José J. Morales’s research while affiliated with University of Puerto Rico at Río Piedras and other places

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Publications (5)


The Structure of Clathrodin, a Novel Alkaloid Isolated from the Caribbean Sea Sponge Agelas clathrodes
  • Article

July 2004

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44 Reads

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46 Citations

Journal of Natural Products

José J. Morales

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A new alkaloid containing a nonbrominated pyrrole and a guanidine moiety, clathrodin, has been isolated from the MeOH extract of the Caribbean sea sponge Agelas clathrodes. The structure of clathrodin was determined to be 1 on the basis of its spectral data.


Single crystal X-ray structure of 11-acetoxy-4-deoxyasbestinin B

August 1993

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8 Reads

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1 Citation

Journal of Crystallographic and Spectroscopic Research

The crystal structure of 11-acetoxy-4-deoxyasbestinin B (C22H34O4, Mr=362.49) crystallized in the orthorhombic space group P212121 with a=10.923(5)Å, b=11.127(5)Å, c=17.047(5)Å, V=2072(3)Å3, Z=4, Dx=1.163g/cm-3. Mo Kα radiation was used for data collection at room temperature. The final R=0.042 for 2464 observed reflections. The stereochemical assignments of the molecule from the 2-D NMR data are verified totally by the overall geometry of the molecule obtained from the X-ray diffraction analysis.


(-)-Agelasidine C and (-)-Agelasidine D, Two New Hypotaurocyamine Diterpenoids from the Caribbean Sea Songe Agelas clathrodes

April 1992

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11 Reads

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29 Citations

Journal of Natural Products

Two new diterpene derivatives of hypotaurocyamine, (-)-agelasidine C [3] and (-)-agelasidine D [5], have been isolated from the Caribbean sea sponge Agelas clathrodes. The structures of 3 and 5 have been established by interpretation and comparison of their spectral data to those of the known antipode (+)-agelasidine C [1].


Application of Two-Dimensional Nmr Spectroscopy in the Structural Determination of Marine Natural Products. Isolation and Total Structural Assignment of 4-Deoxyasbestinin Diterpenes from the Caribbean Gorgonian Briareum asbestinum

September 1991

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14 Reads

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39 Citations

Journal of Natural Products

The structures of four novel asbestinin diterpenes isolated in the toxic extracts of the Caribbean gorgonian Briareum asbestinum are discussed. The major metabolite 11-acetoxy-4-deoxyasbestinin B was subjected to a total structural assignment through the concerted application of several 2D nmr techniques that included 1H-1H COSY, RCT-COSY, RCT2 COSY, HC COSY (HMQC), NOESY, proton-detected long range heteronuclear chemical shift correlation (HMBC) and 13C-13C chemical shift correlation spectroscopy (INADEQUATE).


The structure of euniolide, a new cembranoid diterpene from the Caribbean Gorgonians Eunicea succinea and Eunicea mammosa

December 1990

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12 Reads

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25 Citations

Tetrahedron

Three simple γ-lactonic cembranolides were isolated from the gorgonian Eunicea succinea collected near Palomino Key, Puerto Rico on July,1989. The structure of two were determined from spectral data and chemical correlation experiments to be those of known 12,13-bisepleupalmerin (1) and eunicin (3). The structure of the third metabolite was deduced from spectroscopic data and from chemical degradation experiments to be that of eunlolide (2), a previously undescribed γ-lactonic cembranolide. Extraction of a fresh specimen of Eunicea mammosa collected near Desecheo island Puerto Rico on March, 1989 also afforded sunlolide in addition to known cembranoid diterpene eupalmerin acetate (4).

Citations (4)


... Five new cytotoxic cembranolides (321-325) possessing a rare 4,7-oxa-bridged functionality were isolated from the gorgonian Eunicea mammosa [100]. Other seven cembranolides including eupalmerin (326) [101], eupalmerone (327), chlorohydrin (328) [62], euniolide (329) [102], 12-epieunicin (330), 4epijeunicin (331), 13-epieupalmerin (332) [103], were also isolated from Eunicea mammosa. The first chemical investigation of the gorgonian octocoral Eunicea pinta, lead to the isolation and structure determination of eight new cembranolides, including 12epieupalmerone (333) and uprolides H-M (334-340). ...

Reference:

Cembrane Diterpenes Chemistry and Biological Properties
The structure of euniolide, a new cembranoid diterpene from the Caribbean Gorgonians Eunicea succinea and Eunicea mammosa
  • Citing Article
  • December 1990

Tetrahedron

... Oroidin ( Figure 21, compound 1) was the first PIA to be isolated, and it was obtained from A. oroides, collected in the Bay of Naples in 1971 [148]. Three closely comparable counterparts have now been found: the monobrominated hymenidin ( Figure 21, compound 3), the N-methylated derivative sventrin ( Figure 21, compound 4) from Bahamas A. sventres [149], and the nonbrominated clathrodin ( Figure 21, compound 2) from Caribbean A. clathrodes collected from Desecheo Island [98]. The most basic PIAs, oroidin (compound 1), clathrodin (compound 2), and hymenidin (compound 3), differ only in their bromine concentration. ...

The Structure of Clathrodin, a Novel Alkaloid Isolated from the Caribbean Sea Sponge Agelas clathrodes
  • Citing Article
  • July 2004

Journal of Natural Products

... Bioassay results suggested that compound 24 possessed inhibitory effect on Staphilococcus aureus but no effect on fungi, while 25 and 26 were shown to have antimicrobial activities against S. aureus, Klebsiella pneumoniae and Proteus vulgaris [14]. In vitro cytotoxic test indicated that [15], while 27 and 28 had a moderate antifungal activity against Aspergillus niger [16]. Interestingly, compound 29 contained a nonbrominated pyrrole and a guanidine moiety [17]. ...

(-)-Agelasidine C and (-)-Agelasidine D, Two New Hypotaurocyamine Diterpenoids from the Caribbean Sea Songe Agelas clathrodes
  • Citing Article
  • April 1992

Journal of Natural Products

... The studies performed about their biological activities are scarce, but shows important cytotoxicity against several tumor cellular lines at micromolar and nanomolar levels. [1][2][3][4][5][6][7] Several comprehensive reviews covering the isolation, biological activity and synthesis of these marine metabolites have been published since the first report in 1980. [8][9][10][11][12][13]. ...

Application of Two-Dimensional Nmr Spectroscopy in the Structural Determination of Marine Natural Products. Isolation and Total Structural Assignment of 4-Deoxyasbestinin Diterpenes from the Caribbean Gorgonian Briareum asbestinum
  • Citing Article
  • September 1991

Journal of Natural Products