Chemical studies of marine invertebrates. XLI. Sigmosceptrellin-A methyl ester a nor-sesterterpenoid peroxide from the sponge sigmosceptrella laevis.

Albericci, M.; Collart-Lempereur, M.; Braekman, Jean‐Claude; Dalcze, D.; Tursch, Bernard; Declercq, J.P.; Germain, Gabriel; Meerssche, M. Van

doi:10.1016/s0040-4039(01)86387-5

Cited by 42 publications

(48 citation statements)

References 4 publications

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“…Compound 2 is reported here for the first time; however, its enantiomer had been reported previously reported [6]. Compound 3 is reported here for the first time.…”

Section: H-andmentioning

confidence: 54%

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Structure–Activity Relationship Studies on the Mosquito Toxicity and Biting Deterrency of Callicarpenal Derivatives

Cantrell¹,

Klun

Pridgeon

et al. 2009

Chemistry & Biodiversity

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Callicarpenal (=13,14,15,16-tetranorclerod-3-en-12-al=[(1S,2R,4aR,8aR)-1,2,3,4,4a,7,8,8a-octahydro-1,2,4a,5-tetramethylnaphthalen-1-yl]acetaldehyde; 1) has previously demonstrated significant mosquito bite-deterring activity against Aedes aegypti and Anopheles stephensi in addition to repellent activity against host-seeking nymphs of the blacklegged tick, Ixodes scapularis. In the present study, structural modifications were performed on callicarpenal (1) in an effort to understand the functional groups necessary for maintaining and/or increasing its activity and to possibly lead to more effective insect control agents. All modifications in this study targeted the C(12) aldehyde or the C(3) alkene functionalities or combinations thereof. Mosquito biting deterrency appeared to be influenced most by C(3) alkene modification as evidenced by catalytic hydrogenation that resulted in a compound having significantly less effectiveness than 1 at a test amount of 25 nmol/cm2. Oxidation and/or reduction of the C(12) aldehyde did not diminish mosquito biting deterrency, but, at the same time, none of the modifications were more effective than 1 in deterring mosquito biting. Toxicities of synthesized compounds towards Ae. aegypti ranged from an LD50 value of 2.36 to 40.11 microg per mosquito. Similarly, LD95 values ranged from a low of 5.59 to a high of 104.9 microg.

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“…Compound 2 is reported here for the first time; however, its enantiomer had been reported previously reported [6]. Compound 3 is reported here for the first time.…”

Section: H-andmentioning

confidence: 54%

“…24-ml Fractions were collected and recombined based on TLC similarities providing 51. 4 (6). Using a 100-ml round-bottomed flask, Jones reagent (744 ml) was added to a mixture of 1 (200 mg) in acetone (100 ml) at 08.…”

mentioning

confidence: 99%

Structure–Activity Relationship Studies on the Mosquito Toxicity and Biting Deterrency of Callicarpenal Derivatives

Cantrell¹,

Klun

Pridgeon

et al. 2009

Chemistry & Biodiversity

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“…Cyclic peroxides have also been reported in other sponge genera, mainly Diacarnus [108,109,115,116], Latrunculia [107,117], Negombata [118] and Sigmosceptrella [119], which are all from the order Poecilosclerida. Bicyclic peroxides that share similar structural characteristics to the mycaperoxides include the sigmosceptrellins (e.g., sigmosceptrellin A 133) isolated from the sponge Diacarnus laevis [108,109] and diacarperoxides (e.g., diacarperoxide F 144) from the sponge Diacarnus megaspinorhabdosa [116]. Mycaperoxides A (138) and B (139) inhibited the growth of bacteria (Bacillus subtilis and S. aureus), showed antiviral activity with IC 50 values in the range of 0.25-1.0 µg/mL (against Vesicular stomatitis virus and Herpes simplex virus type-1), and showed cytotoxicity with IC 50 values ranging from 0.5-1.0 µg/mL (against P388, A549, and HT-29 cell lines) [111].…”

Section: Cyclic Peroxidesmentioning

confidence: 86%

“…[113], and mycaperoxide A (138) was reisolated from an Indonesian M. (Arenochalina) euplectellioides [114]. Cyclic peroxides have also been reported in other sponge genera, mainly Diacarnus [108,109,115,116], Latrunculia [107,117], Negombata [118] and Sigmosceptrella [119], which are all from the order Poecilosclerida. Bicyclic peroxides that share similar structural characteristics to the mycaperoxides include the sigmosceptrellins (e.g., sigmosceptrellin A 133) isolated from the sponge Diacarnus laevis [108,109] and diacarperoxides (e.g., diacarperoxide F 144) from the sponge Diacarnus megaspinorhabdosa [116].…”

Section: Cyclic Peroxidesmentioning

confidence: 92%

“…ancorina [107]. This is the enantiomer of sigmosceptrellin A (133), which was originally isolated from the sponge Diacarnus laevis (originally reported as Sigmosceptrella laevis) [108,109] but where the absolute configuration was later corrected by Capon and MacLeod [107]. Later, 132 was again isolated from an Australian M. (Grapelia) ancorina together with the two new cyclic peroxides 134 and 135 that are isomeric with enantio-sigmosceptrellin A (132) [110].…”

Section: Cyclic Peroxidesmentioning

confidence: 99%

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Chemical and Biological Aspects of Marine Sponges from the Family Mycalidae

2016

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Sponges are a useful source of bioactive natural products. Members of the family Mycalidae, in particular, have provided a variety of chemical structures including alkaloids, polyketides, terpene endoperoxides, peptides, and lipids. This review highlights the compounds isolated from Mycalid sponges and their associated biological activities. A diverse group of 190 compounds have been reported from over 40 specimens contained in 49 references. Over half of the studies have reported on the biological activities for the compounds isolated. The polyketides, in particular the macrolides, displayed potent cytotoxic activities (

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Structural aspects of organic peroxides

Gougoutas

1983

PATAI'S Chemistry of Functional Groups

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Chemical studies of marine invertebrates. XLI. Sigmosceptrellin-A methyl ester a nor-sesterterpenoid peroxide from the sponge sigmosceptrella laevis.

Cited by 42 publications

References 4 publications

Structure–Activity Relationship Studies on the Mosquito Toxicity and Biting Deterrency of Callicarpenal Derivatives

Structure–Activity Relationship Studies on the Mosquito Toxicity and Biting Deterrency of Callicarpenal Derivatives

Chemical and Biological Aspects of Marine Sponges from the Family Mycalidae

Structural aspects of organic peroxides

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