New Sesquiterpene Lactones from Illicium floridanum

In continuation of our phytochemical investigation of Illicium floridanum Ellis (American star anise, star bush), three new sesquiterpene lactones possessing the anisatin−type carbon skeleton (8,9-seco-prezizaane skeleton), 14-acetoxy-3-oxofloridanolide (1), 13-acetoxy-14-(n-butyryloxy)floridanolide...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 1998-02, Vol.61 (2), p.230-236
Main Authors: Schmidt, Thomas J, Schmidt, Hildegard M, Müller, Eva, Peters, Wilfried, Fronczek, Frank R, Truesdale, Aimee, Fischer, Nikolaus H
Format: Article
Language:English
Subjects:
Analytical, structural and metabolic biochemistry
Biological and medical sciences
CHEMICAL COMPOSITION
CHEMICAL STRUCTURE
COMPOSICION QUIMICA
COMPOSITION CHIMIQUE
ESPECTROMETRIA
ESTRUCTURA QUIMICA
FEUILLE
FRUITS
FRUTAS
Fundamental and applied biological sciences. Psychology
HOJAS
ILLICIUM
LACTONAS
LACTONE
LACTONES
LEAVES
NERVOUS SYSTEM
NEUROTOXINS
Other biological molecules
SESQUITERPENOID LACTONES
SESQUITERPENOIDE
SESQUITERPENOIDS
SESQUITERPENOS
SISTEMA NERVIOSO
SPECTRAL ANALYSIS
SPECTROMETRIE
SPECTROMETRY
STRUCTURE CHIMIQUE
SYSTEME NERVEUX
Terpenes, steroids. Hormones
TOXINAS
TOXINE
TOXINS
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Summary:In continuation of our phytochemical investigation of Illicium floridanum Ellis (American star anise, star bush), three new sesquiterpene lactones possessing the anisatin−type carbon skeleton (8,9-seco-prezizaane skeleton), 14-acetoxy-3-oxofloridanolide (1), 13-acetoxy-14-(n-butyryloxy)floridanolide (2), and 3β-acetoxy-14-n-butyryloxy-10-deoxyfloridanolide (3), were isolated from fruits of this plant. Their structures were elucidated by 1D and 2D NMR measurements. The molecular structure of 1 was obtained by single crystal X-ray diffraction. The 11,3-δ-lactone structure of the compound previously described as debenzoyldunnianin in our previous communication, on grounds of NMR spectral evidence and X-ray crystallographic analysis is revised to a δ-lactone closed between C-11 and C-7 (compound 4). The neurotoxic sesquiterpene lactone anisatin (5) and its isomer 2α-hydroxyneoanisatin (3-deoxy-2α-hydroxyanisatin, 6) were also isolated and identified by spectroscopic means. The presence of the neurotoxin 5 in relatively high amounts in the fruits and leaves confirms and explains early reports on the toxicity of this plant.
ISSN:0163-3864
1520-6025
DOI:10.1021/np970434g