MetaCyc Pathway: eudesmol biosynthesis
Inferred from experiment

Enzyme View:

Pathway diagram: eudesmol biosynthesis

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Superclasses: BiosynthesisSecondary Metabolites BiosynthesisTerpenoids BiosynthesisSesquiterpenoids Biosynthesis

Some taxa known to possess this pathway include : Atractylodes lancea, Eucalyptus piperita, Guatteriopsis blepharophylla, Guatteriopsis friesiana, Guatteriopsis hispida, Hedychium, Magnolia obovata, Zingiber zerumbet

Expected Taxonomic Range: Viridiplantae

Eudesmol was first identified in Eucalyptus piperita in 1920's, it occurs in the eucalyptus oil in both the liquid and crystal forms [Baker20]. It is also found in a many other plants. Eudesmol is a bicyclic sesquiterpenoid. It has several interesting biological properties and is being investigated as an bioctive agent. It is an effective insect repellent, plant species emit 2-(Decahydro-4a-methyl-1-methylenenaphthalen-7-yl)-propan-2-ol which deter pests.

α-eudesmol is a potent inhibitor of presynaptic omega-agatoxin IVA-sensitive (P/Q-type) Ca(2+) channel. It acts as a channel blocker and is being studied as a useful drug for the treatment of neurogenic inflammation in the trigemino-vascular system, particularly migraine [Asakura00].

β-eudesmol has been isolated from rhizomes of Hedychium spp [Luo09] and Atractylodes lancea [Duan08]. α-humulene, α-humulene and 10-epi-γ-eudesmol are present in significant quantities in the esstential oils of Guatteriopsis blepharophylla and related species and they are considered to contribute to the antimicrobial properties of this oil [Costa08].

The eudesmols in the Japanese herbal extract from barks of Magnolia obovata, along with other consituents are shown to be involved in the inhibition of nitric oxide production in lipopolysaccharide-activated macrophages [Matsuda01].

Very little is known about the biosynthetic route of these sesquiterpenoids and in this pathway the depiction of the reactions catalyzed by zerumbone biosynthesis beta eudesmol synthase in Zingiber zerumbet rhizome bracts indicate that it may be a multifunctional synthase [Yu08b].

Created 10-Jun-2009 by Pujar A, Boyce Thompson Institute


Asakura00: Asakura K, Kanemasa T, Minagawa K, Kagawa K, Yagami T, Nakajima M, Ninomiya M (2000). "alpha-eudesmol, a P/Q-type Ca(2+) channel blocker, inhibits neurogenic vasodilation and extravasation following electrical stimulation of trigeminal ganglion." Brain Res 873(1);94-101. PMID: 10915814

Baker20: Baker, R.T, Smith, H.G (1920). "A Research On The Eucalypts Of Tasmania And Their Essential Oils." Authority of The Government Of The State Of New South Wales, 2nd Edition.

Costa08: Costa EV, Teixeira SD, Marques FA, Duarte MC, Delarmelina C, Pinheiro ML, Trigo JR, Sales Maia BH (2008). "Chemical composition and antimicrobial activity of the essential oils of the Amazon Guatteriopsis species." Phytochemistry 69(9);1895-9. PMID: 18495186

Duan08: Duan JA, Wang L, Qian S, Su S, Tang Y (2008). "A new cytotoxic prenylated dihydrobenzofuran derivative and other chemical constituents from the rhizomes of Atractylodes lancea DC." Arch Pharm Res 31(8);965-9. PMID: 18787781

Luo09: Luo M, Lei L, Lin H (2009). "[Studies on chemical constituents from rhizomes of Hedychium chrysoleucum]." Zhongguo Zhong Yao Za Zhi 34(2);180-2. PMID: 19385181

Matsuda01: Matsuda H, Kageura T, Oda M, Morikawa T, Sakamoto Y, Yoshikawa M (2001). "Effects of constituents from the bark of Magnolia obovata on nitric oxide production in lipopolysaccharide-activated macrophages." Chem Pharm Bull (Tokyo) 49(6);716-20. PMID: 11411523

Yu08b: Yu F, Harada H, Yamasaki K, Okamoto S, Hirase S, Tanaka Y, Misawa N, Utsumi R (2008). "Isolation and functional characterization of a beta-eudesmol synthase, a new sesquiterpene synthase from Zingiber zerumbet Smith." FEBS Lett 582(5);565-72. PMID: 18242187

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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