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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 3.
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marinedrugs-10-02103-f005: 2D NMR correlations of compound 3.

Mentions: Briacavatolide F (3) had a molecular formula of C28H38O13 as deduced by HRESIMS. The IR spectrum of 3 indicated the presence of hydroxy (3501 cm−1), γ-lactone (1778 cm−1), and ester (1736 cm−1) groups. From the 13C NMR data of 3 (Table 1), a trisubstituted olefin (δ 147.4, Cq, C-5; 121.5, CH, C-6) and five carbonyl resonances (δ 170.5, 170.4, 169.6, 168.1, 170.9) were derived. Four esters were identified as acetates by the presence of four methyl resonances in the 1H NMR spectrum of 3 at δ 2.22 (3H, s), 2.07 (3H, s), 2.04 (3H, s), and 2.00 (3H, s) (Table 1). The planar structure of 3 was determined by 2D NMR experiments (Figure 5). The coupling information in the 1H–1H COSY experiment of 3 enabled identification of the C-2/3/4, C-6/16 (by allylic coupling), C-6/7, C-9/10, and C-12/13/14 units. From these data, together with the results of an HMBC experiment of 3, the molecular framework of 3 could be further established. The HMBC data also revealed that the acetate groups are attached at C-2, C-9, C-12, and C-14; thus, the remaining hydroxy groups should be positioned at C-4 and C-11. The relative configurations of 3 elucidated from the NOE correlations (Figure 5) were the same as those of briaexcavatin L except C-11. NOE correlations from H3-20 to H-10/H-12 and from H-10 to H-12 revealed a β-axial orientation of hydroxy at C-11 for 3 [7]. The dd splitting pattern of H-12 (12.0, 5.2 Hz) indicated that H-12 is α axial. The triplet splitting pattern of H-14 is (3.0 Hz) indicated that H-14 is an β equatorial position; this is confirmed by a cross signal with Me-15.


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 3.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

marinedrugs-10-02103-f005: 2D NMR correlations of compound 3.
Mentions: Briacavatolide F (3) had a molecular formula of C28H38O13 as deduced by HRESIMS. The IR spectrum of 3 indicated the presence of hydroxy (3501 cm−1), γ-lactone (1778 cm−1), and ester (1736 cm−1) groups. From the 13C NMR data of 3 (Table 1), a trisubstituted olefin (δ 147.4, Cq, C-5; 121.5, CH, C-6) and five carbonyl resonances (δ 170.5, 170.4, 169.6, 168.1, 170.9) were derived. Four esters were identified as acetates by the presence of four methyl resonances in the 1H NMR spectrum of 3 at δ 2.22 (3H, s), 2.07 (3H, s), 2.04 (3H, s), and 2.00 (3H, s) (Table 1). The planar structure of 3 was determined by 2D NMR experiments (Figure 5). The coupling information in the 1H–1H COSY experiment of 3 enabled identification of the C-2/3/4, C-6/16 (by allylic coupling), C-6/7, C-9/10, and C-12/13/14 units. From these data, together with the results of an HMBC experiment of 3, the molecular framework of 3 could be further established. The HMBC data also revealed that the acetate groups are attached at C-2, C-9, C-12, and C-14; thus, the remaining hydroxy groups should be positioned at C-4 and C-11. The relative configurations of 3 elucidated from the NOE correlations (Figure 5) were the same as those of briaexcavatin L except C-11. NOE correlations from H3-20 to H-10/H-12 and from H-10 to H-12 revealed a β-axial orientation of hydroxy at C-11 for 3 [7]. The dd splitting pattern of H-12 (12.0, 5.2 Hz) indicated that H-12 is α axial. The triplet splitting pattern of H-14 is (3.0 Hz) indicated that H-14 is an β equatorial position; this is confirmed by a cross signal with Me-15.

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