coumarin biosynthesis (via 2-coumarate)

Curini M, Cravotto G, Epifano F, Giannone G. Chemistry and biological activity of natural and synthetic prenyloxycoumarins. Curr Med Chem. 2006;13(2):199–222. doi: 10.2174/092986706775197890. PMID: 16472213.; Lacy A, O'Kennedy R. Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer. Curr Pharm Des. 2004;10(30):3797–811. doi: 10.2174/1381612043382693. PMID: 15579072.; Fylaktakidou KC, Hadjipavlou-Litina DJ, Litinas KE, Nicolaides DN. Natural and synthetic coumarin derivatives with anti-inflammatory/ antioxidant activities. Curr Pharm Des. 2004;10(30):3813–33. doi: 10.2174/1381612043382710. PMID: 15579073.; Oba K, Conn EE, Canut H, Boudet AM. Subcellular Localization of 2-(beta-d-Glucosyloxy)-Cinnamic Acids and the Related beta-glucosidase in Leaves of Melilotus alba Desr. Plant Physiol. 1981 Dec;68(6):1359–63. PMID: 16662108; PMCID: PMC426103.; Poulton JE, McRee DE, Conn EE. Intracellular Localization of Two Enzymes Involved in Coumarin Biosynthesis in Melilotus alba. Plant Physiol. 1980 Feb 01;65(2):171–5. doi: 10.1104/pp.65.2.171.; Gestetner B, Conn EE. The 2-hydroxylation of trans-cinnamic acid by chloroplasts from Melilotus alba desr. Archives of Biochemistry and Biophysics. 1974 Aug;163(2):617–24. doi: 10.1016/0003-9861(74)90522-0.; Kleinhofs A, Haskins FA, Gorz HJ. Ultraviolet-induced isomerization of beta-D-glucosyl omicron-hydroxycinnamic acid on filter paper. J Chromatogr. 1966 Apr;22(1):184–6. doi: 10.1016/s0021-9673(01)97086-4. PMID: 5921806.; Haskins FA, Williams LG, Gorz HJ. Light-Induced Trans to Cis Conversion of ß-d-Glucosyl o-Hydroxycinnamic Acid in Melilotus alba Leaves. Plant Physiol. 1964 Sep 01;39(5):777–81. doi: 10.1104/pp.39.5.777.; Stoker JR. The biosynthesis of coumarin in Melilotus alba. Biochemical and Biophysical Research Communications. 1963 Dec;14(1):17–20. doi: 10.1016/0006-291x(63)90203-1.; Stoker JR, Bellis DM. The Biosynthesis of Coumarin in Melilotus Alba. Journal of Biological Chemistry. 1962 Jul;237(7):2303–5. doi: 10.1016/s0021-9258(19)63437-x.; Kosuge T. Studies on the identity of bound coumarin in sweet clover. Archives of Biochemistry and Biophysics. 1961 Nov;95(2):211–8. doi: 10.1016/0003-9861(61)90137-0.; KOUKOL J, CONN EE. The metabolism of aromatic compounds in higher plants. IV. Purification and properties of the phenylalanine deaminase of Hordeum vulgare. J Biol Chem. 1961 Oct;236():2692–8. PMID: 14458851.; Kosuge T, Conn EE. The Metabolism of Aromatic Compounds in Higher Plants. Journal of Biological Chemistry. 1959 Aug;234(8):2133–7. doi: 10.1016/s0021-9258(18)69879-5.

Metabolites

beta-D-Glucose

Formula: C6H12O6 (180.0633852)

CAS ID: 492-61-5

Copper

Formula: Cu (62.929599)

CAS ID: 7440-50-8

Coumarin

Formula: C9H6O2 (146.0367776)

CAS ID: 91-64-5

H+

Formula: H (1.0078246)

CAS ID: 12408-02-5

H2O

Formula: H2O (18.0105642)

CAS ID: 7732-18-5

Mercury(2+)

Formula: Hg (201.970632)

CAS ID: 14302-87-5

Oxygen

Formula: O2 (31.98983)

CAS ID: 7782-44-7

Zinc cation

Formula: Zn (63.929145)

CAS ID: 23713-49-7

cinnamate

Formula: C9H7O2 (147.0446022)

CAS ID: 4151-45-5

NADPH(4-)

Formula: C21H26N7O17P3 (741.0598016)

CAS ID: 53-57-6

UDP(3-)

Formula: C9H11N2O12P2 (400.9787246)

CAS ID: 86527-70-0

NADP(3-)

Formula: C21H25N7O17P3 (740.051977)

CAS ID: 53-59-8



Enzyme

EC Number name full name note
3.2.1.21 beta-glucosidase beta-D-glucoside glucohydrolase


Proteins

Protein ID name full name