Synthesis, growth inhibitory activity against tumor cells, and structure-activity relationship of CGK733 and its analogs.

CGK733 was reported as a compound that inhibited ATM/ATR kinase activities and blocked their checkpoint signaling pathways with great selectivity. However, this paper was subsequently retracted, and the truth about the activity of CGK733 remains unclear. We synthesized various analogs of CGK733 with a modification of the carboxylic acid moiety and/or the aniline derivative moiety to accumulate knowledge of the structure-activity relationship of this compound.

Advancement in structure elucidation of natural medium-sized lactones through synthesis and theoretical calculations.

Medium-sized lactones are an important class of natural products with diverse biological activities. Unlike conventional organic compounds, these molecules exhibit elevated levels of conformational flexibility. This inherent structural feature occasionally exacerbates the complexities associated with determining their conformation, thereby posing challenges in deciphering their stereochemistry or, in certain instances, leading to incorrect structures.

Chrysin 7-O-β-d-glucopyranoside increases hepatic low-density lipoprotein receptor expression through AMP-activated protein kinase activation.

Elevated plasma low-density lipoprotein (LDL) cholesterol level is a risk factor for developing atherosclerosis. Increased LDL receptor (LDLR) expression is expected to reduce the risk of atherosclerotic disease since hepatic LDLR is essential for clearing plasma LDL cholesterol. Here, we screened human LDLR promoter effectors and observed that extracts from peduncles of sweet cherry (Prunus avium) 'Sato-Nishiki' induce LDLR gene promoter activity.

Divergent Synthesis of Stachyurin and Casuarinin Focusing on C-Glycosidic Bond Reactivity.

Stachyurin and casuarinin are ellagitannins, a class of polyphenols that exhibit various biological activities that have an impact on human health. Casuarinin is a stachyurin stereoisomer. These compounds contain the characteristic C-glycosidic bond between the open-chain d-glucose and the phenol aromatic ring.

Adjacent double branches exist in the branching structure of starch.

Starch is composed of two giant polymers of glucose-linked amylose and amylopectin but is not considered to have a branched structure with adjacent α-1,6-linkages (adjacent double branches). We previously discovered that the oligosaccharide DP6-1 contains adjacent double branches in sake, a Japanese rice wine. In this study, we analyzed the oligosaccharides generated from rice starch following porcine pancreatic α-amylase and glucoamylase digestion by hydrophilic interaction chromatography coupled with time-of-flight/mass spectrometry.

Sulforaphane suppresses the activity of sterol regulatory element-binding proteins (SREBPs) by promoting SREBP precursor degradation.

Sterol regulatory element-binding proteins (SREBPs) are transcription factors that regulate various genes involved in cholesterol and fatty acid synthesis. In this study, we describe that naturally occurring isothiocyanate sulforaphane (SFaN) impairs fatty acid synthase promoter activity and reduces SREBP target gene (e.g.

Synthesis and DFT-NMR-guided structure revision of cremenolide.

The structure of an anti-plant pathogenic and plant growth-promoting nonenolide, namely cremenolide, was revised by an efficient combination of DFT-based theoretical NMR calculations and synthesis of a target diastereomer. Initially, the planar structure of cremenolide was reconsidered by an individual analysis of the reported NMR spectra. Subsequently, the relative configuration was predicted using NMR calculations of all possible diastereomers based on the ωB97X-D functional.

Identification of biosynthetic intermediates for the mating hormone α2 of the plant pathogen Phytophthora.

The heterothallic group of the plant pathogen Phytophthora can sexually reproduce between the cross-compatible mating types A1 and A2. The mating hormone α2, produced by A2 mating type and utilized to promote the sexual reproduction of the partner A1 type, is known to be biosynthesized from phytol. In this study, we identified 2 biosynthetic intermediates, 11- and 16-hydroxyphytols (1 and 2), for α2 by administering the synthetic intermediates to an A2-type strain to produce α2 and by administering phytol to A2 strains to detect the intermediates in the mycelia.

Sulfoquinovosylglyceryl ether, a new group of ether lipids from lake ball-forming green alga Aegagropilopsis moravica (family Pithophoraceae).

Ether lipids are a minor group of glycerolipids but widespread in nature, playing a vital function as membrane lipids, signalling molecules, or buoyant material. We have discovered sulfoquinovosylchimyl alcohol (1), a sulfonate-substituted glyceroglycolipid, from a lake ball-forming green alga Aegagropilopsis moravica (family Pithophoraceae), with the guidance of antimicrobial activity. The structure of 1, including absolute configurations of all sterogenic centers, was established by extensive NMR analysis, chemical degradation studies, and finally by total synthesis.

Studies on analogs of DAMASCENOLIDETM: Part 4. Synthesis and odor evaluation of sulfur-containing analogs of DAMASCENOLIDETM.

DAMASCENOLIDETM [1, 4-(4-methylpent-3-en-1-yl)furan-2(5H)-one], which is isolated from damask rose, is a useful aroma compound with a citrus-like odor. We have previously reported on the synthesis and odor properties of 34 analogs of 1 as part of our new aroma compound development project. In order to develop better aroma compounds and to gather more information on structure-odor relationships, 6 novel sulfur-containing analogs of 1 were synthesized.

Studies on analogs of DAMASCENOLIDETM: Part 3. Synthesis and odor evaluation of dimethylated, cyclopropanated, and other analogs of DAMASCENOLIDETM.

DAMASCENOLIDETM [1, 4-(4-methylpent-3-en-1-yl)furan-2(5H)-one], which has a citrus-like odor, is an important aroma component of roses. We have previously reported on the synthesis and odor evaluation of 24 analogs of 1 as part of our new aroma compound developing project. To accumulate more information on structure-odor relationships, 10 more promising analogs such as dimethylated and cyclopropanated analogs were synthesized and subjected to odor evaluation.

Enantioselective synthesis and stereochemical determination of the highly reduced polyketide ishigamide.

Ishigamide was isolated as a metabolite of a recombinant strain of Streptomyces sp. MSC090213JE08 and its unsaturated fatty acid moiety has been confirmed in vitro to be synthesized by a type II PKS. Biosynthesis of such a highly reduced polyketide by a type II PKS is worthy of note.

Synthesis of both enantiomers of lycoperdic acid, an unusual mushroom-derived amino acid.

An efficient synthesis of both enantiomers of lycoperdic acid, a 4-hydroxyglutamic acid derivative from edible mushroom Lycoperdon perlatum, was achieved from a chiral aminoalcohol. The key steps were a stereoselective introduction of a C3 unit into a bicyclic ketone and oxidative cleavage of a cyclic vicinal diol into a dicarboxylic acid. This report provides the first synthesis of (-)-lycoperdic acid.

Disproof of the Proposed Structures of Bradyoxetin, a Putative Signaling Molecule, and HMCP, a Putative Quorum-Sensing Molecule.

First, we revisited the reported NMR data of bradyoxetin, a putative cell density factor of , and found some inconsistencies in the proposed structure. To elucidate the correct structure, we synthesized model oxetane compounds and confirmed that the NMR data of the synthetic compounds did not match those of the reported bradyoxetin. After reinterpreting the reported NMR data, we concluded that bradyoxetin must be chloramphenicol.

Novel glucoamylase-resistant gluco-oligosaccharides with adjacent α-1, 6 branches at the non-reducing end discovered in Japanese rice wine, sake.

Sake, a traditional Japanese rice wine, contains various oligosaccharides (Sake oligosaccharides; SAOs) derived from rice starch. We previously found that SAOs reach a high degree of polymerization (DP). In this study, we developed a hydrophilic interaction liquid chromatography-time-of-flight/mass spectrometry (HILIC-TOF/MS) based analytical method to separate isomeric SAOs.

Analog synthesis of DAMASCENOLIDE, an important aroma component of roses, and their odor properties.

DAMASCENOLIDE [, 4-(4-methylpent-3-en-1-yl)furan-2(5)-one], which has a citrus-like odor, is an important aroma component of roses. We have previously reported on the synthesis and odor evaluation of double-bond isomers of and concluded that the position and the geometric isomerism of the double-bond had a significant effect on the odor. For the purpose of deepening knowledge about structure-odor relationships, we synthesized 13 analogs of compound and evaluated their odors.

Transglycosylation Forms Novel Glycoside Ethyl α-Maltoside and Ethyl α-Isomaltoside in Sake during the Brewing Process by α-Glucosidase A of .

Sake, the Japanese rice wine, contains a variety of oligosaccharides and glucosides produced by fungal enzymes during the brewing process. This study investigates the effect of knocking out the α-glucosidase () gene on the transglycosylation products in brewed sake. In addition to α-ethyl glucoside and α-glyceryl glucoside, the amount of two compounds that have molecular mass values similar to that of ethyl maltose decreased by gene knockout.

Cucumis sativus secretes 4'-ketoriboflavin under iron-deficient conditions.

A new compound in cucumber, Cucumis sativus, nutrient solution that appears under iron-deficient conditions, but not under ordinary culture conditions, has been revealed by HPLC analysis. The chemical structure of this compound was identified using LC-MS and NMR techniques as that of 4'-ketoriboflavin. This is the first report to show that 4'-ketoriboflavin can be found in metabolites from organisms.

Synthesis of (2RS,8R,10R)-YM-193221 and an improved approach to tyroscherin, bioactive natural compounds from Pseudallescheria sp.

Short-step syntheses of (2RS,8R,10R)-YM-193221 (1) and tyroscherin (2), which are biologically active compounds isolated from Pseudallescheria sp., were accomplished in six and eight steps from L-tyrosine. The relative stereochemistry of natural YM-193221 was determined to be 8R*,10R*.