Kulolide:  A Cytotoxic Depsipeptide from a Cephalaspidean Mollusk, <i>Philinopsis speciosa</i><sup>1</sup>

Reese, Michael T.; Gulavita, Nanda K.; Nakao, Yoichi; Hamann, Mark T.; Yoshida, Wesley Y.; Coval, Stephen J.; Scheuer, Paul J.

doi:10.1021/ja9620301

Cited by 68 publications

(59 citation statements)

References 20 publications

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“…In fact, the isolation of yanucamides A (77) and B (78) [107] from a cyanobacterial assemblage delivered the first support of the hypothesis that the kulolides (79−81) and related metabolites from the marine mollusk Philinopsis speciosa [108,109] are of cyanobacterial origin (see later discussion in this text) (Fig. (16)).…”

Section: Biosynthetic Signatures In Cyanobac-terial Secondary Metabolmentioning

confidence: 79%

“…Chemical investigations of the carnivorous mollusk Philinopsis speciosa have yielded highly diverse metabolites, an alkylpyridine [131], polypropionates [132], depsipeptides {e.g., kulolides 79−81 and kulomo'opunalides 89 and 90 (Fig. (16))} [108,109], and a macrolide {tolytoxin 23-acetate (112) (Fig. (10))} [109], prompting studies on the dietary prey of P. speciosa.…”

Section: More Complex Examples Of Cyanobac-terial Metabolites In Marimentioning

confidence: 99%

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The Cyanobacterial Origin of Potent Anticancer Agents Originally Isolated from Sea Hares

Luesch¹,

Harrigan²,

Goetz³

et al. 2002

CMC

133

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It is increasingly evident that the true biological origin of many metabolites originally isolated from certain marine macroorganisms is cyanobacterial. For example, several dolastatins, potent cytotoxic compounds originally derived from the sea hare Dolabella auricularia, have now been isolated from marine cyanobacteria of the genera Lyngbya and Symploca. This review discusses the isolation of dolastatins and close structural analogues from cyanobacteria. Biosynthetic signatures of metabolites isolated from sea hares, but which are most probably cyanobacterial in origin, are also presented. Finally, some more complex ecology involving movement of cyanobacterial metabolites through the marine food web is presented.

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Section: Biosynthetic Signatures In Cyanobac-terial Secondary Metabolmentioning

confidence: 79%

Section: More Complex Examples Of Cyanobac-terial Metabolites In Marimentioning

confidence: 99%

The Cyanobacterial Origin of Potent Anticancer Agents Originally Isolated from Sea Hares

Luesch¹,

Harrigan²,

Goetz³

et al. 2002

CMC

133

View full text Add to dashboard Cite

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“…8) was isolated from a cephalaspidean mollusk, Philinopsis speciosa Pease, 1860 [40]. The mollusks were collected off Oahu.…”

Section: Kulolidementioning

confidence: 99%

Recent Developments in Depsipeptide Research

Ballard¹,

Yu²,

Wang³

2002

CMC

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This review focuses on the major developments in depsipeptide research since 1995. Depsipeptides are bio-oligomers composed of hydroxy and amino acids linked by amide and ester bonds. Many depsipeptides show very promising biological activities, including anticancer, antibacterial, antiviral, antifungal, anti-inflammatory, and anti-clotting or anti-antherogenic properties. In this report depsipeptides exhibiting these properties are discussed. Their isolation, structural determination, and notable structural features are discussed, but their biological properties and therapeutic potentials are emphasized. Depsipeptides have shown the greatest therapeutic potential as anticancer agents. Four depsipeptides have entered clinical trials for cancer treatment. Among the antiviral compounds discovered, the callipeltins and the quinoxapeptins are particularly promising due to their inhibitory activities against HIV. These compounds have the potential to be developed as anti-AIDS drugs or to serve as lead compounds for the discovery of structurally related anti-AIDS compounds. Antifungal compounds, such as the jaspamides, may lead to therapies against many of the opportunistic infections that accompany AIDS. Anti-inflammatory compounds such as SCH217048 act as neurokinin antagonists and may lead to anti-inflammatory treatments. Some depsipeptides such as micropeptins and A90720A have been found to be effective plasmin inhibitors, which have implications as treatments for cardiovascular diseases. Compounds such as SCH58149 help control the levels of HDL and LDL.

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“…In this report as part of an investigation of active sponge extracts against infectious diseases two new cyclic heptapeptides, stylisin 1 (1) and stylisin 2 (2), and the known peptide phakellistatin 13 (3) were isolated as well as the known alkaloids sceptrin (4), stevensine (5), and oroidin (6). Here we describe the isolation and structure elucidation of the two new cyclic peptides.…”

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confidence: 91%

Cyclic Heptapeptides from the Jamaican Sponge Stylissa caribica

et al. 2006

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Two new cyclic heptapeptides, stylisin 1(1) and stylisin 2 (2), were isolated and characterized from the Jamaican sponge Stylissa caribica, in addition to the cyclic heptapeptide phakellistatin 13 (3) and the known bromopyrrole alkaloids sceptrin (4), stevensine (5), and oroidin (6). The new structures were assigned on the basis of 1D and 2D NMR spectroscopic data, as well as chemical methods for the elucidation of the absolute configuration of amino acids. The peptides and alkaloids have been evaluated for their antimicrobial, antimalarial, anticancer, anti-HIV-1, antiMtb, and antiinflammatory activities.Peptides are well-established bioactive metabolites from marine invertebrates , and include linear peptides, , depsipeptides, , and cyclic -and bicyclic peptides. , Species of the sponge genera Phakellia and Axinella have yielded several bioactive cyclic peptides -reported to have cytotoxic activity against a number of cancer cell lines. It has been noted that most of these cyclic peptides are rich in proline amino acid moieties, which may be in either cis or trans conformation. There is evidence that some of the sponge cyclic peptides are able to bind undetectable quantities of a very potent antineoplastic substance that can only be revealed through biological assays.In this report as part of an investigation of active sponge extracts against infectious diseases two new cyclic heptapeptides, stylisin 1 (1) and stylisin 2 (2), and the known peptide phakellistatin 13 (3) were isolated as well as the known alkaloids sceptrin (4), stevensine (5), and oroidin (6). Here we describe the isolation and structure elucidation of the two new cyclic peptides. Several reports describing the chemistry of different marine sponges belonging to Stylissa spp. have been published including aldisines from Stylissa massa, latonduines from Stylissa carteri, and massadine from Stylissa aff. massa. In a study regarding the chemistry of Stylissa caribica Lehnert & van Soest, 1998 (Halichondrida: Dictyonellidae), a series of bromopyrrole alkaloids have been identified. No cyclic peptides have been previously reported from Stylissa species, and these results have suggested a possible microbial or symbiotic origin for these metabolites. HHS Public Access Results and DiscussionThe sponge extract was dissolved in ethanol and subjected to silica gel vacuum-liquid chromatography followed by column chromatography, Sephadex LH-20, RP HPLC, and PTLC chromatography to yield two new cyclic heptapeptides, stylisin 1 (1) and stylisin 2 (2), the known cyclic peptide phakellistatin 13 (3), and the known alkaloids sceptrin, stevensine, and oroidin (4-6).Stylisin 1 (1) ( (Figures 2 and 3). Each amino acid was connected to the adjacent amino acid in a cyclic form based on the HMBC correlations between the αH and NH with the adjacent CO. An HMBC correlation was assigned between the isoleucine NH and CO of Pro1 at δ 171.48 and generated a partial structure for a Pro1-Ile. The amide proton at δ 7.44 of Phe gave an HMBC correlation to CO of ...

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Kulolide: A Cytotoxic Depsipeptide from a Cephalaspidean Mollusk, Philinopsis speciosa¹

Cited by 68 publications

References 20 publications

The Cyanobacterial Origin of Potent Anticancer Agents Originally Isolated from Sea Hares

The Cyanobacterial Origin of Potent Anticancer Agents Originally Isolated from Sea Hares

Recent Developments in Depsipeptide Research

Cyclic Heptapeptides from the Jamaican Sponge Stylissa caribica

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Kulolide: A Cytotoxic Depsipeptide from a Cephalaspidean Mollusk, Philinopsis speciosa1

Cited by 68 publications

References 20 publications

The Cyanobacterial Origin of Potent Anticancer Agents Originally Isolated from Sea Hares

The Cyanobacterial Origin of Potent Anticancer Agents Originally Isolated from Sea Hares

Recent Developments in Depsipeptide Research

Cyclic Heptapeptides from the Jamaican Sponge Stylissa caribica

Contact Info

Product

Resources

About

Kulolide: A Cytotoxic Depsipeptide from a Cephalaspidean Mollusk, Philinopsis speciosa¹