Prenylated alkylbisphenols from Grevillea whiteana

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

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Eleven new bisresorcinols including four mixtures each of two isomers and one resorcinol/phloroglucinol derivative, together with five known resorcinols have been isolated from the ethyl acetate extract of stems of Grevillea whiteana. The new compounds were identified as 4-(3-hydroxy-3-methylbutyl) grebustol-B (10a), 4′-(3-hydroxy-3-methylbutyl)grebustol-B (10b), 4-(4-hydroxy-3-methylbutyl)grebustol-B (2a) and 4′-(4-hydroxy-3- methylbutyl) rebustol-B (2b), 2,2-dimethyldihydropyrano grebustol-B (11a) and iso-2,2-dimethyldihydropyranogrebustol-B (11b), 2,2-dimethyl-3ξ- hydroxydihydropyranogrebustol-B (7a) and iso-2,2-dimethyl-3ξ- hydroxydihydropyranogrebustol-B (7b), 15-(2-(4-hydroxy-3-methylbutyl)- resorcinol-5-yl)-1-(phloroglucinolyl)-9(Z)pentadecen-one (whiteanone) (4), 5,5′-(hexadecan-diyl)bisresorcinol (12) and 2-methyl-5,5′-(8(Z)- hexadecen-1,16-diyl)bisresorcinol (9). This is the first record of pyranobisresorcinols in the genus and the first report of a phloroglucinol terminal phenolic unit in any Grevillea species.

Original languageEnglish
Pages (from-to)951-958
Number of pages8
JournalNatural Product Communications
Volume4
Issue number7
Publication statusPublished - 2009
Externally publishedYes

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Proteaceae
Phloroglucinol
Grevillea
resorcinol
Resorcinols
resorcinols
isomers
chemical derivatives
stems
extracts

Cite this

Wang, H., Leach, D. N., Thomas, M. C., Blanksby, S. J., Forster, P. I., & Waterman, P. G. (2009). Prenylated alkylbisphenols from Grevillea whiteana. Natural Product Communications, 4(7), 951-958.
Wang, Hao ; Leach, David N. ; Thomas, Michael C. ; Blanksby, Stephen J. ; Forster, Paul I. ; Waterman, Peter G. / Prenylated alkylbisphenols from Grevillea whiteana. In: Natural Product Communications. 2009 ; Vol. 4, No. 7. pp. 951-958.
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abstract = "Eleven new bisresorcinols including four mixtures each of two isomers and one resorcinol/phloroglucinol derivative, together with five known resorcinols have been isolated from the ethyl acetate extract of stems of Grevillea whiteana. The new compounds were identified as 4-(3-hydroxy-3-methylbutyl) grebustol-B (10a), 4′-(3-hydroxy-3-methylbutyl)grebustol-B (10b), 4-(4-hydroxy-3-methylbutyl)grebustol-B (2a) and 4′-(4-hydroxy-3- methylbutyl) rebustol-B (2b), 2,2-dimethyldihydropyrano grebustol-B (11a) and iso-2,2-dimethyldihydropyranogrebustol-B (11b), 2,2-dimethyl-3ξ- hydroxydihydropyranogrebustol-B (7a) and iso-2,2-dimethyl-3ξ- hydroxydihydropyranogrebustol-B (7b), 15-(2-(4-hydroxy-3-methylbutyl)- resorcinol-5-yl)-1-(phloroglucinolyl)-9(Z)pentadecen-one (whiteanone) (4), 5,5′-(hexadecan-diyl)bisresorcinol (12) and 2-methyl-5,5′-(8(Z)- hexadecen-1,16-diyl)bisresorcinol (9). This is the first record of pyranobisresorcinols in the genus and the first report of a phloroglucinol terminal phenolic unit in any Grevillea species.",
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Wang, H, Leach, DN, Thomas, MC, Blanksby, SJ, Forster, PI & Waterman, PG 2009, 'Prenylated alkylbisphenols from Grevillea whiteana', Natural Product Communications, vol. 4, no. 7, pp. 951-958.

Prenylated alkylbisphenols from Grevillea whiteana. / Wang, Hao; Leach, David N.; Thomas, Michael C.; Blanksby, Stephen J.; Forster, Paul I.; Waterman, Peter G.

In: Natural Product Communications, Vol. 4, No. 7, 2009, p. 951-958.

Research output: Contribution to journalArticleResearchpeer-review

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T1 - Prenylated alkylbisphenols from Grevillea whiteana

AU - Wang, Hao

AU - Leach, David N.

AU - Thomas, Michael C.

AU - Blanksby, Stephen J.

AU - Forster, Paul I.

AU - Waterman, Peter G.

PY - 2009

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N2 - Eleven new bisresorcinols including four mixtures each of two isomers and one resorcinol/phloroglucinol derivative, together with five known resorcinols have been isolated from the ethyl acetate extract of stems of Grevillea whiteana. The new compounds were identified as 4-(3-hydroxy-3-methylbutyl) grebustol-B (10a), 4′-(3-hydroxy-3-methylbutyl)grebustol-B (10b), 4-(4-hydroxy-3-methylbutyl)grebustol-B (2a) and 4′-(4-hydroxy-3- methylbutyl) rebustol-B (2b), 2,2-dimethyldihydropyrano grebustol-B (11a) and iso-2,2-dimethyldihydropyranogrebustol-B (11b), 2,2-dimethyl-3ξ- hydroxydihydropyranogrebustol-B (7a) and iso-2,2-dimethyl-3ξ- hydroxydihydropyranogrebustol-B (7b), 15-(2-(4-hydroxy-3-methylbutyl)- resorcinol-5-yl)-1-(phloroglucinolyl)-9(Z)pentadecen-one (whiteanone) (4), 5,5′-(hexadecan-diyl)bisresorcinol (12) and 2-methyl-5,5′-(8(Z)- hexadecen-1,16-diyl)bisresorcinol (9). This is the first record of pyranobisresorcinols in the genus and the first report of a phloroglucinol terminal phenolic unit in any Grevillea species.

AB - Eleven new bisresorcinols including four mixtures each of two isomers and one resorcinol/phloroglucinol derivative, together with five known resorcinols have been isolated from the ethyl acetate extract of stems of Grevillea whiteana. The new compounds were identified as 4-(3-hydroxy-3-methylbutyl) grebustol-B (10a), 4′-(3-hydroxy-3-methylbutyl)grebustol-B (10b), 4-(4-hydroxy-3-methylbutyl)grebustol-B (2a) and 4′-(4-hydroxy-3- methylbutyl) rebustol-B (2b), 2,2-dimethyldihydropyrano grebustol-B (11a) and iso-2,2-dimethyldihydropyranogrebustol-B (11b), 2,2-dimethyl-3ξ- hydroxydihydropyranogrebustol-B (7a) and iso-2,2-dimethyl-3ξ- hydroxydihydropyranogrebustol-B (7b), 15-(2-(4-hydroxy-3-methylbutyl)- resorcinol-5-yl)-1-(phloroglucinolyl)-9(Z)pentadecen-one (whiteanone) (4), 5,5′-(hexadecan-diyl)bisresorcinol (12) and 2-methyl-5,5′-(8(Z)- hexadecen-1,16-diyl)bisresorcinol (9). This is the first record of pyranobisresorcinols in the genus and the first report of a phloroglucinol terminal phenolic unit in any Grevillea species.

KW - Bisresorcinol

KW - Grebustol-B

KW - Grevillea whiteana

KW - Prenyl substituents

KW - Proteaceae

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M3 - Article

VL - 4

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EP - 958

JO - Natural Product Communications

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SN - 1555-9475

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Wang H, Leach DN, Thomas MC, Blanksby SJ, Forster PI, Waterman PG. Prenylated alkylbisphenols from Grevillea whiteana. Natural Product Communications. 2009;4(7):951-958.