A sedge plant as the source of Kangaroo Island propolis rich in prenylated p-coumarate ester and stilbenes

Colin C. Duke, Van H. Tran, Rujee K. Duke, Abdallah Abu-Mellal, George T. Plunkett, Douglas I. King, Kaiser Hamid, Karen L. Wilson, Russell L. Barrett, Jeremy J. Bruhl

Research output: Contribution to journalArticle

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Abstract

Propolis samples from Kangaroo Island, South Australia, were investigated for chemical constituents using high-field nuclear magnetic resonance spectral profiling. A type of propolis was found containing a high proportion of prenylated hydroxystilbenes. Subsequently, the botanical origin of this type of propolis was identified using a beehive propolis depletion method and analysis of flora. Ligurian honey bees, Apis mellifera ligustica Spinola, were found to produce propolis from resin exuded by the Australian native sedge plant Lepidosperma sp. Montebello (Cyperaceae). The plants, commonly known as sword sedge, were found to have resin that matched with the propolis samples identified as the most abundant propolis type on the island containing C- and O-prenylated tetrahydroxystilbenes (pTHOS) in addition to a small amount of prenylated p-coumarate. The isolation of five pTHOS not previously characterized are reported: (E)-4-(3-methyl-2-buten-1-yl)-3,4′,5-trihydroxy-3′-methoxystilbene, (E)-2,4-bis(3-methyl-2-buten-1-yl)-3,3′,4′,5-tetrahydroxystilbene, (E)-2-(3-methyl-2-buten-1-yl)-3-(3-methyl-2-butenyloxy)-3′,4′,5-trihydroxystilbene, (E)-2,6-bis(3-methyl-2-buten-1-yl)-3,3′,5,5′-tetrahydroxystilbene and (E)-2,6-bis(3-methyl-2-buten-1-yl)-3,4′,5-trihydroxy-3′-methoxystilbene. A National Cancer Institute 60 human cell line anticancer screen of three of these compounds showed growth inhibitory activity. The large Australasian genus Lepidosperma is identified as a valuable resource for the isolation of substances with medicinal potential. © 2016 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license

Original languageEnglish
Pages (from-to)87-97
Number of pages11
JournalPhytochemistry
Volume134
Early online date24 Nov 2016
DOIs
Publication statusPublished - 1 Feb 2017

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Propolis
Macropodidae
Stilbenes
propolis
stilbenes
Islands
Esters
esters
Bees
resins
Cyperaceae
Ligusticum
Resins
Apis mellifera ligustica
beehives
South Australia
human cell lines
Honey
National Cancer Institute (U.S.)
Licensure

Cite this

Duke, C. C., Tran, V. H., Duke, R. K., Abu-Mellal, A., Plunkett, G. T., King, D. I., ... Bruhl, J. J. (2017). A sedge plant as the source of Kangaroo Island propolis rich in prenylated p-coumarate ester and stilbenes. Phytochemistry, 134, 87-97. https://doi.org/10.1016/j.phytochem.2016.11.005
Duke, Colin C. ; Tran, Van H. ; Duke, Rujee K. ; Abu-Mellal, Abdallah ; Plunkett, George T. ; King, Douglas I. ; Hamid, Kaiser ; Wilson, Karen L. ; Barrett, Russell L. ; Bruhl, Jeremy J. / A sedge plant as the source of Kangaroo Island propolis rich in prenylated p-coumarate ester and stilbenes. In: Phytochemistry. 2017 ; Vol. 134. pp. 87-97.
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abstract = "Propolis samples from Kangaroo Island, South Australia, were investigated for chemical constituents using high-field nuclear magnetic resonance spectral profiling. A type of propolis was found containing a high proportion of prenylated hydroxystilbenes. Subsequently, the botanical origin of this type of propolis was identified using a beehive propolis depletion method and analysis of flora. Ligurian honey bees, Apis mellifera ligustica Spinola, were found to produce propolis from resin exuded by the Australian native sedge plant Lepidosperma sp. Montebello (Cyperaceae). The plants, commonly known as sword sedge, were found to have resin that matched with the propolis samples identified as the most abundant propolis type on the island containing C- and O-prenylated tetrahydroxystilbenes (pTHOS) in addition to a small amount of prenylated p-coumarate. The isolation of five pTHOS not previously characterized are reported: (E)-4-(3-methyl-2-buten-1-yl)-3,4′,5-trihydroxy-3′-methoxystilbene, (E)-2,4-bis(3-methyl-2-buten-1-yl)-3,3′,4′,5-tetrahydroxystilbene, (E)-2-(3-methyl-2-buten-1-yl)-3-(3-methyl-2-butenyloxy)-3′,4′,5-trihydroxystilbene, (E)-2,6-bis(3-methyl-2-buten-1-yl)-3,3′,5,5′-tetrahydroxystilbene and (E)-2,6-bis(3-methyl-2-buten-1-yl)-3,4′,5-trihydroxy-3′-methoxystilbene. A National Cancer Institute 60 human cell line anticancer screen of three of these compounds showed growth inhibitory activity. The large Australasian genus Lepidosperma is identified as a valuable resource for the isolation of substances with medicinal potential. {\circledC} 2016 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license",
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Duke, CC, Tran, VH, Duke, RK, Abu-Mellal, A, Plunkett, GT, King, DI, Hamid, K, Wilson, KL, Barrett, RL & Bruhl, JJ 2017, 'A sedge plant as the source of Kangaroo Island propolis rich in prenylated p-coumarate ester and stilbenes' Phytochemistry, vol. 134, pp. 87-97. https://doi.org/10.1016/j.phytochem.2016.11.005

A sedge plant as the source of Kangaroo Island propolis rich in prenylated p-coumarate ester and stilbenes. / Duke, Colin C.; Tran, Van H.; Duke, Rujee K.; Abu-Mellal, Abdallah; Plunkett, George T.; King, Douglas I.; Hamid, Kaiser; Wilson, Karen L.; Barrett, Russell L.; Bruhl, Jeremy J.

In: Phytochemistry, Vol. 134, 01.02.2017, p. 87-97.

Research output: Contribution to journalArticle

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AU - Tran, Van H.

AU - Duke, Rujee K.

AU - Abu-Mellal, Abdallah

AU - Plunkett, George T.

AU - King, Douglas I.

AU - Hamid, Kaiser

AU - Wilson, Karen L.

AU - Barrett, Russell L.

AU - Bruhl, Jeremy J.

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N2 - Propolis samples from Kangaroo Island, South Australia, were investigated for chemical constituents using high-field nuclear magnetic resonance spectral profiling. A type of propolis was found containing a high proportion of prenylated hydroxystilbenes. Subsequently, the botanical origin of this type of propolis was identified using a beehive propolis depletion method and analysis of flora. Ligurian honey bees, Apis mellifera ligustica Spinola, were found to produce propolis from resin exuded by the Australian native sedge plant Lepidosperma sp. Montebello (Cyperaceae). The plants, commonly known as sword sedge, were found to have resin that matched with the propolis samples identified as the most abundant propolis type on the island containing C- and O-prenylated tetrahydroxystilbenes (pTHOS) in addition to a small amount of prenylated p-coumarate. The isolation of five pTHOS not previously characterized are reported: (E)-4-(3-methyl-2-buten-1-yl)-3,4′,5-trihydroxy-3′-methoxystilbene, (E)-2,4-bis(3-methyl-2-buten-1-yl)-3,3′,4′,5-tetrahydroxystilbene, (E)-2-(3-methyl-2-buten-1-yl)-3-(3-methyl-2-butenyloxy)-3′,4′,5-trihydroxystilbene, (E)-2,6-bis(3-methyl-2-buten-1-yl)-3,3′,5,5′-tetrahydroxystilbene and (E)-2,6-bis(3-methyl-2-buten-1-yl)-3,4′,5-trihydroxy-3′-methoxystilbene. A National Cancer Institute 60 human cell line anticancer screen of three of these compounds showed growth inhibitory activity. The large Australasian genus Lepidosperma is identified as a valuable resource for the isolation of substances with medicinal potential. © 2016 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license

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