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Proposal for structure revision of pinofuranoxin A through total syntheses of stereoisomers
2024 / Journal of Natural MedicinesThe relative configuration of the epoxide functionality in pinofuranoxin A (1), α-alkylidene-β-hydroxy-γ-methyl-γ-butyrolactone with trans-epoxy side chain isolated by Evidente et al. in 2021, was revised by DFT-based spectral reinvestigations and stereo-controlled synthesis. The present investigation demonstrates the difficulty of the config...
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Absolute Configuration of Oxabornyl Polyenes Prugosenes A1–A3 and Structural Revision of Prugosene A2
2024 / Journal of Natural ProductsOxabornyl polyenes represent a unique group of polyketides characterized by a central polyene core flanked by a conserved oxabornyl moiety and a structurally diverse oxygen heterocyclic ring. They are widely distributed in fungi and possess a variety of biological activities. Due to the significant spatial separation between the two stereogenic ring systems, it is ...
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Retinestatin, a Polyol Polyketide from a Termite Nest-Derived Streptomyces sp.
2024 / Journal of Natural ProductsA new polyol polyketide, named retinestatin (1), was obtained and characterized from the culture of a Streptomyces strain, which was isolated from a subterranean nest of the termite Reticulitermes speratus kyushuensis Morimoto. The planar structure of 1 was elucidated on the basis of the cumulative analysis of ultraviolet, infrared, mass spectrometry, and nuclear m...
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C2-Symmetrical 3,4-Ethylenedioxythiophene Monomers through a Divergent Approach
2024 / The Journal of Organic ChemistryWe present a divergent synthetic approach to C2-symmetrical 3,4-Ethylenedioxythiophene (EDOT) monomers in which functionalities can be introduced as pendant chains from the ethylene bridge. The key synthon, obtained through a high yielding trans-etherification, is the chiral EDOT with bromomethyl pendant groups and is prone to substitution reactions with oxygen-bas...
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Quinoline, Indole, and Isogranatanine Alkaloids from Malayan Leuconotis eugeniifolia
2024 / Journal of Natural ProductsNine new alkaloids, eugeniinalines A–H (1–8) and (+)-eburnamenine N-oxide (9), comprising one quinoline, six indole, and two isogranatanine alkaloids, were isolated from the stem-bark extract of the Malayan Leuconotis eugeniifolia. The structures and absolute configurations of these alkaloids were established based on the analysis of the spectroscopic d...
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De Novo Access to BODIPY C-Glycosides as Linker-Free Nonsymmetrical BODIPY-Carbohydrate Conjugates
2024 / The Journal of Organic ChemistryRecent years have witnessed an increasing interest in the synthesis and study of BODIPY-glycoconjugates. Most of the described synthetic methods toward these derivatives involve postfunctional modifications of the BODIPY core followed by the covalent attachment of the fluorophore and the carbohydrate through a “connector”. Conversely, few de novo synthe...
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Pseudoceranoids A–J, Sesquiterpene-Based Meroterpenoids with Cytotoxicity from the Sponge Pseudoceratina purpurea
2023 / Journal of Natural ProductsPseudoceranoid A (1), a rare merosesquiterpene featuring a rearranged 4,9-friedodrimane-type core with a crotonolactone moiety, two new rearranged 4,9-friedodrimane-type sesquiterpene cyclopentanones (2 and 3), and three new rearranged 4,9-friedodrimane-type sesquiterpene hydroquinones (4–6), along with two new drimane-type sesquiterpene derivatives (7 and 8)...
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Tetramic acid-motif natural products from a marine fungus Tolypocladium cylindrosporum FB06 and their anti-Parkinson activities
2023 / Marine Life Science & TechnologyTetramic acid-containing natural products are attracting significantly increasing attention from biologists and chemists due to their intriguing structures and biological activities. In the present study, two new tetramic acid alkaloids tolypyridone I (1) and tolypyridone J (2), together with five known ones (3–7), were isolated from cultures of a marine fu...
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Oligomerization Mechanisms of Tea Catechins Involved in the Production of Black Tea Thearubigins
2024 / Journal of Agricultural and Food ChemistryThearubigins (TRs) are chemically ill-defined black tea pigments composed of numerous catechin oxidation products. TRs contain oligomeric components; however, the oligomerization mechanisms are poorly understood. The comparison of the 13C nuclear magnetic resonance (NMR) spectra of TRs with different molecular sizes suggested the participation of A-ring methine car...
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Antimalarial Lanostane Dimers from Artificially Cultivated Fruiting Bodies of Ganoderma weberianum
2023 / Journal of Natural ProductsInvestigation of cultivated fruiting bodies of Ganoderma weberianum led to the isolation of 11 previously unreported lanostane dimers, ganoweberianones C (3a), D (4a), E (5a), F (6a), G (7a), and H (8a) and isoganoweberianones A (1b), B (2b), D (4b), G (7b), and H (8b). Six new ganodermanontriol derivatives as three pairs of diastereomers (11/12, 13/14, and 15/16) ...
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Phenyl dialkynylcarbinols, a Bioinspired Series of Synthetic Antitumor Acetylenic Lipids
2023 / Journal of Medicinal ChemistryA series of 25 chiral anti-cancer lipidic alkynylcarbinols (LACs) were devised by introducing an (hetero)aromatic ring between the aliphatic chain and the dialkynylcarbinol warhead. The resulting phenyl-dialkynylcarbinols (PACs) exhibit enhanced stability, while retaining cytotoxicity against HCT116 and U2OS cell lines with IC50 down to 40 nM for resolved eutomers....
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Identification of novel metabolites of abiraterone in human serum and their metabolic pathways
2023 / Analytical SciencesTwo novel abiraterone (Abi, 3β-OH-Abi) metabolites in human serum were identified as 3α-OH-Abi and Δ5-Abi (D5A). Both metabolites were confirmed by their retention times on LC/MS and their product-ion mass spectra on LC–MS/MS compared to those of authentic compounds, which were chemically synthesized. The plausible metabolic pathways of these...
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Semisynthesis of 5-O-ester derivatives of renieramycin T and their cytotoxicity against non-small-cell lung cancer cell lines
2023 / Scientific ReportsThe semisynthesis of 5-O-ester derivatives of renieramycin T was accomplished through the photoredox reaction of renieramycin M (1), a bistetrahydroisoquinolinequinone alkaloid isolated from the Thai blue sponge Xestospongia sp. This process led to the conversion of compound 1 to renieramycin T (2), which was subsequently subjected to Steglich esterification with...
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Kaemtakols A–D, highly oxidized pimarane diterpenoids with potent anti-inflammatory activity from Kaempferia takensis
2023 / Natural Products and BioprospectingFour highly oxidized pimarane diterpenoids were isolated from Kaempferia takensis rhizomes. Kaemtakols A–C possess a tetracyclic ring with either a fused tetrahydropyran or tetrahydrofuran motif. Kaemtakol D has an unusual rearranged A/B ring spiro-bridged pimarane framework with a C-10 spirocyclic junction and an adjacent 1-methyltricyclo[3.2.1.02,7]octene r...
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Synthesis and Conformational Analysis of FR901464-Based RNA Splicing Modulators and Their Synergism in Drug-Resistant Cancers
2023 / Journal of Medicinal Chemistryv FR901464 is a cytotoxic natural product that binds splicing factor 3B subunit 1 (SF3B1) and PHD finger protein 5A (PHF5A), the components of the human spliceosome. The amide-containing tetrahydropyran ring binds SF3B1, and it remains unclear how the substituents on the ring contribute to the binding. Here, we synthesized meayamycin D, an analogue of FR901464, ...
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