Abstract
Crude CH2Cl2-MeOH extracts prepared from Alangium javanicum and A. grisolleoides were found to induce DNA strand breakage in the presence of Cu2+ and were subjected to bioassay-guided fractionation to permit identification of the active principle(s). Javaniside (1), a novel alkaloid possessing an unusual monoterpenoid oxindole skeleton, was identified as an active principle contributing to the DNA cleavage activity observed for the crude extract of A. javanicum. Alangiside (2), a tetrahydroisoquinoline monoterpene glucoside widely distributed in the genus Alangium, was also isolated from A. grisolleoides as a new type of Cu2+-dependent DNA cleavage agent. The relative configuration of the asymmetric centers in javaniside was established by analysis of 1H-1H coupling constants and NOESY correlations. Semisynthesis of javaniside from secologanin (3) established the absolute stereochemistry of javaniside.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 1147-1152 |
| Number of pages | 6 |
| Journal | Journal of Natural Products |
| Volume | 68 |
| Issue number | 8 |
| DOIs | |
| State | Published - Aug 2005 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Plant Science
- Chemistry (miscellaneous)
- Drug Discovery
- Organic Chemistry
- Pharmacology
Cite this
Alkaloids from Alangium javanicum and Alangium grisolleoides that mediate Cu2+-dependent DNA strand scission. / Pham, Van Cuong; Ma, Ji; Thomas, Shannon J.; Xu, Zhidong; Hecht, Sidney.
In: Journal of Natural Products, Vol. 68, No. 8, 08.2005, p. 1147-1152.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Alkaloids from Alangium javanicum and Alangium grisolleoides that mediate Cu2+-dependent DNA strand scission
AU - Pham, Van Cuong
AU - Ma, Ji
AU - Thomas, Shannon J.
AU - Xu, Zhidong
AU - Hecht, Sidney
PY - 2005/8
Y1 - 2005/8
N2 - Crude CH2Cl2-MeOH extracts prepared from Alangium javanicum and A. grisolleoides were found to induce DNA strand breakage in the presence of Cu2+ and were subjected to bioassay-guided fractionation to permit identification of the active principle(s). Javaniside (1), a novel alkaloid possessing an unusual monoterpenoid oxindole skeleton, was identified as an active principle contributing to the DNA cleavage activity observed for the crude extract of A. javanicum. Alangiside (2), a tetrahydroisoquinoline monoterpene glucoside widely distributed in the genus Alangium, was also isolated from A. grisolleoides as a new type of Cu2+-dependent DNA cleavage agent. The relative configuration of the asymmetric centers in javaniside was established by analysis of 1H-1H coupling constants and NOESY correlations. Semisynthesis of javaniside from secologanin (3) established the absolute stereochemistry of javaniside.
AB - Crude CH2Cl2-MeOH extracts prepared from Alangium javanicum and A. grisolleoides were found to induce DNA strand breakage in the presence of Cu2+ and were subjected to bioassay-guided fractionation to permit identification of the active principle(s). Javaniside (1), a novel alkaloid possessing an unusual monoterpenoid oxindole skeleton, was identified as an active principle contributing to the DNA cleavage activity observed for the crude extract of A. javanicum. Alangiside (2), a tetrahydroisoquinoline monoterpene glucoside widely distributed in the genus Alangium, was also isolated from A. grisolleoides as a new type of Cu2+-dependent DNA cleavage agent. The relative configuration of the asymmetric centers in javaniside was established by analysis of 1H-1H coupling constants and NOESY correlations. Semisynthesis of javaniside from secologanin (3) established the absolute stereochemistry of javaniside.
UR - http://www.scopus.com/inward/record.url?scp=24744444933&partnerID=8YFLogxK
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U2 - 10.1021/np058013j
DO - 10.1021/np058013j
M3 - Article
VL - 68
SP - 1147
EP - 1152
JO - Journal of Natural Products
JF - Journal of Natural Products
SN - 0163-3864
IS - 8
ER -