Chemoecological studies on marine natural products: terpene chemistry from marine mollusks

Mudianta, I Wayan; White, Andrew M.; Suciati, Suciati; Katavic, Peter L.; Krishnaraj, Rahul R.; Winters, Anne E.; Mollo, Ernesto; Cheney, Karen L.; Garson, Mary J.

doi:10.1515/pac-2013-1111

Cited by 15 publications

(29 citation statements)

References 24 publications

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“…In addition, some known sesquiterpenes, including dendrolasin (12) (Figure 3), are found in the Patagonian doridacean Tyrinna nobilis [89]. Furthermore, (5R,6Z)-dendrolasin-5-acetate was isolated from Hypselodoris jacksoni from Australia [90]. The dendronotid slug Doto pinnatifida from the Atlantic presents dotofide (13) (Figure 3), a guanidine-interrupted terpenoid with an unknown ecological role [91].…”

Section: Monocyclic Sesquiterpenoidsmentioning

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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Section: Monocyclic Sesquiterpenoidsmentioning

confidence: 99%

Terpenoids in Marine Heterobranch Molluscs

Ávila

2020

Marine Drugs

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“…Here we presented an initial chemical investigation of nudibranch Hypselodoris infucata collected from Tulamben-Bali, a less-explored waters but rich in species diversity. Our research group have pioneered the chemical investigation of marine invertebrate mainly sponges and nudibranchs from this prolific site (Mańdi et al, 2015;Mudianta et al, 2014). We also reported for the first time the development of a method to assay nudibranch extracts for their feeding deterrent activity against local shrimps Penaeus vannamei.…”

Section: Introductionmentioning

confidence: 99%

“…However, despite slow movements and the absence of physical attributes, only few predators have been documented. Chemoecological studies showed that nudibranchs may employ secondary metabolites as chemical defence mechanism against predators (Cimino and Ghiselin, 2009;Mudianta et al, 2014). The metabolites are either derived from their diets mainly sponges or biosynthesized in de novo fashion (Fontana et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

BIOACTIVE TERPENOID FROM THE BALINESE NUDIBRANCH Hypselodoris infucata

Mudianta

Martiningsih²,

Prasetia³

et al. 2016

Indonesian J. Pharm.

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Marine organisms, in particular nudibranchs (Mollusca: nudibranchia), are known as a rich source of chemically diverse secondary metabolites exhibiting potential as antimalarial, antiinflammatory, antiviral and anticancer activity. We presented the chemical investigation of an extract of nudibranch Hypselodoris infucata collected from Bali, an unexplored water but rich in nudibranch diversity. The extract contained the known (-)furodysinin (1), a furanosesquiterpene that for the first time isolated from this species. Metabolite 1 was purified by chromatography and the structure was characterised by comparison of 1 H NMR data with that of the reported data. The absolute configuration was determined by comparing the optical rotation values with the known enantiomer. In vitro cytotoxic activity of compound 1 against HeLa cell line displayed an IC50 at 102.7µg/mL. We also report for the first time the development of a method to assay nudibranch extracts for their feeding deterrence activity against local shrimps Penaeus vannamei. The extract show food rejection with highly significant difference in respect to the control (P = 0.0061) at natural concentration of 3.0mg/mL.

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“…The feeding deterrence activity of compounds 1-3 was evaluated against the cooccurring generalist shrimp Palaemon elegans Rathke, 1837, following an approach already used to assess the palatability of other bioactive metabolites (31), including marine furanosesquiterpenes (32,33). Like other palaemonid species (34,35), P. elegans is suitable for evaluations of this kind, which require a good view of the ingested food in the digestive system (31). Given that decapod crustaceans exhibit complex learning ability (36,37), the possibility that the shrimp learn to avoid the compounds after experiencing aversive olfactory stimuli was also considered.…”

mentioning

confidence: 99%

Volatile secondary metabolites as aposematic olfactory signals and defensive weapons in aquatic environments

Giordano

Carbone

Ciavatta

et al. 2017

Proc. Natl. Acad. Sci. U.S.A.

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Olfaction is considered a distance sense; hence, aquatic olfaction is thought to be mediated only by molecules dissolved in water. Here, we challenge this view by showing that shrimp and fish can recognize the presence of hydrophobic olfactory cues by a "tactile" form of chemoreception. We found that odiferous furanosesquiterpenes protect both the Mediterranean octocoral Maasella edwardsi and its specialist predator, the nudibranch gastropod Tritonia striata, from potential predators. Food treated with the terpenes elicited avoidance responses in the cooccurring shrimp Palaemon elegans. Rejection was also induced in the shrimp by the memory recall of postingestive aversive effects (vomiting), evoked by repeatedly touching the food with chemosensory mouthparts. Consistent with their emetic properties once ingested, the compounds were highly toxic to brine shrimp. Further experiments on the zebrafish showed that this vertebrate aquatic model also avoids food treated with one of the terpenes, after having experienced gastrointestinal malaise. The fish refused the food after repeatedly touching it with their mouths. The compounds studied thus act simultaneously as (i) toxins, (ii) avoidance-learning inducers, and (iii) aposematic odorant cues. Although they produce a characteristic smell when exposed to air, the compounds are detected by direct contact with the emitter in aquatic environments and are perceived at high doses that are not compatible with their transport in water. The mouthparts of both the shrimp and the fish have thus been shown to act as "aquatic noses," supporting a substantial revision of the current definition of the chemical senses based upon spatial criteria. T raditionally, the sense of smell has been regarded as a distance sense (like vision), whereas the sense of taste has been treated as a contact sense (like touch). This classification of the chemical senses (olfaction and gustation) based on their spatial range persists in contemporary literature. Accordingly, biomolecules smaller than ∼300 Da, which can be transported through air, and which finally bind to odorant receptors expressed in olfactory neurons, are generally considered odorant molecules. Conversely, the molecules sensed by taste have to be in solution and in contact with the receptor (1). However, the claim that "only olfaction can provide information on the identity of the water mass encountered" by marine organisms (2) implies that water-soluble compounds, which are typically "tasted" by the tongues of terrestrial animals, act as olfactory cues in aquatic environments. Consequently, it may be asked how typical odorant molecules such as small terpenes from plants and marine sponges that combine high volatility in air with insolubility in water can produce olfactory sensations in marine organisms, thereby giving protection from predators and cues to finding food and mates.

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Chemoecological studies on marine natural products: terpene chemistry from marine mollusks

Cited by 15 publications

References 24 publications

Terpenoids in Marine Heterobranch Molluscs

Terpenoids in Marine Heterobranch Molluscs

BIOACTIVE TERPENOID FROM THE BALINESE NUDIBRANCH Hypselodoris infucata

Volatile secondary metabolites as aposematic olfactory signals and defensive weapons in aquatic environments

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