On the Toxin of Illicium Anisatum. I. The Isolation and Characterization of a Convulsant Principle: Anisatin<sup>1</sup>

Lane, John F.; Koch, W.; Leeds, Norma S.; Gorin, George

doi:10.1021/ja01133a002

Cited by 82 publications

(43 citation statements)

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“…Anisatin is a secoprezizaane sesquiterpene isolated from the seeds and carpels of I. anisatum (6) and also from the fruits and leaves of Illicium floridanum J.Ellis (7) and the pericarps of Illicium merrillianum A.C.Sm. (8).…”

Section: Introductionmentioning

confidence: 99%

Distinguishing Chinese Star Anise from Japanese Star Anise Using Thermal Desorption−Gas Chromatography−Mass Spectrometry

Howes

Kite

Simmonds

2009

J. Agric. Food Chem.

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The volatile compounds from the pericarps of Illicium anisatum L., Illicium brevistylum A.C.Sm., Illicium griffithii Hook.f. & Thomson, Illicium henryi Diels, Illicium lanceolatum A.C.Sm., Illicium majus Hook.f. & Thomson, Illicium micranthum Dunn, and Illicium verum Hook.f. were examined by thermal desorption-gas chromatography-mass spectrometry (TD-GC-MS). The volatiles desorbed from the pericarps of I. verum (Chinese star anise), the species traded for culinary purposes, were generally characterized by a high proportion of (E)-anethole (57.6-77.1%) and the presence of foeniculin; the latter was otherwise only detected in the pericarps of I. lanceolatum. In the pericarps of all other species analyzed, the percentage composition of (E)-anethole was comparatively lower (

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Section: Introductionmentioning

confidence: 99%

Distinguishing Chinese Star Anise from Japanese Star Anise Using Thermal Desorption−Gas Chromatography−Mass Spectrometry

Howes

Kite

Simmonds

2009

J. Agric. Food Chem.

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“…1,2 For decades, these natural products have attracted significant synthetic attention owing to their diverse oxidation patterns and notable biological activities (Figure 1). Pseudoanisatin ( 1 ) and its congeners contain a bridging ε-lactone, while anisatin ( 2 ) and associated compounds present an unusual spiro β-lactone motif.…”

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confidence: 99%

Oxidative Entry into the Illicium Sesquiterpenes: Enantiospecific Synthesis of (+)-Pseudoanisatin

et al. 2016

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Illicium sesquiterpenes have been the subject of numerous synthetic efforts due to their ornate and highly oxidized structures as well as significant biological activities. Herein we report the first chemical synthesis of (+)-pseudoanisatin from the abundant feedstock chemical cedrol (~$50 USD/kg) in 12-steps using extensive site-selective C(sp3)–H bond functionalization. Significantly, this work represents a novel oxidative strategic template for future approaches to these natural products and their analogs.

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“…Anisatin 17 and neoanisatin 18 are convulsant principles isolated from the fruits of the toxic plant Illicium anisatum L [139]. Salinosporamide A (19) is a bioactive product of a marine microorganism [140].…”

Section: Natural or Bioactive Compoundsmentioning

confidence: 99%

Four‐Membered Heterocycles: Structure and Reactivity

Rousseau

Robin

2011

Modern Heterocyclic Chemistry

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On the Toxin of Illicium Anisatum. I. The Isolation and Characterization of a Convulsant Principle: Anisatin¹

Cited by 82 publications

References 4 publications

Distinguishing Chinese Star Anise from Japanese Star Anise Using Thermal Desorption−Gas Chromatography−Mass Spectrometry

Distinguishing Chinese Star Anise from Japanese Star Anise Using Thermal Desorption−Gas Chromatography−Mass Spectrometry

Oxidative Entry into the Illicium Sesquiterpenes: Enantiospecific Synthesis of (+)-Pseudoanisatin

Four‐Membered Heterocycles: Structure and Reactivity

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On the Toxin of Illicium Anisatum. I. The Isolation and Characterization of a Convulsant Principle: Anisatin1

Cited by 82 publications

References 4 publications

Distinguishing Chinese Star Anise from Japanese Star Anise Using Thermal Desorption−Gas Chromatography−Mass Spectrometry

Distinguishing Chinese Star Anise from Japanese Star Anise Using Thermal Desorption−Gas Chromatography−Mass Spectrometry

Oxidative Entry into the Illicium Sesquiterpenes: Enantiospecific Synthesis of (+)-Pseudoanisatin

Four‐Membered Heterocycles: Structure and Reactivity

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On the Toxin of Illicium Anisatum. I. The Isolation and Characterization of a Convulsant Principle: Anisatin¹