Chlorovulones, new halogenated marine prostanoids with an antitumor activity from the stolonifer clavularia viridis Quoy and Gaimard

Iguchi, Kazuo; Kaneta, Soichiro; Mori, Kenichiro; Yamada, Yasuji; Honda, Akira; Mori, Yo

doi:10.1016/s0040-4039(00)98927-5

Cited by 100 publications

(51 citation statements)

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“…The correlations from the signals at δ ϭ 2.53 and 2.38 (13-H) ppm to the quaternary carbon signal at δ ϭ 78.6 (C-12) ppm, quaternary carbon signal at δ ϭ 140.1 (C-8) ppm, and the olefinic carbon signal at δ ϭ 162.7 (C-11) ppm reveal that the ω-side chain is connected to the C-12 carbon atom on the cyclopentenone ring. The correlations from the 2-H methylene signal at δ ϭ 2.36 ppm and the methyl ester signal at δ ϭ 3.65 ppm to the ester The configuration of the olefinic bond at C-7 is assigned on the basis of the chemical shift values of the 7-H signals of compound 1 and similar natural substances reported by Iguchi [8,9,12] [δ ϭ 7.35 ppm for the (E) isomer, δ ϭ 6.99 ppm for the (Z) isomer]. Because of the anisotropy effect (shielding effect) of the C-9 carbonyl moiety, the signal of proton 7-H in the (7Z) configuration should appear at a higher field than that of the corresponding (7E) isomer.…”

Section: Resultsmentioning

confidence: 90%

“…The IR spectrum of 1 shows absorptions due to hydroxy group (3490 cm Ϫ1 ), methyl ester (1738, 1233 cm Ϫ1 ), and α,β-unsaturated cyclopentenone (1706 cm Ϫ1 ). The conjugated system in 1, corresponding to that of bromovulone, [12] is demonstrated by absorptions at 248 (log ε ϭ 4.08) and 313 (log ε ϭ 4.01) nm, indicating the presence of a cross-conjugated system (α-halogenocyclopentenone and dienone).…”

Section: Resultsmentioning

confidence: 99%

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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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Section: Resultsmentioning

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Brominated Oxylipins and Oxylipin Glycosides from Red Sea Corals

Řezanka

Dembitsky

2002

Eur J Org Chem

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“…Several of these products have received much attention due to their potential antitumour activity (e.g. Iguchi et al, 1985Iguchi et al, , 1986Honda et al, 1988;Iwashima et al, 1999). Their functional significance in the animals producing such compounds is unclear, but they may provide defence against predation by fish (Gerhart, 1991) as well as protecting against microbial attack (Ř ezanka and Dembitsky, 2003).…”

Section: Prostaglandins In Non-insectan Invertebratesmentioning

confidence: 99%

Prostaglandins in non-insectan invertebrates: recent insights and unsolved problems

Rowley

Vogan

Taylor

et al. 2005

Journal of Experimental Biology

119

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Prostaglandins, together with thromboxanes (collectively termed prostanoids), are fatty acid derivatives of significant importance in many physiological processes. These compounds are formed following the action of cyclooxygenases (COX) and associated enzymes on C20 polyunsaturated fatty acid precursors released from phospholipids in membranes. Nearly all mammalian cell types have the biosynthetic machinery to produce at least one type of prostanoid. The same C20 fatty acid substrates can also be acted upon by lipoxygenases to produce mono-di-and trihydroxy derivatives such as leukotrienes, lipoxins and resolvins. The final route is the cytochrome P 450 pathway that can convert C20 fatty acids to hydroxylated derivatives.Collectively these compounds are called eicosanoids; the term derived from the Greek eikosi that refers to the C20 backbone in the parent fatty acid.Prostaglandins (PGs) were first discovered in the 1930s by von Euler and colleagues, who found a substance produced by the prostate gland that caused smooth muscle contraction. They christened the active substance 'prostaglandin', but it was over 30 years until the structure and mode of biosynthesis of these fatty acid derivatives became fully understood. PGs have many basic physiological functions where they act as 'local' hormones. For example, thromboxane (Tx) A 2 and prostacyclin (PGI 2 ) generated by platelets and endothelial cells, respectively, regulate the aggregatory behaviour of

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“…In Clavularia viridis, which inhabits coral reefs around Ishigaki Island, Okinawa, Japan, prostanoids including CV I, II, III, and IV (Scheme 1) (6,7) and halovulones, which contain halogen atoms (12,13) such as chlorovulones (14), have been detected. CV are C. viridis-specific prostanoids that have not been detected in other species of Clavularia.…”

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confidence: 99%

Localization of clavulons, prostanoids with antitumor activity, within the Okinawan soft coral Clavularia viridis (alcyonacea, clavulariidae): Preparation of a high‐purity Symbiodinium faction using a protease and a detergent

Hashimoto

Fujiwara

Watanabe

et al. 2003

Lipids

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To investigate the localization of clavulones (CV), prostanoids with antitumor activity, in the Okinawan soft coral Clavularia viridis, we developed a method for the isolation of Symbiodinium cells from the coral, i.e., treatment of a coral homogenate with a protease, pronase E, and a detergent, Nonidet P-40. The conditions for the treatment were optimized by monitoring the morphology microscopically and the amount of chlorophyll in the Symbiodinium fraction (SymF) optically. To evaluate the purity of SymF and a Symbiodinium-free coral fraction (CorF), we analyzed them for proteins and lipids using cultivated Symbiodinium as a reference. TLC of lipids revealed that SymF contained a greater amount of glycolipids, whereas CorF comprised mostly phospholipids. SDS-PAGE of proteins in SymF and CorF revealed their distinct profiles. Thus, we could obtain each fraction with high purity; we reached the conclusion that CV and arachidonic acid, their possible precursor, are localized exclusively in the insoluble fraction of host coral cells.

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Chlorovulones, new halogenated marine prostanoids with an antitumor activity from the stolonifer clavularia viridis Quoy and Gaimard

Cited by 100 publications

References 9 publications

Brominated Oxylipins and Oxylipin Glycosides from Red Sea Corals

Brominated Oxylipins and Oxylipin Glycosides from Red Sea Corals

Prostaglandins in non-insectan invertebrates: recent insights and unsolved problems

Localization of clavulons, prostanoids with antitumor activity, within the Okinawan soft coral Clavularia viridis (alcyonacea, clavulariidae): Preparation of a high‐purity Symbiodinium faction using a protease and a detergent

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