Kaurane and trachylobane diterpenes from Xylopia aethiopica

George G. Harrigan; Vanderlan da S.Bolzani; A. A. Leslie Gunatilaka; David G.I. Kingston

doi:10.1016/S0031-9422(00)97022-5

Kaurane and trachylobane diterpenes from Xylopia aethiopica

George G. Harrigan, Vanderlan da S.Bolzani, A. A. Leslie Gunatilaka, David G.I. Kingston

Research output: Contribution to journal › Article › peer-review

51 Scopus citations

Abstract

Phytochemical investigation of Xylopia aethiopica (Annonaceae) has resulted in the isolation of two novel diterpenes, 15-oxo-(-)-trachyloban-19-oic acid and (-)-kaur-15-en-17-al-19-oic acid. Also encountered were the known compounds 15-hydroxy-(-)-trachyloban-19-oic acid, 15β-hydroxy-(-)-kaur-16-en-19-oic acid (as an inseperable mixture), 15-oxo-(-)-kaur-16-en-19-oic acid and sitosterol glucoside. ¹³C NMR assignments of 15-hydroxy-(-)- trachyloban-19-oic acid and the assignment of the configuration of its hydroxyl group at C-15 have been carried out for the first time.

Original language	English (US)
Pages (from-to)	109-113
Number of pages	5
Journal	Phytochemistry
Volume	36
Issue number	1
DOIs	https://doi.org/10.1016/S0031-9422(00)97022-5
State	Published - May 1994
Externally published	Yes

Keywords

Annonaceae
Xylopia aethiopica
kaurane and trachylobane diterpenes
structure elucidation.

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Plant Science
Horticulture

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10.1016/S0031-9422(00)97022-5

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title = "Kaurane and trachylobane diterpenes from Xylopia aethiopica",

abstract = "Phytochemical investigation of Xylopia aethiopica (Annonaceae) has resulted in the isolation of two novel diterpenes, 15-oxo-(-)-trachyloban-19-oic acid and (-)-kaur-15-en-17-al-19-oic acid. Also encountered were the known compounds 15-hydroxy-(-)-trachyloban-19-oic acid, 15β-hydroxy-(-)-kaur-16-en-19-oic acid (as an inseperable mixture), 15-oxo-(-)-kaur-16-en-19-oic acid and sitosterol glucoside. 13C NMR assignments of 15-hydroxy-(-)- trachyloban-19-oic acid and the assignment of the configuration of its hydroxyl group at C-15 have been carried out for the first time.",

keywords = "Annonaceae, Xylopia aethiopica, kaurane and trachylobane diterpenes, structure elucidation.",

author = "Harrigan, {George G.} and {da S.Bolzani}, Vanderlan and {Leslie Gunatilaka}, {A. A.} and Kingston, {David G.I.}",

note = "Funding Information: Acknowledgements-This work was supported by a National Cooperative Drug Discovery Group awarded to the University of Virginia (I UOl CA 50771)[ Dr S. M. Hecht, Principal Investigator]. We thank SmithKline Beecham Pharmaceuticals for the provision of plant material, Mr Tom E. Glass for 2D NMR spectra, Mr Kim Harich for high resolution mass spectra and MS Nina Baj for expert technical assistance.W e also thank Forestry Enterprises of Ghana through Biotics (U.K.) for the supply of X. uethiopica plant material. One of us (V. da S. B.) acknowledges FAPESP (Fundacao de Amiparo a Pesquisa do Estado de S. Paulo) and UNESP (Uni-versidade Estadual Paulista) for financial support.",

year = "1994",

month = may,

doi = "10.1016/S0031-9422(00)97022-5",

language = "English (US)",

volume = "36",

pages = "109--113",

journal = "Phytochemistry",

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publisher = "Elsevier Ltd",

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AU - Harrigan, George G.

AU - da S.Bolzani, Vanderlan

AU - Leslie Gunatilaka, A. A.

AU - Kingston, David G.I.

N1 - Funding Information: Acknowledgements-This work was supported by a National Cooperative Drug Discovery Group awarded to the University of Virginia (I UOl CA 50771)[ Dr S. M. Hecht, Principal Investigator]. We thank SmithKline Beecham Pharmaceuticals for the provision of plant material, Mr Tom E. Glass for 2D NMR spectra, Mr Kim Harich for high resolution mass spectra and MS Nina Baj for expert technical assistance.W e also thank Forestry Enterprises of Ghana through Biotics (U.K.) for the supply of X. uethiopica plant material. One of us (V. da S. B.) acknowledges FAPESP (Fundacao de Amiparo a Pesquisa do Estado de S. Paulo) and UNESP (Uni-versidade Estadual Paulista) for financial support.

PY - 1994/5

Y1 - 1994/5

N2 - Phytochemical investigation of Xylopia aethiopica (Annonaceae) has resulted in the isolation of two novel diterpenes, 15-oxo-(-)-trachyloban-19-oic acid and (-)-kaur-15-en-17-al-19-oic acid. Also encountered were the known compounds 15-hydroxy-(-)-trachyloban-19-oic acid, 15β-hydroxy-(-)-kaur-16-en-19-oic acid (as an inseperable mixture), 15-oxo-(-)-kaur-16-en-19-oic acid and sitosterol glucoside. 13C NMR assignments of 15-hydroxy-(-)- trachyloban-19-oic acid and the assignment of the configuration of its hydroxyl group at C-15 have been carried out for the first time.

AB - Phytochemical investigation of Xylopia aethiopica (Annonaceae) has resulted in the isolation of two novel diterpenes, 15-oxo-(-)-trachyloban-19-oic acid and (-)-kaur-15-en-17-al-19-oic acid. Also encountered were the known compounds 15-hydroxy-(-)-trachyloban-19-oic acid, 15β-hydroxy-(-)-kaur-16-en-19-oic acid (as an inseperable mixture), 15-oxo-(-)-kaur-16-en-19-oic acid and sitosterol glucoside. 13C NMR assignments of 15-hydroxy-(-)- trachyloban-19-oic acid and the assignment of the configuration of its hydroxyl group at C-15 have been carried out for the first time.

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KW - structure elucidation.

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ER -

Kaurane and trachylobane diterpenes from Xylopia aethiopica

Abstract

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