Three new compounds, 1-3, together with 22 known compounds, were isolated from the fruits of Piper retrofractum. The structures of the new compounds were elucidated on the basis of spectroscopic data analysis and comparison with literature values. Compound 1 was found to enhance the neurite outgrowth of NGF-mediated PC12 cells at concentrations ranging from 0.1 to 10 μM.

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Bangle (Zingiber purpureum) is a tropical ginger that is used as a spice in Southeast Asia. Phenylbutenoid dimers isolated from Bangle have exhibited neurotrophic effects in primary cultured rat cortical neurons and PC12 cells. Furthermore, chronic treatment with phenylbutenoid dimers enhances hippocampal neurogenesis in olfactory bulbectomized mice. In this study, we investigated the effects of Bangle extract on behavior and hippocampal neurogenesis in vivo. SAMP8 mice, which are an established model for accelerated aging, with age-related learning and memory impairments, were given a Bangle-containing diet for 1 month, and subsequent behavioral tests and immunohistochemistry for Ki67, a proliferating cell marker, were performed. We found that the Bangle-containing diet improved spatial learning and memory deficits in the Morris water maze and significantly increased the numbers of Ki67-positive cells in the dentate gyrus of the SAMP8 mice. In addition, the Bangle extract exhibited a neurotrophin-like activity as indicated by the induction of neurite sprouting in PC12 cells. Our results suggest that Bangle is beneficial for the prevention of age-related progression of cognitive impairment.

To develop the Javanese ginger Bangle (Zingiber purpureum), which contains neurotrophic phenylbutenoid compounds named banglenes 1 and 2, as a functional food additive for protection of neurodegenerative disease, we investigated conversion method from 3 to 1 and 2 under practical conditions available in food processing steps. After several trials, we found that dimerization of 3 proceeded smoothly under refluxing EtOH/H 2 O (1/3) in the presence of ubiquinone (0.1 eq) in sealed tube, giving rise to 1 and 2 in 54% yield. When this condition was applied for 70% EtOH extract of bangle, content of 1 and 2 in the extract was increased 2-fold by 2.1%.

Novel Neurotrophic Phenylbutenoids from Indonesian Ginger Bangle, Zingiber purpureum. -Two new curcuminoids (I), and a new phenylbutenoid dimer (II) are isolated from Bangle (Zingiber purpureum). Compounds (I) promote neurite outgrowth of NGF-mediated PC12 cells. In addition, (Ia) accelerates the prevention of A42 aggregation. -(KUBO*, M.; GIMA, M.; BABA, K.; NAKAI, M.; HARADA, K.; SUENAGA, M.; MATSUNAGA, Y.; KATO, E.; HOSODA, S.; FUKUYAMA, Y.; Bioorg. Med. Chem. Lett. 25 (2015) 7, 1586-1591, http://dx.