A New Isocyanosesquiterpene from the Nudibranch <i>Phyllidiella pustulosa</i>

Jomoria, Takahiro; Shibutani, Takahiro; Ahmadi, Peni; Suzuka, Toshimasa; Tanaka, Junichi

doi:10.1177/1934578x1501001126

Cited by 7 publications

(15 citation statements)

References 9 publications

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“…Many other phyllidid species ( P. rosans (P. bourguini) , P. coelestis , P. ocellata , Phyllidia sp, Phyllidiella pustulosa , Phyllidiopsis krempfi , etc.) contain a wide variety of these and other nitrogenated compounds, but these have not been tested for toxicity [ 101 , 102 , 103 , 111 , 114 , 118 , 119 , 120 , 122 , 373 , 374 , 375 , 376 , 377 ].…”

Section: Ecological Activitymentioning

confidence: 99%

“…Since the isolation of 9- iso cyanopupukeanane ( 21 ) from Phillidia varicosa [ 106 ], phyllidids have been shown to be chemically rich, presenting many nitrogenous mono-, bi- and tri-cyclic sesquiterpenes, usually traced back to their sponge prey [ 1 , 4 , 22 , 101 , 102 , 103 , 104 , 105 , 106 , 107 , 110 , 111 , 114 , 116 , 118 , 119 , 120 , 122 , 374 , 375 , 376 , 377 , 437 ]. Some of these compounds are potent antifouling agents, effective against barnacle larvae, such as the bisabolene 3- iso cyanotheonellin ( 161 ) of P. varicosa from Sri Lanka, and a sesquiterpene isonitrile from the Japanese Phyllidiella pustulosa [ 102 , 103 , 114 , 115 , 116 , 437 ].…”

Section: Ecological Activitymentioning

confidence: 99%

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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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Section: Ecological Activitymentioning

confidence: 99%

Section: Ecological Activitymentioning

confidence: 99%

Bioactive Compounds from Marine Heterobranchs

Ávila

Angulo‐Preckler

2020

Marine Drugs

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“…Sea slugs of the genus Phyllidiella and Phyllidia are prolific in the South China Sea. They are well known for their ability to ingest toxic nitrogenous sesquiterpenoids from their diets, and use either these metabolites themselves or their biosynthetically transformed derivatives as a weapon for chemical defense [1,2,3,4,5,6,7]. An intriguing ecological study showed that when sea slugs are under attack, they release a lot of mucus containing these nitrogenous metabolites to poison their enemies [8].…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic Nitrogenous Terpenoids from Two South China Sea Nudibranchs Phyllidiella pustulosa, Phyllidia coelestis, and Their Sponge-Prey Acanthella cavernosa

Chen

et al. 2019

Marine Drugs

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A detailed chemical investigation of two South China Sea nudibranchs Phyllidiella pustulosa and Phyllidia coelestis, as well as their possible sponge-prey Acanthella cavernosa, led to the isolation of one new nitrogenous cadinane-type sesquiterpenoid xidaoisocyanate A (1), one new naturally occurring nitrogen-containing kalihinane-type diterpenoid bisformamidokalihinol A (16), along with 17 known nitrogenous terpenoids (2–15, 17–19). The structures of all the isolates were elucidated by detailed spectroscopic analysis and by the comparison of their spectroscopic data with those reported in the literature. In addition, the absolute stereochemistry of the previously reported axiriabiline A (5) was determined by X-ray diffraction (XRD) analysis. In a bioassay, the bisabolane-type sesquiterpenoids 8, 10, and 11 exhibited cytotoxicity against several human cancer cell lines.

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“…229 Subsequent studies have found a number of related nitrogenous mono-, bi-and tricyclic sesquiterpenes from Phyllidia sp., 230 P. varicosa, 231,232 P. ocellata, 232-234 P. coelestis, 235 and P. pustulosa. 231,232,236,237 Phyllidia pustulosa has been reclassied as Phyllidiella pustulosa 413 so unsurprisingly, several studies of the animal reported as Phyllidiella pustulosa also yielded nitrogenous sesquiterpenes, [238][239][240][241][242] although one additionally yielded nitrogenous diterpenes, 240 which had also been isolated previously from a sponge. 240 Phyllidiopsis kremp also yielded nitrogenous sesquiterpenes and a sesquiterpene peroxide.…”

Section: Phyllidioideamentioning

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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A New Isocyanosesquiterpene from the Nudibranch Phyllidiella pustulosa

Cited by 7 publications

References 9 publications

Bioactive Compounds from Marine Heterobranchs

Bioactive Compounds from Marine Heterobranchs

Cytotoxic Nitrogenous Terpenoids from Two South China Sea Nudibranchs Phyllidiella pustulosa, Phyllidia coelestis, and Their Sponge-Prey Acanthella cavernosa

The chemistry and chemical ecology of nudibranchs

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