Toshinori Nakagawa

Multiple uses of Essential Oil and By-Products from Various Parts of the Yakushima Native Cedar (Cryptomeria Japonica)

This article presents multiple potential uses of the Yakushima native cedar (Cryptomeria japonica), known in Japan as the Yaku-sugi tree. The Yaku-sugi was divided into four parts: leaves, branches with leaves, branches, and stems. We obtained the essential oil, hydrosol, distillation residue, and distillation wastewater from the trees. Essential oil and hydrosol were determined to be volatile organic compounds. All samples were screened for the following bioactivities: antioxidative, antibacterial, and anti-melanogenesis activities. Freeze-dried distillation residue was tested to assess whether it had a deodorizing effect. The main component of the leaf essential oil was found to be monoterpenes. In contrast, the stem essential oil mainly contained sesquiterpenes. In terms of bioactivities, the leaf essential oil showed antibacterial activity and the stem essential oil showed anti-melanogenesis activity. Distillation residue and wastewater showed many activities, including antioxidant, antibacterial, and anti-melanogenesis activities. Moreover, the residue had a deodorizing effect against ammonia.

Effect of polyphenols from Vicia faba L on lipase activity and melanogenesis

Abstract Two new flavonoid glycosides, kaempferol 3-O-α-L-rhamnopyranosyl (1→6) (3′′-acetyl)-β-D-galactopyranoside 1 and kaempferol 3-O-α-L-arabinopyranosyl-5-O-α-L-rhamnopyranoside 2, along with six known ones 3–8 were isolated from the flowers of Vicia faba L. (Fabaceae). Methanol extract and the isolated compounds were tested against lipase and melanogenesis inhibition activities and resulted in that compound 2 showed 53 and 77% lipase inhibition activity in concentrations of 400 and 800 μg/mL, respectively. For melanogenesis, compounds 2, 3 and 4 exhibited potent melanogenesis inhibition activity where the melanin content in melanoma cells was decreased to be about 57.5, 56 and 61%, respectively, with no obvious melanocytotoxicity. The rest of compounds showed weak to moderate activity. The results of melanogenesis inhibition activity of this study suggested the potential use of Vicia faba flowers as a skin-whitening agent and reveal the flowers to be a rich source of important phytochemicals with antilipase and melanogenesis inhibitory activity.

Determination of seed soundness in conifers cryptomeria japonica and chamaecyparis obtusa using narrow-multiband spectral imaging in the short-wavelength infrared range

Regeneration of planted forests of Cryptomeria japonica (sugi) and Chamaecyparis obtuse (hinoki) is the pressing importance to the forest administration in Japan. Low seed germination rate of these species, however, has hampered low-cost production of their seedlings for reforestation. The primary cause of the low germinability has been attributed to highly frequent formation of anatomically unsound seeds, which are indistinguishable from sound germinable seeds by visible observation and other common criteria such as size and weight. To establish a method for sound seed selection in these species, hyperspectral imaging technique was used to identify a wavelength range where reflectance spectra differ clearly between sound and unsound seeds. In sound seeds of both species, reflectance in a narrow waveband centered at 1,730 nm, corresponding to a lipid absorption band in the short-wavelength infrared (SWIR) range, was greatly depressed relative to that in adjacent wavebands on either side. Such depression was absent or less prominent in unsound seeds. Based on these observations, a reflectance index SQI, abbreviated for seed quality index, was formulated using reflectance at three narrow SWIR wavebands so that it represents the extent of the depression. SQI calculated from seed area-averaged reflectance spectra and spatial distribution patterns of pixelwise SQI within each seed area were both proven as reliable criteria for sound seed selection. Enrichment of sound seeds was accompanied by an increase in germination rate of the seed lot. Thus, the methods described are readily applicable toward low-cost seedling production in combination with single seed sowing technology.

Biological Activities of Oleanolic Acid Derivatives from Calendula officinalis Seeds

Phytochemical examination of butanol fraction of Calendula officinalis seeds led to the isolation of two compounds identified as 28‐O‐β‐D‐glucopyranosyl‐oleanolic acid 3‐O‐β‐D–glucopyranosyl (1→3)‐β‐D‐glucopyranosiduronic acid (CS1) and oleanolic acid 3‐O‐β‐D–glucopyranosyl (1→3)‐β‐D‐glucopyranosiduronic acid (CS2). Biological evaluation was carried out for these two compounds such as melanin biosynthesis inhibitory, hyaluronic acid production activities, anti obesity using lipase inhibition and adipocyte differentiation as well as evaluation of the protective effect against hydrogen peroxide induced neurotoxicity in neuro‐2A cells. The results showed that, compound CS2 has a melanin biosynthesis stimulatory activity; however, compound CS1 has a potent stimulatory effect for the production of hyaluronic acid on normal human dermal fibroblast from adult (NHDF‐Ad). Both compounds did not show any inhibitory effect on both lipase and adipocyte differentiation. Compound CS2 could protect neuro‐2A cells and increased cell viability against H2O2. These activities (melanin biosynthesis stimulatory and protective effect against H2O2 of CS2 and hyaluronic acid productive activities of these triterpene derivatives) have been reported for the first time. Copyright

Changes in content of triterpenoids and polysaccharides in Ganoderma lingzhi at different growth stages

Ganoderma lingzhi is a traditional medicinal mushroom, and its extract contains many bioactive compounds. Triterpenoids and polysaccharides are the primary bioactive components that contribute to its medicinal properties. In this study, we quantified 18 triterpenoids, total triterpenoid content and total polysaccharide content in the ethanol and water extracts of G. lingzhi at different growth stages. Triterpenoids were quantified by liquid chromatograph–tandem mass spectrometry in the multiple-reaction-monitoring mode. Total triterpenoid and total polysaccharide content were determined by colorimetric analysis. The results indicated that the fruit bodies at an early growth stage had a higher content of ganoderic acid A, C2, I and LM2, as well as of ganoderenic acid C and D, than those at a later growth stage. In contrast, ganoderic acid K, TN and T–Q contents were higher in mature fruit bodies (maturation stage). The highest total triterpenoid and total polysaccharide contents were found in fruit bodies before maturity (stipe elongation stage or early stage of pileus formation). Our results provide information which will contribute to the establishment of an efficient cultivation system for G. lingzhi with a higher content of triterpenoids.

Improved Biological Activities of Isoepoxypteryxin by Biotransformation

Isoepoxypteryxin is the major coumarin of a Japanese medicinal plant Angelica shikokiana. This research was designed to study the effect of structural changes through fungal biotransformation on the reported biological activities of isoepoxypteryxin. Among the tested microorganisms, only Cordyceps sinensis had enzymes that could catalyze the ester hydrolysis and the reductive cleavage of the epoxide ring of isoepoxypteryxin, separately, to give two more polar metabolites (+)‐cis‐khellactone (P1) and a new coumarin derivative (+)‐cis‐3′‐[(2‐methyl‐3‐hydroxybutanoyl)oxy]‐4′‐acetoxy‐3′,4′‐dihydroseselin (P2), respectively. The polar metabolite P2 showed stronger cytotoxicity and higher selectivity than isoepoxypteryxin. On the molecular level, P2 showed more in vitro inhibition of both tubulin polymerization and histone deacetylase 8 (HDAC8). Similarly, P2 showed more neuroprotection against amyloid beta fragment 1 – 42 (Aβ1 – 42)‐induced neurotoxicity in human neuroblastoma cells (SH‐SY5Y) and exhibited more inhibition of the in vitro aggregation of Aβ1 – 42. Both metabolites showed stronger antiplatelet aggregation by increased inhibition of thromboxane‐A2 synthase (TXS) activity and thromboxane‐A2 (TXA2) production. This study is the first to describe the improved cytotoxic, neuroprotective, and antiplatelet aggregation activities of isoepoxypteryxin through its biotransformation by C. sinensis.