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Picrotoxanes

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Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, Vol. 93

Abstract

Shortly after Sertürner’s isolation of morphine in 1806, which signified the start of plant secondary products research, picrotoxin was isolated by the French scientist Boullay (1811) from the dried fruits of a liana growing in India and Southeast Asia (1). Although the plant had no value as therapeutic in Western medicine, picrotoxin was isolated even prior to such therapeutically most important plant constituents as emetine (1816) and quinine (1820). Its high toxicity and the ease of isolation by crystallization from water were responsible for the very early discovery of this first member of the picrotoxanes or tutinanolides. Picrotoxanes are a group of sesquiterpenes, sesquiterpene alkaloids, and “norditerpenes” with highly complex, mostly tetra- or pentacyclic structures and up to 12 stereogenic centers. Thus, it is not surprising that it took 70 years to learn that the crystalline substance picrotoxin is a molecular compound consisting of equal amounts of picrotoxinin (1), one of the most potent plant toxins, comparable in lethality with strychnine, and the less active hydrated derivative picrotin (2). An additional 80 years were to pass until the advent of modern spectroscopy allowed Conroy to complete his pioneering elucidation of the structure of picrotoxinin and picrotin. In the meantime more than ten new structural relatives had been isolated from very diverse plant families. In 1866, coriamyrtin (9) was isolated from the toxic berries of the tanner’s brush, the only European plant known to contain picrotoxanes.

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Notes

  1. 1.

    For other unexplained occurrences of secondary metabolites in marine sponges and phylogenetically very distant species see references (282, 283).

  2. 2.

    Note that the structures of capenicin and its derivatives are incorrectly depicted in (2).

  3. 3.

    Unfortunately this name has also been given to a peptide toxin.

  4. 4.

    However, the authors depicted 65 and 66 with C(18) in the (R)-configuration in this publication (53) whereas in a later publication (55) 65 and 66 are depicted with C(18) in the (S)-configuration without comment.

Abbreviations

Ac:

Acetyl

acac:

acetyacetone

ACCN:

1,1′-Azobis(cyclohexanecarbonitrile)

AIBN:

2,2′-Azobisisobutyronitrile

aq:

aqueous

Bn:

Benzyl

BSA:

Bistrimethylsilylacetamide

brsm:

Based on recovered starting material

Bu:

n-butyl

Bz:

Benzoyl

cat:

catalytic

CD:

Circular dichroism

COLOC:

Correlation spectroscopy of long range coupling

COSMIC:

Force field calculation

COSY:

Correlation spectroscopy

Cp:

Cyclopentadienyl

CSA:

Camphorsulfonic acid

Cy:

Cyclohexyl

d:

day(s)

dba:

dibenzylidene acetone

DBU:

1,8-Diazabicyclo[5.4.0]undec-7-ene

DCC:

1,3-Dicyclohexylcarbodiimide

DDQ:

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

DEAD:

Diethylazodicarboxylate

DEPT:

Distortionless enhanced polarization transfer

DHF:

4,5-Dihydrofuran

DIBAH:

Diisobutylaluminum hydride

dicot:

dicotyledon (flowering plant with two seed leafs)

diglyme:

Bis-β-Hydroxyethyl ether

dil:

diluted

DMAP:

4-dimethylaminopyridine

DME:

1,2-Dimethoxyethane

DMF:

N,N-Dimethylformamide

DMSO:

Dimethylsulfoxide

2D-NMR:

Two-dimensional nuclear magnetic resonance

ee :

enantiomeric excess

EPC:

Enantiomerically pure compound

ESIMS:

Electron spray ionization mass spectrum

Et:

ethyl

exc:

excess

FAB:

Fast atom bombardment

FVP:

Flash vacuum pyrolysis

GABA:

γ-Aminobutyric acid

GLC:

Gas–liquid chromatography

glyme:

1,2-Dihydroxyethane

h:

hours

hν:

Irradiation with light

HMBC:

Heteronuclear multiple bond correlation

HMDS:

Hexamethyldisilazane

HMPA:

Hexamethylphosphoramide

HMQC:

Heteronuclear multiple quantum correlation

HOHAHA:

Homonuclear single quantum correlation

HPLC:

High pressure liquid chromatography

HR-TOF-MS:

High resolution time of flight-mass spectrum

HSQC:

Heteronuclear single quantum correlation

IMDA :

Intramolecular Diels–Alder reaction

iPr:

Isopropyl

IR:

infrared (spectroscopy)

LAH:

Lithium aluminum hydride

LDA:

Lithium diisopropylamide

LHMDS:

Lithium hexamethyldisilazide

MCPBA:

meta-chloroperbenzoic acid

Me:

Methyl

MOM:

Methoxymethyl

monocot:

monocotyledon (flowering plant with only one seed leaf)

Mp:

Melting point

Ms:

Methansulfonyl

MS:

Molecular sieve

MS:

Mass spectrum

MPTA Cl:

(+)-α-Methoxy-α-(trifluoromethyl)phenylacetyl chloride

NBS:

N-Bromosuccinimide

NMO:

Morpholine-N-oxide

NMR:

Nuclear magnetic resonance (spectroscopy)

NOE:

Nuclear Overhauser effect

ODS:

Octadecyl silica gel

ORD:

Optical rotation dispersion (spectroscopy)

PCC:

Pyridinium chlorochromate

PDC:

Pyridinium dichromate

Ph:

Phenyl

PhH:

Benzene

PhCH3 :

Toluene

PMB:

p-Methoxybenzyl

PMBOM:

p-Methoxybenzyloxymethyl

PP:

Diphosphate

PPTS:

Pyridinium p-toluenesulfonate

pyr:

pyridine

quant:

quantitative yield

rfl:

reflux

rt:

room temperature

s.l.:

sensu lato

t-Am:

tert-amyl = 2-methylbut-2-yl

t-Bu:

tert-butyl

TBAF:

Tetrabutylammonium fluoride

TBS:

tert-butyldimethylsilyl

TFA:

Trifluoroacetic acid

TFAA:

Trifluoroacetic anhydride

Tf (OTf):

triflate=trifluoromethanesulfonate

thexyl:

2,3-dimethyl-2-butyl

THF:

Tetrahydrofuran, tetrahydrofuranyl

TLC:

Thin-layer chromatography

TMS:

Trimethylsilyl

TosMIC:

Tosylmethylisocyanide = p-toluenesulfonylmethylisonitrile

Troc:

Trichloroethoxycarbonyl

Ts:

Tosyl = p-Toluenesulfonyl

UV:

ultraviolet (spectroscopy)

Z:

Benzyloxycarbonyl

Δ:

High temperature

′:

Minutes

″:

Seconds

[α]D :

Optical rotation at λ = 589 nm

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Acknowledgments

The author thanks Dr. F. Wuggenig for reading through the manuscript. She is grateful to Prof. P. K. Endress for the valuable advice and to Prof. Wei-Min Zhao for his information on the structure of dendronobiline A. Her special thanks go to Prof. Jie Yan for translating Chinese written publications. For their assistance concerning the early literature on the picrotoxanes, she wishes to thank Dr. U. Rinner, Prof. W. Schmid, and Dr. K. Zimmermann. The author is grateful to Mag. C. Lentsch for his help concerning EDV problems.

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  1. Institut für Organische Chemie der Universität Wien, Währinger Strasse 38, 1090, Vienna, Austria

    Edda Gössinger

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  1. Edda Gössinger
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  1. College of Pharmacy, Div. Medicinal Chemistry &, Ohio State University, West 12th Ave. 500, Columbus, 43210, USA

    A. Douglas Kinghorn

  2. Leonfeldner Str. 150, Linz, 4040, Austria

    Heinz Falk

  3. Graduate School of Medical Sciences, Dept. Developmental, Kyushu University, Maidashi 3-1-1, Fukuoka, 812-8582, Japan

    Junichi Kobayashi

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Gössinger, E. (2010). Picrotoxanes. In: Kinghorn, A., Falk, H., Kobayashi, J. (eds) Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, Vol. 93. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 93. Springer, Vienna. https://doi.org/10.1007/978-3-7091-0140-7_2

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