Structures and possible functions of epoxypukalide and pukalide

Coll, John C.; Bowden, Bruce F.; Heaton, Andrew; Scheuer, Paul J.; Li, M. K. W.; Clardy, Jon; Schulte, Gayle K.; Finer-Moore, J.

doi:10.1007/bf01014821

Cited by 35 publications

(17 citation statements)

References 21 publications

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“…Its spectroscopic data were identical with those reported [14]. The structure of 3 was confirmed by X-ray crystallography [16]. Pukalide (3) protects the soft coral against the settling by cyprid larvae of Balanus amphitrite by a nontoxic mechanism [17].…”

supporting

confidence: 68%

“…The isopropenyl group is located at C(1). This showed the HMBC cross-peaks between C(1) and CH 2 (16) and Me (17). The location of the EtO group at C(3) could be deduced from the HMBC correlation C(3)/MeCH 2 ÀOÀC(3), and the HMBC signal C(18)/MeOÀC(18) established the position of the MeO group at C (18).…”

mentioning

confidence: 86%

“…These data together with HMBC interactions CH 2 (2)/C(3), CH 2 (2)/C(4), HÀC(5)/C(4), HÀC(5)/C(6), HÀC(7)/C(6), Me(19)/C(7), Me(19)/C(8), Me(19)/C(9), HÀC(10)/C(11), HÀC(10)/C(20), HÀC(11)/C (20), and HÀC(11)/C(13) established that 1 possessed a furanocembranoid diterpene skeleton with a g-lactone moiety. The HMBC crosspeaks of C(1) with CH 2 (16) and Me (17) indicated the position of the isopropenyl group. The MeO group at C(18) was established by HMBC correlation C(18)/ MeOÀC (18).…”

mentioning

confidence: 99%

“…Compound 7 (for the 13 C-NMR data, see Table 2 in Exper. Part) has been isolated for the first time from the gorgonian coral Leptogorgia setacea, and its configuration was established by X-ray crystallography [16]. This furanocembranoid diterpene is a potent feeding deterrent of corals against fish [13].…”

mentioning

confidence: 99%

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Furanocembranoids from the Soft Corals Sinularia asterolobata and Litophyton arboreum

Grote

Dahse

Seifert

2008

Chemistry & Biodiversity

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The new cembranoid diterpene danielid (1) along with 3alpha-ethoxyfuranocembranoid 2, pukalide (3), 13alpha-acetoxypukalide (4), furanocembranoid 5, and furanosesquiterpene 6 have been isolated from the soft coral Sinularia asterolobata. The furanocembranoid diterpene 11beta,12beta-epoxypukalide (7) and the sesquiterpene (-)-bicyclogermacrene (8) have been obtained from the soft coral Litophyton arboreum. The structures were elucidated primarily by NMR spectroscopy. The furanocembranoids 2, 4, and 5 show good antiproliferative activities against the cell lines L-929 and K-562, and weak cytotoxic effects on HeLa cells.

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supporting

confidence: 68%

mentioning

confidence: 86%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Furanocembranoids from the Soft Corals Sinularia asterolobata and Litophyton arboreum

Grote

Dahse

Seifert

2008

Chemistry & Biodiversity

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“…In vitro anti-inflammatory activity assays were carried out using lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophage cells. At a concentration of 10 mm, compounds 40,44,46,59,61,67,84,195,196, and 235 could reduce both the levels of the pro-inflammatory iNOS and COX-2 proteins [16] 3.3. Antifouling Activity.…”

Section: Chemical and Biological Studies Of Soft Corals Of The Nephthmentioning

confidence: 99%

Chemical and Biological Studies of Soft Corals of the Nephtheidae Family

Yang

Lin

et al. 2011

Chemistry & Biodiversity

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Total Synthesis of 7‐epi‐Pukalide and 7‐Acetylsinumaximol B

McAulay

Clark

2017

Chemistry A European J

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Convergent total syntheses of the furanocembranoids 7-epi-pukalide and 7-acetylsinumaximol B have been achieved using a one-pot Knoevenagel condensation and thioether-mediated furan-forming reaction. Furan formation proceeds via a sulfur ylide and results in rapid introduction of structural complexity during the coupling of two highly functionalised fragments. The targets have been prepared in 16 steps from (R)-perillyl alcohol.The furanocembrane family of natural products comprises structurally diverse diterpenoids that have been isolated from several octocoral species (Figure 1). [1][2][3][4][5] The first furanocembranoid to be fully characterised was pukalide, a compound that was first isolated from the alcynacean octocoral Sinularia abrupta by Scheuer and co-workers in 1975 [6] and has been isolated from several other species of coral more recently. [7] Figure 1. Selected furanocembranoid marine natural products.[a]Prof. Dr. J. S. Clark and K. McAulay WestCHEM, School of Chemistry Joseph Black Building, University of Glasgow University Avenue, Glasgow G12 8QQ (UK) E-mail: stephen.clark@glasgow.ac.uk Homepage: http://www.chem.gla.ac.uk/staff/stephenc/ Supporting information for this article is given via a link at the end of the document Pukalide and the other furanocembranoids possess a 14-membered carbocyclic skeleton that includes a bridging furan (C3-C6) and a five-membered lactone (C10-C12), and bears an isopropenyl substituent at C1 and a methyl substituent at C8 (Figure 1). Structural variation occurs at the C4 position, where an ester, aldehyde or methyl group can be present, and at the C7-C8 and C11-C12 positions, which can be unsaturated or bear an epoxide (Figure 1). Positions C2, C7, C8 and C13 can be substituted with hydroxyl or acetate groups in some cases.Several furanocembranoids have been reported to possess significant biological activities. For example, lophotoxin is an irreversible antagonist of the nicotinic acetylcholine receptor [8] and pukalide has emetic activity in fish (Figure 1).[7d] As a consequence of their pharmacological activities and interesting molecular structures, the furanocembranoids have received considerable attention as synthetic targets. [9][10][11][12][13][14][15][16][17][18][19][20] The first synthesis of a furanocembrane natural product -acerosolide (Figure 1) -was reported by Paquette and co-workers in 1993.[10] Subsequent pioneering studies by the groups of Pattenden, [11] Marshall [12] and Trauner [13] resulted in total syntheses of deoxypukalide, rubifolide and bipinnatin J (Figure 1). Total syntheses of furanocembranoids have also been reported by the groups of Donohoe (Z-deoxypukalide) [14] and Rawal (bipinnatin J). [15] In addition, the groups of Paterson [16] and Wipf [17] have made important contributions with regard to the synthesis of lophotoxin and pukalide, the groups of Bach [18] and Honda [19] have prepared advanced intermediates to bipinnatin J, and Mulzer and co-workers assembled the complete skeleton of providencin. [20] In spi...

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Structures and possible functions of epoxypukalide and pukalide

Cited by 35 publications

References 21 publications

Furanocembranoids from the Soft Corals Sinularia asterolobata and Litophyton arboreum

Furanocembranoids from the Soft Corals Sinularia asterolobata and Litophyton arboreum

Chemical and Biological Studies of Soft Corals of the Nephtheidae Family

Total Synthesis of 7‐epi‐Pukalide and 7‐Acetylsinumaximol B

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