Bisresorcinols and arbutin derivatives from Grevillea banksii R. Br.

Hao Wang, David Leach, Michael C. Thomas, Stephen J. Blanksby, Paul I. Forster, Peter G. Watermana

Research output: Contribution to journalArticleResearchpeer-review

Abstract

This work is part of a series of chemical investigations of the genus Grevillea. Two new arbutin derivatives, seven new bisresorcinols, including a mixture of two isomers, three known flavonol glycosides, and four known resorcinols, including a mixture of two homologous compounds, were isolated from the ethyl acetate extract of the leaves and methanol extract of the stems of Grevillea banksii. The new compounds were identified, on the basis of spectroscopic data, as 6′-O-(3-(2-(hydroxymethyl)acryloyloxy)-2- methylpropanoyl)arbutin (1), 6′-O-(2-methylacryloyl)arbutin (2), 5,5′-(4(Z)-dodecen-1,12-diyl)bisresorcinol (6), 2′-methyl-5, 5′-(4(Z)-tetradecen-1,14-diyl)bisresorcinol (8), 2,2′-di(4- hydroxyprenyl)-5,5′-(6(Z)-tetradecen-1,14-diyl)bisresorcinol (9), 2-(4-acetoxyprenyl)-2′-(4-hydroxyprenyl) 5,5′-(6(Z)-tetradecen-1,14- diyl)bisresorcinol (10), 2-(4-acetoxyprenyl)-2′-(4-hydroxyprenyl)5, 5′-(8(Z)-tetradecen-1,14-diyl)bisresorcinol (11), 5,5′-(10(Z)- tetradecen-1-ondiyl) bisresorcinol (12) and 5,5′-(4(Z)-tetradecen-1-on- diyl)bisresorcinol (13).

Original languageEnglish
Pages (from-to)57-64
Number of pages8
JournalNatural Product Communications
Volume3
Issue number1
Publication statusPublished - 2008
Externally publishedYes

Fingerprint

Proteaceae
Arbutin
Grevillea
resorcinols
chemical derivatives
Resorcinols
flavonols
leaf extracts
isomers
glycosides
methanol
Glycosides
stems
Methanol
extracts

Cite this

Wang, H., Leach, D., Thomas, M. C., Blanksby, S. J., Forster, P. I., & Watermana, P. G. (2008). Bisresorcinols and arbutin derivatives from Grevillea banksii R. Br. Natural Product Communications, 3(1), 57-64.
Wang, Hao ; Leach, David ; Thomas, Michael C. ; Blanksby, Stephen J. ; Forster, Paul I. ; Watermana, Peter G. / Bisresorcinols and arbutin derivatives from Grevillea banksii R. Br. In: Natural Product Communications. 2008 ; Vol. 3, No. 1. pp. 57-64.
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abstract = "This work is part of a series of chemical investigations of the genus Grevillea. Two new arbutin derivatives, seven new bisresorcinols, including a mixture of two isomers, three known flavonol glycosides, and four known resorcinols, including a mixture of two homologous compounds, were isolated from the ethyl acetate extract of the leaves and methanol extract of the stems of Grevillea banksii. The new compounds were identified, on the basis of spectroscopic data, as 6′-O-(3-(2-(hydroxymethyl)acryloyloxy)-2- methylpropanoyl)arbutin (1), 6′-O-(2-methylacryloyl)arbutin (2), 5,5′-(4(Z)-dodecen-1,12-diyl)bisresorcinol (6), 2′-methyl-5, 5′-(4(Z)-tetradecen-1,14-diyl)bisresorcinol (8), 2,2′-di(4- hydroxyprenyl)-5,5′-(6(Z)-tetradecen-1,14-diyl)bisresorcinol (9), 2-(4-acetoxyprenyl)-2′-(4-hydroxyprenyl) 5,5′-(6(Z)-tetradecen-1,14- diyl)bisresorcinol (10), 2-(4-acetoxyprenyl)-2′-(4-hydroxyprenyl)5, 5′-(8(Z)-tetradecen-1,14-diyl)bisresorcinol (11), 5,5′-(10(Z)- tetradecen-1-ondiyl) bisresorcinol (12) and 5,5′-(4(Z)-tetradecen-1-on- diyl)bisresorcinol (13).",
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Wang, H, Leach, D, Thomas, MC, Blanksby, SJ, Forster, PI & Watermana, PG 2008, 'Bisresorcinols and arbutin derivatives from Grevillea banksii R. Br.', Natural Product Communications, vol. 3, no. 1, pp. 57-64.

Bisresorcinols and arbutin derivatives from Grevillea banksii R. Br. / Wang, Hao; Leach, David; Thomas, Michael C.; Blanksby, Stephen J.; Forster, Paul I.; Watermana, Peter G.

In: Natural Product Communications, Vol. 3, No. 1, 2008, p. 57-64.

Research output: Contribution to journalArticleResearchpeer-review

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T1 - Bisresorcinols and arbutin derivatives from Grevillea banksii R. Br.

AU - Wang, Hao

AU - Leach, David

AU - Thomas, Michael C.

AU - Blanksby, Stephen J.

AU - Forster, Paul I.

AU - Watermana, Peter G.

PY - 2008

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N2 - This work is part of a series of chemical investigations of the genus Grevillea. Two new arbutin derivatives, seven new bisresorcinols, including a mixture of two isomers, three known flavonol glycosides, and four known resorcinols, including a mixture of two homologous compounds, were isolated from the ethyl acetate extract of the leaves and methanol extract of the stems of Grevillea banksii. The new compounds were identified, on the basis of spectroscopic data, as 6′-O-(3-(2-(hydroxymethyl)acryloyloxy)-2- methylpropanoyl)arbutin (1), 6′-O-(2-methylacryloyl)arbutin (2), 5,5′-(4(Z)-dodecen-1,12-diyl)bisresorcinol (6), 2′-methyl-5, 5′-(4(Z)-tetradecen-1,14-diyl)bisresorcinol (8), 2,2′-di(4- hydroxyprenyl)-5,5′-(6(Z)-tetradecen-1,14-diyl)bisresorcinol (9), 2-(4-acetoxyprenyl)-2′-(4-hydroxyprenyl) 5,5′-(6(Z)-tetradecen-1,14- diyl)bisresorcinol (10), 2-(4-acetoxyprenyl)-2′-(4-hydroxyprenyl)5, 5′-(8(Z)-tetradecen-1,14-diyl)bisresorcinol (11), 5,5′-(10(Z)- tetradecen-1-ondiyl) bisresorcinol (12) and 5,5′-(4(Z)-tetradecen-1-on- diyl)bisresorcinol (13).

AB - This work is part of a series of chemical investigations of the genus Grevillea. Two new arbutin derivatives, seven new bisresorcinols, including a mixture of two isomers, three known flavonol glycosides, and four known resorcinols, including a mixture of two homologous compounds, were isolated from the ethyl acetate extract of the leaves and methanol extract of the stems of Grevillea banksii. The new compounds were identified, on the basis of spectroscopic data, as 6′-O-(3-(2-(hydroxymethyl)acryloyloxy)-2- methylpropanoyl)arbutin (1), 6′-O-(2-methylacryloyl)arbutin (2), 5,5′-(4(Z)-dodecen-1,12-diyl)bisresorcinol (6), 2′-methyl-5, 5′-(4(Z)-tetradecen-1,14-diyl)bisresorcinol (8), 2,2′-di(4- hydroxyprenyl)-5,5′-(6(Z)-tetradecen-1,14-diyl)bisresorcinol (9), 2-(4-acetoxyprenyl)-2′-(4-hydroxyprenyl) 5,5′-(6(Z)-tetradecen-1,14- diyl)bisresorcinol (10), 2-(4-acetoxyprenyl)-2′-(4-hydroxyprenyl)5, 5′-(8(Z)-tetradecen-1,14-diyl)bisresorcinol (11), 5,5′-(10(Z)- tetradecen-1-ondiyl) bisresorcinol (12) and 5,5′-(4(Z)-tetradecen-1-on- diyl)bisresorcinol (13).

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Wang H, Leach D, Thomas MC, Blanksby SJ, Forster PI, Watermana PG. Bisresorcinols and arbutin derivatives from Grevillea banksii R. Br. Natural Product Communications. 2008;3(1):57-64.