1. Miscellaneous Natural Products
Young Soo Keum

2. 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

3. Natural Lignans in Food!

4. Lignans Backbone Structure of Lignans Furan Furofuran Dibenzylbutane
Dibenzylbutyrolactone
Miscellaneous

5. Backbone Structure of Lignans
Furan
Furofuran

6. Backbone Structure of Lignans
Dibenzylbutane
Dibenzylbutyrolactone

7. Backbone Structure of Lignans
Miscellaneous
Dibenzocyclooctane Lignans from Schisandra chinensis

8. 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

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

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

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

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

13. Bioactivities of Lignans
Enzyme inhibition
Cytochrome P450: Sesamin

14. Bioactivities of Lignans example
Cytochrome P450: Sesamin

15. Bioactivities of Lignans
Anti-allergic/hepatoprotective
Kadsura japonica

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

17. Biosynthesis of Lignans 1

18. Biosynthesis of Lignans 2
Podophyllum hexandrum

19. Biosynthesis of Podophyllotoxin