Abstract
Three lines of hairy root culture of Ambrosia maritima induced by Agrobacterium rhizogenes ATCC15834 were established. Thiarubrine A, thiarubrine A epoxide, thiarubrine A diol and their precursor pentayneene were produced by the hairy roots after elicitation with methyl jasmonate, the common signal molecule in the plant defense and development. Thiarubrine A diol was the main form detected in the medium. Maximum yield was achieved when the 13-day-old hairy root cultures were exposed to 40 μM methyl jasmonate for 72 h. Callus and cell suspension cultures were established and maintained on Murashige and Skoog medium supplied with α-naphthylacetic acid (NAA) and kinetin. When the cell suspension cultures were elicited with methyl jasmonate, pentayneene was the only polyacetylene produced. The yield of pentayneene in hairy root cultures was much higher (9.6 times) than that of cell suspension cultures.
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Abbreviations
- DEPT:
-
distortionless enhancement by polarization transfer
- FAB-MS:
-
fast atom bombardment mass spectroscopy
- HMBC:
-
heteronuclear multiple bond correlation
- MeJ:
-
methyl jasmonate
References
LM Abou Basha MH El Sayed AF Allam MM Osman (1992) ArticleTitleThe effects of Ambrosia maritima on the viability of Lymnaea Cailliaudi; an experimental study J. Egypt. Soc. Parasit. 24 513–517
RRJ Arroo APM Brouwer ParticleDe AF Croes GJ Wullems (1995) ArticleTitleThiophene interconversion in elicitor-treated roots of Tagetes patula L Plant Cell Rep. 15 133–137
J Bakker FJ Gommers I Nieuwenhuis H Wunberg (1979) ArticleTitlePhotoactivation of the nematicidal compound α-terthienyl from roots of marigolds (Tagetes species) J. Biol. Chem. 254 1841–1847
SG Bhagwath MA Hjortso (2000) ArticleTitleStatistical analysis of elicitation strategies for thiarubrine A production in hairy root cultures of Ambrosia artemisiifolia J. Biotech 80 159–167
F Bohlmann K Kleine (1965) ArticleTitleUber rote naturliche schwefelaceylenverbin dungen Chem. Ber. 98 3081–3086
F Bohlmann T Burkhardt C Zdero (1973) Naturally Occurring Acetylenes Academic Press London
F Bourgaud V Bouque E Gontier A Guckert (1997) ArticleTitleHairy root cultures for the production of secondary metabolites AgBiotech News Inform 9 205N–208N
GFQ Chan GHN Towers JC Mitchell (1975) ArticleTitleUltraviolet mediated antibiotic activity of thiophene compounds of Tagetes Phytochemistry 14 2295–2296
RA Creelman JE Mullet (1995) ArticleTitleJasmonic acid distribution and action in plant: regulation during development and response to biotic and abiotic stress Proc. Natl. Acad. Sci. 92 4114–4119
SM Ellis F Balza P Constabel JB Hudson GHN Towers (1995) Thiarubrines: novel dithiacyclohexadiene polyne photosensitizers from higher plants JR Heitz KR Downum (Eds) Light-Activated Pest Control American Chemical Society Washington, DC 165–178
ML Gomez-barrios FJ Parodi D Vargas L Quijano MA Hjortso HE Flores NH Fischer (1992) ArticleTitleStudies on the biosynthesis of thiarubrine A in hairy root cultures of Ambrosia artemisiifolia using 13C-labelled acetates Phytochemistry 31 2703–2707
G Guillet GJR Philogene J O’Meara T Durst JT Arnason (1997) ArticleTitleMultiple modes of insecticidal action of three classes of polyacetylene derivatives from Rudbeckia hirta Phytochemistry 46 495–498
JB Hudson EA Graham N Miki GHN Towers LL Hudson R Rossi A Carpita D Neri (1989) ArticleTitlePhotoactive antiviral and cytotoxic activities of synthetic thiophenes and their acetylenic derivatives Chemosphere 19 1329–1343
S Iyengar JT Arnason BJR Philogene P Murand NH Werstink G Timmins (1987) ArticleTitleToxicokinetics of the phototoxic allelochemical α-terthienyl in three herbivorous Lepidoptera Pestic. Biochem. Physiol. 29 1–9
NR Lersten JD Curtis (1989) ArticleTitlePolyacetylene reservoir developments in Ambrosia trifida staminate flowers Amer. J. Botany 76 1000–1005
Misawa M (1994) Plant tissue culture: an alternative for production of useful metabolites. FAO Agricultural Services Bulletin 108
JT Mortensen JS Soerensen NA Sorerensen (1964) ArticleTitleStudies related to naturally occuring acetylene compounds Acta Chem. Scand. 18 2392–2394
T Murashige F Skoog (1962) ArticleTitleA revised medium for rapid growth and bioassays with tobacco cultures Physiol. Plant. 15 473–497
K Saito M Yamazaki I Murakoshi (1992) ArticleTitleTransgenic medicinal plants: Agrobacterium-mediated foreign gene transfer and production of secondary metabolites J. Nat. Prod. 55 149–162
L Toivonen (1993) ArticleTitleUtilization of hairy root cultures for production of secondary metabolites Biotech. Prog. 9 12–20
GHN Towers Z Abramowski AJ Finlayson A Zuconi (1985) ArticleTitleAntibiotic properties of thiarubrine A, a naturally occurring dithiacyclohexadiene polyine Planta Med. 51 225–229
Towers GHN, Bruening RC, Balza F, Abramowski Z & Lopez-Bazzochi I (1993) Thiarubrine antifungal agents. U.S. Patent 5,202,348
Troung TV, Bierer DE, Dener JM, Hector R, Tempesta MS, Love B, Yang W & Koreeda M (1997) Novel 1,2-dithiin antiinfective agents. U.S. Patent 5,668,168
Y Wang M Koreeda (1998) ArticleTitleChemistry of 1,2-dithiins. Synthesis of the potent antibiotic thiarubrine A J. Org. Chem. 63 8644–8645
L Fits Particlevan der J Memelink (2000) ArticleTitleORCA3, a jasmonate-responsive transcriptional regulator of plant primary and secondary metabolism Science 289 295–297 Occurrence Handle10.1126/science.289.5477.295 Occurrence Handle10894776
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Zid, S.A., Orihara, Y. Polyacetylenes accumulation in Ambrosia maritima hairy root and cell cultures after elicitation with methyl jasmonate. Plant Cell Tiss Organ Cult 81, 65–75 (2005). https://doi.org/10.1007/s11240-004-2776-8
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DOI: https://doi.org/10.1007/s11240-004-2776-8