A new xenicane diterpene named 4α-acetoxyisodictyohemiacetal (1) was isolated from the brown alga Dictyota coriacea, along with 11 known diterpenoids. The structure of 1 was established by spectroscopic analyses, and its absolute configuration was determined by comparing the experimental and theoretical electronic circular dichroism (ECD) spectra. Two dictyodiacetal diastereomers (5 and 6) were isolated and the full NMR assignments were performed. The anti-inflammatory activities of the isolated compounds were evaluated using the lipopolysaccharide-stimulated mouse macrophage cell line, RAW264. The hemiacetal-containing xenicanes and dictyol-type diterpene inhibited not only the production of nitric oxide, but also the expression of inducible nitric oxide synthase, interleukin-6, and cyclooxygenase-2 mRNA in RAW264 cells. This study demonstrated that diterpenes from Dictyota coriacea may be useful as natural anti-inflammatory agents.
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http://dx.doi.org/10.1093/bbb/zbae163 | DOI Listing |
Biosci Biotechnol Biochem
November 2024
Department of Chemistry, Graduate School of Science, Osaka Metropolitan University, Osaka, Japan.
A new xenicane diterpene named 4α-acetoxyisodictyohemiacetal (1) was isolated from the brown alga Dictyota coriacea, along with 11 known diterpenoids. The structure of 1 was established by spectroscopic analyses, and its absolute configuration was determined by comparing the experimental and theoretical electronic circular dichroism (ECD) spectra. Two dictyodiacetal diastereomers (5 and 6) were isolated and the full NMR assignments were performed.
View Article and Find Full Text PDFJ Nat Prod
January 2024
School of Pharmacy, Jiangxi Medical College, Nanchang University, Nanchang 330006, People's Republic of China.
A phytochemical investigation of an East China Sea collection of the brown alga has led to the isolation of four novel nitrogen-containing crenulide diterpenoids, named coriaceumins A-D (-), two rare nitrogenous xenicane diterpenoids, dictyolactams C () and D (), and one known crenulide diterpenoid, hydroxycrenulide (). The structures of the new compounds were elucidated by detailed spectroscopic data analyses, including HRESIMS and 1D/2D NMR. The absolute configurations were determined by a comparison of the experimental ECD spectra with the spectra computed by DFT-based quantum chemical calculations.
View Article and Find Full Text PDFACS Omega
February 2023
School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou, Zhejiang 325035, People's Republic of China.
Five new xenicane diterpenes, including three rare nitrogen-containing derivatives, dictyolactams A () and B () and 9-demethoxy-9-ethoxyjoalin (), a rare diterpene with a cyclobutanone moiety, named 4-hydroxyisoacetylcoriacenone (), and 19--acetyldictyodiol (), were isolated from an East China Sea collection of the brown alga , along with 15 known analogues (-). The structures of the new diterpenes were elucidated by spectroscopic analyses and theoretical ECD calculations. All compounds had cytoprotective effects against oxidative stress in neuron-like PC12 cells.
View Article and Find Full Text PDFOrg Lett
September 2019
Molecular Targets Program, Center for Cancer Research , National Cancer Institute, Frederick , Maryland 21702 , United States.
The challenging structural motif of dictyospiromide (), a spirosuccinimide alkaloid with antioxidant properties that are associated with activation of the Nrf2/ARE signaling pathway, was assigned using contemporary NMR experiments complemented with anisotropic NMR, chiroptical, and computational methodologies. Anisotropic NMR parameters provided critical orthogonal verification of the configuration of the difficult to assign spiro carbon and the other stereogenic centers in .
View Article and Find Full Text PDFNat Prod Commun
April 2013
Bio-Conversion Center, Jeju Technopark, Jeju 690-121, Korea.
This study was conducted to identify the anti-melanogenesis constituents from a seaweed Dictyota coriacea (Holmes). Three known compounds, viz. 1,9-dihydroxycrenulide (1), epiloliolide (2) and D-mannitol (3), were isolated from the ethanol extract.
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