Abstract
As part of our continuing interest in identifying anticancer drug leads from Red Sea marine organisms, we have investigated the sponge Theonella swinhoei. We report here the isolation and structure elucidation of swinholide A (1) and two new macrolides, swinholide I (2) and hurghadolide A (3). Swinholide I is the first derivative of swinholide A with hydroxylation at the side chain. Hurghadolide A possesses an unprecedented asymmetric 42-membered dilactone moiety and presents a novel skeleton of macrolides. The structural determinations were based on extensive interpretation of high-field NMR spectra and HRFABMS data. Swinholide I and hurghadolide A showed in vitro cytotoxicity against human colon adenocarcinoma (HCT-116) with IC50 values of 5.6 and 365 nM, respectively. Furthermore, swinholide I and hurghadolide A caused disruption of the actin cytoskeleton at concentrations of 70 and 7.3 nM, respectively. In addition, both compounds were active against Candida albicans.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 154-157 |
| Number of pages | 4 |
| Journal | Journal of Natural Products |
| Volume | 69 |
| Issue number | 1 |
| DOIs | |
| State | Published - Jan 2006 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Plant Science
- Chemistry (miscellaneous)
- Drug Discovery
- Organic Chemistry
- Pharmacology
Cite this
Hurghadolide A and swinholide I, potent actin-microfilament disrupters from the red sea sponge Theonella swinhoei. / Youssef, Diaa T A; Mooberry, Susan L.
In: Journal of Natural Products, Vol. 69, No. 1, 01.2006, p. 154-157.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Hurghadolide A and swinholide I, potent actin-microfilament disrupters from the red sea sponge Theonella swinhoei
AU - Youssef, Diaa T A
AU - Mooberry, Susan L
PY - 2006/1
Y1 - 2006/1
N2 - As part of our continuing interest in identifying anticancer drug leads from Red Sea marine organisms, we have investigated the sponge Theonella swinhoei. We report here the isolation and structure elucidation of swinholide A (1) and two new macrolides, swinholide I (2) and hurghadolide A (3). Swinholide I is the first derivative of swinholide A with hydroxylation at the side chain. Hurghadolide A possesses an unprecedented asymmetric 42-membered dilactone moiety and presents a novel skeleton of macrolides. The structural determinations were based on extensive interpretation of high-field NMR spectra and HRFABMS data. Swinholide I and hurghadolide A showed in vitro cytotoxicity against human colon adenocarcinoma (HCT-116) with IC50 values of 5.6 and 365 nM, respectively. Furthermore, swinholide I and hurghadolide A caused disruption of the actin cytoskeleton at concentrations of 70 and 7.3 nM, respectively. In addition, both compounds were active against Candida albicans.
AB - As part of our continuing interest in identifying anticancer drug leads from Red Sea marine organisms, we have investigated the sponge Theonella swinhoei. We report here the isolation and structure elucidation of swinholide A (1) and two new macrolides, swinholide I (2) and hurghadolide A (3). Swinholide I is the first derivative of swinholide A with hydroxylation at the side chain. Hurghadolide A possesses an unprecedented asymmetric 42-membered dilactone moiety and presents a novel skeleton of macrolides. The structural determinations were based on extensive interpretation of high-field NMR spectra and HRFABMS data. Swinholide I and hurghadolide A showed in vitro cytotoxicity against human colon adenocarcinoma (HCT-116) with IC50 values of 5.6 and 365 nM, respectively. Furthermore, swinholide I and hurghadolide A caused disruption of the actin cytoskeleton at concentrations of 70 and 7.3 nM, respectively. In addition, both compounds were active against Candida albicans.
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UR - http://www.scopus.com/inward/citedby.url?scp=32644452774&partnerID=8YFLogxK
U2 - 10.1021/np050404a
DO - 10.1021/np050404a
M3 - Article
C2 - 16441091
AN - SCOPUS:32644452774
VL - 69
SP - 154
EP - 157
JO - Journal of Natural Products
JF - Journal of Natural Products
SN - 0163-3864
IS - 1
ER -