Dolastane and Secodolastane Diterpenes from the Marine Brown Alga, Dictyota cericornis

Teixeira, Valéria Laneuville; Tomassini, Therezinha Coelho Barbosa; Fleury, Beatriz G.; Kelecom, Alphonse

doi:10.1021/np50046a002

Cited by 49 publications

(37 citation statements)

References 6 publications

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“…Chemical characteristics of the compounds (4R, 9S, 14S)-4α-Acetoxy-9β,14α-dihydroxydolast-1 (15),7-diene (1): yellowish gum (430 mg); with physical and spectroscopic properties identical to those previously reported (González et al 1983); (4R,7R,14S)-4α,7α-diacetoxy-14-hydroxydolast-1(15),8-diene (2): colorless gum (450 mg); with physical and spectroscopic properties identical to those previously reported (González et al 1983); Isolinearol (3): yellowish gum (25 mg); with physical and spectroscopic properties identical to those previously reported (Teixeira et al 1986). …”

Section: Isolation Of Compoundssupporting

confidence: 81%

“…The brown seaweed Canistrocarpus cervicornis (Kützing) De Paula and De Clerck (= Dictyota cervicornis Kützing) possesses a biosynthetic pathway that produces dolastane and seco-dolastane diterpenes, encompassing a total of 11 compound types (Teixeira et al 1986), but little is known about the ecological roles of these compounds, aside from the fact that the seco-dolastane diterpenes linearol/isolinearol mixture acts as a feeding deterrent against the gastropod Astraea latispina (Pereira et al 2002b).…”

Section: Introductionmentioning

confidence: 99%

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Antifoulant diterpenes produced by the brown seaweed Canistrocarpus cervicornis

et al. 2008

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This paper reports the antifouling properties of the dichloromethane crude extract (DC) and 3 pure compounds isolated from the Brazilian brown seaweed Canistrocarpus cervicornis against establishment of the mussel Perna perna. DC extract showed a strong inhibition activity against byssal threads. Two natural dolastanes and one seco-dolastane diterpene, namely (4R, 9S, 14S)-4α-acetoxy-9β,14α-dihydroxydolast-1(15),7-diene (1), (4R,7R,14S)-4α,7α-diacetoxy-14-hydroxydolast-1(15),8-diene (2) and isolinearol (3), were isolated from DC extract. Dolastane (1) inhibited 60% of byssal fixation, while compound 2 and the seco-dolastane (3) strongly inhibited (82%) the establishment of P. perna. This is the first report of this type of chemical skeleton in three powerful compounds that could be further explored for the development of antifouling technology.

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Section: Isolation Of Compoundssupporting

confidence: 81%

Section: Introductionmentioning

confidence: 99%

Antifoulant diterpenes produced by the brown seaweed Canistrocarpus cervicornis

et al. 2008

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“…Thus, treatment of methyl 4-methyl-2-pentynoate (9) with lithium (phenylthio)(trimethylstannyl)cuprate (10) (23) under appropriate reaction conditions (24) provided the Z enoate 11. Reduction of this material with diisobutylaluminum hydride, followed by reaction of the resultant allylic alcohol 12 with triphenylphosphine dibromide in the presence of triethylarnine, produced the required bromide 13 in 69% overall yield from 9.…”

Section: Resultsmentioning

confidence: 99%

“…Again the 'H nmr spectrum of 45 did not furnish unambiguous corroboration for the stereochemical assignment. 10 It should be noted that, in their total synthesis of (f )-isoamijiol, Pattenden and co-workers carried out a comparable methylation on a substrate structurally similar to 44 (16).…”

mentioning

confidence: 99%

Annulations leading to diene systems. Total syntheses of the dolastane-type diterpenoids (±)-(5S,12R,14S)-dolasta-1(15),7,9-trien-14-ol and (±)-amijitrienol

Piers¹,

Friesen²

1992

Can. J. Chem.

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Annulations leading to diene systems. Total syntheses of the dolastane-type diterpenoids (~)-(5S,12R,14S)-dolasta-1(15),7,9-trien-14-01 and (2)-amijitrienol Chem. 70, 1204Chem. 70, (1992. Alkylation of the substituted cycloalkanones 14ci-el and 30 with (Z)-l-bromo-4-methyl-3-trimethylstannyl-2-pentene (13) produced compounds 150-d and 33, which were readily converted into the corresponding en01 trifluoromethanesulfonates (triflates) 160-el and 34. Intramolecular Pd(0)-catalyzed coupling of the vinylstannane and en01 triflate functions in 160-d and 34 provided the dienes 170-d and 35. The annulation product 35 served as a suitable starting material for the total syntheses of the dolastane diterpenoids (5)-(5S, 12R, 14s)-dolasta-1(15),7,9-trien-14-01 (2) and (?)-amijitrienol (3). The key steps of the synthesis of (5) [Traduit par la rCdaction]

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“…As algas desse grupo pertencem ao gênero Canistrocarpus e sintetizam dolastanos e secodolastanos. 38,[44][45][46] Muitos artigos sobre a atividade biológica dos diterpenos dessas algas foram publicados. A parceria entre o ALGAMAR e outros grupos de pesquisa foi crucial para o estabelecimento dessas atividades.…”

Section: Produtos Naturais De Algas Pardas Marinhasunclassified

Marine Natural Products from Seaweeds

Teixeira¹

2013

Revista Virtual De Química

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Marine Natural Products from SeaweedsAbstract: Natural products from seaweeds have been studied with the aim of finding new drugs of industrial value, understanding their ecological role, and well as establishing the limits of taxonomic species, genera and families of marine algae. The present review shows the main features of natural products from seaweeds of the Divisions Chlorophyta -Class Ulvophyceae (green seaweeds), Ochrophyta -Class Phaeophyceae (Brown seaweeds) and Rhodophyta (red seaweeds). The most important examples of natural products isolated in the Brazilian coast are presented along with their main biological activities and their ecological, evolutionary and taxonomic importance.

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Dolastane and Secodolastane Diterpenes from the Marine Brown Alga, Dictyota cericornis

Cited by 49 publications

References 6 publications

Antifoulant diterpenes produced by the brown seaweed Canistrocarpus cervicornis

Antifoulant diterpenes produced by the brown seaweed Canistrocarpus cervicornis

Annulations leading to diene systems. Total syntheses of the dolastane-type diterpenoids (±)-(5S,12R,14S)-dolasta-1(15),7,9-trien-14-ol and (±)-amijitrienol

Marine Natural Products from Seaweeds

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