Terpenoids from Acamptopappus sphaerocephalus and A. shockleyi

Shivanand D. Jolad; Joseph J. Hoffmann; Barbara N. Timmermann; Steven P. McLaughlin; Robert B. Bates; Fernando A. Camou; Jack R. Cole

doi:10.1016/0031-9422(88)80025-6

Terpenoids from Acamptopappus sphaerocephalus and A. shockleyi

Shivanand D. Jolad, Joseph J. Hoffmann, Barbara N. Timmermann, Steven P. McLaughlin, Robert B. Bates, Fernando A. Camou, Jack R. Cole

Pharmacy Practice and Science

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Abstract

Eight new labdane diterpenoids were isolated from the sodium carbonate-soluble acid fraction of Acamptopappus sphaerocephalus and their structures were deduced from the spectral properties of their methyl esters and other derivatives. They are 7,E-13- or 8,E-13-labdadienes having oxygen-containing substituents at C-2, C-7, C-15 and/or C-19. These same diterpenoids were also present in A. shockleyi. Eight previously reported sesquiterpenoids, namely, bisabolene-1,4-endoperoxide, caryophyllene oxide, β-eudesmol, trans-nerolidol, 1-oxobisabolene, shiromool, spathulenol and viridiflorol, were isolated from the non-polar fraction of A. sphaerocephalus and identified by their ¹H NMR spectra.

Original language	English (US)
Pages (from-to)	3197-3204
Number of pages	8
Journal	Phytochemistry
Volume	27
Issue number	10
DOIs	https://doi.org/10.1016/0031-9422(88)80025-6
State	Published - 1988

Keywords

A. shockleyi
Acamptopappus sphaerocephalus
Asteraceae
Astereae
Solidagininae
labdane diterpenoids
sesquiterpenoids.

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Plant Science
Horticulture

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10.1016/0031-9422(88)80025-6

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title = "Terpenoids from Acamptopappus sphaerocephalus and A. shockleyi",

abstract = "Eight new labdane diterpenoids were isolated from the sodium carbonate-soluble acid fraction of Acamptopappus sphaerocephalus and their structures were deduced from the spectral properties of their methyl esters and other derivatives. They are 7,E-13- or 8,E-13-labdadienes having oxygen-containing substituents at C-2, C-7, C-15 and/or C-19. These same diterpenoids were also present in A. shockleyi. Eight previously reported sesquiterpenoids, namely, bisabolene-1,4-endoperoxide, caryophyllene oxide, β-eudesmol, trans-nerolidol, 1-oxobisabolene, shiromool, spathulenol and viridiflorol, were isolated from the non-polar fraction of A. sphaerocephalus and identified by their 1H NMR spectra.",

keywords = "A. shockleyi, Acamptopappus sphaerocephalus, Asteraceae, Astereae, Solidagininae, labdane diterpenoids, sesquiterpenoids.",

author = "Jolad, {Shivanand D.} and Hoffmann, {Joseph J.} and Timmermann, {Barbara N.} and McLaughlin, {Steven P.} and Bates, {Robert B.} and Camou, {Fernando A.} and Cole, {Jack R.}",

note = "Funding Information: Ackno~lrdgements~~~Wet hank Dr Meredith A. Lane, Dirk and Erik Timmermann for assistance in collection of A. shockleyi and Mr Peter Baker for mass spectral data. This work was supported in part by the National Science Foundation (Grant No. PCM-8304771) and the Arizona Disease Control Research Commission (Grant No. 8277~000000-l-l-Z-7493) whom we gratefully acknowledge.",

year = "1988",

doi = "10.1016/0031-9422(88)80025-6",

language = "English (US)",

volume = "27",

pages = "3197--3204",

journal = "Phytochemistry",

issn = "0031-9422",

publisher = "Elsevier Limited",

number = "10",

}

TY - JOUR

T1 - Terpenoids from Acamptopappus sphaerocephalus and A. shockleyi

AU - Jolad, Shivanand D.

AU - Hoffmann, Joseph J.

AU - Timmermann, Barbara N.

AU - McLaughlin, Steven P.

AU - Bates, Robert B.

AU - Camou, Fernando A.

AU - Cole, Jack R.

N1 - Funding Information: Ackno~lrdgements~~~Wet hank Dr Meredith A. Lane, Dirk and Erik Timmermann for assistance in collection of A. shockleyi and Mr Peter Baker for mass spectral data. This work was supported in part by the National Science Foundation (Grant No. PCM-8304771) and the Arizona Disease Control Research Commission (Grant No. 8277~000000-l-l-Z-7493) whom we gratefully acknowledge.

PY - 1988

Y1 - 1988

N2 - Eight new labdane diterpenoids were isolated from the sodium carbonate-soluble acid fraction of Acamptopappus sphaerocephalus and their structures were deduced from the spectral properties of their methyl esters and other derivatives. They are 7,E-13- or 8,E-13-labdadienes having oxygen-containing substituents at C-2, C-7, C-15 and/or C-19. These same diterpenoids were also present in A. shockleyi. Eight previously reported sesquiterpenoids, namely, bisabolene-1,4-endoperoxide, caryophyllene oxide, β-eudesmol, trans-nerolidol, 1-oxobisabolene, shiromool, spathulenol and viridiflorol, were isolated from the non-polar fraction of A. sphaerocephalus and identified by their 1H NMR spectra.

AB - Eight new labdane diterpenoids were isolated from the sodium carbonate-soluble acid fraction of Acamptopappus sphaerocephalus and their structures were deduced from the spectral properties of their methyl esters and other derivatives. They are 7,E-13- or 8,E-13-labdadienes having oxygen-containing substituents at C-2, C-7, C-15 and/or C-19. These same diterpenoids were also present in A. shockleyi. Eight previously reported sesquiterpenoids, namely, bisabolene-1,4-endoperoxide, caryophyllene oxide, β-eudesmol, trans-nerolidol, 1-oxobisabolene, shiromool, spathulenol and viridiflorol, were isolated from the non-polar fraction of A. sphaerocephalus and identified by their 1H NMR spectra.

KW - A. shockleyi

KW - Acamptopappus sphaerocephalus

KW - Asteraceae

KW - Astereae

KW - Solidagininae

KW - labdane diterpenoids

KW - sesquiterpenoids.

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DO - 10.1016/0031-9422(88)80025-6

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VL - 27

SP - 3197

EP - 3204

JO - Phytochemistry

JF - Phytochemistry

SN - 0031-9422

IS - 10

ER -

Terpenoids from Acamptopappus sphaerocephalus and A. shockleyi

Abstract

Keywords

ASJC Scopus subject areas

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