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Excavatoids O and P, new 12-hydroxybriaranes from the octocoral Briareum excavatum.

Sung PJ, Li GY, Su YD, Lin MR, Chang YC, Kung TH, Lin CS, Chen YH, Su JH, Lu MC, Kuo J, Weng CF, Hwang TL - Mar Drugs (2010)

Bottom Line: Two new 12-hydroxybriarane diterpenoids, designated as excavatoids O (1) and P (2), were isolated from the octocoral Briareum excavatum.The structures of briaranes 1 and 2 were established on the basis of extensive spectral data analysis.Excavatoid P (2) is the first metabolite which possesses a 6β -chlorine atom in briarane analogues.

View Article: PubMed Central - PubMed

Affiliation: Graduate Institute of Marine Biotechnology, National Dong Hwa University, Pingtung 944, Taiwan. pjsung@nmmba.gov.tw

ABSTRACT
Two new 12-hydroxybriarane diterpenoids, designated as excavatoids O (1) and P (2), were isolated from the octocoral Briareum excavatum. The structures of briaranes 1 and 2 were established on the basis of extensive spectral data analysis. Excavatoid P (2) is the first metabolite which possesses a 6β -chlorine atom in briarane analogues.

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Selective NOESY correlations of 1.
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f1-marinedrugs-08-02639: Selective NOESY correlations of 1.

Mentions: Based on previous studies, all naturally occurring briarane-type diterpenoids have the C-15 methyl group as trans to H-10, and these two groups are assigned as β - and α-oriented, respectively, as shown in most briarane derivatives [1–3]. The relative stereochemistry of 1 was established from a NOESY experiment (Figure 1). In the NOESY experiment of 1, the correlations of H-10 with H-2, H-3, H-6, H-9, and H-11; and H-11 correlated with H-12, indicated that these protons are situated on the same face and were assigned as α protons since the C-15 methyl is the β -substituent at C-1. H-14 was found to exhibit a correlation with H3-15, revealing the β -orientation of this proton. The correlations between H3-16 and H-3, H-6, reflected the α-orientation of H3-16. H-7 correlated with H3-15, indicating this proton should be β -oriented. Furthermore, H3-18 showed a correlation with H-9. By detailed analysis of molecular models, H3-18 was found to be reasonably close to H-9 when H3-18 was placed on the β face in the γ-lactone moiety. Based on the above findings, the structure of 1 was elucidated unambiguously.


Excavatoids O and P, new 12-hydroxybriaranes from the octocoral Briareum excavatum.

Sung PJ, Li GY, Su YD, Lin MR, Chang YC, Kung TH, Lin CS, Chen YH, Su JH, Lu MC, Kuo J, Weng CF, Hwang TL - Mar Drugs (2010)

Selective NOESY correlations of 1.
© Copyright Policy - open-access
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC2992997&req=5

f1-marinedrugs-08-02639: Selective NOESY correlations of 1.
Mentions: Based on previous studies, all naturally occurring briarane-type diterpenoids have the C-15 methyl group as trans to H-10, and these two groups are assigned as β - and α-oriented, respectively, as shown in most briarane derivatives [1–3]. The relative stereochemistry of 1 was established from a NOESY experiment (Figure 1). In the NOESY experiment of 1, the correlations of H-10 with H-2, H-3, H-6, H-9, and H-11; and H-11 correlated with H-12, indicated that these protons are situated on the same face and were assigned as α protons since the C-15 methyl is the β -substituent at C-1. H-14 was found to exhibit a correlation with H3-15, revealing the β -orientation of this proton. The correlations between H3-16 and H-3, H-6, reflected the α-orientation of H3-16. H-7 correlated with H3-15, indicating this proton should be β -oriented. Furthermore, H3-18 showed a correlation with H-9. By detailed analysis of molecular models, H3-18 was found to be reasonably close to H-9 when H3-18 was placed on the β face in the γ-lactone moiety. Based on the above findings, the structure of 1 was elucidated unambiguously.

Bottom Line: Two new 12-hydroxybriarane diterpenoids, designated as excavatoids O (1) and P (2), were isolated from the octocoral Briareum excavatum.The structures of briaranes 1 and 2 were established on the basis of extensive spectral data analysis.Excavatoid P (2) is the first metabolite which possesses a 6β -chlorine atom in briarane analogues.

View Article: PubMed Central - PubMed

Affiliation: Graduate Institute of Marine Biotechnology, National Dong Hwa University, Pingtung 944, Taiwan. pjsung@nmmba.gov.tw

ABSTRACT
Two new 12-hydroxybriarane diterpenoids, designated as excavatoids O (1) and P (2), were isolated from the octocoral Briareum excavatum. The structures of briaranes 1 and 2 were established on the basis of extensive spectral data analysis. Excavatoid P (2) is the first metabolite which possesses a 6β -chlorine atom in briarane analogues.

Show MeSH