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Briacavatolides D-F, new briaranes from the Taiwanese octocoral Briareum excavatum.

Wang SK, Yeh TT, Duh CY - Mar Drugs (2012)

Bottom Line: In the continued search for novel bioactive substances from the Taiwanese octocoral Briareum excavatum collected at Orchid Island, three new briarane-type diterpenoids, briacavatolides D-F (1-3) were isolated from the acetone extract.The structures of these compounds were elucidated by extensive NMR spectroscopic analysis and physical data.The anti-HCMV (human cytomegalovirus) activity of 1-3 and their cytotoxicity against selected cancer cell lines were evaluated.

View Article: PubMed Central - PubMed

Affiliation: Asia-Pacific Ocean Research Center, National Sun Yat-Sen University, Kaohsiung 804, Taiwan. skwang@cc.kmu.edu.tw

ABSTRACT
In the continued search for novel bioactive substances from the Taiwanese octocoral Briareum excavatum collected at Orchid Island, three new briarane-type diterpenoids, briacavatolides D-F (1-3) were isolated from the acetone extract. The structures of these compounds were elucidated by extensive NMR spectroscopic analysis and physical data. The anti-HCMV (human cytomegalovirus) activity of 1-3 and their cytotoxicity against selected cancer cell lines were evaluated.

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2D NMR correlations of compound 2.
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marinedrugs-10-02103-f004: 2D NMR correlations of compound 2.

Mentions: The gross structure of 2 and all of the 1H and 13C chemical shifts associated with the molecule were determined by a series of 2D NMR experiments (Figure 4). In the HMBC spectrum of 2, the n-butyrate positioned at C-12 was confirmed from the long-range coupling between H-12 (δH 4.82) with the carbonyl carbon (δC 171.0) of the n-butyryloxyl group. Furthermore, the HMBC correlations also revealed that two acetates were attached to C-2 and C-14. These data, together with the other 1H-13C long-range correlations (Table 1), unambiguously established the molecular framework of 2. The relative configurations of 2 were identical to those of briaexcavatin L except that of C-12. H3-20 were found to exhibit NOE correlations (Figure 4) with H-12 and H-9, revealing the β-orientation of H-12 [7]. Splitting patterns of H-12 and H-14 as triplets (3.0 Hz) indicated that both are β equatorial.


Briacavatolides D-F, new briaranes from the Taiwanese octocoral Briareum excavatum.

Wang SK, Yeh TT, Duh CY - Mar Drugs (2012)

2D NMR correlations of compound 2.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3475276&req=5

marinedrugs-10-02103-f004: 2D NMR correlations of compound 2.
Mentions: The gross structure of 2 and all of the 1H and 13C chemical shifts associated with the molecule were determined by a series of 2D NMR experiments (Figure 4). In the HMBC spectrum of 2, the n-butyrate positioned at C-12 was confirmed from the long-range coupling between H-12 (δH 4.82) with the carbonyl carbon (δC 171.0) of the n-butyryloxyl group. Furthermore, the HMBC correlations also revealed that two acetates were attached to C-2 and C-14. These data, together with the other 1H-13C long-range correlations (Table 1), unambiguously established the molecular framework of 2. The relative configurations of 2 were identical to those of briaexcavatin L except that of C-12. H3-20 were found to exhibit NOE correlations (Figure 4) with H-12 and H-9, revealing the β-orientation of H-12 [7]. Splitting patterns of H-12 and H-14 as triplets (3.0 Hz) indicated that both are β equatorial.

Bottom Line: In the continued search for novel bioactive substances from the Taiwanese octocoral Briareum excavatum collected at Orchid Island, three new briarane-type diterpenoids, briacavatolides D-F (1-3) were isolated from the acetone extract.The structures of these compounds were elucidated by extensive NMR spectroscopic analysis and physical data.The anti-HCMV (human cytomegalovirus) activity of 1-3 and their cytotoxicity against selected cancer cell lines were evaluated.

View Article: PubMed Central - PubMed

Affiliation: Asia-Pacific Ocean Research Center, National Sun Yat-Sen University, Kaohsiung 804, Taiwan. skwang@cc.kmu.edu.tw

ABSTRACT
In the continued search for novel bioactive substances from the Taiwanese octocoral Briareum excavatum collected at Orchid Island, three new briarane-type diterpenoids, briacavatolides D-F (1-3) were isolated from the acetone extract. The structures of these compounds were elucidated by extensive NMR spectroscopic analysis and physical data. The anti-HCMV (human cytomegalovirus) activity of 1-3 and their cytotoxicity against selected cancer cell lines were evaluated.

Show MeSH
Related in: MedlinePlus