Secondary Metabolite Changes in Tedara (Bituminaria bituminosa L.) Genotypes in Different Growing Period

Abstract

In this study, secondary metabolite amounts of leaf samples belonging to 12 different Bituminaria bituminosa (L.) C.H. Stirtion genotypes were determined at the beginning of growth, budding and at the beginning of flowering periods. Leaf samples belonging to B. bituminosa genotypes were dried under natural conditions and extracted using a microwave system (NEOS). Furanocumarins (psoralen and angelicin), isoflavonoids (daidzein, genistein) and isoflovan glycosides (daidzin and genistin) obtained by LC-MS / MS. While the secondary metabolite contents determined in B. bituminosa differed among growth periods, genotype difference was found to be more effective on these metabolite contents. As a result, all genotypes performed remarkably in terms of secondary metabolites. Besides, the number 12 genotype (Samsun-Kavak) was prominent in terms of angelicin, daidzein, genistein, daidzin, and genistin compared to the other genotypes.

Keywords

• Animal health
• Furanocoumarin
• Isoflavonoid
• Tedera

References

1. Adlercreutz H, Mousavi Y, Loukovaara M & Hämäläinen E (1991). Lignans, isoflavones, sex hormone metabolism and breast cancer. In: R B Hochberg & F Naftolin (Eds.) The New Biology of Steroid Hormones, New York, Raven Press, pp.145–154.
2. Ahandani E A, Abdel Gawwad M R & Yavari A (2013). Extraction and preparation of Psoralen from different plant part of Psoralea corylifolia and Psoralen increasing with some elicitors. Journal of Plant Biology Research 2(1): 25-37.
3. Arjmandi B H, Alekel L, Hollis B W, Amin D, Stacewicz-Sapuntzakis M, Guo P & Kukreja S C (1996). Dietary soybean protein prevents bone loss in an ovariectomized rat model of osteoporosis. The Journal of Nutrition 126(1): 161–67. . https://doi.org/ 10.1093/jn/126.1.161.
4. Alekel D L, Germain A S, Peterson C T, Hanson K B, Stewart J W, Toda T (2000). Isoflavone- rich soy protein isolate attenuates bone loss in the lumbar spine of perimenopausal perimenopausal women. The American Journal of Clinical Nutrition 72(3): 679–80. https://doi.org/10.1093/ajcn/72.3.844.
5. Anderson J J, Ambrose W W & Garner S C (1995). Orally dosed genistein from soy and prevention of cancellous bone loss in two ovariectomized rat models. The Journal of Nutrition 125: 799S.
6. Baskaran P I & Jayabalan N (2001). Effect of growth regulators on rapid micropropagation and psoralen production in Psoralea corylifolia L. Acta Physiologiae Plantarum 30:345–351.
7. Cappelletti E M, Innocenti G & Caporale G (1984). Furocoumarins localization in the fruit and seed of Psoralea corylifolia L. Plantes Medicinales-etPhytotherapie 18: 181-1189. Correal E (2012). Bituminaria bituminosa Workshop, 28-30 Novembe, Sassari/İtalya.
8. Davis PH (1965). Flora of Turkey and The East Aegean Islands. Edinburgh University Press, Edinburgh.

9. Del Río JA, Ortuño A, Pérez I, Bennett RG, Real D et al. (2010). Furanocoumarin content in Bituminaria bituminos a varieties and Cullen s pecies. In : C Porqu eddu & S Ríos (Eds.). The contributions of grasslands to the conservation of Mediterranean biodiversity. Option s Méditerranéennes: Série A. Sémin aires Méditerranéen, pp. 69-70.
10. Hsu Y T, Wu C J, Chen J M, Yang Y C & Wang S Y (2001). The presence of three isoflavonoid compounds in Psoralea corylifolia. Journal of Chromatographic Science 39: 441-444. https://doi.org/10.1093/chromsci/39.10.441.
11. Kallela K, Saastamoinen I, Huokuna E & Hakkola H (1988). Variation in plant oestrogen content between certain red clover cultivars in northern and southern Finland. Suomen Eläinlääkärilehti 94: 287−291.
12. Kittler L, Hradecna Z & Suhnel J (1980). Cross-link formation of phage lambda DNA in situ photochemically induced by the furocoumarin derivative angelicin. Biochim Biophys Acta 607: 215-220. https://doi.org/10.1016/0005-2787(80)90074-x.
13. Li X, Yu C, Hu Y, Xia X, Liao Y, Zhang J, Chen H, Lu W, Zhou W & song Z (2018). New application of psoralen and angelicin on periodontitis with anti-bacterial, anti-inflammatory, and osteogenesis effects. Front Cell Infect Microbiol 5: 8:178. . https://doi.org/10.3389/fcimb.2018.00178.
14. Lojza J, Schulzová V & Hajšlová J (2004). Changes of phytoestrogens daidzein, genistein and their glycosides daidzin and genistin and coumestrol during processing of soyabeans. Czech Journal of Food Sciences 22 (Special Issue): 223-226. . https://doi.org/10.17221/10666-CJFS.
15. Martínez S, Correal E, Real D, Ortuño A Río JA (2010). Bituminaria bituminosa: a source of furanocoumarins of pharmaceutical interest. Drug plants I: 307-322.
16. Milesi S, Massot B, Gontier E, Bourgaud F & Guckert A (2001). Ruta graveolens L.: A promising species for the production of furanocoumarins. Plant Science 161:189-199. https://doi.org/10.1016/S0168-9452(01)00413-7.
17. Mustonen E, Tuori M, Kurki P, Isolahti M, Taponen J & Vanhatalo A (2018). Variety, time of harvest and conditions during growing season have impact on red clover isoflavone content. Agricultural and Food science 27: 102–109.
18. Oliveira A M A G, Manuela M, Raposo M, Oliveira-Campos A M F, Machado A E H, Puapairoj P, Pedro M, Nascimento M S C, Portela C, Afonso C & Madalena P (2006). Psoralen analogues: synthesis, inhibitory activity of growth of human tumor cell lines and computational studies. European Journal of Medicinal Chemistry 41: 367–372. https://doi.org/10.1016/j.ejmech.2005.10.016.
19. Pazos-Navarro M, Del Rı´o J A, Ortun˜o A, Romero-Espinar P, Correal E & Dabauza M (2013). Plant regeneration from different explant types of Bituminaria bituminosa and furanocoumarin content along plant regeneration stages. Plant Growth Regulation 70: 123–129. https://doi.org/10.1007/s10725-013-9784-9.
20. Pecetti L, Tava A, Pagnotta M A & Russi L (2007). Variation in forage quality and chemical composition among Italian accessions of Bituminaria bituminosa (L.) Stirt. Journal of the Science of Food and Agriculture 87: 985–991. https://doi.org/10.1002/jsfa.2792.
21. Pistelli L, Noccioli C, Appendino G, Bianchi F, Sterner O & Ballero M (2003). Pterocarpans from Bituminaria morisiana and Bituminaria bituminosa. Phytochemistry 64: 595–598.
22. Rakhmankulov U & Korotkova E E (1975). Dynamics of furocoumarine content in different parts of Psoralea drupacea. Rastitel, nye-Resursy 11: 98-104.
23. Real D (2012). Tedera a modern model of species domestication and breeding. Booklet. Department of Agriculture and Food Government of Western Australia.
24. Saloniemi H, Wähälä K, Nykänen-Kurki P, Kallela K & Saastamoinen I (1995). Phytoestrogen content and estrogenic effect of legume fodder. Proceedings of the Society for Experimental Biology and Medicine 208: 13−17. https://doi.org/10.3181/00379727-208-43825.
25. Setchell K D R, Lawson A M, Borriello S P, Harkness R, Gordon H, Morgan D M, Kirk D N, Adlercreatz H, Anderson L C & Axelson M (1981). Lignan formation in man-microbial involvement and possible roles in relation to cancer. The Lancet 2: 4–7. https://doi.org/10.1016/S0140-6736(81)90250-6.
26. Sivesind E & Seguin P (2005). Effects of the environment, cultivar, maturity, and preservation method on red clover isoflavone concentration. Journal of Agricultural and Food Chemistry 53: 6397−6402. https://doi.org/10.1021/jf0507487.
27. Tava A, Pecetti L, Ricci M, Pagnotta M A & Russi L (2007). Volatile compounds from leaves and flowers of Bituminaria bituminosa (L.) Stirt. (Fabaceae) from Italy. Flavour Flavour and Fragrance Journal 22: 363–370. https://doi.org/10.1002/ffj.1806.
28. Walker D J, Moñino I & Correal E (2006). Genome size in Bituminaria bituminosa (L.) C.H. Stirton (Fabaceae) populations: Separation of “true” differences from environmental effects on DNA determination. Environmental and Experimental Botany 55: 258–265. https://doi.org/10.1016/j.envexpbot.2004.11.005.