Malyngamides O and P from the Sea Hare <i>Stylocheilus longicauda</i>

Gallimore, Winklet A.; Scheuer, Paul J.

doi:10.1021/np0000365

Cited by 45 publications

(34 citation statements)

References 14 publications

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“…For example, a number of lipopeptides structurally derived from the cyanobacterial metabolite malyngamide A (29) [54] have been isolated from sea hares in recent times [55,56]. Malyngamides O (30) and P (31) have been reported from an extract of S. longicauda [55], and malyngamide S (32) was recently found in the sea hare Bursatella leachii [56] (Fig. (7)).…”

Section: Other Sea Hare Isolates Of Postulated Cyanobacterial Originmentioning

confidence: 99%

“…(18)), lyngbyaloside (57), and lyngbyaloside B (59) (Fig. (11)) the bromine is substituent of a conjugated diene moiety as in aurisides A (55) and B (56) (Fig. (11)).…”

Section: Biosynthetic Signatures In Cyanobac-terial Secondary Metabolmentioning

confidence: 99%

“…. Glycoside macrolides isolated from the sea hare Dolabella auricularia(55,56) and from Lyngbya spp. (57−59).…”

mentioning

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: Other Sea Hare Isolates Of Postulated Cyanobacterial Originmentioning

confidence: 99%

“…(18)), lyngbyaloside (57), and lyngbyaloside B (59) (Fig. (11)) the bromine is substituent of a conjugated diene moiety as in aurisides A (55) and B (56) (Fig. (11)).…”

Section: Biosynthetic Signatures In Cyanobac-terial Secondary Metabolmentioning

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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“…Recently, malyngamide C and its 8-epi-isomer were shown to inhibit bacterial quorum sensing [198,199]. Although malyngamides were primarily isolated from marine cyanobacteria Lyngbya sp., some are derived from sea hares, such as Stylocheilus longicauda (malyngamides O and P) [200], and Bursatella leachii (malyngamides S [201] and X [202]), which are known to accumulate a wide variety of secondary metabolites from their diet (Fig. 33.24).…”

Section: Polyketidesmentioning

confidence: 99%

Antitumor Effects of Sea Hare-Derived Compounds in Cancer

Kigoshi

Kita

2014

Handbook of Anticancer Drugs From Marine Origin

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Sea hares (family Aplysiidae) are a rich source of bioactive substances. Especially, over the past 40 years, the genera Aplysia and Dolabella have afforded numerous bioactive secondary metabolites that exhibit antitumor activity. For example, the depsipeptide dolastatin 10 and its analogue are currently in cancer clinical trials. Meanwhile, the chemical probe approach has revealed that the antitumor macrolide aplyronine A inhibits microtubule assembly in association with actin. This article highlights the recent findings regarding the chemical biology of antitumor and antineoplastic compounds from sea hares, as well as molecules that have been discovered and characterized after 2000.Keywords Antitumor · Sea hare · Aplysia · Antitumor · Actin-deplymerization · Cytotoxicity · Tubulin IntroductionSea hares, which belong to the opisthobranch group of mollusks (clade Aplysiomorpha), are shell-less, slow-moving benthic marine mollusks [1]. The order Anaspidea includes two families, Akeridae and Aplysiidae [2]. Almost all chemical studies have focused on Aplysiidae specimens. The family Aplysiidae includes nine genera, Aplysia (Linnaeus 1767), Bursatella (Blainville 1817), Dolabella (Lamarck 1801), Dolabrifera (Gray 1847), Notarchus (Cuvier 1817), Petalifera (Gray 1847), Phyllaplysia (Fischer 1872), Syphonota (Adams 1854), and Stylocheilus (Gould 1852). Sea hares are herbivorous, and are typically found on seaweed in shallow water. They are not eaten by other marine animals and have been postulated to contain chemical defense substances. The poisonous properties of sea hare secretions were known in Roman times. In addition, sea hares release ink from their ink glands, which deter predators. This ink acts as a screen, while at the

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“…2,3 In addition, malyngamides M and N were isolated from the red alga Gracilaria coronopifolia . 4 However, it is likely that the original natural product sources in these latter cases were also Lyngbya species as these cyanobacteria are reported to be eaten by Bursatella and Stylocheilus , 2,3 and form epiphytic associations with Gracilaria . 4 …”

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confidence: 99%

Malyngamide 2, an Oxidized Lipopeptide with Nitric Oxide Inhibiting Activity from a Papua New Guinea Marine Cyanobacterium

et al. 2010

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A Papua New Guinea collection of the marine cyanobacterium cf. Lyngbya sordida yielded three known compounds as well as a new PKS-NRPS-derived malyngamide with anti-inflammatory and cytotoxic activity. Malyngamide 2 features an extensively oxidized cyclohexanone ring. Resolution of the ring core as a 6,8,9-triol rather then a 7,8,9-triol and relative configuration was based on chemical shift and bond geometry modeling in conjunction with homonuclear and heteronuclear coupling constants, NOE and ROE correlations, and other structural information. Malyngamide 2 exhibited anti-inflammatory activity in LPS-induced RAW macrophage cells (IC50 = 8.0 μM) with only modest cytotoxicity to the mammalian cell line.

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Malyngamides O and P from the Sea Hare Stylocheilus longicauda

Abstract: Two new malyngamides, O (1) and P (2), were isolated from the sea hare Stylocheilus longicauda. The structures were elucidated by analysis of their 1D and 2D NMR spectra.

Cited by 45 publications

References 14 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

Antitumor Effects of Sea Hare-Derived Compounds in Cancer

Malyngamide 2, an Oxidized Lipopeptide with Nitric Oxide Inhibiting Activity from a Papua New Guinea Marine Cyanobacterium

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