Quantitative profiling of polyacetylenes in tissue cultures and plant parts of three species of the Asteraceae
- 192 Downloads
Polyacetylenes are a group of fatty-acid derived specialized metabolites with several C–C-triple bonds and derived compounds which are widely distributed in the plant kingdom, but are especially abundant and structurally diverse in the Asteraceae family. Despite their interesting structural and biological properties, the biosynthesis of polyacetylenes is only poorly understood. We have used three species of the Asteraceae (Carthamus tinctorius, Tagetes patula, and Arctium lappa) to compare their suitability for studies of polyacetylene biosynthesis when used after cultivation on soil or as tissue culture. The polyacetylene profiles detected in different plant parts together with information from the literature indicate that C. tinctorius seedlings and flowers as well as T. patula roots and flower buds are major sites of polyacetylene biosynthesis. Highest levels of polyacetylenes were detected in T. patula [about 30 µmol/g dry weight (d.w.) thiophenes in roots] while A. lappa contained less than 1 µmol/g d.w.. Methyljasmonate (MeJ)-induced T. patula hairy root cultures proved to be an excellent source of butenynyl-bithiophene (200 µmol/g d.w., 43 mg/g d.w.) while T. patula flower buds could serve as a source of pentenynyl-bithiophene and α-terthienyl (5–10 µmol/g d.w.) and C. tinctorius flowers or seedlings as a source of polyacetylenic C13 hydrocarbons, the biosynthetic precursors of thiophenes (5–10 µmol/g d.w.). Upon addition of elicitors to tissue cultures, highest elicitation factors (between four and seven) were reached for 1,11-tridecadiene-3,5,7,9-tetrayne in C. tinctorius cell suspension cultures with 40 µM MeJ and α-terthienyl in T. patula hairy root cultures with 100 µM MeJ.
KeywordsCarthamus tinctorius Tagetes patula Arctium lappa Thiophenes α-Terthienyl 1,11-Tridecadiene-3,5,7,9-tetrayne
Dr. Till Beuerle is thanked for advice on compound identification and quantification by GC. Financial support of N.F.A.E. by a PhD Fellowship of the Libyan Government is gratefully acknowledged.
N.F.A.E. designed and performed experiments and analyzed data. U.W. conceived the study with contributions from N.F.A.E., discussed results, and wrote the manuscript based on a draft prepared by N.F.A.E.
Compliance with ethical standards
Conflict of interest
The authors declare that they have no conflict of interest.
- Bohlmann F, Mannhardt HJ (1957) Acetylenverbindungen im Pflanzenreich. In: Zechmeister L (ed) Fortschritte der Chemie Organischer Naturstoffe. Springer, Wien, p 1–70Google Scholar
- Bohlmann F, Burkhardt T, Zdero C (1973) Naturally occurring acetylenes. Academic, LondonGoogle Scholar
- Hjortso M, Mukundan U (1994) Genetic transformation in Tagetes species (marigolds) for thiophene contents. In: Bajaj YPS (ed) Plant protoplasts and genetic engineering V. Biotechnology in agriculture and forestry, vol 29. Springer, Berlin, p 365–382. https://doi.org/10.1007/978-3-662-09366-5_25
- Hinds L, Kenny O, Hossain MB, Walsh D, Sheehy E, Evans P, Gaffney M, Rai DK (2017) Evaluating the antibacterial properties of polyacetylene and glucosinolate compounds with further identification of their presence within various carrot (Daucus carota) and broccoli (Brassica oleracea) cultivars using high-performance liquid chromatography with a diode array detector and ultra performance liquid chromatography–tandem mass spectrometry analyses. J Agric Food Chem 65:7186–7191CrossRefPubMedGoogle Scholar
- Ichihara KI, Noda M (1975) Polyacetylenes from immature seeds of safflower (Carthamus tinctorius L.). Agric Biol Chem 39:1103–1108Google Scholar
- Nakada H, Kobayashi A, Yamashita K (1977) Stereochemistry and biological activity of phytoalexin “safynol” from safflower. Agric Biol Chem 41:1761–1765Google Scholar
- Offringa IA, Melchers LS, Regensburg-Tuink AJG, Costantino P, Schilperoort RA, Hooykaas PJJ (1986) Complementation of Agrobacterium tumefaciens tumor-inducing aux mutants by genes from the T(R)-region of the Ri plasmid of Agrobacterium rhizogenes. Proc Natl Acad Sci USA 83:6935–6939CrossRefPubMedGoogle Scholar
- Pitta-Alvarez SI, Giulietti AM (1999) Influence of chitosan, acetic acid and citric acid on growth and tropane alkaloid production in transformed roots of Brugmansia candida: effect of medium pH and growth phase. Plant Cell Tissue Organ Cult 59:31–38. https://doi.org/10.1023/A:1006359429830 CrossRefGoogle Scholar
- Sambrook J, Fritsch EF, Maniatis T (1989) Molecular cloning: a laboratory manual. Cold Spring Harbor Laboratory Press, New YorkGoogle Scholar
- Schulte KE (1978) Occurence of polyacetylenes—chemistry and biosynthesis. Korean J Pharmacogn 9:11–32Google Scholar
- Šejvčík J (1976) Detectors in gas chromatography. Journal of Chromatography Library, vol 4. Elsevier, AmsterdamGoogle Scholar
- Washino T, Yoshikura M, Obata S (1986) New sulfur-containing acetylenic compounds from Arctium lappa. Agric Biol Chem 50:263–269Google Scholar