Three further dolabellane diterpenoids from Dictyota sp.

Tringali, Corrado; Nicolosi, Giovanni; Piattelli, Mario; Rocco, Cláudia Seely

doi:10.1016/s0031-9422(00)83468-8

Cited by 13 publications

(5 citation statements)

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“…A xeniane compound, also found in D. menstrualis, may deter feeding by sea urchins, but not by pinfish or amphipods (Cronin and Hay 1996). Dolabellane diterpenes are also the main secondary metabolites in Dictyota bartayresiana Lamouroux (Bheemasankara Rao et al 1991, Trimurtulu et al 1992, D. dichotoma (Hudson) Lamouroux (Pullaiah et al 1985, Bheemasankara Rao et al 1986, D. pardalis f. pseudohamata Cribb (Wright et al 1990a,b, 1991, all collected in the Indo-West tropical region, and D. dichotoma (Amico et al 1980, 1981, Durá n et al 1997 and Dilophus fasciola (Roth) Howe (Tringali et al 1984a(Tringali et al ,b,c, 1985(Tringali et al , 1986, both from the warm-temperate Mediterranean-Atlantic region. This is the first report showing that a dolabellane compound constitutes a structural class of defensive diter-Brought to you by | University of Connecticut Authenticated Download Date | 6/8/15 1:52 AM penes found in Dictyota species.…”

Section: Resultsmentioning

confidence: 99%

A dolabellane diterpene from the brown alga Dictyota pfaffii as chemical defense against herbivores

Barbosa¹,

Teixeira²,

Pereira³

2004

Botanica Marina

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Laboratory and field experiments assessed the defensive properties of the crude extract and major secondary metabolite found in the Brazilian brown alga Dictyota pfaffii. Natural concentrations of the crude organic extract of D. pfaffii significantly inhibited feeding by the sea urchin Lytechinus variegatus and generalist herbivore fishes in the field. In contrast, the crude extract did not inhibit feeding by the crab Pachygrapsus transversus. Chemical defensive action against the sea urchin and the generalist fishes was due to the diterpenoid 10,18-diacetoxy-8-hydroxy-2,6-dolabelladiene found as the major natural product in D. pfaffii. However, this compound did not inhibit feeding by P. transversus as readily as the crude extract. This is the first report showing that Dictyota species produce dolabellane diterpenes as chemical defense against herbivory. In addition, these results widen the action spectrum of secondary metabolites found in species of this brown algal genus. Since dolabellanes constitute the major skeleton type found in Dictyota, we suggest that these diterpenes may play an important ecological function as defenses to the Dictyota species worldwide.

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Section: Resultsmentioning

confidence: 99%

A dolabellane diterpene from the brown alga Dictyota pfaffii as chemical defense against herbivores

Barbosa¹,

Teixeira²,

Pereira³

2004

Botanica Marina

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“…Seventeen diterpenoids 1-17 isolated from brown algae of the family Dictyotaceae (8)(9)(10)(11)(12)(13)(14), most of them dolabellane derivatives, have been screened for molluscicidal and antifungal activities.…”

Section: Resultsmentioning

confidence: 99%

Molluscicidal and Antifungal Activity of Diterpenoids from Brown Algae of the FamilyDictyotaceae

Tringali¹,

Piattelli²,

Nicolosi³

et al. 1986

Planta Med

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“…1(1? *), 11(5*), 12(R*)-FASCIOLA-7,18-DIEN-I7-AL (6).-The natural diterpenoid 6 was obtained on recrystallization from EtOH as white needles (100 mg), mp 103-104°, [a]25D= -150.9 (c= 1 in EtOH); ir v max(CHCl3) 1678, 1450, 1000, 860 cm-1; uv X max (cyclohexane) 195 (e= 11,000), 247 (e=8,500), 323 nm (e=50); hrms 284.2131 (M+, 89%)obsd (C20H28O requires 284.2140); ms m/z 284, 268 (M+ -CH3, 30%), 255 (M+ -CHO, 25%), 241 (81%), 215 (29%), 187 (32%), 173 (34%), 159 (36%), 145 (52%), 131 (56%), 121 (60%), 119 (74%), 105 (98%), 91 (90%), 81 (80%). For and 13C nmr, see Tables 1 and 2, respectively.…”

Section: Methodsmentioning

confidence: 99%

Fasciola-7, 18-dien-17-al, a Diterpenoid with a New Tetracyclic Ring System from the Brown Alga Dilophus fasciola

Tringali¹,

Piattelli²,

Nicolosi³

1986

J. Nat. Prod.

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From the brown alga Dilophus fasciola the di terpenoid 6 with a new tetracyclic ring system was isolated. The structure and relative stereochemistry of this compound were determined essentially by spectral data including two-dimensional nmr methods.A bewildering array of mono-, di-, and tri-cyclic diterpenoids have been isolated from brown algae of the family Dictyotaceae. Representative examples of these classes are dilophol (1), obtained from Dilophus ligulatus (1), pachydictyol A (2) from Pachydictyon coriaceum (2), and amijol (3) isolated from Dictyota linearis (3).In previous papers, we described the isolation of a number of diterpenoids based on the dolabellane skeleton, for example, 4 and 5, from a brown alga provisionally classified as Dictyota sp. (4-7). From this same alga, which, after a more accurate morphological examination, turned out to be a species belonging to the closely related genus Dilophus, namely Dilophus fasciola (Roth) Howe, we have now isolated a diterpenoid, fasciola-7, lS-dien-17-al1 (6) with a novel 3,6,6,5-carbotetracyclic framework. We wish to describe here the structure elucidation of this new algal metabolite.Compound 6, C20H28O (hrms) was isolated by repeated chromatography of the CHClj extract of the alga as an optically active, crystalline solid. Its spectral properties revealed remarkable, albeit partial, similarities with those of the dolabellane-based diterpenoids. Thus, the eims of 6 contains intense peaks at mlz 121 (C9H13) and 81 (C6H9) which are present in the mass spectrum of all the dolabellanes we have so far investigated and can be assigned to fragments I and II.However, the molecular formula combined with the presence of a conjugated formyl group [ir: 1678 cm-1; *H nmr:9-48 (s, 17-H) and 6.94 (t,_/=3 Hz, 7-H);13C nmr: (C-7), 148.0 (C-8), and 194.3 ppm (C-17)} and a terminal double bond { 4.77 and 4.82 (1H each, bs, 19-Ha and 19-Hb); 13C nmr: 147.4 (C-18), 111.0 (C-19), and 26.1 ppm (C-20)}, which accounted for all the 13C-nmr resonances for sp2-hybridized carbons, required 6 to have a tetracyclic framework. A preliminary examination of the 'H-nmr (Table 1) and 13C-nmr (Table 2) spectra pointed to a novel ring system, and, therefore, efforts were directed toward the preparation of a single crystal amenable to X-ray structural elucidation. Since these attempts were frustrated by the fact that 6 crystallized in a form unsuitable for X-ray analysis, we tried to solve the structure by spectroscopic methods only.1 We have named the adlehyde (6) as a derivative of the hypothetical hydrocarbon "fascioiane." The numbering system follows that for the related dolabellane diterpenoids.

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Three further dolabellane diterpenoids from Dictyota sp.

Cited by 13 publications

References 4 publications

A dolabellane diterpene from the brown alga Dictyota pfaffii as chemical defense against herbivores

A dolabellane diterpene from the brown alga Dictyota pfaffii as chemical defense against herbivores

Molluscicidal and Antifungal Activity of Diterpenoids from Brown Algae of the FamilyDictyotaceae

Fasciola-7, 18-dien-17-al, a Diterpenoid with a New Tetracyclic Ring System from the Brown Alga Dilophus fasciola

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