Studies of Australian Soft Corals. XLVII. New Halogenated Briaran Diterpenes From a Briareum Species (Octocorallia, Gorgonacea)

Bowden, BF; Coll, JC; Vasilescu, I; Alderslade, PN

doi:10.1071/ch9891727

Cited by 14 publications

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“…Briaran diterpenes continue to attract the attention of investigators because of the structural complexity and interesting bioactivity (e.g., cytotoxicity, ,, antiinflammatory, ,, antiviral, , insecticidal 3 ) associated with several compounds of this type. The genus Briareum has been found to be situated near the transition between the Gorgonacea and Alcyonacea, both in chemical and taxonomic terms. , Previous studies have shown that species identification could be assisted by investigation of secondary metabolites from organisms of the Briareum sp. ,, In connection with our continuing studies of bioactive secondary metabolites from marine organisms, the chemistry of a specimen of Briareum sp., originally identified as Pachyclavularia violacea on the basis of similarity in colonial morphology, was studied. The specimen identification was subsequently revised on the basis of its chemical constituents.…”

supporting

confidence: 77%

“…Gorgonians (order Gorgonacea) and soft corals (Alcyonacea) are known to be important sources of diterpenoids in the marine environment. The gorgonacean genus Briareum has been the subject of many investigations that have led to the discovery of oxygenated diterpenes, including briareins, − asbestinins, − cladiellins, and cembranes . Briaran diterpenes continue to attract the attention of investigators because of the structural complexity and interesting bioactivity (e.g., cytotoxicity, ,, antiinflammatory, ,, antiviral, , insecticidal 3 ) associated with several compounds of this type.…”

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confidence: 99%

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New Cytotoxic Briaran Diterpenes from the Formosan Gorgonian Briareum sp.

et al. 1996

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Three new briaran diterpenes, 2β-acetoxy-2-(debutyryloxy)stecholide E (3), 9-deacetylstylatulide lactone (4), and 4β-acetoxy-9-deacetylstylatulide lactone (5), and two known diterpenes, brianthein W (1) and 9-deacetylbriareolide H (2), have been isolated from a Briareum sp. of gorgonian. The structures and relative stereochemistry of these compounds were determined by spectroscopic and chemical methods. Diterpenes 2−4 and the corresponding 9-acetyl derivatives 6, 7, and 12 exhibited cytotoxicity toward various cancer cell lines.

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confidence: 77%

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confidence: 99%

New Cytotoxic Briaran Diterpenes from the Formosan Gorgonian Briareum sp.

et al. 1996

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“…Compound 7 can be assigned nearly the same conformation as found for 4-6 since the H-15 resonance is downfield (1.55 ppm) as in the latter set of compounds and the H-14/H-13 coupling is large indicating a 14-axial (and ß) hydrogen orientation. The epoxide on the lactone ring is assigned an a orientation by virtue of the nOe between H-l 8 and H-9 and correspondence of the 13C-nmr resonances for C-8 and C-17 in the group of diterpenes reported here and related compounds (1,3,4,12).…”

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confidence: 53%

New Diterpenes from the Gorgonian Solenopodium excavatum

Mm²,

Siripitayananon³

et al. 1993

J. Nat. Prod.

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Seven new briariane diterpene lactones were isolated from the gorgonian Solenopodium excavatum collected in New Guinea. One structure (4) was determined by X-ray diffraction and the remainder were elucidated by spectroscopic analysis. Six of the new briareolides, 4-9, exist in a conformation that is quite uncommon for representatives of this fairly large family of compounds, namely one in which the bonds joining the 10-membered ring to the 6-membered ring are nearly diaxially oriented. Conformational energy calculations are discussed as are the structural features that are responsible for the uncommon conformation. Mild cytotoxic activity was confirmed for 4.

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“…[1] Among them, halogenated compounds Ϫ predominantly steroids, [2] diterpenes, [3] alkaloids, [4] and prostanoids [5] Ϫ have received much attention because of their strong antiinflammatory and antitumor activities. The chemistry of prostaglandins has now entered a new stage, thanks to newly discovered, predominantly halogenated, compounds.…”

Section: Introductionmentioning

confidence: 99%

Brominated Oxylipins and Oxylipin Glycosides from Red Sea Corals

Řezanka

Dembitsky

2002

Eur J Org Chem

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Eight new brominated oxylipins 1−8, including two glycosides, were isolated from the Red Sea invertebrates Dendrophyllia sp., Dendronephthya sp. (red variety), Dendronephthya sp. (yellow variety), and Tubipora musica. Their structures were elucidated mainly on the basis of NMR spectroscopic data. The relative and absolute configurations were determined by analysis of NOESY and CD data and by the IntroductionThe ongoing investigation of the chemical constituents of soft corals of the Anthozoa class has resulted in the isolation of a number of different active metabolites.[1] Among them, halogenated compounds Ϫ predominantly steroids, [2] diterpenes, [3] alkaloids, [4] and prostanoids [5] Ϫ have received much attention because of their strong antiinflammatory and antitumor activities. The chemistry of prostaglandins has now entered a new stage, thanks to newly discovered, predominantly halogenated, compounds. The first paper describing the isolation of prostaglandins from a Caribbean gorgonian coral [6] was published more than 30 years ago; 16 years later, halogen-substituted prostaglandins were isolated for the first time from an octocoral. [5] Marine prostanoids, predominantly halogenated, are distributed among a number of different marine sources and include, for example, chloro-punaglandins [7Ϫ10] from octocorals living in the Pacific ocean, chloro-epoxy prostanoids from Clavularia viridis, [11] punaglandins from Hawaiian octocorals, [5] and also substituted chloro-, bromo-, and iodovulones [12Ϫ16] from corals.Further metabolites with different but similar structures Ϫ including a cyclopentenone ring Ϫ were found in Dendrophyllia sp. They are similar to chromomoric acids B and F, isolated from Chromolaena morii and C. chasleae. [17,18] Chromomoric acid B methyl ester has also been found in other species such as Schistostepnium, [19] Montanoa, [20] and [a] 309 modified Mosher method. The compounds gave positive results in a brine shrimp toxicity assay, a sea urchin eggs test (Paracentrotus lividus), and a crown gall tumor on potato disks test (Agrobacterium tumefaciens).

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Studies of Australian Soft Corals. XLVII. New Halogenated Briaran Diterpenes From a Briareum Species (Octocorallia, Gorgonacea)

Cited by 14 publications

References 0 publications

New Cytotoxic Briaran Diterpenes from the Formosan Gorgonian Briareum sp.

New Cytotoxic Briaran Diterpenes from the Formosan Gorgonian Briareum sp.

New Diterpenes from the Gorgonian Solenopodium excavatum

Brominated Oxylipins and Oxylipin Glycosides from Red Sea Corals

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