Seco-Abietanoids from Cryptomeria japonica and Their Inhibitory Activity Toward Xanthine Oxidase

Chemistry of Natural Compounds - A new seco-abietanoid, 12-methoxy-7-oxo-6,7-secoabieta-8,11,13-trien-6-oic acid (1), and a known seco-abietanoid,12-hydroxy-6,7-secoabieta-8,11,13-triene-6,7-dial...     

Improved Synthesis of Asymmetric Curcuminoids and Their Assessment as Antioxidants

In this paper, the syntheses of twelve asymmetric curcumin analogs using Pabon’s method are reported. Generally, the previously reported yields of asymmetric curcuminoids, such as 9a (53%), 9c (38%), and 9k (38%), have been moderate or low. Herein, we propose that the low yields were due to the presence of water and n-BuNH₂ in the reaction media. To prove this formulated hypothesis, we have demonstrated that the yields can be improved by adding molecular sieves (MS) (4 Å) to the reaction mixture, thus reducing the interference of water. Therefore, improved yields (41–76%) were obtained, except for 9b (36.7%), 9g (34%), and 9l (39.5%). Furthermore, compounds 9b, 9d, 9e, 9f, 9g, 9h, 9i, 9j, and 9l are reported herein for the first time. The structures of these synthetic compounds were determined by spectroscopic and mass spectrometry analyses. The free radical scavenging ability of these synthetic asymmetric curcuminoids was evaluated and compared to that of the positive control butylated hydroxytoluene (BHT). Among the synthesized asymmetric curcuminoids, compounds 9a (IC₅₀ = 37.57 ± 0.89 μM) and 9e (IC₅₀ = 37.17 ± 1.76 μM) possessed effective 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging abilities, and compounds 9h (IC₅₀ = 11.36 ± 0.65 μM) and 9i (IC₅₀ = 10.91 ± 0.77 μM) displayed potent 2,2’-azinobis-(3-ethylbenzthiazoline-6-sulphonate) (ABTS) radical scavenging abilities comparable to that of curcumin (IC₅₀ = 10.14 ± 1.04 μM). Furthermore, all the synthetic asymmetric curcuminoids were more active than BHT.     

Secondary Metabolites with Anti-Inflammatory from the Roots of Cimicifuga taiwanensis

The genus Cimicifuga is one of the smallest genera in the family Ranunculaceae. Cimicifugae Rhizoma originated from rhizomes of Cimicifuga simplex, and C. dahurica, C. racemosa, C. foetida, and C. heracleifolia have been used as anti-inflammatory, analgesic and antipyretic remedies in Chinese traditional medicine. Inflammation is related to many diseases. Cimicifuga taiwanensis was often used in folk therapy in Taiwan for inflammation. Phytochemical investigation and chromatographic separation of extracts from the roots of Cimicifuga taiwanensis has led to the isolation of six new compounds: cimicitaiwanins A–F (1–6, respectively). The structures of the new compounds were unambiguously elucidated on the basis of extensive spectroscopic data analysis (1D- and 2D-NMR, MS, and UV) and comparison with the literature data. The effect of some isolates on the inhibition of NO production in lipopolysaccharide-activated RAW 264.7 murine macrophages was evaluated. Of the isolates, 3–6 exhibited potent anti-NO production activity, with IC₅₀ values ranging from 6.54 to 24.58 μM, respectively, compared with that of quercetin, an iNOS inhibitor with an IC₅₀ value of 34.58 μM. This is the first report on metabolite from the endemic Taiwanese plant-C. taiwanensis.     

Metabolites from a New Actinobacteria,Herbidospora yilanensis

Chemistry of Natural Compounds -     

Rumphellolides A-F, six new caryophyllane-related derivatives from the Formosan Gorgonian coral Rumphella antipathies

Six new caryophyllane-related natural products, including two carboxylated sesquiterpenoids, rumphellolides A (1) and B (2), and four norsesquiterpene alcohols, rumphellolides C-F (3-6), were isolated from the Formosan gorgonian coral Rumphella antipathies. The structures of the above new natural products were established on the basis of extensive spectral data analysis. Rumphellolides A (1), D (4), E (5), and F (6) showed weak antibacterial activity.     

Secondary Metabolites with Antimycobacterial Activities from One Actinobacteria: Herbidospora yilanensis

The cultivation of one actinobacteria strain, Herbidospora yilanensis, was isolated from sediment samples collected from Yilan County City in Taiwan, resulting in the isolation of five previously undescribed compounds: herbidosporayilanensins A–E (1–5), and four compounds isolated from nature for the first time: herbidosporayilanensins F–I (6–9). Their structures were elucidated by spectroscopic analyses, including 1D- and 2D-NMR experiments with those of known analogues, and on the basis of HR-EI-MS mass spectrometry, their antimycobacterial activities were also evaluated.     

Saccharpiscinols A–C: Flavans with Potential Anti-Inflammatory Activities from One Actinobacteria Saccharomonospora piscinae

Phytochemical investigation and chromatographic separation of extracts from the actinobacteria strain Saccharomonospora piscinae that was isolated from dried fishpond sediment of Kouhu township, in the south of Taiwan, led to the isolation of three new compounds, saccharpiscinols A–C (1–3, respectively), and three new natural products, namely (2S)-5,7,3′,4′-tetrahydroxy-6,8-dimethylflavanone (4), methyl-4-hydroxy-2-methoxy-6-methylbenzoate (5), and (±)-7-acetyl-4,8-dihydroxy-6-methyl-1-tetralone (6). Compounds 4–6 were reported before as synthesized products, herein, they are reported from nature for the first time. The structures of the new compounds were unambiguously elucidated on the basis of extensive spectroscopic data analysis (1D- and 2D-NMR, MS, and UV) and comparison with literature data. The effect of some isolates on the inhibition of NO production in lipopolysaccharide-activated RAW 264.7 murine macrophages was evaluated. Saccharpiscinol A showed inhibitory activities against LPS-induced NO production.     

Briarenolide E: the first 2-ketobriarane diterpenoid from an octocoral Briareum sp. (Briareidae)

A novel 2-ketobriarane diterpenoid, briarenolide E (1), was isolated from an octocoral Briareum sp. The structure of briarane 1 was elucidated by interpretations of spectral data. Compound 1 displayed modestly inhibitory effects on the generation of superoxide anions and the release of elastase by human neutrophils.