The potential of immature poken (Citrus reticulata) extract in the weight management, lipid and glucose metabolism.

OBJECTIVES: The prevalence of obesity was increasing globally, with nearly half a billion of the world's population now considered to be overweight or obese. The immature poken (Citrus reticulata) was a good source of flavonoids and phenolic acids, which may exert an anti-obesity effect. However, the current efficacy in clinical trials was still unclear. Thus, the object of this study was to explore whether immature poken had an anti-obesity effect in the clinical trial. METHODS: In this study, we identified nine major compounds from immature poken extract (IPE), and most compounds significantly decreased the lipid accumulation in adipocytes. In addition, 20 subjects with body mass index (BMI) ≥ 24 or body fat > 30 were recruited and randomly allocated to placebo and experimental (IPE) groups for 6 week intervention and 2 week follow-up. RESULTS: In comparison with the baseline results (week 0), the body weight, body fat, and waist circumference at week 6 in the IPE group were significantly decreased by 1.49 kg, 0.33%, 2.1 cm. Moreover, in blood biochemical analysis, total cholesterol (TC), triglyceride (TG), fasting blood sugar (FBS), and insulin levels at week 6 in IPE group were also decreased by 3.6, 4.6, 2.1 (mg/dL), and 2.9 (µU/mL), respectively. CONCLUSIONS: The finding showed that immature poken had important roles in fat metabolism by suppressing adipogenesis, and immature poken may provide new weight loss strategies for obese people.

Novel 11-norbetaenone isolated from an entomopathogenic fungus Lecanicillium antillanum.

A novel nor-betaenone compound, 11-norbetaenone (1), was isolated from the culture broth of an entomopathogenic fungus Lecanicillium antillanum. The structure was determined on the basis of 1D and 2D NMR spectroscopic data. The absolute stereochemistry of 1 was further confirmed by X-ray single crystallography analysis. It is the first secondary metabolite reported from the species Lecanicillium antillanum. And it is also the first time that a betaenone-type compound was isolated from the genus Lecanicillium. Furthermore, 11-norbetaenone (1) displayed significant anti-angiogenic effect by suppressing tube formation.

Alkaloids from Pandanus amaryllifolius: Isolation and Their Plausible Biosynthetic Formation.

Pandanus amaryllifolius Roxb. (Pandanaceae) is used as a flavor and in folk medicine in Southeast Asia. The ethanolic crude extract of the aerial parts of P. amaryllifolius exhibited antioxidant, antibiofilm, and anti-inflammatory activities in previous studies. In the current investigation, the purification of the ethanolic extract yielded nine new compounds, including N-acetylnorpandamarilactonines A (1) and B (2); pandalizines A (3) and B (4); pandanmenyamine (5); pandamarilactones 2 (6) and 3 (7), and 5(E)-pandamarilactonine-32 (8); and pandalactonine (9). The isolated alkaloids, with either a γ-alkylidene-α,ß-unsaturated-γ-lactone or γ-alkylidene-α,ß-unsaturated-γ-lactam system, can be classified into five skeletons including norpandamarilactonine, indolizinone, pandanamine, pandamarilactone, and pandamarilactonine. A plausible biosynthetic route toward 1-5, 7, and 9 is proposed.

Suberoylanilide hydroxamic acid, a histone deacetylase inhibitor, induces the production of anti-inflammatory cyclodepsipeptides from Beauveria felina.

The addition of the histone deacetylase inhibitor suberoylanilide hydroxamic acid to a culture of the filamentous fungus Beauveria felina significantly changed its secondary metabolite profile and led to the isolation of eight compounds, including three new cyclodepsipeptides, desmethylisaridin E (1), desmethylisaridin C2 (2), and isaridin F (3), along with five known cyclodepsipeptide compounds. Isaridin F (3) possesses a cyclodepsipeptide ring with N-methylbutyric acid, which is rare in natural peptides. Absolute configurations of the new cyclodepsipeptides were achieved by Marfey's method. The anti-inflammatory activity of the isolated compounds was investigated through evaluating their effect on superoxide anion production and elastase release by FMLP-induced human neutrophils. Among the tested compounds, desmethylisaridin E (1) inhibited superoxide anion production and desmethylisaridin C2 (2) inhibited elastase release, with IC50 values of 10.00 ± 0.80 and 10.01 ± 0.46 µM, respectively.

An epigenetic modifier enhances the production of anti-diabetic and anti-inflammatory sesquiterpenoids from Aspergillus sydowii.

The addition of a DNA methyltransferase inhibitor, 5-azacytidine, to Aspergillus sydowii fungus culture broth changed its secondary metabolites profile. Analysis of the culture broth extract led to the isolation of three new bisabolane-type sesquiterpenoids: (7S)-(+)-7-O-methylsydonol (1), (7S,11S)-(+)-12-hydroxysydonic acid (2) and 7-deoxy-7,14-didehydrosydonol (3), along with eight known compounds. The isolated compounds were evaluated for their anti-diabetic and anti-inflammatory activities. Among the isolates, (S)-(+)-sydonol (4) did not only potentiate insulin-stimulated glucose consumption but also prevented lipid accumulation in 3T3-L1 adipocytes. Additionally, (S)-(+)-sydonol (4) exhibited significant anti-inflammatory activity through inhibiting superoxide anion generation and elastase release by fMLP/CB-induced human neutrophils. This is the first report on isolating a secondary metabolite with anti-diabetic and anti-inflammatory activities from microorganisms.

Tenuipyrone, a novel skeletal polyketide from the entomopathogenic fungus, Isaria tenuipes, cultivated in the presence of epigenetic modifiers.

The concomitant addition of the histone deacetylase inhibitor and the DNA methyltransferase inhibitor to the culture medium of an entomopathogenic fungus, Isaria tenuipes, greatly enhanced its secondary metabolite production and led to the isolation of tenuipyrone (1), a novel polyketide with an unprecedented tetracyclic ring system bearing a spiroketal structural component, along with two known C(10)-polyketides, cephalosporolide B (2), which is a plausible biosynthetic precursor of 1, and cephalosporolide F (3).

Antioxidant and tyrosinase inhibitory constituents from a desugared sugar cane extract, a byproduct of sugar production.

Recycling agricultural resources has become an important issue worldwide promoting the economical value of agricultural production processes. Desugared sugar cane extract (DSE) from Saccharum officinarum is a byproduct obtained during sugar production. Two new neolignan glucosides, saccharnan A (1) and saccharnan B (2), together with 10 known phenolics (3-12) were isolated from DSE, and their structures were elucidated on the basis of NMR spectral analysis. Compounds 3, 4, 8, and 9 showed good activity against DPPH radical (IC(50) ≤ 51.20 µM) and compounds 3-8 and 12 exhibited strong ABTS(+) free radical scavenging activity (IC(50) ≤ 51.57 µM) compared to those of the positive controls, ascorbic acid and Trolox. Moreover, compounds 7 and 12 acted as potent tyrosinase inhibitors (IC(50) ≤ 42.59 µM) compared to the positive control arbutin. Our results highlighted the economical value of recycling DSE for the future development of natural antioxidants and/or tyrosinase inhibitors.

A novel alkaloid, aristopyridinone A and anti-inflammatory phenanthrenes isolated from Aristolochia manshuriensis.

A novel alkaloid, aristopyridinone A (1) and a new phenanthrene, aristolamide II (2), were isolated from Aristolochia manshuriensis (Guanmutong) together with eight known phenanthrenes (3-10). All structures were elucidated by spectroscopic methods. Compound 2 showed a selective inhibitory effect on elastase release by human neutrophils in response to fMLP with an IC(50) value of 4.11 µg/mL. Compound 7 exhibited significant inhibitory effects on superoxide anion generation and elastase release with IC(50) values of 0.12 and 0.20 µg/mL, respectively.

Anti-inflammatory and antioxidant components from Hygroryza aristata.

Twenty-six known compounds and two new compounds, including a new lignan, (7S*,8R*,7'R*,8'S*)-icariol A2-9-O-ß-xylopyranoside (1), and a new indole alkaloid, hygarine (2), were isolated from the extracts of Hygroryza aristata (Gramineae). The structures of all compounds were elucidated on the basis of NMR spectral analysis. The compounds (-)-epigallocatechin-3-O-gallate (4) and (-)-epicatechin-3-O-gallate (5) possess free radical scavenging activities and compound 1 could inhibit superoxide anion generation and elastase release by fMLP/CB-induced human neutrophils with IC50 values of 19.33 ± 0.86 and 24.14 ± 1.59 µM, respectively.

The inhibition of superoxide anion generation in human neutrophils by Viscum coloratum.

One new 1,3-diphenylpropane, viscolin (1), and one new flavanone, (2S)-7,4'-dihydroxy-5,3'-dimethoxyflavanone (2), together with thirty-nine known compounds, which included eleven known flavanones, two chromones, fourteen benzenoids, one inositol, two pyrimidines, four triterpenoids and five steroids, were isolated and characterized from Viscum coloratum. Structures of new compounds were determined by spectral analysis. Among them, viscolin (1) showed the most significant inhibition on superoxide anion generation by human neutrophils in response to fMLP (formyl-L-methionyl-L-leucyl-L-phenylalanine).