Marine natural products: parguerol, deoxyparguerol, and isoparguerol. New brominated diterpenes with modified pimarane skeletons from the sea hare Aplysia dactylomela

Schmitz, Francis J.; Michaud, Dennis P.; Schmidt, Paul G.

doi:10.1021/ja00387a045

Cited by 63 publications

(71 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…C 24 H 35 BrO 6 was obtained in 1.34% yield (58 mg) of the fraction (b) and its spectral data was identical to isoparguerol-16-acetate isolated from the sea hare Aplysia dectylomela (Schmitz et al, 1982 and acetate group at 1730 cm −1 . MS spectrum together with other spectral data proved that compound 3 was isoparguerol 7,16 diacetate which previously isolated from the sea hare Aplysia dactylomela and red alga Laurancia obtuse (Schmitz et al, 1982;Higgs and Faulkner, 1982).…”

Section: Compoundmentioning

confidence: 59%

“…C 22 H 33 BrO 5 was obtained in 1.67% yield (72 mg) of the fraction (c) and showed all characters of the marine natural compound isoparguerol isolated from the sea hare Aplysia dectylomela (Schmitz et al, 1982). IR spectra revealed the presence of hydroxyl and acetate groups (3484, 1724, 1246 cm…”

Section: Compoundmentioning

confidence: 95%

“…Parguerene and isoparguerene carbon skeletons were first isolated as natural products in 1982 from the Caribbean sea hare Aplysia dectylomela (Schmitz et al, 1982) and marine red alga Laurencia obtusa (Higgs and Faulkner, 1982). Investigations of Laurencia spp.…”

Section: Introductionmentioning

confidence: 99%

“…revealed the isolation of brominated diterpenes parguerene, deoxyparguerene and isoparguerene (Takeda et al, 1990;Rochfort and Capon, 1996;Kurata and Taniguchi, 1998). Schmitz et al (1982) reported that parguerol, parguerol-16-acetate, deoxyparguerol, isoparguerol and isoparguerol-16-acetate, isolated from Aplysia dactylomela, are assumed to be of algal origin…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Bioactive brominated diterpenes from the marine red alga Jania Rubens (L.) Lamx.

Awad

2004

Phytotherapy Research

View full text Add to dashboard Cite

Seven brominated diterpenes of the parguerene and isoparguerene series were isolated for the first time from the red alga Jania rubens (L.) Lamx., collected from the Red Sea coast at Hurghada, Egypt. The diterpenes were identified as isoparguerol (1), isoparguerol-16-acetate (2), isoparguerol-7,16-diacetate (3), parguerol-16-acetate (4), parguerol-7,16-diacetate (5), deoxyparguerol (6) and deoxyparguerol-7-acetate (7). The isolated diterpenes had a marked antitumour activity. Isoparguerol derivatives were slightly more effective than parguerol derivatives. Moreover, the data implied that the cytotoxicity of these compounds were dependent on the number of acetoxy groups. Also, anthelmintic activities of the isolated compounds on earthworms (Allolobophora caliginosa) were studied.

show abstract

Section: Compoundmentioning

confidence: 59%

Section: Compoundmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Bioactive brominated diterpenes from the marine red alga Jania Rubens (L.) Lamx.

Awad

2004

Phytotherapy Research

View full text Add to dashboard Cite

show abstract

“…Sea hare species have attracted the interest of many workers investigating the chemical compounds secreted by the purple gland or present in different tissues, possibly involved in the defense of these invertebrates. Thus, some sea hare species have been shown to contain low molecular mass substances with antimicrobial (2-6) and antitumor activities (7)(8)(9)(10) and also high molecular mass compounds such as those from Aplysia kurodai, Aplysia juliana and Dolabella auricularia with similar activities, and which were named aplysianins (11,12), julianins (13,14) and dolabellanins (15,16), respectively. This study describes some biological properties (antibacterial, antifungal, hemagglutinating and toxic activities) of the purple fluid of the sea hare Aplysia dactylomela, which is an opistobranch widespread along the Brazilian coast and also occurring in the intertidal zones from Southern Florida in the United States to Eastern India (17).…”

Section: Introductionmentioning

confidence: 99%

Toxic, antimicrobial and hemagglutinating activities of the purple fluid of the sea hare Aplysia dactylomela Rang, 1828

Melo¹,

Fonseca²,

Vasconcelos

et al. 1998

Braz J Med Biol Res

View full text Add to dashboard Cite

Rhodophyceae (Red Algae)

Kornprobst

2014

Encyclopedia of Marine Natural Products

View full text Add to dashboard Cite

The article contains sections titled: Special Features of Red Algae Classification of Rhodophyceae Photosynthetic Pigments Storage Monosaccharides and Polysaccharides Skeleton Polysaccharides Matrix Polysaccharides: Carrageenans and Agars Carrageenophytes and Agarophytes Gelling Agents and Thickeners Other Types of Matrix Polysaccharides Phospholipids and Fatty Acids Oxylipins and Prostaglandins Sterols and Ecdysteroids General Comments on the Secondary Metabolites Secondary Metabolites of Cryptonemiales Secondary Metabolites of Gelidiales Secondary Metabolites of Rhodymeniales Polyhalogenated Monoterpenes of Gigartinales Diterpenes of Sphaerococcus coronopifolius (Gigartinales, Sphaerococcaceae) Macrocyclic Pyrones of Phacelocarpus labillardieri (Gigartinales, Sphaerococcaceae) Polycavernosides of Polycavernosa tsudai (Gigartinales, Gracilariaceae) Brominated Meroditerpenes of Callophycus serratus (Gigartinales, Solieriaceae) Halogenated Phloroglucinols of Rhabdonia verticillata (Gigartinales, Solieriaceae) Sulfated Aromatic Derivatives of Tichocarpus crinitus (Gigartinales, Tichocarpaceae) Nitrogen‐Containing Derivatives of Gigartinales Halogenated Compounds of Ceramiales: General Comments Polyhalogenated Monoterpenes of Pantoneura plocamioides (Ceramiales, Delesseriaceae) Sesquiterpenes of Laurencia (Ceramiales, Rhodomelaceae) Halogenated Diterpenes of Laurencia Squalenoids of Laurencia species and Chondria armata Cyclic Halogenated C 15 Ethers and Polyethers of Laurencia and Chondria Bromo‐ and Polybromophenols of Ceramiales Nitrogen‐Containing Bromophenols of Rhodomela confervoides and Osmundaria colensoi Other Nitrogen‐Containing Derivatives of Ceramiales Cyclic Polysulfides of Chondria californica Arsenic‐Containing Derivative of Chondria crassicaulis Some Atypical Derivatives of Laurencia Species Macrocyclic α ‐ Pyrones of Neurymenia fraxinifolia Halogenated Derivatives of Nemaliales Acetylenic Acids of Liagora farinosa Sulfated Triterpene Alcohols of Tricleocarpa fragilis Cyclic Peptide from Galaxaura filamentosa

show abstract

Marine natural products: parguerol, deoxyparguerol, and isoparguerol. New brominated diterpenes with modified pimarane skeletons from the sea hare Aplysia dactylomela

Cited by 63 publications

References 0 publications

Bioactive brominated diterpenes from the marine red alga Jania Rubens (L.) Lamx.

Bioactive brominated diterpenes from the marine red alga Jania Rubens (L.) Lamx.

Toxic, antimicrobial and hemagglutinating activities of the purple fluid of the sea hare Aplysia dactylomela Rang, 1828

Rhodophyceae (Red Algae)

Contact Info

Product

Resources

About