Abstract
Cancer cell cytotoxicity was used to guide the isolation of nine new swinholide-related compounds, named samholides A-I (1-9), from an American Samoan marine cyanobacterium cf. Phormidium sp. Their structures were determined by extensive analysis of 1D and 2D NMR spectroscopic data. The new compounds share an unusual 20-demethyl 44-membered lactone ring composed of two monomers, and they demonstrate structural diversity arising from geometric isomerization of double bonds, sugar units with unique glyceryl moieties and varied methylation patterns. All of the new samholides were potently active against the H-460 human lung cancer cell line with IC50 values ranging from 170 to 910 nM. The isolation of these new swinholide-related compounds from a marine cyanobacterium reinvigorates questions concerning the evolution and biosynthetic origin of these natural products.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 3034-3046 |
| Number of pages | 13 |
| Journal | Journal of Organic Chemistry |
| Volume | 83 |
| Issue number | 6 |
| DOIs | |
| State | Published - Mar 16 2018 |
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All Science Journal Classification (ASJC) codes
- Organic Chemistry
Cite this
Samholides, Swinholide-Related Metabolites from a Marine Cyanobacterium cf. Phormidium sp. / Tao, Yiwen; Li, Pinglin; Zhang, Daojing; Glukhov, Evgenia; Gerwick, Lena; Zhang, Chen; Murray, Thomas F.; Gerwick, William H.
In: Journal of Organic Chemistry, Vol. 83, No. 6, 16.03.2018, p. 3034-3046.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Samholides, Swinholide-Related Metabolites from a Marine Cyanobacterium cf. Phormidium sp.
AU - Tao, Yiwen
AU - Li, Pinglin
AU - Zhang, Daojing
AU - Glukhov, Evgenia
AU - Gerwick, Lena
AU - Zhang, Chen
AU - Murray, Thomas F.
AU - Gerwick, William H.
PY - 2018/3/16
Y1 - 2018/3/16
N2 - Cancer cell cytotoxicity was used to guide the isolation of nine new swinholide-related compounds, named samholides A-I (1-9), from an American Samoan marine cyanobacterium cf. Phormidium sp. Their structures were determined by extensive analysis of 1D and 2D NMR spectroscopic data. The new compounds share an unusual 20-demethyl 44-membered lactone ring composed of two monomers, and they demonstrate structural diversity arising from geometric isomerization of double bonds, sugar units with unique glyceryl moieties and varied methylation patterns. All of the new samholides were potently active against the H-460 human lung cancer cell line with IC50 values ranging from 170 to 910 nM. The isolation of these new swinholide-related compounds from a marine cyanobacterium reinvigorates questions concerning the evolution and biosynthetic origin of these natural products.
AB - Cancer cell cytotoxicity was used to guide the isolation of nine new swinholide-related compounds, named samholides A-I (1-9), from an American Samoan marine cyanobacterium cf. Phormidium sp. Their structures were determined by extensive analysis of 1D and 2D NMR spectroscopic data. The new compounds share an unusual 20-demethyl 44-membered lactone ring composed of two monomers, and they demonstrate structural diversity arising from geometric isomerization of double bonds, sugar units with unique glyceryl moieties and varied methylation patterns. All of the new samholides were potently active against the H-460 human lung cancer cell line with IC50 values ranging from 170 to 910 nM. The isolation of these new swinholide-related compounds from a marine cyanobacterium reinvigorates questions concerning the evolution and biosynthetic origin of these natural products.
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U2 - 10.1021/acs.joc.8b00028
DO - 10.1021/acs.joc.8b00028
M3 - Article
VL - 83
SP - 3034
EP - 3046
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 6
ER -