Structures of dictyodial and dictyolactone, unusual marine diterpenoids

Finer, Janet; Clardy, Jon; Fenical, William; Minale, L.; Riccio, Raffaele; Battaile, J.; Kirkup, Michael P.; Moore, Richard E.

doi:10.1021/jo01326a040

Cited by 92 publications

(71 citation statements)

References 2 publications

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“…Xenicanes are a class of diterpenes and norditerpenes (Faulkner, 1993) which have been isolated not only from many brown algae belonging to the family Dictyotaceae (Finer et al, 1979;Enoki et al, 1982;Shono and Kashimura, 1983;Pathirana and Andersen, 1984;Ishitsuka et al, 1982Ishitsuka et al, , 1988Norte et al, 1990;König et al, 1991aKönig et al, , 1991bBouaïcha et al, 1993aBouaïcha et al, , 1993bPatil et al, 1993;Siamopoulou et al, 2004) but also from soft corals and gorgonians (Faulkner, 2000). Some of them showed interesting biological activities including cytotoxicity (Ishitsuka et al, 1988;Bouaïcha et al, 1993aBouaïcha et al, , 1993bRho et al, 2001) and antimicrobial (Iwagawa et al, 1996).…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic Xenicane Diterpenes from the Brown Alga Padina pavonia (L.) Gaill.

Awad

Selim

Metawe

et al. 2008

Phytotherapy Research

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Column chromatography of the hexane fraction of a methanol extract of Padina pavonia (L.) Gaill. collected from the Red Sea at Hurghada, Egypt yielded 18,19-epoxyxenic-19-methoxy-18-hydroxy-4-acetoxy-6,9,13-triene (1) and 18,19-epoxyxenic-18,19-dimethoxy-4-hydroxy-6,9,13-triene (2). The isolated compounds have various antitumor activities against lung carcinoma (H460) and liver carcinoma (HepG2) human cell lines (in vitro).

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Section: Introductionmentioning

confidence: 99%

Cytotoxic Xenicane Diterpenes from the Brown Alga Padina pavonia (L.) Gaill.

Awad

Selim

Metawe

et al. 2008

Phytotherapy Research

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“…Here we describe the structure elucidation and the biological activity of two new xenicane diterpenes, ciliolatale (1) and 17-acetoxy-dictyodial (2), isolated from the lipophilic extract of D. ciliolata along with dictyodial (Finer et al, 1979), and the guaiane homologs, dictyol C (Danise et al, 1977) and dictyol H (Alvarado and Gerwick, 1985). The previously reported pachydictyol A and dictyol B acetate were not detected in the sample analyzed in the present work.…”

Section: Introductionmentioning

confidence: 51%

“…Dictyodial, dictyol C and dictyol H, which are typical algal terpenes previously isolated from different species of Dictyota (Finer et al, 1979;Alvarado & Gerwick, 1985;Danise et al, 1977;Enoki et al, 1982;Cronin et al, 1995;Schmitt et al, 1998;Siamopoulou et al, 2004;De Nys et al, 1993;Freitas et al, 2007;De-Paula et al, 2008;Cavalcanti et al, 2006) as well as from mollusks associated with the algae by dietary relationships (Danise et al, 1977), were identified by comparison of the NMR and mass spectrometric data and [a] D 25 values with the data from literature.…”

Section: Resultsmentioning

confidence: 99%

Diterpene content of the alga Dictyota ciliolata from a Moroccan lagoon

Manzo

Ciavatta

Bakkas

et al. 2009

Phytochemistry Letters

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“…They were identified as 18-hydroxy-3,7-dolabelladiene (1) [3], dictyolactone (2) [4], dilopholide (3) [5], and dictyotin B (4) [6]. Diterpenoids 2 and 3 were isolated for the first time from D. dichotoma.…”

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confidence: 99%

“…Diterpenoids 2 and 3 were isolated for the first time from D. dichotoma. They were previously known as secondary metabolites of the algal-toxic mollusk Aplysia depilans [4] and brown alga Dilophus ligulatus [5], respectively. Recently 2 was isolated from the alga Dilophus okamurae [7].…”

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confidence: 99%

Slightly polar secondary metabolites from the far-eastern brown alga Dictyota dichotoma

2007

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The brown alga Dictyota dichotoma is well-known as a source of terpenoids with bactericidal, antifungal, insectidical, antitumor, and antiviral activity. Secondary metabolites from populations of this alga growing near the shores of Japan, Australia, India, Pakistan, Greece, Italy, and Spain have been previously studied. It has been shown that the terpenoid composition depends on the collection site [1]. Nevertheless, the chemical composition of the Russian population of D. dichotoma inhabiting the northwest shore of the Sea of Japan has not been studied.In continuation of our research on natural compounds from this alga species collected in Troits Bay of the Sea of Japan [2], we communicate the isolation from the ethanol extract of D. dichotoma (dry alga weight 53 g) another four diterpenoids (1-4).Compound 1 (2.5 mg, 0.008% of dry weight) was isolated by column chromatography over silica gel (hexane:EtOAc, 25:1) followed by normal-phase HPLC over a column of Ultrasphere ™ Si (5 µm, 9.4 × 250 mm, hexane:EtOAc, 30:1). We isolated analogously using hexane:EtOAc (10:1) and HPLC compound 2 (19.4 mg, 0.06% of dry wt.), fractions containing 3 (9.3 mg) as the main constituent, and fractions containing 4 (8.6 mg). Compounds 3 (2 mg, 0.007% of dry wt.) and 4 (3.7 mg, 0.01% of dry wt.) were purified by HPLC over columns of Ultrasphere ™ Si (5 µm, 4.6 × 250 mm, hexane:EtOAc, 20:1 for 3; 15:1 for 4).The structures and relative stereochemistries of 1-4 were found using one-dimensional and two-dimensional NMR spectroscopy (PMR and 13 C NMR, 1 H-1 H COSY, DEPT, HSQC, HMBC, and NOESY) and GC-MS spectra. They were identified as 18-hydroxy-3,7-dolabelladiene (1) [3], dictyolactone (2) [4], dilopholide (3) [5], and dictyotin B (4) [6]. Diterpenoids 2 and 3 were isolated for the first time from D. dichotoma. They were previously known as secondary metabolites of the algal-toxic mollusk Aplysia depilans [4] and brown alga Dilophus ligulatus [5], respectively. Recently 2 was isolated from the alga Dilophus okamurae [7]. We report for the first time the NMR spectra of dictyotin B in C 6 D 6 . Compounds 1 and 4 were found previously in Italian and Japanese populations of D. dichotoma, respectively [3,6]. 18-Hydroxy-3,7-dolabelladiene (1). Colorless oil, [α] D 25 +20.0° (c 0.1, CHCl 3 ), lit. [3] [α] D +27.5° (c 1, CHCl 3 ). The PMR and 13 C NMR spectra (CDCl 3 ) agreed with those reported earlier [3]. GC-MS (m/z, I rel , %) 290 (3) [M] + , 272 (

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Structures of dictyodial and dictyolactone, unusual marine diterpenoids

Abstract: The structures and stereochem. of dictyodial, dictyodiol, and dictyolactone (I-III, resp.) ,marine diterpenoids isolated from Dictyota species and from Aplysia depilans, were confirmed by 13C NMR and 1H NMR and by crystal structure of II, which was obtained by redn. of I

Cited by 92 publications

References 2 publications

Cytotoxic Xenicane Diterpenes from the Brown Alga Padina pavonia (L.) Gaill.

Cytotoxic Xenicane Diterpenes from the Brown Alga Padina pavonia (L.) Gaill.

Diterpene content of the alga Dictyota ciliolata from a Moroccan lagoon

Slightly polar secondary metabolites from the far-eastern brown alga Dictyota dichotoma

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