Relative configuration of luminaolide

Maru, Norihito; Inuzuka, Toshiyasu; Yamamoto, Keita; Kikuchi, Makoto; Schupp, Peter J.; Yamada, Kaoru; Uemura, Daisuke

doi:10.1016/j.tetlet.2013.05.143

Cited by 8 publications

(8 citation statements)

References 7 publications

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“…11deoxyfistularin-3 induced low levels of metamorphosis in larvae of the stony coral Pseudosiderastrea tayami, but when provided in combination with isolated CCA pigments (βcarotene, lycopene) larval metamorphosis increased to high levels (Kitamura et al, 2007). Luminaolide, a macrodiolide isolated from the CCA Hydrolithon reinboldii, was capable to enhance the metamorphosis activity in larvae of the stony coral Leptastrea purpurea, particularly when combined with a second fraction derived from the same CCA but with so far unknown chemical composition (Kitamura et al, 2009;Maru et al, 2013).…”

Section: Introductionmentioning

confidence: 99%

Photosensitivity of the Bacterial Pigment Cycloprodigiosin Enables Settlement in Coral Larvae—Light as an Understudied Environmental Factor

et al. 2021

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The survival of coral reefs largely depends among other factors on the recruitment of a new generation of coral individuals that are more adapted to a rapidly changing climate and other anthropogenic stressors (e.g., pollution, sedimentation). Therefore, a better understanding of the coral settlement process, the molecules involved as well as crucial environmental drivers that control settlement success are needed. In this study, we identified a novel settlement inducer for the brooding scleractinian coral Leptastrea purpurea and highlight the importance of light for the settlement process. Crude extract of the red-pigmented bacterium Pseudoalteromonas rubra reliably triggered attachment and metamorphosis in L. purpurea larvae in less than 24 h. Prodigiosin (II) and the two derivatives, cycloprodigiosin (I) and 2-methyl-3-hexyl prodiginine (III) were isolated and structurally elucidated from the crude extract of P. rubra. We demonstrated that the photosensitive pigment cycloprodigiosin (I) was the responsible compound for attachment and metamorphosis in L. purpurea larvae. Under the tested light regimes (i.e., darkness, constant light and a dark-light alternation), cycloprodigiosin (I) triggered approximately 90% settlement at a concentration of 0.2 μg mL–1 under a 12 h alternating dark-light cycle, mimicking the light-flooded coral reef environment. Our findings enable for the first time a mechanistic understanding of the light-dependent larva to polyp transformation by discovering the novel bacterial settlement cue cycloprodigiosin and its photosensitivity as a determining factor for coral settlement.

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Section: Introductionmentioning

confidence: 99%

Photosensitivity of the Bacterial Pigment Cycloprodigiosin Enables Settlement in Coral Larvae—Light as an Understudied Environmental Factor

et al. 2021

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“…The absolute configurations of compounds 439 – 443 and 446 were determined by NMR spectroscopy with the relative stereochemistry at C-9 in 446 remaining unassigned [ 265 ]. The metamorphosis-enhancing macrodiolide luminaolide ( 447 ) was isolated from the crustose coralline alga Hydrolithon reinboldii and its absolute relative configuration was determined by NMR spectroscopy with the relationships of the two side chains to the macrolide ring remaining unassigned [ 266 , 267 ].…”

Section: Chemical and Biological Diversity Of Marine-derived Macrolidesmentioning

confidence: 99%

Marine-Derived Macrolides 1990–2020: An Overview of Chemical and Biological Diversity

et al. 2021

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Macrolides are a significant family of natural products with diverse structures and bioactivities. Considerable effort has been made in recent decades to isolate additional macrolides and characterize their chemical and bioactive properties. The majority of macrolides are obtained from marine organisms, including sponges, marine microorganisms and zooplankton, cnidarians, mollusks, red algae, bryozoans, and tunicates. Sponges, fungi and dinoflagellates are the main producers of macrolides. Marine macrolides possess a wide range of bioactive properties including cytotoxic, antibacterial, antifungal, antimitotic, antiviral, and other activities. Cytotoxicity is their most significant property, highlighting that marine macrolides still encompass many potential antitumor drug leads. This extensive review details the chemical and biological diversity of 505 macrolides derived from marine organisms which have been reported from 1990 to 2020.

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“…8.9; exemplarily shown for coral larvae), it is questionable if a single cue can induce the settlement chain or if sev- Fig. 8.8 (a) Jacaranone (Yvin et al 1985), (b) histamine (Williamson et al 2000), (c) tetrabromopyrrole (Tebben et al 2011), (d) 11-deoxyfistularin-3 (Kitamura et al 2007), and (e) luminaolide (Maru et al 2013) (created with ChemDraw, v. 16.0.1.4) Fig. 8.9 Settlement and early life stages of scleractinian corals.…”

Section: Marine Invertebrate Larvae Settlement: Role Of Secondary Metmentioning

confidence: 99%

“…8.8e). The macrodiolide luminaolide was originally isolated from the CCA H. reinboldii and greatly enhanced the metamorphosis activity in Leptastrea purpurea when combined with another fraction that eluted at 80% aqueous methanol by octadecyl silica gel column chromatography (Kitamura et al 2009;Maru et al 2013). Interestingly, chemical inducers for larval settlement were also discovered in coral rubble and the skeleton of the massive coral Goniastrea sp.…”

Section: Coral Larvae Settlement: Search For Novel Settlement Cuesmentioning

confidence: 99%

Secondary Metabolites of Marine Microbes: From Natural Products Chemistry to Chemical Ecology

Petersen

Kellermann

Schupp

2019

YOUMARES 9 - The Oceans: Our Research, Our Future

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Marine natural products (MNPs) exhibit a wide range of pharmaceutically relevant bioactivities, including antibiotic, antiviral, anticancer, or anti-inflammatory properties. Besides marine macroorganisms such as sponges, algae, or corals, specifically marine bacteria and fungi have shown to produce novel secondary metabolites (SMs) with unique and diverse chemical structures that may hold the key for the development of novel drugs or drug leads. Apart from highlighting their potential benefit to humankind, this review is focusing on the manifold functions of SMs in the marine ecosystem. For example, potent MNPs have the ability to exile predators and competing organisms, act as attractants for mating purposes, or serve as dye for the expulsion or attraction of other organisms. A large compilation of literature on the role of MNPs in marine ecology is available, and several reviews evaluated the function of MNPs for the aforementioned topics. Therefore, we focused the second part of this review on the importance of bioactive compounds from crustose coralline algae (CCA) and their role during coral settlement, a topic that has received less attention. It has been shown that certain SMs derived from CCA and their associated bacteria are able to induce attachment and/or metamorphosis of many benthic invertebrate larvae, including globally threatened reef-building scleractinian corals. This review provides an overview on bioactivities of MNPs from marine microbes and their potential use in medicine as well as on the latest findings of the chemical ecology and settlement process of scleractinian corals and other invertebrate larvae.

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Relative configuration of luminaolide

Cited by 8 publications

References 7 publications

Photosensitivity of the Bacterial Pigment Cycloprodigiosin Enables Settlement in Coral Larvae—Light as an Understudied Environmental Factor

Photosensitivity of the Bacterial Pigment Cycloprodigiosin Enables Settlement in Coral Larvae—Light as an Understudied Environmental Factor

Marine-Derived Macrolides 1990–2020: An Overview of Chemical and Biological Diversity

Secondary Metabolites of Marine Microbes: From Natural Products Chemistry to Chemical Ecology

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