Methyl jasmonate elicits the production of methyl (E)-2-hexenoate from (Z)-2-hexenol via (Z)-2-hexenal in Achyranthes bidentata plant.

Methyl jasmonate elicits the production of methyl (E)-2-hexenoate from (Z)-2-hexenol via (Z)-2-hexenal in Achyranthes bidentata plant.

FEBS letters (2015-01-13)

Shigeru Tamogami, Koji Noge, Ganesh K Agrawal, Randeep Rakwal

ABSTRACT

The medicinal herbal plant Achyranthes bidentata (A. bidentata) produces the sweet-odor ester - methyl (E)-2-hexenoate (1) as the major volatile in response to methyl jasmonate (MeJA). Here, we investigated the biosynthetic pathway of methyl (E)-2-hexenoate (1). The common plant precursor (Z)-3-hexenal was only slightly metabolized into methyl (E)-2-hexenoate (1), and its application scarcely enhanced the production of this ester. By contrast, a structurally related alcohol, (Z)-2-hexenol, as well as a deuteride derivative thereof could be efficiently metabolized into methyl (E)-2-hexenoate (1). Thus, we hypothesize that A. bidentata possess a specific pathway for the production of methyl (E)-2-hexenoate (1) from (Z)-2-hexenol in response to MeJA.

MATERIALS

Product Number

Brand

Product Description

178810

Sigma-Aldrich

Tetrahydrofuran, ReagentPlus^®, ≥99.0%, contains 250 ppm BHT as inhibitor

360589

Sigma-Aldrich

Tetrahydrofuran, contains 250 ppm BHT as inhibitor, ACS reagent, ≥99.0%

224316

Sigma-Aldrich

Zirconyl chloride octahydrate, reagent grade, 98%

87368

Sigma-Aldrich

Tetrahydrofuran, contains 250 ppm BHT as inhibitor, puriss. p.a., ACS reagent, reag. Ph. Eur., ≥99.9%

34865

Sigma-Aldrich

Tetrahydrofuran, inhibitor-free, suitable for HPLC, ≥99.9%

630829

Sigma-Aldrich

2-Hexyn-1-ol, 97%

78445

Supelco

Tetrahydrofuran, analytical standard

87369

Supelco

Tetrahydrofuran, Selectophore^™, ≥99.5%

401757

Sigma-Aldrich

Tetrahydrofuran, anhydrous, ≥99.9%, inhibitor-free

190144

Sigma-Aldrich

Pyridinium chlorochromate, 98%

270385

Supelco

Tetrahydrofuran, HPLC grade, ≥99.9%, inhibitor-free

186562

Sigma-Aldrich

Tetrahydrofuran, anhydrous, contains 250 ppm BHT as inhibitor, ≥99.9%

244430

Sigma-Aldrich

3-Hexyn-1-ol, 98%

PHR1561

Supelco

Tetrahydrofuran, Pharmaceutical Secondary Standard; Certified Reference Material

676764

Sigma-Aldrich

Tetrahydrofuran, ACS reagent, ≥99.0%, contains 250 ppm BHT as inhibitor

66742

Supelco

Dichloromethane, Selectophore^™, ≥99.5%

439223

Sigma-Aldrich

Dichloromethane, suitable for HPLC, ≥99.9%, contains 40-150 ppm amylene as stabilizer

270997

Sigma-Aldrich

Dichloromethane, anhydrous, ≥99.8%, contains 40-150 ppm amylene as stabilizer

34856

Sigma-Aldrich

Dichloromethane, suitable for HPLC, ≥99.8%, contains amylene as stabilizer

PHR1557

Supelco

Methylene Chloride, Pharmaceutical Secondary Standard; Certified Reference Material

02575

Supelco

Dichloromethane, analytical standard

650463

Sigma-Aldrich

Dichloromethane, HPLC Plus, for HPLC, GC, and residue analysis, ≥99.9%, contains 50-150 ppm amylene as stabilizer

676853

Sigma-Aldrich

Dichloromethane, ACS reagent, ≥99.5%, contains 40-150 ppm amylene as stabilizer

D65100

Sigma-Aldrich

Dichloromethane, contains 40-150 ppm amylene as stabilizer, ACS reagent, ≥99.5%

494453

Sigma-Aldrich

Dichloromethane, biotech. grade, 99.9%, contains 40-150 ppm amylene as stabilizer

24233

Sigma-Aldrich

Dichloromethane, puriss., meets analytical specification of Ph. Eur., NF, ≥99% (GC)

320269

Sigma-Aldrich

Dichloromethane, ACS reagent, ≥99.5%, contains 40-150 ppm amylene as stabilizer

32222

Sigma-Aldrich

Dichloromethane, puriss. p.a., ACS reagent, reag. ISO, ≥99.9% (GC)