by inhibition of membrane localization of Tec and subsequently interfered with the activation of PLCγ2, protein kinase C, and p47(phox).

New Sesquiterpenoids and Anti-Platelet Aggregation Constituents from the Rhizomes of Curcuma zedoaria

Two new sesquiterpenoids—13-hydroxycurzerenone (1) and 1-oxocurzerenone (2)—have been isolated from the rhizomes of Curcuma zedoaria, together with 13 known compounds (3–15). The structures of two new compounds were determined through spectroscopic and MS analyses. Among the isolated compounds, 13-hydroxycurzerenone (1), 1-oxocurzerenone (2), curzerenone (3), germacrone (4), curcolone (5), procurcumenol (6), ermanin (7), curcumin (8), and a mixture of stigmast-4-en-3,6-dione (12) and stigmasta-4,22-dien-3,6-dione (13) exhibited inhibition (with inhibition % in the range of 21.28%–67.58%) against collagen-induced platelet aggregation at 100 μM. Compounds 1, 5, 7, 8, and the mixture of 12 and 13 inhibited arachidonic acid (AA)-induced platelet aggregation at 100 μM with inhibition % in the range of 23.44%–95.36%.

New pterosin sesquiterpenes and antitubercular constituents from Pteris ensiformis.

Two new pterosin sesquiterpenes, (2S)‐13‐hydroxypterosin A (1) and (2S,3S)‐12‐hydroxypterosin Q (2), were isolated from the whole plants of Pteris ensiformis, together with six known compounds. The structures of 1 and 2 were determined through extensive 1D/2D‐NMR and MS analyses. Compound 2 exhibited antitubercular activity (MIC 6.25 μg/ml) against Mycobacterium tuberculosis H37Rv in vitro.

A New Benzenoid and Anti-Inflammatory Constituent of Capparis acutifolia

A new benzenoid, propyl 7-methoxybenzo[d][1,3]dioxole-5-carboxylate (1), has been isolated from the stems of Capparis acutifolia, together with five known compounds, rutin (2), 3β-hydroxystigmast-5-en-7-one (3), 6β-hydroxystigmast-4-en-3-one (4), sitosterol trans-ferulate (5), and sitosterol cis-ferulate (6). The structure of the new compound 1 was determined through spectroscopic and MS analyses. Rutin (2) exhibited potent inhibition, with IC50 value of 1.26 ± 0.15 μg/mL, against formyl-L-methionyl-L-leucyl-L-phenylalanine (fMLP)-induced superoxide anion (O2·–) generation.

A New 2H-Pyran-2-One Derivative and Anti-inflammatory Constituents of Alpinia zerumbet

A new 2H-pyran-2-one derivative, 4-hydroxy-6-(4-methoxyphenethyl)-2H-pyran-2-one (1), together with four known compounds, 5,6-dehydrokawain (2), dihydro-5,6-dehydrokawain (3), (E)-labda-8(17),12-diene-15,16-dial (4), and quercetin (5) were isolated from the rhizomes of Alpinia zerumbet. (E)-Labda-8(17),12-diene-15,16-dial (4) and quercetin (5) exhibited potent inhibition, with IC50 values of 3.18 ± 1.13 and 1.17 ± 0.13 μg/mL, respectively, against formyl-L-methionyl-L-leucyl-L-phenylalanine (fMLP)-induced superoxide anion (O2−) generation.