Protective effect of UV-irradiated red perilla (Perilla frutescens (L.) Britton) on carbon tetrachloride-induced liver injury in mice.

UV-irradiated red perilla demonstrated promising protective effects against carbon tetrachloride-induced liver injury in mice. UV exposure significantly enhanced the accumulation of rosmarinic acid, malonylshisonin, and shisonin in red perilla, and increased 1,1-diphenyl-2-picrylhydrazyl radical scavenging capacity. The hepatoprotective effect of UV-irradiated red perilla may be attributed to the high level of its polyphenolic compounds, which exhibit antioxidant activity.

Anti-Obesity Effects of Matoa (Pometia pinnata) Fruit Peel Powder in High-Fat Diet-Fed Rats.

Fruit peels, pericarps, or rinds are rich in phenolic/polyphenolic compounds with antioxidant properties and potentially beneficial effects against obesity and obesity-related non-communicable diseases. This study investigated the anti-obesity effects of matoa (Pometia pinnata) and salak (Salacca zalacca) fruit peel. Neither matoa peel powder (MPP) nor salak peel powder (SPP) affected the body weight, visceral fat weight, or serum glucose or lipid levels of Sprague-Dawley rats when included as 1% (w/w) of a high-fat diet (HFD). However, MPP significantly decreased the hepatic lipid level. MPP at a dose of 3% (w/w) of the HFD decreased body weight, visceral fat, and serum triglyceride levels as well as the hepatic lipid content. The inhibitory effect of MPP on hepatic lipid accumulation was not enhanced when its concentration was increased from 1% to 3% of the HFD. The anti-obesity effect of matoa was partly explained by the inhibitory effect of the matoa peel extract on fatty acid-induced secretion of ApoB-48 protein, a marker of intestinal chylomicrons, in differentiated Caco-2 cell monolayers. We identified hederagenin saponins that are abundant in MPP as potential anti-obesity substances. These results will contribute towards the development of functional foods with anti-obesity effects using the matoa fruit peel.

Changes in the extracted amounts and seasonally variable constituents of Diospyros kaki at different growth stages.

Persimmon Calyx is a crude drug derived from the persistent calyx of mature fruit of Diospyros kaki Thunberg (Ebenaceae) and is used for the treatment of intractable hiccups. Although there are several reports on the isolation of constituents from Persimmon Calyx, its active constituents have not been elucidated. In this study, by focusing on the medicinal part of Persimmon Calyx, calyx on mature fruit of D. kaki, we examined the changes in the extraction amounts of 3 cultivars of D. kaki ('Hiratanenashi', 'Jiro', and 'Tonewase') to identify and quantify seasonally variable constituents during the maturation process by analysing their chemical compositions. We found that the extraction weight of the calyx, fruit of persimmons, and total tannin content in calyxes were significantly increased during maturation. Lupeol (1), betulinic acid (2), pomolic acid (3), ursolic acid (4), ß-sitosterol (5), rotungenic acid (6), barbinervic acid (7), catechin (8), gallocatechin (9), and sucrose (10) were identified in the calyx of D. kaki. Compounds 1, 6, and 7 were isolated from Persimmon Calyx for the first time. Moreover, the isolated compounds (1-7) and their analogue (oleanolic acid) were quantitatively analysed, and the results showed that the amounts of 4 and oleanolic acid were reduced during maturation, whereas that of 2, 3, 6, and 7 were increased.

Drying the leaves of Perilla frutescens increases their content of anticancer nutraceuticals.

A regular intake of plant-derived bioactive agents has gained popularity because of the health benefits. Fresh leafy greens, however, normally have a low concentration of such bioactive agents. In this study, we found that drying markedly affected the accumulation of secondary metabolites and that dried leaves of Perilla frutescens L. (perilla) contained more anticancer flavonoids than fresh leaves. Drying is a major method of food preparation, particularly for plant-based foods, but the quality of the bioactive agents contained in the fresh and dried leaves of perilla has received only scant attention. Quantitative analysis of the concentrations of perillaldehyde, rosmarinic acid, apigenin, luteolin, 4-hydroxyphenyllactic acid, and 4-coumaric acid, some of which are known as nutraceuticals, revealed that the effect of drying significantly increased apigenin (28-fold) and luteolin (86-fold), but decreased rosmarinic acid in all leaf stages. We examined the positive effect on flavonoid levels on perilla leaves and confirmed that, by comparison with fresh perilla leaves, the dried leaves contained greater concentrations of anticancer flavonoids regardless of variety, form, or manner of cultivation. This indicates that drying can significantly increase the level of flavonoids in perilla leaves without a loss of flavor. Therefore, drying is a simple and effective method to improve the concentrations of bioactive agents, which increases the intake of beneficial substances derived from herbs and edible plants. This finding serves as a method for the supply of raw plant materials rich in bioactive agents that are suitable for labeling as edible nutraceuticals.

Palladium-catalyzed beta-allylation of 2,3-disubstituted indoles.

Given the prevalence of the indole nucleus in biologically active compounds, the direct C3-functionalization of 2,3-disubstituted indoles represents an important problem. Described is a general, high-yielding method for the palladium-catalyzed beta-allylation of carba- and heterocycle fused indoles, including complex natural product substrates.

Growth and Accumulation of Secondary Metabolites in Perilla as Affected by Photosynthetic Photon Flux Density and Electrical Conductivity of the Nutrient Solution.

The global demand for medicinal plants is increasing. The quality of plants grown outdoors, however, is difficult to control. Myriad environmental factors influence plant growth and directly impact biosynthetic pathways, thus affecting the secondary metabolism of bioactive compounds. Plant factories use artificial lighting to increase the quality of medicinal plants and stabilize production. Photosynthetic photon flux density (PPFD) and electrical conductivity (EC) of nutrient solutions are two important factors that substantially influence perilla (Perilla frutescens, Labiatae) plant growth and quality. To identify suitable levels of PPFD and EC for perilla plants grown in a plant factory, the growth, photosynthesis, and accumulation of secondary metabolites in red and green perilla plants were measured at PPFD values of 100, 200, and 300 µmol m-2 s-1 in nutrient solutions with EC values of 1.0, 2.0, and 3.0 dS m-1. The results showed significant interactive effects between PPFD and EC for both the fresh and dry weights of green perilla, but not for red perilla. The fresh and dry weights of shoots and leafy areas were affected more by EC than by PPFD in green perilla, whereas they were affected more by PPFD than by EC in red perilla. Leaf net photosynthetic rates were increased as PPFD increased in both perilla varieties, regardless of EC. The perillaldehyde concentration (mg g-1) in red perilla was unaffected by the treatments, but accumulation in plants (mg per plant) was significantly enhanced as the weight of dry leaves increased. Perillaldehyde concentrations in green perilla showed significant differences between combinations of the highest PPFD with the highest EC and the lowest PPFD with the lowest EC. Rosmarinic acid concentration (mg g-1) was increased in a combination of low EC and high PPFD conditions. Optimal cultivation conditions of red and green perilla in plant factory will be discussed in terms of plant growth and contents of medicinal ingredients.

Total synthesis of (+)-mycalamide A.

A convergent total synthesis of (+)-mycalamide A is described. A Yb(OTf)3-TMSCl catalytic system is used to synthesize a trioxadecalin ring system, which contains the right segment of mycalamide A. In addition, a tetrahydropyran ring, which is the left segment, is constructed with use of a novel one-pot delta-lactonization protocol. Both segments are prepared from a common starting material, d-mannitol. These segments are then coupled and the functional groups are transformed to synthesize (+)-mycalamide A.

One-Carbon Homologation of Primary Alcohols to Carboxylic Acids, Esters, and Amides via Mitsunobu Reactions with MAC Reagents.

A method is reported for the one-carbon homologation of an alcohol to the extended carboxylic acid, ester, or amide. The process involves the Mitsunobu reaction with an alkoxymalononitrile, followed by unmasking in the presence of a suitable nucleophile. The homologation and unmasking can even be performed in a one-pot process in high yield.

Palladium-catalyzed decarboxylative allylation and benzylation of N-alloc and N-Cbz indoles.

A set of general methods for the palladium-catalyzed decarboxylative C3-allylation and C3-benzylation of indoles, starting from the corresponding N-alloc and N-Cbz indoles, respectively, is reported. This chemistry provides ready access to a wide range of functionalized indolenines in good to excellent yields. A tandem process, wherein the palladium catalyzed allylation chemistry is coupled with a Mizoroki-Heck reaction, offers a simple route to cinnamylated products.

Rh(I)-catalyzed CO gas-free carbonylative cyclization reactions of alkynes with 2-bromophenylboronic acids using formaldehyde.

The rhodium(I)-catalyzed reaction of alkynes with 2-bromophenylboronic acids in the presence of paraformaldehyde resulted in a CO gas-free carbonylative cyclization, yielding indenone derivatives. [RhCl(BINAP)](2) and [RhCl(cod)](2) were responsible for the decarbonylation of formaldehyde and the subsequent carbonylation of alkynes with 2-haloboronic acids, respectively, leading to efficient whole carbonylation. Sterically bulky and electron-withdrawing groups on unsymmetrically substituted alkynes favored the alpha-position of indenones.

Convergent total synthesis of (+)-mycalamide A.

The details of a convergent total synthesis of (+)-mycalamide A are described. Yb(OTf)3-TMSCl-catalyzed cross-aldol reaction conditions are used to synthesize the right segment of mycalamide A. In this reaction, an acid-sensitive aldehyde reacts with methyl trimethylsilyl dimethylketene acetal without epimerization to provide the desired aldol adduct. Additionally, a tetrahydropyran ring, which is the left segment of mycalamide A, is prepared using a novel one-pot delta-lactone formation methodology. Both segments are constructed from a common starting material, d-mannitol. These segments are then coupled in the presence of BuLi, and the functional groups are transformed to complete the synthesis of (+)-mycalamide A.