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Young Soo Keum Miscellaneous Natural Products. Sulfur-Containing N.P. Alkyldisulfide/sulfones Glucosinolates Thiophenes and Related Compounds Cruciferae.

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Presentation on theme: "Young Soo Keum Miscellaneous Natural Products. Sulfur-Containing N.P. Alkyldisulfide/sulfones Glucosinolates Thiophenes and Related Compounds Cruciferae."— Presentation transcript:

1 Young Soo Keum Miscellaneous Natural Products

2 Sulfur-Containing N.P. Alkyldisulfide/sulfones Glucosinolates Thiophenes and Related Compounds Cruciferae phytoalexins

3 Structures of Representative N.P. with Sulfur Allicin SinigrinSinalbin Progoitrin Terthienyl Camalexin

4 Alkyl disulfides and related. Taxanomic distribution Limited to Liliaceae plants Allium cepa Allium sativum

5 Allicin Analogues in Liliaceae Plants

6 Bioactivity of Allicin Antibacterial Antiviral Antimalarial Antioxidant/Cardiovascular activity Anticancer

7 Bioactivity of Allicin: Example

8 Bioactivity of Allicin

9 Biosynthesis of Allicin

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12 Glucosinolates Glucosinolates constitute a natural class of organic compounds that contain sulfur and nitrogen and are derived from glucose and an amino acid Belong to the glucosides. Every glucosinolate contains a central carbon atom, bound via a sulfur atom to the thioglucose group and nitrogen atom to a sulfate group. In addition, the central carbon is bound to a side group; different glucosinolates have different side groups, and it is variation in the side group that is responsible for the variation in the biological activities of these plant compounds. Sinigrin is the precursor to allyl isothiocyanate Glucotropaeolin is the precursor to benzyl isothiocyanate Gluconasturtiin is the precursor to phenethyl isothiocyanate Glucoraphanin is the precursor to sulforaphane

13 Taxanomic Distribution of Glucosinolates Limited to Cruciferae Arabidopsis thalianaRaphanus sativusBrassica campestris

14 Representative Glucosinolates

15 Classification of Glucosinoates Depending on the R-Groups From methionine From Branched A.A. Valine, Leucine, Isoleucine From Aromatic A.A. Phenylalanine Tyrosine Tryptophan

16 Structural Diversities From methionine From Branched A.A.

17 From Aromatic A.A. Structural Diversities

18 Bioactivity of Glucosinolates Anti-nutritive (Iodine-uptake inhibitor) Anti-microbial (antifungal and antibacterial) Anti-cancer Anti-oxidant

19 An Important Process to be Bioactive! Metabolism of Glucosinolates An Important Process to be Bioactive! Catalytic Enzyme: Myrosinase, Unique Thioether-link Cleavage Enzyme

20 Biosynthesis of Glucosinolates Outline 1: Chain-Type R group

21 Biosynthesis of Glucosinolates Outline 2: Chain-Type R group

22 Biosynthesis of Glucosinolates Outline 3: Aromatic R group

23 Biosynthesis of Glucosinolates Example


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