MALONIC PATHWAY and POLYKETIDE PHENOLIC COMPOUNDS Melody A

MALONIC PATHWAY and POLYKETIDE & PHENOLIC COMPOUNDS Melody A. Salvador BS Chemistry for Teachers

Malonic Pathway • primary pathway for the production of secondary metabolites • also known as polyketide pathway • Produces Ø fatty acids Ø quinones Ø phenols Øprostaglandins

Polyketide Biosynthesis

Polyketide Biosynthesis

Polyketide Pathway

Malonic Pathway ketosynthase

Malonic Pathway

Malonic Pathway d e h y d r a t i o n e n o l i z a t i o n

Polyketides • • complex small molecules came from natural sources Antibiotics Ø Ø Ø Erythromicin Refamycin B Oxytetracycline Avermactin FK 506 Doxorubicin Ø Epothilone Ø Geldanamycin Ø Discodermolide Ø

Polyketide Biosynthesis

Polyketide Biosynthesis

Polyketides Erythromicin Refamycin B Oxytetracycline

Polyketides Avermactin FK 506 Doxorubicin

Polyketides Epothilone Geldanamycin Discodermolide

Polyketides Aflotoxins Patulin Zearalenone

Phenolic Compounds • composed of one or more aromatic benzene rings with one or more hydroxyl groups (C-OH) • includes numerous plant compounds that are chemically distinct from terpenes.

Phenolic Compounds • represent a large group of molecules with a variety of functions in; – plants’ growth and development (lignin) – protection (salicylic acid) • also included in signaling molecules, pigments and flavors that can attract or repel insects, fungi or bacteria.

Classification • according to the number of carbon atoms. q phenol qphenolic acid q cinnamic acid q coumarins q. Flavonoids q chalcones q lignin

Phenolic Compounds humulone

Phenolic Compounds malvin

Phenolic Compounds 2, 6 -dimethoxybenzoquinone

Phenolic Compounds juglone

Phenolic Compounds emodin

Phenolic Compounds griseofulvin

Phenolic Compounds Biosynthesis of phloroglucinol

Phenolic Compounds Plumbagin Biosynthesis of plant naphthoquinones

Phenolic Compounds

Phenolic Compounds

Phenolic Compounds qmethyl salicylate q. Raspberry ketone q Thymol (2 -Isopropyl-5 -methyl phenol) q BHT (butylated hydroxy toluene) q Porpolis q Guaiacol (2 -methoxyphenol) q Salicylic acid q Orthophenyl phenol q Phenolphthalein, phenol red, bromothymol blue, thymolphthalein and bromophenol blue

Phenolic Compounds • Spices contain phenolic substances q gallic q tannic q caffeic q chlorogenic q ferulic q vanillic qcinnamic

"Drinking a cup of coffee induces an increase in the resistance of LDL cholesterol to oxidative changes, probably as a result of the incorporation of phenolic acids found in coffee into LDL cholesterol. That caffeine coffee is good or bad?

THANK YOU FOR LISTENING! Salvador, Melody A. IV-BSCT