dehydroabietic acid biosynthesis

Kersten PJ, Kopper BJ, Raffa KF, Illman BL. Rapid Analysis of Abietanes in Conifers. Journal of Chemical Ecology. 2006 Nov 03;32(12):2679–85. doi: 10.1007/s10886-006-9191-z.; Ro DK, Bohlmann J. Diterpene resin acid biosynthesis in loblolly pine (Pinus taeda): functional characterization of abietadiene/levopimaradiene synthase (PtTPS-LAS) cDNA and subcellular targeting of PtTPS-LAS and abietadienol/abietadienal oxidase (PtAO, CYP720B1). Phytochemistry. 2006 Aug;67(15):1572–8. doi: 10.1016/j.phytochem.2006.01.011. PMID: 16497345.; Ro D, Arimura G, Lau SYW, Piers E, Bohlmann J. Loblolly pine abietadienol/abietadienal oxidase PtAO (CYP720B1) is a multifunctional, multisubstrate cytochrome P450 monooxygenase. Proc. Natl. Acad. Sci. U.S.A. 2005 May 23;102(22):8060–5. doi: 10.1073/pnas.0500825102.; Trapp S, Croteau R. DEFENSIVE RESIN BIOSYNTHESIS IN CONIFERS. Annu. Rev. Plant. Physiol. Plant. Mol. Biol. 2001 Jun;52(1):689–724. doi: 10.1146/annurev.arplant.52.1.689.; Tomlin ES, Antonejevic E, Alfaro RI, Borden JH. Changes in volatile terpene and diterpene resin acid composition of resistant and susceptible white spruce leaders exposed to simulated white pine weevil damage. Tree Physiol. 2000 Oct;20(16):1087–95. doi: 10.1093/treephys/20.16.1087. PMID: 11269960.; Lafever RE, Vogel BS, Croteau R. Diterpenoid Resin Acid Biosynthesis in Conifers: Enzymatic Cyclization of Geranylgeranyl Pyrophosphate to Abietadiene, the Precursor of Abietic Acid. Archives of Biochemistry and Biophysics. 1994 Aug;313(1):139–49. doi: 10.1006/abbi.1994.1370.

Metabolites

(-)-Abietadiene

Formula: C20H32 (272.2503872)

CAS ID: 35241-40-8

Dehydroabietic acid

Formula: C20H28O2 (300.2089188)

CAS ID: 1740-19-8

H+

Formula: H (1.0078246)

CAS ID: 12408-02-5

H2O

Formula: H2O (18.0105642)

CAS ID: 7732-18-5

Oxygen

Formula: O2 (31.98983)

CAS ID: 7782-44-7

5alpha,9alpha,10beta-labda-8(20),13-dien-15-yl diphosphate(3-)

Formula: C20H33O7P2 (447.1701428)

CAS ID:

2-trans,6-trans,10-trans-geranylgeranyl diphosphate(3-)

Formula: C20H33O7P2 (447.1701428)

CAS ID:

NADPH(4-)

Formula: C21H26N7O17P3 (741.0598016)

CAS ID: 53-57-6

NADP(3-)

Formula: C21H25N7O17P3 (740.051977)

CAS ID: 53-59-8



Enzyme

EC Number name full name note
1.14.14.145 abieta-7,13-dien-18-ol hydroxylase abieta-7,13-dien-18-ol,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (18-hydroxylating)
4.2.3.132 neoabietadiene synthase (+)-copaly-diphosphate diphosphate-lyase (cyclizing, neoabietadiene-forming)
4.2.3.18 abieta-7,13-diene synthase (+)-copalyl-diphosphate diphosphate-lyase [cyclizing, abieta-7,13-diene-forming]
4.2.3.32 levopimaradiene synthase (+)-copalyl-diphosphate diphosphate-lyase [abieta-8(14),12-diene-forming]
4.2.3.44 isopimara-7,15-diene synthase copalyl diphosphate-lyase (isopimara-7,15-diene-forming)
5.5.1.12 copalyl diphosphate synthase (+)-copalyl-diphosphate lyase (decyclizing)


Pathway Source

Organism Taxonomy Group Enzyme List Source Ratio
Streptomyces anulatus bacteria 5.5.1.12 16.67%
Talaromyces verruculosus MAGs 5.5.1.12 16.67%
Diaporthe amygdali fungi 5.5.1.12 16.67%
Streptomyces cyslabdanicus bacteria 5.5.1.12 16.67%