Fumiyuki Kiuchi

Induction of Sesquiterpenoid Production by Methyl Jasmonate in Aquilaria sinensis Cell Suspension Culture

Abstract A suspension cell culture was established from Aquilaria sinensis, a timber species producing fragrant woody material called “Agarwood.” Methyl jasmonate was added to this culture in order to induce production of fragrant compounds. Cells were harvested after seven days of incubation and subjected to solid phase micro-extraction to produce an extract that was analyzed by GC/MS. Three peaks appeared on GC and were identifi ed as α-guaiene, γ-guaiene (= 1(10),11-guaiadiene), and α-humulene based on their mass fragmentation patterns and 13C-NMR data. The production of the guaiene derivatives and α-humulene showed different kinetics, which may mean they are the products of different induced biosynthetic enzymes.

Antichagasic Activity of Komaroviquinone Is Due to Generation of Reactive Oxygen Species Catalyzed by Trypanosoma cruzi Old Yellow Enzyme

ABSTRACT A novel potent trypanocidal diterpene, komaroviquinone, was reduced by Trypanosoma cruzi old yellow enzyme (TcOYE) to its semiquinone radical. The reductase activity in trypanosome lysates was completely immunoabsorbed by anti-TcOYE antibody. Since TcOYE is expressed throughout the T. cruzi life cycle, komaroviquinone is an interesting candidate for developing new antichagasic drugs.

Anticarcinogenic compounds in the Uzbek medicinal plant, Helichrysum maracandicum

An ethanol extract of Helichrysum maracandicum showed antiproliferative activity against cultured cells of SENCAR mouse in an in vitro assay, and activity-guided fractionation of the extract resulted in the isolation of isosalipurposide as an active substance. Naringenin chalcone, the aglycone of isosalipurposide, also showed strong antiproliferative activity. An in vivo assay of two-stage carcinogenesis on mouse skin revealed that epidermal application of isosalipurposide resulted in delayed formation of papillomas. Western blot analysis showed that the expression of p38 mitogen-activated protein kinase was suppressed by the administration of naringenin chalcone or isosalipurposide, which might be related to the anticarcinogenic activity.

Chirality transmission in flexible 5,5′-dinitrodiphenic esters connected with chiral secondary alcohols

Abstract Induced circular dichroism (CD) was observed with dinitrodiphenic esters of chiral secondary alcohols. The CD spectra of the esters prepared from a pair of antipodal alcohols were symmetrical to each other relative to the x -axis, indicating the enantiomeric nature of the esters. The sign of the Cotton effect at around 270 nm was found to reflect the absolute configuration of the original alcohol. In the case of aliphatic mono-alcohols, negative Cotton effect was observed for the esters of ( R )-alcohols and a positive effect for the esters of ( S )-alcohols. On the contrary, unsaturation or an oxygen atom at the vicinal position reversed the sign of the Cotton effect.

Bioactive constituents from Dracocephalum subcapitatum (O. Kuntze) Lipsky

From an EtOAc extract of Dracocephalum subcapitatum, five flavonoids, calycopterin, xanthomicrol, isokaempferide, luteolin and apigenin, together with five terpenoids, oleanolic acid, ursolic acid, geranial, neral and limonene-10-al, were isolated. Among them, citral and limonene-10-al were the most effective components against epimastigotes of Trypanosoma cruzi, the parasitic agent of Chagas disease.

A guanidine derivative from seeds of Plantago asiatica.

AbstractsA new guanidine derivative named plantagoguanidinic acid was isolated from the seeds of Plantagoxa0asiatica. The structure was elucidated by two-dimensional (2D) nuclear magnetic resonance (NMR) spectral and other spectral methods.

A new phenolic glucoside from an Uzbek medicinal plant, Origanum tyttanthum

A new phenolic glucoside was isolated from the aerial parts of Origanumtyttanthum, an Uzbek medicinal plant, together with 12 known compounds. The structure of the new compound was elucidated as 4-O-β-d-glucopyranosylbenzyl-3′-hydroxyl-4′-methoxybenzoate (1) based on the spectral and chemical evidence.

An unusual sesquiterpene derivative from Ferula kuhistanica

An unusual new sesquiterpene derivative, kuhistaferone (1), was isolated from the fruits of the Uzbekistan medicinal plant Ferula kuhistanica. The structure of 1 was established on the basis of spectroscopic evidence. Compound 1 showed moderate cytotoxicity against the human colon tumor cell line HCT116.

Chemical Composition of Essential Oils from Perilla setoyensis, A New Species of Wild Perilla in Japan

Abstract The essential oil of Perilla setoyensis G. Honda, a newly discovered wild perilla in Japan, was examined by GC and GC/MS. The principal volatile constituent of the leaves was revealed to be a novel monoterpene, shisofuran, which was fully characterized by spectroscopic means. Nonetheless, shisofuran (18.3–196%) was labile and decomposed during steam distillation, leaving 1-octen-3-ol (16.2–21.8%) and β-caryophyllene (18.3–19.6%) as the major constituents of the oil.

Genetic and Phenotypic Analyses of a Papaver somniferum T-DNA Insertional Mutant with Altered Alkaloid Composition

The in vitro shoot culture of a T-DNA insertional mutant of Papaver somniferum L. established by the infection of Agrobacterium rhizogenes MAFF03-01724 accumulated thebaine instead of morphine as a major opium alkaloid. To develop a non-narcotic opium poppy and to gain insight into its genetic background, we have transplanted this mutant to soil, and analyzed its alkaloid content along with the manner of inheritance of T-DNA insertion loci among its selfed progenies. In the transplanted T0 primary mutant, the opium (latex) was found to be rich in thebaine (16.3% of dried opium) by HPLC analysis. The analyses on T-DNA insertion loci by inverse PCR, adaptor-ligation PCR, and quantitative real-time PCR revealed that as many as 18 copies of T-DNAs were integrated into a poppy genome in a highly complicated manner. The number of copies of T-DNAs was decreased to seven in the selected T3 progenies, in which the average thebaine content was 2.4-fold that of the wild type plant. This may indicate that the high thebaine phenotype was increasingly stabilized as the number of T-DNA copies was decreased. In addition, by reverse transcription PCR analysis on selected morphine biosynthetic genes, the expression of codeine 6-O-demethylase was clearly shown to be diminished in the T0 in vitro shoot culture, which can be considered as one of the key factors of altered alkaloid composition.