title: A sedge plant as the source of Kangaroo Island propolis rich in prenylated p-coumarate ester and stilbenes.
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.
authors.affiliation: Faculty of Pharmacy, The University of Sydney, New South Wales, Australia. Electronic address: colin.duke@sydney.edu.au.
authors.forename: Colin C
authors.initials: CC
authors.lastname: Duke
authors.affiliation: Faculty of Pharmacy, The University of Sydney, New South Wales, Australia.
authors.forename: Van H
authors.initials: VH
authors.lastname: Tran
authors.affiliation: Department of Pharmacology, Faculty of Medicine, The University of Sydney, New South Wales, Australia.
authors.forename: Rujee K
authors.initials: RK
authors.lastname: Duke
authors.affiliation: Faculty of Pharmacy, The University of Sydney, New South Wales, Australia; Faculty of Pharmacy, Al Ain University of Science and Technology, Abu Dhabi, United Arab Emirates.
authors.forename: Abdallah
authors.initials: A
authors.lastname: Abu-Mellal
authors.affiliation: Botany, School of Environmental and Rural Science, University of New England, Armidale, New South Wales, Australia.
authors.forename: George T
authors.initials: GT
authors.lastname: Plunkett
authors.affiliation: Faculty of Pharmacy, The University of Sydney, New South Wales, Australia.
authors.forename: Douglas I
authors.initials: DI
authors.lastname: King
authors.affiliation: Faculty of Pharmacy, The University of Sydney, New South Wales, Australia.
authors.forename: Kaiser
authors.initials: K
authors.lastname: Hamid
authors.affiliation: National Herbarium of New South Wales, Royal Botanic Gardens and Domain Trust, Sydney, New South Wales, Australia.
authors.forename: Karen L
authors.initials: KL
authors.lastname: Wilson
authors.affiliation: Kings Park & Botanic Garden, West Perth, Western Australia, Australia; The University of Western Australia, Nedlands, Western Australia, Australia; Australian National Herbarium, Centre for Australian National Biodiversity Research, CSIRO, Canberra, Australian Capital Territory, Australia.
authors.forename: Russell L
authors.initials: RL
authors.lastname: Barrett
authors.affiliation: Botany, School of Environmental and Rural Science, University of New England, Armidale, New South Wales, Australia.
authors.forename: Jeremy J
authors.initials: JJ
authors.lastname: Bruhl
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001315:Australia; D001516:Bees; D003374:Coumarins / Q000737:chemistry / Q000302:isolation & purification; D029785:Cyperaceae / Q000737:chemistry*; D007614:Macropodidae; D054876:Prenylation; D011429:Propolis / Q000737:chemistry*; D013267:Stilbenes / Q000737:chemistry / Q000302:isolation & purification*
chemical_list: C551466:3,3',5,5'-tetrahydroxystilbene; D000970:Antineoplastic Agents; D003374:Coumarins; D013267:Stilbenes; C041525:3,3',4,5'-tetrahydroxystilbene; D011429:Propolis
keywords: Anticancer activity; Cyperaceae; Honey bee; Lepidosperma; Prenylated hydroxystilbenes; Propolis