Insecticidal sesquiterpene pyridine alkaloids from Maytenus chiapensis.
The new sesquiterpene pyridine alkaloids chiapenines ES-I (1), ES-II (2), ES-III (3), and ES-IV (4), in addition to the known alkaloids wilfordine (5), alatamine (6), wilforidine (7), alatusinine (8), euonine (9), euonymine (10), ebenifoline E-I (11), forrestine (12), mayteine (13), and 4-hydroxy-7-epi-chuchuhuanine E-V (14), were isolated from the leaves of Maytenus chiapensis. Their structures were elucidated by 1D and 2D NMR spectroscopy, including homonuclear and heteronuclear correlation (COSY, ROESY, HSQC, and HMBC) experiments. Wilfordine, alatusinine, and euonine exhibited strong antifeedant activity against Spodoptera littoralis.
Núñez
Marvin J
MJ
Instituto Universitario de Bio-Orgánica Antonio González, Universidad de La Laguna, Avenida Astrofísico Francisco Sánchez 2, 38206 La Laguna, Tenerife, Canary Islands, Spain.
Guadaño
Ana
A
Jiménez
Ignacio A
IA
Ravelo
Angel G
AG
González-Coloma
Azucena
A
Bazzocchi
Isabel L
IL
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D001042:Aphids / Q000187:drug effects; D002478:Cells, Cultured; D004544:El Salvador; D005247:Feeding Behavior / Q000187:drug effects; D007306:Insecticides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D029755:Maytenus / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018411:Spodoptera / Q000187:drug effects
D000470:Alkaloids; D007306:Insecticides; D011725:Pyridines; D012717:Sesquiterpenes; C023666:pyridine