Excavatolides U−Z, New Briarane Diterpenes from the Gorgonian <i>Briareum excavatum</i>

Sheu, Jyh‐Horng; Sung, Ping‐Jyun; Su, Jui‐Hsin; Wang, Guey‐Horng; Duh, Chang‐Yih; Shen, Ya‐Ching; Chiang, Michael Y.; Chen, I-Ting

doi:10.1021/np990302i

Cited by 58 publications

(46 citation statements)

References 25 publications

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“…1), the cembrane group (Fig. 2), as well as some meroditerpenoid-related metabolites (275)(276)(277)(278)(279)(280)(281)(282)(283) from Nephthea chabroli [138]. Dolabellane diterpenoids were discovered in two species of the genus Clavularia.…”

Section: Coelenteratesmentioning

confidence: 99%

“…Five briarane analogues, brianthein W (627), 9-deacetylbriareolide H (628), 2β-acetoxy-2-(debutyryloxy) stecholide E (629), 9-deacetylstylatulide lactone (630), and 4β-acetoxy-9-deacetylstylatulide lactone (631) [274], were isolated from an unidentified species of the genus Briareum which is known for generating the first briarane diterpenoid, briarein A [275]. Extensive chemical investigation on B. excavatum resulted in the isolation of a large group of briaranes, namely the excavatolides A-M (632-644) [276,277] and U-Z (645-650) [278], the briaexcavatolides A-Z (651-676) [279][280][281][282][283][284], as well as the brianolides 677 and 678 [276,280]. The natural briarane diterpenoids are commonly cytotoxic compounds.…”

Section: Gorgoniansmentioning

confidence: 99%

“…The natural briarane diterpenoids are commonly cytotoxic compounds. Many briareins, such as brianthein W (627), 9-deacetylbriareolide H (628), 2β-acetoxy-2-(debutyryloxy) stecholide E (629), 9-deacetylstylatulide lactone (630) [274], the excavatolides A (632), D (635) [276], U (645), and Z (650) [278], the briaexcavatolides B (652), F (656) [279], and L (662) and brianolide 678 [280], displayed potent selective cytotoxic activities against one or several of the P-388, KB, A549, and HT-29 cell lines. The excavatolides C (634), E (636), K (642), and M (644) were broadly cytotoxic against a limited panel of these cells [276,277] with an extraordinarily low ED 50 value of 0.001 µg/mL being observed for excavatolide M (644) against P-388 [277].…”

Section: Gorgoniansmentioning

confidence: 99%

“…For example, variations in the functional groups at the C-2, C-3, C-9, and C-12 positions can influence the cytotoxicity of these compounds [277]. The presence of a large substituent at C-3 significantly reduces the cytotoxicity of this class of compounds [278] while oxidation at C-9 increases the level of activity of these diterpenoids [274].…”

Section: Gorgoniansmentioning

confidence: 99%

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Secondary Metabolites from the South China Sea Invertebrates: Chemistry and Biological Activity

Zhang

Guo²,

Gu³

2006

CMC

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The increasing demand for new lead compounds in the pharmaceutical and agrochemical industries has driven scientists to search for new sources of bioactive natural products. Marine invertebrates are a rich source of novel, bioactive secondary metabolites and they have attracted a great deal of attention from scientists in the fields of chemistry, pharmacology, ecology, and molecular biology. During the past 25 years, many complex and structurally unique secondary metabolites have been isolated from the invertebrates inhabiting the South China Sea. These metabolites are responsible for various bioactivities such as anti-tumor, anti-inflammation and antioxidant activities, and/or they act on the cardiovascular system. This review will focus on the marine natural product chemistry of invertebrates from the South China Sea, aiming to give the reader a brief view of the compounds isolated from these invertebrates, as well as their biological activities. The article covers the literature published during the period from the beginning of 1980 to the end of 2005, with 340 citations and 811 compounds from invertebrates from the South China Sea, including sponges, coelenterates, molluscs and echinoderms.

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Section: Coelenteratesmentioning

confidence: 99%

Section: Gorgoniansmentioning

confidence: 99%

Section: Gorgoniansmentioning

confidence: 99%

Section: Gorgoniansmentioning

confidence: 99%

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Secondary Metabolites from the South China Sea Invertebrates: Chemistry and Biological Activity

Zhang

Guo²,

Gu³

2006

CMC

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“…A spectrum of different novel marine compounds have been identified, and their bioactivities evaluated for potential pharmaceutical application [13]. Among these compounds, we isolated and identified a group of briarane-type diterpenes (BrDs) from Briareum excavatum , a Formosan gorgonian coral [14,15]. …”

Section: Introductionmentioning

confidence: 99%

Topical application of marine briarane-type diterpenes effectively inhibits 12-O-tetradecanoylphorbol-13-acetate-induced inflammation and dermatitis in murine skin

et al. 2011

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BackgroundSkin is the largest organ in the body, and is directly exposed to extrinsic assaults. As such, the skin plays a central role in host defense and the cutaneous immune system is able to elicit specific local inflammatory and systemic immune responses against harmful stimuli. 12-O-tetradecanoylphorbol-13-acetate (TPA) can stimulate acute and chronic inflammation and tumor promotion in skin. TPA-induced dermatitis is thus a useful in vivo pharmacological platform for drug discovery. In this study, the inhibitory effect of briarane-type diterpenes (BrDs) from marine coral Briareum excavatum on TPA-induced dermatitis and dendritic cell (DC) function was explored.MethodsEvans blue dye exudation was used to determine vascular permeability. H&E-stained skin section was used to determine the formation of edema in mouse abdominal skin. We also used immunohistochemistry staining and western blot assays to evaluate the activation of specific inflammation makers and key mediators of signaling pathway in the mouse skin. Furthermore, mouse bone marrow DCs were used to determine the relationship between the chemical structure of BrDs and their regulation of DC function.ResultsBrD1 remarkably suppressed TPA-induced vascular permeability and edema in skin. At the biochemical level, BrD1 inhibited TPA-induced expression of cyclooxygenase-2, inducible nitric oxide synthase and matrix metalloproteinase-9, the key indicators of cutaneous inflammation. This inhibition was apparently mediated by interference with the Akt/NF-κB-mediated signaling network. BrD1 also inhibited TNF-α and IL-6 expression in LPS-stimulated BMDCs. The 8, 17-epoxide of BrDs played a crucial role in the inhibition of IL-6 expression, and replacement of the C-12 hydroxyl group with longer esters in BrDs gradually decreased this inhibitory activity.ConclusionsOur results suggest that BrDs warrant further investigation as natural immunomodulatory agents for control of inflammatory skin diseases.

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Cnidaria and Ctenophora–1

Kornprobst

2014

Encyclopedia of Marine Natural Products

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The article contains sections titled: General Introduction Simplified Classification of Cnidaria Hermatypic and Ahermatypic Corals: Coral Bleaching General Information on Metabolites of Cnidaria Membrane Constituents and Secondary Metabolites of Octocorallia (Anthozoa) Prostaglandins and Prostanoids Phospholipid Fatty Acids, Glycolipids, and Other Lipidic Derivatives General Remarks on the Sterols of Octocorallia Gorgosterol and Other Cyclopropane‐Containing Sterols 19‐Oxygenated‐ and 19‐ nor ‐Steroids Polyoxygenated Steroids Sterones and Chlorinated Sterones Sulfur‐Containing Steroids Cyclized Side‐Chain Sterols Secosterols Sterosides, Pregnane, and nor ‐Pregnane Derivatives Sesquiterpenic Hydrocarbons Halogen‐, Nitrogen‐, and Sulfur‐Containing Sesquiterpenes Sesquiterpenes with Original Carbon Skeletons Examples of Sesquiterpenes with a Classical Carbon Skeleton General Account of Diterpenes Linear and Monocyclic Diterpenes General Information on Bicyclic Diterpenes Chlorinated Diterpenes Other examples of Briarane Derivatives Nitrogen‐Containing Diterpenes of Cladiellane/Eunicellane: Eleutherobin and Analogs, Labiatamides Other Examples of Cladiellane/Eunicellane Diterpenes Diterpenes of Serrulatane and Other Bicyclic Carbon Skeletons Bicyclic C 5 /C 11 Diterpenes Bicyclic Diterpenes Containing a Cyclopropane Some Other Examples of Bicyclic Diterpenes General Account of Tricyclic Diterpenes Pseudopterosins, Other Amphilectane Derivatives and Analogs Other Examples of Tricyclic and Tetracyclic Diterpenes Comments on the Origin of Terpenes Non‐Terpenic Nitrogenous Derivatives of Octocorallia Uncommon Sulfur‐Containing Compounds

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Excavatolides U−Z, New Briarane Diterpenes from the Gorgonian Briareum excavatum

Cited by 58 publications

References 25 publications

Secondary Metabolites from the South China Sea Invertebrates: Chemistry and Biological Activity

Secondary Metabolites from the South China Sea Invertebrates: Chemistry and Biological Activity

Topical application of marine briarane-type diterpenes effectively inhibits 12-O-tetradecanoylphorbol-13-acetate-induced inflammation and dermatitis in murine skin

Cnidaria and Ctenophora–1

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