Structural Elucidation of Kurodainol, a Novel Halogenated Monoterpene from Sea Hare (<i>Aplysia Kurodai</i>)

Masuda, Hideki; Ina, Kazuo; Nozaki, Hirōshi; Nakayama, Mitsuru

doi:10.1080/00021369.1982.10865164

Cited by 7 publications

(6 citation statements)

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“…Goniobranchus albopunctatus (previously known as Chromodoris albopunctata) from Australia presents 12α-acetoxyspongian-16-one, 20-acetoxyspongian-16-one, (+)-spongian-16-one, and 7α-acetoxyspongian-16-one, together with some propionates and (+)-isoagatholactone [90]. The same study reports that Chromodoris splendida from Australia presents aplysulphurin (61) (Figure 8), probably from its diet, the demosponge Darwinella tango, together with gracilin metabolites, such as gracilin C 20, not found in the sponge. A recent study on 19 species of Chromodoridid nudibranchs from Australia, mentioned above, reported many diterpenoids, among other compounds, found in mantle and internal glands [154].…”

Section: Tricyclic Diterpenoidsmentioning

confidence: 77%

“…Within anaspideans, the sea hare Aplysia kurodai from Japan presents halogenated and brominated monoterpenoids distributed in different body parts, such as kurodainol (1) [61] and aplysiaterpenoid B (2) ( Figure 2) [62,63]. Mediterranean specimens of Aplysia fasciata contain polyhalogenated monoterpenes similar to those of Plocamium red algae [64].…”

Section: Linear Monoterpenoidsmentioning

confidence: 99%

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Terpenoids in Marine Heterobranch Molluscs

Ávila

2020

Marine Drugs

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Heterobranch molluscs are rich in natural products. As other marine organisms, these gastropods are still quite unexplored, but they provide a stunning arsenal of compounds with interesting activities. Among their natural products, terpenoids are particularly abundant and diverse, including monoterpenoids, sesquiterpenoids, diterpenoids, sesterterpenoids, triterpenoids, tetraterpenoids, and steroids. This review evaluates the different kinds of terpenoids found in heterobranchs and reports on their bioactivity. It includes more than 330 metabolites isolated from ca. 70 species of heterobranchs. The monoterpenoids reported may be linear or monocyclic, while sesquiterpenoids may include linear, monocyclic, bicyclic, or tricyclic molecules. Diterpenoids in heterobranchs may include linear, monocyclic, bicyclic, tricyclic, or tetracyclic compounds. Sesterterpenoids, instead, are linear, bicyclic, or tetracyclic. Triterpenoids, tetraterpenoids, and steroids are not as abundant as the previously mentioned types. Within heterobranch molluscs, no terpenoids have been described in this period in tylodinoideans, cephalaspideans, or pteropods, and most terpenoids have been found in nudibranchs, anaspideans, and sacoglossans, with very few compounds in pleurobranchoideans and pulmonates. Monoterpenoids are present mostly in anaspidea, and less abundant in sacoglossa. Nudibranchs are especially rich in sesquiterpenes, which are also present in anaspidea, and in less numbers in sacoglossa and pulmonata. Diterpenoids are also very abundant in nudibranchs, present also in anaspidea, and scarce in pleurobranchoidea, sacoglossa, and pulmonata. Sesterterpenoids are only found in nudibranchia, while triterpenoids, carotenoids, and steroids are only reported for nudibranchia, pleurobranchoidea, and anaspidea. Many of these compounds are obtained from their diet, while others are biotransformed, or de novo biosynthesized by the molluscs. Overall, a huge variety of structures is found, indicating that chemodiversity correlates to the amazing biodiversity of this fascinating group of molluscs.

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Section: Tricyclic Diterpenoidsmentioning

confidence: 77%

Section: Linear Monoterpenoidsmentioning

confidence: 99%

Terpenoids in Marine Heterobranch Molluscs

Ávila

2020

Marine Drugs

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“…In Japan, A. kurodai specimens also contain aplysiaterpenoid A (298) and aplysiapyranoids A-D (299), displaying moderate cytotoxicities against Vero, MDCK, and B16 cell lines (IC 50 19-96 µg/mL) [668,669]. Moreover, mono-and di-terpenes, such as kurodainol (300), aplysiaterpenoids A-D ( 298), aplysin-20 (301), iso-aplysin-20, aplysiadiol (302), epi-aplysin-20, and ent-isoconcinndiol (303), are found in A. kurodai specimens and are suggested to originate from isoconncindiol of the red algae Laurencia snyderae [668][669][670][671][672][673][674]. A. kurodai also contains other compounds, including aplydilactone, a dieicosanoid lactone, aplysepsine, and a 1,4-benzoidiasepine alkaloid [675,676].…”

Section: Anaspideamentioning

confidence: 99%

Bioactive Compounds from Marine Heterobranchs

Ávila

Angulo‐Preckler

2020

Marine Drugs

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The natural products of heterobranch molluscs display a huge variability both in structure and in their bioactivity. Despite the considerable lack of information, it can be observed from the recent literature that this group of animals possesses an astonishing arsenal of molecules from different origins that provide the molluscs with potent chemicals that are ecologically and pharmacologically relevant. In this review, we analyze the bioactivity of more than 450 compounds from ca. 400 species of heterobranch molluscs that are useful for the snails to protect themselves in different ways and/or that may be useful to us because of their pharmacological activities. Their ecological activities include predator avoidance, toxicity, antimicrobials, antifouling, trail-following and alarm pheromones, sunscreens and UV protection, tissue regeneration, and others. The most studied ecological activity is predation avoidance, followed by toxicity. Their pharmacological activities consist of cytotoxicity and antitumoral activity; antibiotic, antiparasitic, antiviral, and anti-inflammatory activity; and activity against neurodegenerative diseases and others. The most studied pharmacological activities are cytotoxicity and anticancer activities, followed by antibiotic activity. Overall, it can be observed that heterobranch molluscs are extremely interesting in regard to the study of marine natural products in terms of both chemical ecology and biotechnology studies, providing many leads for further detailed research in these fields in the near future.

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“…However, as far as we know, there are no studies concerning to the bioactivity of compounds 61 and 62 . Kurodainol ( 63 ) was found in the gut of A. kurodai , its structure being determined by X-ray analysis [ 96 ]. A. punctata from Sancti Petri, Cádiz (Spain), contained four new unusual acetates of linear polyhalogenated monoterpenes ( 64 – 67 ) [ 97 ].…”

Section: Terpenoidsmentioning

confidence: 99%

Chemical Diversity and Biological Properties of Secondary Metabolites from Sea Hares of Aplysia Genus

2016

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The marine environment is an important source of structurally-diverse and biologically-active secondary metabolites. During the last two decades, thousands of compounds were discovered in marine organisms, several of them having inspired the development of new classes of therapeutic agents. Marine mollusks constitute a successful phyla in the discovery of new marine natural products (MNPs). Over a 50-year period from 1963, 116 genera of mollusks contributed innumerous compounds, Aplysia being the most studied genus by MNP chemists. This genus includes 36 valid species and should be distinguished from all mollusks as it yielded numerous new natural products. Aplysia sea hares are herbivorous mollusks, which have been proven to be a rich source of secondary metabolites, mostly of dietary origin. The majority of secondary metabolites isolated from sea hares of the genus Aplysia are halogenated terpenes; however, these animals are also a source of compounds from other chemical classes, such as macrolides, sterols and alkaloids, often exhibiting cytotoxic, antibacterial, antifungal, antiviral and/or antifeedant activities. This review focuses on the diverse structural classes of secondary metabolites found in Aplysia spp., including several compounds with pronounced biological properties.

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Structural Elucidation of Kurodainol, a Novel Halogenated Monoterpene from Sea Hare (Aplysia Kurodai)

Cited by 7 publications

References 1 publication

Terpenoids in Marine Heterobranch Molluscs

Terpenoids in Marine Heterobranch Molluscs

Bioactive Compounds from Marine Heterobranchs

Chemical Diversity and Biological Properties of Secondary Metabolites from Sea Hares of Aplysia Genus

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