Miscellaneous Natural Products

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Presentation transcript:

Miscellaneous Natural Products Young Soo Keum

Definition of Natural Lignans -Lignans are a class of secondary plant metabolites produced by oxidative dimerization of two phenylpropanoid units. The term lignan is applied to the optically active dimers of phenylpropanoids linked by the central carbon atoms of their side chains. -Derived from phenylalanine via dimerization of substituted cinnamic alcohols (see cinnamic acid), known as monolignols, to a dibenzylbutane skeleton. -This reaction is catalyzed by oxidative enzymes and is often controlled by divergent proteins

Natural Lignans in Food!

Lignans Backbone Structure of Lignans Furan Furofuran Dibenzylbutane Dibenzylbutyrolactone Miscellaneous

Backbone Structure of Lignans Furan Furofuran

Backbone Structure of Lignans Dibenzylbutane Dibenzylbutyrolactone

Backbone Structure of Lignans Miscellaneous Dibenzocyclooctane Lignans from Schisandra chinensis

Taxanomic Distribution Thymelaeaceae (팥꽃나무과): Daphne genkwa (팥꽃나무) Oleaceae (물푸레나무과): Forsythia koreana (개나리) Compositae (국화과): Aster spp. (국화 및 근연종) Apocynaceae (협죽도과): Nerium oleander Euphorbiaceae (대극과): Ricinus communis (피마자) Rutaceae (운향과): Zanthoxylum spp. (산초) Pinaceae (소나무과): Pinus spp. (소나무) Cupressaceae (측백나무과): Chamaecyparis obtusa (편백) Araucariaceae (남양삼나무과): Araucaria spp. Podocarpaceae (나한송과): Podocarpus spp. (나한송) Schisandraceae (오미자과): Schisandra chinensis (오미자) Linaceae (아마과): Linum usitatissimum (아마) Berberidaceae (매자나무과): Podophyllum spp. Many others

Bioactivities of Lignans Anticancer : Podophyllotoxins Anti-inflammatory: 5’-Methoxyyatein Antimicrobial: Justicidin B Antioxidant: Schisandra lignans Immunosuppresive: Nemerosin Enzyme inhibition: Sesamin

Bioactivities of Lignans Anticancer R = Me, Justicidin A Justicia procumbens (쥐꼬리망초)

Bioactivities of Lignans Anticancer Arctium lappa, Centaurea imperialis, Trachelospermum asiaticum, Saussurea heteromalla, Forsythia viridissima Arctium lappa

Bioactivities of Lignans Anti-inflammatory Acanthopanax chiisanensis (지리오가피) Helioxanthin

Bioactivities of Lignans Enzyme inhibition Cytochrome P450: Sesamin

Bioactivities of Lignans example Cytochrome P450: Sesamin

Bioactivities of Lignans Anti-allergic/hepatoprotective Kadsura japonica

Biosynthesis of Lignans 1 Biosynthesis of Sesamin from Sesamum indicum Biosynthesis of Sesamin: Aspects of Life Stage

Biosynthesis of Lignans 1

Biosynthesis of Lignans 2 Podophyllum hexandrum

Biosynthesis of Podophyllotoxin