Takagi M.,Nihon University |
Tachi Y.,Nihon University |
Zhang J.,Nihon University |
Shinozaki T.,Nihon University |
And 6 more authors.
Chemistry and Biodiversity | Year: 2014
Seventeen limonoids (tetranortriterpenoids), 1-17, including three new compounds, i.e., 17-defurano-17-(2,5-dihydro-2-oxofuran-3-yl)-28-deoxonimbolide (14), 17-defurano-17-(2ξ-2,5-dihydro-2-hydroxy-5-oxofuran-3-yl)-28- deoxonimbolide (15), and 17-defurano-17-(5ξ-2,5-dihydro-5-hydroxy-2-oxofuran- 3-yl)-2′,3′-dehydrosalannol (17), were isolated from an EtOH extract of the leaf of neem (Azadirachta indica). The structures of the new compounds were elucidated on the basis of extensive spectroscopic analyses and comparison with literature. Upon evaluation of the cytotoxic activities of these compounds against leukemia (HL60), lung (A549), stomach (AZ521), and breast (SK-BR-3) cancer cell lines, seven compounds, i.e., 1-3, 12, 13, 15, and 16, exhibited potent cytotoxicities with IC50 values in the range of 0.1-9.9 μM against one or more cell lines. Among these compounds, cytotoxicity of nimonol (1; IC50 2.8 μM) against HL60 cells was demonstrated to be mainly due to the induction of apoptosis by flow cytometry. Western blot analysis suggested that compound 1 induced apoptosis via both the mitochondrial and death receptor-mediated pathways in HL60 cells. In addition, when compounds 1-17 were evaluated for their inhibitory activities against melanogenesis in B16 melanoma cells, induced with α-melanocyte-stimulating hormone (α-MSH), seven compounds, 1, 2, 4-6, 15, and 16, exhibited inhibitory activities with 31-94% reduction of melanin content at 10 μM concentration with no or low toxicity to the cells (82-112% of cell viability at 10 μM). All 17 compounds were further evaluated for their inhibitory effects against the Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13- acetate (TPA) in Raji cells. Copyright © 2014 Verlag Helvetica Chimica Acta AG, Zürich.
ICHIMARU PHARCOS Co. | Date: 2006-03-28
Chemical reagents for use in manufacturing cosmetics and excipients for medicated cosmetics made of botanical extracts.
Tsuchiya Y.,Tohoku Womens College |
Tomita M.,Tohoku Womens College |
Tsuboi M.,ICHIMARU PHARCOS Co. |
Takahashi T.,ICHIMARU PHARCOS Co. |
And 5 more authors.
Bioscience, Biotechnology and Biochemistry | Year: 2013
The mechanism underlying proteoglycan (PG) absorption in the intestine is not clear. Hence we analyzed the transport of salmon PG in the rat jejunum, ileum, and colon by the everted-sac method. The jejunum showed the largest capacity for PG transport. Jejunal transport of PG was also greater than that of chondroitin A and C. An inhibitor of clathrin-mediated endocytosis reduced jejunal PG transport. We conclude that intestinal PG transport is highest in the jejunum, and is partially dependent on clathrin-mediated endocytosis.
Akazawa H.,Nihon University |
Fujita Y.,ICHIMARU PHARCOS Co. |
Banno N.,ICHIMARU PHARCOS Co. |
Watanabe K.,Nihon University |
And 4 more authors.
Journal of Oleo Science | Year: 2010
Ten cyclic diarylheptanoids (1-10), including three new compounds: myricanone 5-O-a-Larabinofuranosyl-(1→6)-b-D-glucopyranoside (7), myricanone 17-O-β-D-(6'-O-galloyl)-glucopyranoside (8), and 16-methoxy acerogenin B 9-O-β-D-apiofuranosyl-(1→6)-b-D-glucopyranoside (10), along with two flavonoids (11, 12), were isolated from the extracts of Myrica rubra (Myricaceae) bark. The structures of new compounds were determined on the basis of spectroscopic methods. On evaluation of compounds 1-12 against the melanogenesis in the B16 melanoma cells, six compounds, 3, 5, 7, 8, 10, and 12, exhibited inhibitory effects with 30-56% reduction of melanin content at 25 μg/mL with no or very weak toxicity to the cells (82-103% of cell viability at 25 μg/mL). In addition, upon evaluation of compounds 1-12 against the scavenging activities of free radicals [against the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical], seven compounds, 1, 3, 5, 6, 8, 11, and 12, showed potent scavenging activity [IC50 2-21 μM (0.6-7.3 μg/mL)]. © 2010 by Japan Oil Chemists' Society.
Zhang J.,Nihon University |
Koike R.,Nihon University |
Yamamoto A.,Nihon University |
Ukiya M.,Nihon University |
And 6 more authors.
Chemistry and Biodiversity | Year: 2013
A new flavonoid glycoside, chrysin 6-C-β-rutinoside (chrysin α-L-rhamnopyranosyl-(1→6)-C-β-glucopyranoside; 2), and two new triterpene glycosides, (31R)-31-O-methylpassiflorine (7) and (31S)-31-O-methylpassiflorine (8), along with 14 known glycosides, including three flavonoid glycosides, 1, 3, and 4, six triterpene glycosides, 5, 6, and 9-12, three cyano glycosides, 13-15, and two other glycosides, 16 and 17, were isolated from a MeOH extract of the leaves of Passiflora edulis (passion flower; Passifloraceae). The structures of new compounds were elucidated on the basis of extensive spectroscopic analysis and comparison with literature data. Upon evaluation of compounds 1-17 against the melanogenesis in the B16 melanoma cells induced with α-melanocyte-stimulating hormone (α-MSH), three compounds, isoorientin (1), 2, and (6S,9R)-roseoside (17), exhibited inhibitory effects with 37.3-47.2% reduction of melanin content with no, or almost no, toxicity to the cells (90.8-100.2% cell viability) at 100 μM. Western blot analysis showed that compound 2 reduced the protein levels of MITF, TRP-1, and tyrosinase, in a concentration-dependent manner while exerted almost no influence on the level of TRP-2, suggesting that this compound inhibits melanogenesis on the α-MSH-stimulated B16 melanoma cells by, at least in part, inhibiting the expression of MITF, followed by decreasing the expression of TRP-1 and tyrosinase. In addition, compounds 1-17 were evaluated for their inhibitory effects against the Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells. Copyright © 2013 Verlag Helvetica Chimica Acta AG, Zürich.