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Defensive sesterterpenoids with unusual antipodal cyclopentenones from the leaves of Leucosceptrum canum. 2011

Shi-Hong Luo, and Lin-Hong Weng, and Ming-Jin Xie, and Xiao-Nian Li, and Juan Hua, and Xu Zhao, and Sheng-Hong Li
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, PR China.

Two novel sesterterpenoids, leucosceptroids C (1) and D (2), possessing unusual antipodal cyclopentenones while maintaining the stereochemistry and functionality of the tricyclic cores, were discovered from the leaves of Leucosceptrum canum (Labiatae). Their structures including absolute stereochemistries were determined by comprehensive NMR, MS, and single-crystal X-ray diffraction analyses. The potent antifeedant activity of 1 against the generalist plant-feeding insect Helicoverpa armigera (EC(50) = 0.017 μmol/cm(2)) suggested them to be new defensive sesterterpenoids of L. canum.

UI MeSH Term Description Entries
D007915 Lepidoptera A large order of insects comprising the butterflies and moths.
D008958 Models, Molecular Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures. Molecular Models,Model, Molecular,Molecular Model
D003500 Cyclization Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Cyclizations
D003517 Cyclopentanes A group of alicyclic hydrocarbons with the general formula R-C5H9. Cyclopentadiene,Cyclopentadienes,Cyclopentene,Cyclopentenes,Cyclopentane
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D054830 Sesterterpenes Terpenes of five units of HEMITERPENES, formed from geranylfarnesyl pyrophosphate.
D018515 Plant Leaves Expanded structures, usually green, of vascular plants, characteristically consisting of a bladelike expansion attached to a stem, and functioning as the principal organ of photosynthesis and transpiration. (American Heritage Dictionary, 2d ed) Plant Leaf,Leaf, Plant,Leave, Plant,Leaves, Plant,Plant Leave
D019686 Lamiaceae The mint plant family. They are characteristically aromatic, and many of them are cultivated for their oils. Most have square stems, opposite leaves, and two-lipped, open-mouthed, tubular corollas (united petals), with five-lobed, bell-like calyxes (united sepals). Glechoma,Labiatae,Leonotis,Mesona,Micromeria,Schizonepeta,Tetradenia,Glechomas,Leonoti,Mesonas,Micromerias,Schizonepetas,Tetradenias

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