Sesquiterpenoids of Cinnamosma fragrans baillon

Canonica, L.; Corbella, A.; Gariboldi, Pierluigi; Jommi, G.; Krˇepinský, J.; Ferrari, G.; Casagrande, C

doi:10.1016/s0040-4020(01)82921-5

Cited by 58 publications

(22 citation statements)

References 4 publications

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“…With the exception of 8 all other compounds have been found previously in other species of the family Canellaceae (Table 1). In each case the identification, achieved by analysis of UV, IR, 1 H NMR, 13 C NMR and mass spectra, was confirmed by comparison of mp, specific rotation and with published data.…”

Section: Resultsmentioning

confidence: 54%

Drimane-Type Sesquiterpenoids as Chemosystematic Markers of Canellaceae

Bastos¹,

Kaplan²,

Gottlieb³

1999

J. Braz. Chem. Soc.

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Poligodial, isopoligodial, mukaadial, e poligonona foram isoladas pela primeira vez de Capsicodendron dinisii. O isolamento dessas substâncias pertencentes ao grupo de sesquiterpenos do tipo eudesmano, presentes em Canellaceae, permitiu estabelecer maior afinidade do gênero Sulamericano Capsicodendron com o gênero Africano Warburgia do que com o gênero Cinnamosma de Madagascar.Polygodial, isopolygodial, mukaadial and polygonone were isolated for the first time from Capsicodendron dinisii. Thus, with respect to drimane-type sesquiterpenoids of the Canellaceae, the close affinity of the South American genus Capsicodendron with the African genus Warburgia rather than the Madagascarian genus Cinnamosma is established.

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Section: Resultsmentioning

confidence: 54%

Drimane-Type Sesquiterpenoids as Chemosystematic Markers of Canellaceae

Bastos¹,

Kaplan²,

Gottlieb³

1999

J. Braz. Chem. Soc.

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“…These physical data are in agreement with those reported for ugandensolide (5) (4), and the identity was confirmed (mmp, pmr, ms, tic) by comparison with an authentic sample.10 Ugandensolide (5, 10 mg) was treated overnight with acetic anhydride-pyridine (1:1, 0.5 ml). Following removal of excess reagents and crystallization from acetone, the acetylation product (7, 6 mg), mp, 103-104°, exhibited the following spectral properties, uv, max (MeOH) 212 nm (log e 3.9), ir, v max (KBr) 1770, 1760, 1390, 1370 and 1240 cm-1: pmr (CDC13) 1.04 Í6H, s, 4,4'-CH3), 1.50 (3H, s, 10-CH3), 2.07 (3H, s, -OCOCHs), 2.14 (3H, s, -OCOCH3), 2.56 Í1H, d of m, 7=12 Hz, 1-3H), 4.64 (2H, br s, 12-H2), 5.14 (1H, m, 7-H) and 5.54 (1H, m, 6-H): ms, m/e M* 350 (4%), 308 (7), 290 (26), 248 (37), 230 (3), 109 (11) and 55 (100).…”

Section: Experimental6mentioning

confidence: 99%

“…In a continuing search for anticancer and cytotoxic agents from plants, chloroform extracts of stem bark and leaf-twig samples of the South American arboreal species Capsicodendron dinisii (Canellaceae) were found to exhibit cytotoxic activity against the Eagle's 9KB carcinoma of the nasopharynx in cell culture (l). 3 Separation of active fractions from the root bark by column chromatography over silica gel4 resulted in the isolation of two cytotoxic compounds, cinnamodial (1) and capsicodendrin (2). Three inactive compounds.…”

mentioning

confidence: 99%

Potential Anticancer Agents. XVI. Isolation of Bicyclofarnesane Sesquiterpenoids From Capsicodendron dinisii

Mahmoud¹,

Kinghorn²,

Cordell³

et al. 1980

J. Nat. Prod.

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“…White solid; all spectroscopic data were in agreement with those reported. 88,89 Dendocarbin A (36): White solid; all spectroscopic data were in agreement with those reported. Fraction 1 from one of the columns was backloaded onto a 20 mL HP20 column (2 × 6 cm) and eluted with 60 mL MeOH.…”

Section: Cinnamolide (35)supporting

confidence: 84%

“…They are typified by furodysin (86), and the rearranged furodysinin (83), 117 which was isolated in this study. Interestingly, in addition to various oxygenated derivatives, several sulfur-containing dysin sesquiterpenes have been isolated, such as thiofurodysin acetate (87), thiofurodysinin acetate (88), methylthiofurodysinin (89) and thiofurodysinin (90) from sponges of the genus Dysidea and the nudibranch Ceratosoma brevicaudatum. [117][118][119] C. brevicaudatum also contained the unusual dimer dithiofurodysinin disulfide (91), possibly an artifact arising from the oxidative coupling of the free thiol 90 as thiols readily dimerize in air.…”

Section: Ceratosoma Amoenummentioning

confidence: 99%

Isolation of New Secondary Metabolites from New Zealand Marine Invertebrates

Wojnar¹

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<p>This study describes the isolation and structure elucidation of several known and 13 new compounds from New Zealand marine organisms. Furthermore, it describes the development of a digital mask program for the analysis of HSQC spectra of crude sponge extracts. This was used as a screening tool to identify secondary metabolite producers that warranted further analysis. As reports of metabolites from New Zealand nudibranchs are poorly represented in the literature, a study of five New Zealand nudibranch species was undertaken. These coloured and seemingly undefended nudibranchs are known to concentrate or sequester toxic metabolites from their prey, facilitating rapid isolation and structure elucidation of these metabolites. This study resulted in the isolation of a variety of metabolite classes; two new compounds, 13alpha- acetoxypukalide diol (30) and lopholide diol (31) from the nudibranch Tritonia incerta, are described. Examination of the sponge Raspailia agminata resulted in the isolation of a novel family of partially acetylated glycolipids which contain up to six glucose residues. The chromatographic separation of these compounds was a challenge due to the similarity of the congeners and their lack of a chromophore. MSguided isolation eventually led to the purification of agminosides A-E (145-149). An unidentified sponge of the order Dictyoceratida was found to contain a new isomer (186) of the known sesterterpene variabilin. As variabilin-type compounds are predominantly found from sponges of the family Irciniidae, the unidentified sponge is most likely an irciniid. In addition, the sponge contained two prenylated quinones, one of which, 189, is a new isomer of a known sponge metabolite. The sponge Darwinella oxeata contained four new nitrogenous diterpenes of the aplysulphurane (rearranged spongian) skeleton, oxeatamide A (214), isooxeatamide A (215), oxeatamide A 23-methyl ester (216) and oxeatamide B (217).</p>

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Sesquiterpenoids of Cinnamosma fragrans baillon

Cited by 58 publications

References 4 publications

Drimane-Type Sesquiterpenoids as Chemosystematic Markers of Canellaceae

Drimane-Type Sesquiterpenoids as Chemosystematic Markers of Canellaceae

Potential Anticancer Agents. XVI. Isolation of Bicyclofarnesane Sesquiterpenoids From Capsicodendron dinisii

Isolation of New Secondary Metabolites from New Zealand Marine Invertebrates

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