Xenicane Diterpenoids Research Articles

Coriaceumins A-D, the First Nitrogen-Containing Crenulide Diterpenoids from the Brown Alga Dictyota coriacea Collected in the East China Sea.

A phytochemical investigation of an East China Sea collection of the brown alga Dictyota coriacea has led to the isolation of four novel nitrogen-containing crenulide diterpenoids, named coriaceumins A-D (1-4), two rare nitrogenous xenicane diterpenoids, dictyolactams C (5) and D (6), and one known crenulide diterpenoid, hydroxycrenulide (7). 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. Coriaceumins A-D (1-4) represent the first examples of nitrogen-containing crenulide diterpenoids. In a bioassay, compounds 2, 3, 5, and 7 were found to exhibit different levels of inhibitory effects against protein tyrosine phosphatase 1B (PTP1B) with IC50 values ranging from 7.3 to 19 μM. In addition, the primary structure-activity relationships of all the isolates were summarized.

Targeted Isolation of Xenicane Diterpenoids From Taiwanese Soft Coral Asterospicularia laurae

Application of LC-MS/MS-based molecular networking indicated the ethanol extract of octocoral Asterospicularia laurae is a potential source for the discovery of new xenicane derivatives. A natural product investigation of this soft coral resulted in the isolation of four new xenicane diterpenoids, asterolaurins O–R (1–4), together with six known compounds, xeniolide-A (5), isoxeniolide-A (6), xeniolide-B (7), 7,8-epoxyxeniolide-B (8), 7,8-oxido-isoxeniolide-A (9), and 9-hydroxyxeniolide-F (10). The structures of isolated compounds were characterized by employing spectroscopic analyses, including 2D-NMR (COSY, HMQC, HMBC, and NOESY) and high-resolution electrospray ionization mass spectrometry (HRESIMS). Asterolaurin O is the first case of brominated tricarbocyclic type floridicin in the family Xeniidae. Concerning bioactivity, the cytotoxic activity of those isolates was evaluated. As a result, compounds 1 and 2 demonstrated a selective cytotoxic effect against the MCF-7 cell line at IC50 of 14.7 and 25.1 μM, respectively.

ChemInform Abstract: Synthesis of Xenia Diterpenoids and Related Metabolites Isolated from Marine Organisms

AbstractReview: [71 refs.

Synthesis of Xenia diterpenoids and related metabolites isolated from marine organisms.

This review describes strategies for the chemical synthesis of xenicane diterpenoids and structurally related metabolites. Selected members from the four different subclasses of the Xenia diterpenoid family, the xenicins, xeniolides, xeniaphyllanes and xeniaethers, are presented. The synthetic strategies are discussed with an emphasis on the individual key reactions for the construction of the uncommon nine-membered carbocycle which is the characteristic structural feature of these natural products. Additionally, the putative biosynthetic pathway of xenicanes is illustrated.

Bioactive Xenicane Diterpenoids from the Taiwanese Soft Coral Asterospicularia laurae

Chemical investigation of the Taiwanese soft coral Asterospicularia laurae has led to the isolation of three new xenicane diterpenoids, named asterolaurins K-M (1-3, resp.). Their chemical structures were determined through extensive spectroscopic analyses ((1) H- and (13) C-NMR, (1) H,(1) H-COSY, HMBC, and NOESY). Compound 2 exhibited cytotoxic activity against HEp-2, Daoy, MCF-7, and WiDr tumor cells.

Asterolaurins G – J, New Xenicane Diterpenoids from the Taiwanese Soft Coral Asterospicularia laurae

AbstractFour new xenicane diterpenoids, asterolaurins G–J (1–4, resp.) have been isolated from the Taiwanese soft coral Asterospicularia laurae. Their structures were determined by extensive spectroscopic analyses (UV, CD, IR, 1H‐ and 13C‐NMR, 1H,1H‐COSY, HMBC, and NOESY). The cytotoxic activities of all compounds were evaluated.

ChemInform Abstract: Three New Xenicane Diterpenoids from Okinawan Soft Coral of the Genus, Xenia.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Xenimanadins A—D, a Family of Xenicane Diterpenoids from the Indonesian Soft Coral Xenia sp.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Xenimanadins A–D, a family of xenicane diterpenoids from the Indonesian soft coral Xenia sp.

Four novel xenicane diterpenoids, xenimanadins A–D ( 1– 4), characterized by the unusual 2,6-dimethoxytetrahydropyran functionality, have been isolated from the Indonesian soft coral Xenia sp., together with three known xeniolides. The stereostructure of these metabolites has been established through extensive interpretation of NMR data and application of the modified Mosher method. Xenimanadins were tested against tumor cell lines, revealing details about the cytotoxic potential of xenicane diterpenoids.

New Xenicanes from Xenia viridis

The dichloromethane extract of Xenia viridis afforded two new xenicane diterpenoids (3 and 4) by silica gel chromatography. The oxirane ring of 3 was found to be susceptible to a slow ring opening under acidic conditions to afford 5. Their structures were elucidated by extensive 1D and 2D NMR spectroscopy.

Cytotoxic Xenia Diterpenoids from the Soft Coral Xenia umbellata

Eleven new xenia diterpenoids, umbellacins A-G (1-7), 14,15-epoxy-xeniolide H (8), 3-acetyl-14,15-epoxy-xeniolide H (9), and umbellacins H and I (10, 11), were isolated from a methylene chloride-soluble fraction of the soft coral Xenia umbellata. The structures were elucidated by extensive spectroscopic analysis, and their cytotoxicity against selected cancer cells was measured in vitro.

New Xenicane Diterpenoids from Xenia florida.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Xenia Diterpenoids from the Formosan Soft Coral Xenia blumi

Eight new xenia diterpenoids, blumiolide-A (1) (novel carbon skeleton), blumiolide-B (2), 9-deoxy-isoxeniolide-A (3), 9-deoxy-7,8-epoxy-isoxeniolide-A (4), 9-deacetoxy-7,8-epoxy-13-epi-xenicin (5), 9-deoxy-7,8-epoxy-xeniolide-A (6), blumiolide-C (7), and blumicin-A (8), were isolated from the methylene chloride solubles of the Formosan soft coral Xenia blumi. Their structures were elucidated by extensive spectroscopic analysis, and their cytotoxicity against selected cancer cells was measured in vitro.

New xenicane diterpenoids from Xenia florida

Three new xenicane diterpenoids, designated xeniolactones A ( 1 ), B ( 2 ), and C ( 3 ), were isolated from Xenia florida collected in Taiwan. Compound 1 possesses a novel structure having a heterotricyclic skeleton in cyclononane system. The structures of 1– 3 were elucidated on the basis of extensive spectroscopic analysis. The cytotoxicity of 1– 3 was also evaluated against human cancer cell lines.

Two New Xenicane Diterpenoids from Okinawan Soft Coral of the Genus, Xenia

AbstractFor Abstract see ChemInform Abstract in Full Text.

Two New Xenicane Diterpenoids from Okinawan Soft Coral of the Genus, Xenia

Two New Xenicane Diterpenoids from Okinawan Soft Coral of the Genus, Xenia

Three new xenicane diterpenoids from Okinawan soft coral of the genus, Xenia

Three new xenicane diterpenoids, xeniaol, xeniadiol and xeniatriol, were isolated from the Okinawan soft coral of the genus, Xenia. Their structures were elucidated by spectroscopic analysis.

ChemInform Abstract: New Xenia Diterpenoids from Xenia sp. collected at Sata Cape, Kagoshima Prefecture. Part 2. New Xenia Diterpenoids from a Xenia Species of a Soft Coral.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

New xenia diterpenoids from a Xenia species of a soft coral

Seven new xenia diterpenoids including seco-type variants have been isolated from a soft coral, Xenia sp., and their structures elucidated on the basis of spectroscopy.

ChemInform Abstract: New Xenia Diterpenoids from Xenia sp. collected at Bonotsu, Kagoshima Prefecture. Part 3. New Xenia Diterpenoids from a Soft Coral, Xenia Species Containing Fatty Acyl Side Chains

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.