Abstract
Lyngbyabellin A (1), a significantly cytotoxic compound with unusual structural features, was isolated from a Guamanian strain of the marine cyanobacterium Lyngbya majuscula. This novel peptolide is structurally related to dolabellin (2) in that both depsipeptides bear a dichlorinated β- hydroxy acid and two functionalized thiazole carboxylic acid units. Its gross structure has been elucidated by spectral analysis, including 2D NMR techniques. The absolute stereochemistry of 1 was determined by chiral HPLC analysis of hydrolysis products and by characterization of the degradation products methyl 7,7-dichloro-3-hydroxy-2,2-dimethyloctanoate (3) and the corresponding acid 4. The total structure was further supported by molecular modeling studies. The isolation of 1 from L. majuscula once more supports the proposal that many compounds originally isolated from the sea hare Dolabella auricularia are of cyanobacterial origin. Lyngbyabellin A (1) was shown to be a potent disrupter of the cellular microfilament network.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 611-615 |
| Number of pages | 5 |
| Journal | Journal of Natural Products |
| Volume | 63 |
| Issue number | 5 |
| DOIs | |
| State | Published - May 2000 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Plant Science
- Chemistry (miscellaneous)
- Drug Discovery
- Organic Chemistry
- Pharmacology
Cite this
Isolation, structure determination, and biological activity of lyngbyabellin A from the marine cyanobacterium Lyngbya majuscula. / Luesch, Hendrik; Yoshida, Wesley Y.; Moore, Richard E.; Paul, Valerie J.; Mooberry, Susan L.
In: Journal of Natural Products, Vol. 63, No. 5, 05.2000, p. 611-615.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Isolation, structure determination, and biological activity of lyngbyabellin A from the marine cyanobacterium Lyngbya majuscula
AU - Luesch, Hendrik
AU - Yoshida, Wesley Y.
AU - Moore, Richard E.
AU - Paul, Valerie J.
AU - Mooberry, Susan L
PY - 2000/5
Y1 - 2000/5
N2 - Lyngbyabellin A (1), a significantly cytotoxic compound with unusual structural features, was isolated from a Guamanian strain of the marine cyanobacterium Lyngbya majuscula. This novel peptolide is structurally related to dolabellin (2) in that both depsipeptides bear a dichlorinated β- hydroxy acid and two functionalized thiazole carboxylic acid units. Its gross structure has been elucidated by spectral analysis, including 2D NMR techniques. The absolute stereochemistry of 1 was determined by chiral HPLC analysis of hydrolysis products and by characterization of the degradation products methyl 7,7-dichloro-3-hydroxy-2,2-dimethyloctanoate (3) and the corresponding acid 4. The total structure was further supported by molecular modeling studies. The isolation of 1 from L. majuscula once more supports the proposal that many compounds originally isolated from the sea hare Dolabella auricularia are of cyanobacterial origin. Lyngbyabellin A (1) was shown to be a potent disrupter of the cellular microfilament network.
AB - Lyngbyabellin A (1), a significantly cytotoxic compound with unusual structural features, was isolated from a Guamanian strain of the marine cyanobacterium Lyngbya majuscula. This novel peptolide is structurally related to dolabellin (2) in that both depsipeptides bear a dichlorinated β- hydroxy acid and two functionalized thiazole carboxylic acid units. Its gross structure has been elucidated by spectral analysis, including 2D NMR techniques. The absolute stereochemistry of 1 was determined by chiral HPLC analysis of hydrolysis products and by characterization of the degradation products methyl 7,7-dichloro-3-hydroxy-2,2-dimethyloctanoate (3) and the corresponding acid 4. The total structure was further supported by molecular modeling studies. The isolation of 1 from L. majuscula once more supports the proposal that many compounds originally isolated from the sea hare Dolabella auricularia are of cyanobacterial origin. Lyngbyabellin A (1) was shown to be a potent disrupter of the cellular microfilament network.
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UR - http://www.scopus.com/inward/citedby.url?scp=0034092263&partnerID=8YFLogxK
U2 - 10.1021/np990543q
DO - 10.1021/np990543q
M3 - Article
C2 - 10843570
AN - SCOPUS:0034092263
VL - 63
SP - 611
EP - 615
JO - Journal of Natural Products
JF - Journal of Natural Products
SN - 0163-3864
IS - 5
ER -