Sterols in marine invertebrates. 51. Isolation and structure elucidation of C-18 functionalized sterols from the soft coral Sinularia dissecta

Jagodzinska, Barbara; Trimmer, James S.; Fenical, William; Djerassi, Carl

doi:10.1021/jo00216a036

Cited by 27 publications

(31 citation statements)

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“…Danach fuhrt der Oxiranring und die 8,14-Doppelbindung auch zu einer weitgehenden Einebnung im Bereich der C-Atome 6, 7, 8,14, 15 und 16, rnit der Folge, daI3 7a-H und 15a-H in eine pseudoaquatoriale Lage gebracht werden. Bei einem Abstand von 1.9 8, wird nur zwischen diesen beiden Protonen ein starker NOE-Effekt beobachtet, was die pseudoaxiale 7P-Stellung der Hydroxygruppe bestatigt.…”

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Isolierung und Strukturaufklärung von Ergokonin A und B; zwei neue antifungische Sterol‐Antibiotika aus Trichoderma koningii

Augustiniak¹,

Forche²,

Reichenbach³

et al. 1991

Liebigs Ann. Chem.

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Isolation and Structure Elucidation of Ergokonin A and B Two New Antifungal Sterol Antibiotics from Trichoderma koningiiIsolation and structure elucidation by 2D-NMR spectroscopy of the two new antifungal sterol antibiotics ergokonin A (1) and B (2a) from Trichoderma koningii are described. The structures of 1 and 2a are derived from ergosterol and characterized by an 18-carboxy group. In addition ergokonin A (1) is esterified at the 3-hydroxy group with (2S,3S)-3-hydroxyleucine 3-0-sulfate (3c). In the course of structure elucidation of the amino acid residue the stereoisomers of 3-hydroxyleucine N-sulfamate and 3-0-sulfate (3b, c) have been synthesized and characterized by NMR spectroscopy.

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Isolierung und Strukturaufklärung von Ergokonin A und B; zwei neue antifungische Sterol‐Antibiotika aus Trichoderma koningii

Augustiniak¹,

Forche²,

Reichenbach³

et al. 1991

Liebigs Ann. Chem.

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“…Djerassi et al have reported both the *H and I3 C spectra of a number of oxysterols derived from marine sources or from intermediates in their chemical synthesis (Taylor and Djerassi, 1977;Cho and Djerassi, 1987;Jagodzinska et al, 1985;Catalan et al, 1983;Hirano and Djerassi, 1982). Anastasia et al (1979aAnastasia et al ( ,b,c, 1983Anastasia et al ( ,1986 have also published many examples of the carbon and proton spectra of a variety of oxysterols produced during the chemical synthesis of biologically significant steroids.…”

Section: Because Of Their Potent Action As Inhibitors Of Sterol Biosymentioning

confidence: 99%

Analysis of Oxysterols

Parish

1989

Analysis of Sterols and Other Biologically Significant Steroids

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“…There have been many reports documenting the diversity of secondary metabolites produced by soft corals from the genus Sinularia , including sesquiterpenes [ 1 , 2 ], diterpenes [ 3 , 4 , 5 , 6 , 7 ], cembranoids [ 8 , 9 , 10 , 11 ], polyhydroxylated steroids [ 12 ], glycosides [ 13 ], sphingosines [ 14 ], farnesyl quinols [ 15 , 16 ], and polyamines [ 17 ]. These metabolites have been shown to possess a range of biological activities including antimicrobial [ 5 ], antiviral [ 4 ], anti-inflammatory [ 4 , 11 ], cytotoxic [ 8 , 9 , 10 , 17 ], anticancer [ 3 , 18 ], antifouling [ 19 ], antifeedant [ 20 ], and allelopathic [ 21 , 22 ] activities.…”

Section: Introductionmentioning

confidence: 99%

A Great Barrier Reef Sinularia sp. Yields Two New Cytotoxic Diterpenes

et al. 2012

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The methanol extract of a Sinularia sp., collected from Bowden Reef, Queensland, Australia, yielded ten natural products. These included the new nitrogenous diterpene (4R*,5R*,9S*,10R*,11Z)-4-methoxy-9-((dimethylamino)-methyl)-12,15-epoxy-11(13)-en-decahydronaphthalen-16-ol (1), and the new lobane, (1R*,2R*,4S*,15E)-loba-8,10,13(14),15(16)-tetraen-17,18-diol-17-acetate (2). Also isolated were two known cembranes, sarcophytol-B and (1E,3E,7E)-11,12-epoxycembratrien-15-ol, and six known lobanes, loba-8,10,13(15)-triene-16,17,18-triol, 14,18-epoxyloba-8,10,13(15)-trien-17-ol, lobatrientriol, lobatrienolide, 14,17-epoxyloba-8,10,13(15)-trien-18-ol-18-acetate and (17R)-loba-8,10,13(15)-trien-17,18-diol. Structures of the new compounds were elucidated through interpretation of spectra obtained after extensive NMR and MS investigations and comparison with literature values. The tumour cell growth inhibition potential of 1 and 2 along with loba-8,10,13(15)-triene-16,17,18-triol, 14,17-epoxyloba-8,10,13(15)-trien-18-ol-18-acetate, lobatrienolide, (1E,3E,7E)-11,12-epoxycembratrien-15-ol and sarcophytol-B were assessed against three human tumour cell lines (SF-268, MCF-7 and H460). The lobanes and cembranes tested demonstrated 50% growth inhibition in the range 6.8–18.5 µM, with no selectivity, whilst 1 was less active (GI50 70–175 µM).

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Sterols in marine invertebrates. 51. Isolation and structure elucidation of C-18 functionalized sterols from the soft coral Sinularia dissecta

Abstract: The isolation and identification of over a dozen C-18 functionalized polyhydroxylated sterols from the soft coral Sinularia dissecta are described. All three levels of oxidation (CH20H, CHO, and C02H) at C-18 were encountered in this rare class of sterols.

Cited by 27 publications

References 1 publication

Isolierung und Strukturaufklärung von Ergokonin A und B; zwei neue antifungische Sterol‐Antibiotika aus Trichoderma koningii

Isolierung und Strukturaufklärung von Ergokonin A und B; zwei neue antifungische Sterol‐Antibiotika aus Trichoderma koningii

Analysis of Oxysterols

A Great Barrier Reef Sinularia sp. Yields Two New Cytotoxic Diterpenes

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