Selected Bioactive Compounds from Japanese Anaspideans and Nudibranchs

Miyamoto, Tomofumi

doi:10.1007/978-3-540-30880-5_9

Cited by 6 publications

(7 citation statements)

References 29 publications

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“…There is a strong bias in the natural product literature towards research on marine heterobranch gastropods (Figs 6, 7), in which the shell is often reduced or completely absent. Several reviews focus on the chemical ecology of these soft‐bodied opisthobranchs ( Karuso, 1987; Cimino and Sodano, 1989; Faulkner, 1992 a ; Avila, 1995; 2006; Cimino et al , 2001; Wägele, Ballesteros & Avila, 2006; Wahidullah et al , 2006; Miyamoto, 2006; Fontana, 2006). The taxonomy of Heterobranchia is yet to be fully resolved (Thollesson, 1999; Wägele et al , 2008; Mordan & Wade, 2008), but further knowledge of their phylogenetic relationships will be beneficial for understanding the full chemical diversity of this group and the potential for shared biosynthetic pathways among taxa.…”

Section: Taxonomic Distribution Of Molluscan Metabolitesmentioning

confidence: 99%

“…These reviews have been continued in recent years by Blunt et al (2003Blunt et al ( , 2004Blunt et al ( , 2005Blunt et al ( , 2006Blunt et al ( , 2007Blunt et al ( , 2008Blunt et al ( , 2009) reporting a further 190 distinct compounds from 75 species. Cimino & Gavagnin (2006) provide a modern review of marine molluscan chemistry and biotechnology, including chapters on secondary metabolites from marine gastropods from Antarctica, Southern Africa and South America (Davies-Coleman, 2006); Australia and New Zealand (Garson, 2006), Indo-Pacific (Wahidullah et al, 2006) and Japan (Miyamoto, 2006). These references offer excellent opportunities to examine the chemical diversity of marine molluscs (Table 1, Figs 3,4), with respect to structural diversity ( Fig.…”

Section: (1) Molluscan Biological Diversitymentioning

confidence: 99%

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Molluscan biological and chemical diversity: secondary metabolites and medicinal resources produced by marine molluscs

2010

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The phylum Mollusca represents an enormous diversity of species with eight distinct classes. This review provides a taxonomic breakdown of the published research on marine molluscan natural products and the medicinal products currently derived from molluscs, in order to identify priority targets and strategies for future research. Some marine gastropods and bivalves have been of great interest to natural products chemists, yielding a diversity of chemical classes and several drug leads currently in clinical trials. Molluscs also feature prominently in a broad range of traditional natural medicines, although the active ingredients in the taxa involved are typically unknown. Overall secondary metabolites have only been investigated from a tiny proportion (<1%) of molluscan species. At the class level, the number of species subject to chemical studies mirrors species richness and our relative knowledge of the biology of different taxa. The majority of molluscan natural products research is focused within one of the major groups of gastropods, the opisthobranchs (a subgroup of Heterobranchia), which are primarily comprised of soft-bodied marine molluscs. Conversely, most molluscan medicines are derived from shelled gastropods and bivalves. The complete disregard for several minor classes of molluscs is unjustified based on their evolutionary history and unique life styles, which may have led to novel pathways for secondary metabolism. The Polyplacophora, in particular, have been identified as worthy of future investigation given their use in traditional South African medicines and their abundance in littoral ecosystems. As bioactive compounds are not always constitutively expressed in molluscs, future research should be targeted towards biosynthetic organs and inducible defence reactions for specific medicinal applications. Given the lack of an acquired immune system, the use of bioactive secondary metabolites is likely to be ubiquitous throughout the Mollusca and broadening the search field may uncover interesting novel chemistry.

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Section: Taxonomic Distribution Of Molluscan Metabolitesmentioning

confidence: 99%

Section: (1) Molluscan Biological Diversitymentioning

confidence: 99%

Molluscan biological and chemical diversity: secondary metabolites and medicinal resources produced by marine molluscs

2010

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“…These aspects will not be evaluated here. In addition, previous reviews covered the literature on "opisthobranch" chemistry and chemical ecology in particular geographical areas, in selected groups of compounds, or for certain heterobranch groups [27,[44][45][46][47][48][49][50][51][52][53]. Other wide reviews have also been published regarding molluscs, general marine chemical ecology, or marine chemistry [23,28,33,50,[54][55][56][57][58][59][60].…”

Section: Introductionmentioning

confidence: 99%

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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“…24,25 Many focus on specic groups of metabolites such as diterpenes, 26 terpenoids, 27 cyanide and isothiocyanates 28 and isocyanides 29 (but all also include other marine invertebrates). A number of these reviews are regional in their focus, dealing with nudibranchs and other molluscs found in New Zealand, 30,31 Australia, 31,32 North America, 33 Japan, 34 Africa, 35 South America 35 and Antarctica. 35 The annual review of marine natural products that appears in Natural Product Reports has a section on molluscs 36a-f but given the wide scope of this review, there is no capacity to discuss nudibranchs in any detail or in a comprehensive manner over a considerable time period.…”

Section: Scope Of Reviewmentioning

confidence: 99%

The chemistry and chemical ecology of nudibranchs

Dean

Prinsep

2017

Nat. Prod. Rep.

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Covering: up to the end of February 2017Nudibranchs have attracted the attention of natural product researchers due to the potential for discovery of bioactive metabolites, in conjunction with the interesting predator-prey chemical ecological interactions that are present. This review covers the literature published on natural products isolated from nudibranchs up to February 2017 with species arranged taxonomically. Selected examples of metabolites obtained from nudibranchs across the full range of taxa are discussed, including their origins (dietary or biosynthetic) if known and biological activity.

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Selected Bioactive Compounds from Japanese Anaspideans and Nudibranchs

Cited by 6 publications

References 29 publications

Molluscan biological and chemical diversity: secondary metabolites and medicinal resources produced by marine molluscs

Molluscan biological and chemical diversity: secondary metabolites and medicinal resources produced by marine molluscs

Terpenoids in Marine Heterobranch Molluscs

The chemistry and chemical ecology of nudibranchs

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