Chloriolins A-C, Chlorinated Sesquiterpenes Produced by Fungal Cultures Separated from a Jaspis Marine Sponge

Cheng, Xing; Varoglu, Mustafa; Abrell, Leif; Crews, Phillip; Lobkovsky, Emil; Clardy, Jon

doi:10.1021/jo00100a041

Cited by 68 publications

(62 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Previous chemical investigations of the A. albocinnamomea led to the isolation of novel degraded steroids albocisterols A-C and new humulane-type sesquiterpenes [6,7]. In our continuous search for new and bioactive natural products from higher fungi, five new triquinane-type sesquiterpenes, antrodins A-E (1-5) and a new gymnomitranetype sesquiterpene, antrodin F (6), together with three known compounds coriolin (7) [8], dihydrocoriolin C (8) [9], and chloriolin B (9) [10] were isolated from fermentation of A. albocinnamomea (see Scheme 1). The structures of the new compounds were determined on the basis of extensive spectroscopic analysis and single-crystal X-ray diffraction method.…”

Section: Introductionmentioning

confidence: 99%

New triquinane and gymnomitrane sesquiterpenes from fermentation of the basidiomycete Antrodiella albocinnamomea

Chen

Wang

et al. 2015

Fitoterapia

View full text Add to dashboard Cite

Section: Introductionmentioning

confidence: 99%

New triquinane and gymnomitrane sesquiterpenes from fermentation of the basidiomycete Antrodiella albocinnamomea

Chen

Wang

et al. 2015

Fitoterapia

View full text Add to dashboard Cite

“…An unidentified fungus isolated from the sponge Jaspis aff. johnstoni and cultured on a complex marine medium produced a number of sesquiterpenoid chlorinated metabolites two of which had already been reported from the terrestrial fungus Coriolus consors [23]. 4.…”

Section: Associationsmentioning

confidence: 83%

Biological Effects and Biosynthesis of Brominated Metabolites

Neilson

2003

The Handbook of Environmental Chemistry

View full text Add to dashboard Cite

Abstract. On the basis of halogenated metabolites assembled by Gribble, an attempt is made to provide a hypothesis for the biosynthesis of representative groups. Examples of brominated and iodinated metabolites are drawn from the major classes of terpenoids and acetogenins, and related to the biosynthesis of their putative precursors. Brominated and iodinated carbocyclic and heterocyclic aromatic compounds are discussed as weil as mechanisms for the oxidative coupling of phenolic substrates. A few chlorinated metabolites are introduced for additional illustration. Halogenation by cationoid (Hai+) reactions catalyzed by haloperoxidases is discussed, and attention drawn to the alternative role of anionoid (Hal-) halogenation. The presentation is extended to the biosynthesis of isonitriles and dichloroimines by anionoid reaction of precursors with cyanide. The range of biota that produce brominated substrates is briefly indicated, and comments made on the ecological significance of metabolites and associations among biota.

show abstract

“…Selected examples include Xestenone, [20] Chloriolin-A, [21] Spergulagenin-A [22] and Saussureal. [23] Methods for the construction of these highly substituted carbocycles are rare in literature.…”

Section: Resultsmentioning

confidence: 99%

“…Highly substituted five-membered rings bearing a quaternary carbon tethered to a carbonyl group, are often found in natural products or biologically active compounds. Selected examples include Xestenone, [20] Chloriolin-A, [21] Spergulagenin-A [22] and Saussureal. [23] Methods for the construction of these highly substituted carbocycles are rare in literature.…”

Section: Resultsmentioning

confidence: 99%

Gold‐Catalyzed, Intramolecular, Oxygen‐Transfer Reactions of 2‐Alkynyl‐1,5‐diketones or 2‐Alkynyl‐5‐ketoesters: Scope, Expansion, and Mechanistic Investigations on a New [4+2] Cycloaddition

Liu

Malhotra

Jin

et al. 2011

Chemistry A European J

View full text Add to dashboard Cite

The gold-catalyzed intramolecular oxygen-transfer reactions of 2-alkynyl-1,5-diketones or 2-alkynyl-5-ketoesters-obtained from tetra-n-butylammonium fluoride mediated Michael addition of activated allenes to electron-deficient olefins-furnished cyclopentenyl ketones under very mild conditions. These reactions proceeded much easier and faster than similar reactions reported in literature, and the corresponding products were obtained in very good yields. Mechanistic investigations on the cycloisomerization were carried out by means of both (18) O isotopic experiments and quantum chemical calculations. The results from both, the designed isotopic experiments and theoretical calculations, satisfactorily supported the novel proposed intramolecular [4+2] cycloaddition of a gold-containing furanium intermediate to a carbonyl group, instead of the previous well-accepted [2+2] pathway.

show abstract

Chloriolins A-C, Chlorinated Sesquiterpenes Produced by Fungal Cultures Separated from a Jaspis Marine Sponge

Cited by 68 publications

References 0 publications

New triquinane and gymnomitrane sesquiterpenes from fermentation of the basidiomycete Antrodiella albocinnamomea

New triquinane and gymnomitrane sesquiterpenes from fermentation of the basidiomycete Antrodiella albocinnamomea

Biological Effects and Biosynthesis of Brominated Metabolites

Gold‐Catalyzed, Intramolecular, Oxygen‐Transfer Reactions of 2‐Alkynyl‐1,5‐diketones or 2‐Alkynyl‐5‐ketoesters: Scope, Expansion, and Mechanistic Investigations on a New [4+2] Cycloaddition

Contact Info

Product

Resources

About