In search of photosensitising compounds in the annual forage legume Biserrula pelecinus L.
E. Swinny A , C. K. Revell B C D , N. Campbell A , E. Spadek A and C. Russo A
+ Author Affiliations
- Author Affiliations
A ChemCentre, Resources and Chemistry Precinct, Level 2, South Wing, Building 500, Cnr Manning Road and Townsing Drive, Bentley, WA 6102, Australia.
B Department of Agriculture and Food Western Australia, 3 Baron-Hay Court, South Perth, WA 6151, Australia.
C Centre for Plant Genetics and Breeding, University of Western Australia, 35 Stirling Highway, Crawley, WA 6009, Australia.
D Corresponding author. Email: clinton.revell@agric.wa.gov.au
Crop and Pasture Science 66(11) 1161-1166 https://doi.org/10.1071/CP14342
Submitted: 2 December 2014 Accepted: 6 May 2015 Published: 8 October 2015
Abstract
Biserrula is an annual pasture legume endemic to the Mediterranean basin and has been recently domesticated for use in Mediterranean environments in southern Australia. Over the past 10 years the species has been associated with isolated cases of what appears to be a primary photosensitisation in sheep that graze green pastures in winter and spring. Whole-top samples of biserrula pasture were taken from a range of farmers’ paddocks over 2 years (including paddocks where photosensitisation had been observed) and methanolic extracts were screened by high-performance liquid chromatography and liquid chromatography coupled to mass spectrometry for known primary photosensitising compounds belonging to the classes furanocoumarins and dianthrones. None of these were detected. Pyrrolizidine alkaloids were also not detected and this supports the view that a secondary photosensitisation is not involved. Chlorophyll profiles were relatively unchanged between samples and this suggested that chlorophyll metabolites are unlikely to be responsible for a primary photosensitisation. A series of luteolin and apigenin mono- and diglycosides were identified in the extracts, but these are not regarded as photosensitising compounds. Further work is required to establish the photosensitising agent(s) in biserrula.
Additional keywords: chlorophyll, flavones, HPLC, LCMS, photosensitisation.
References
Banik B, Durmic Z, Erskine W, Ghamkar K, Revell C (2013) In vitro ruminal fermentation and methane production differ in selected key pasture species in Australia. Crop & Pasture Science 64, 935–942.| In vitro ruminal fermentation and methane production differ in selected key pasture species in Australia.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhvVGms7bF&md5=377a915f947265ce7d7b1ad208eb986cCAS |
Bisby FA, Buckingham J, Harbourne JB (1994) ‘Phytochemical dictionary of the Leguminosae.’ (Chapman and Hall: London)
Boppré M, Colegate SM, Edgar JA (2005) Pyrrolizidine alkaloids of Echium vulgare honey found in pure pollen. Journal of Agricultural and Food Chemistry 53, 594–600.
| Pyrrolizidine alkaloids of Echium vulgare honey found in pure pollen.Crossref | GoogleScholarGoogle Scholar | 15686407PubMed |
Campbell WM, Dombroski GS, Sharma I, Partridge AC, Collett MG (2010) Photodynamic chlorophyll a metabolites, including phytoporphyrin (phylloerythrin), in the blood of photosensitive livestock: overview and measurement. New Zealand Veterinary Journal 58, 146–154.
| Photodynamic chlorophyll a metabolites, including phytoporphyrin (phylloerythrin), in the blood of photosensitive livestock: overview and measurement.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXpt1ajs7k%3D&md5=29f59ec4206ca6cd86df8bc531ecd4a9CAS | 20514089PubMed |
Encyclopedia of Life (2014) Biserrula pelecinus. Available at: http://eol.org/pages/1230348/names?all=1 (accessed 24 November 2014).
Ferrer LM, Ortin A, Loste A, Fernandez A, Verde MT, Ramos JJ (2007) Photosensitisation in sheep grazing alfalfa infested with aphids and ladybirds. The Veterinary Record 161, 312–314.
| Photosensitisation in sheep grazing alfalfa infested with aphids and ladybirds.Crossref | GoogleScholarGoogle Scholar | 1:STN:280:DC%2BD2srhs1GlsA%3D%3D&md5=d72468e6358ec4e0a06f61ccfd174ec5CAS | 17766813PubMed |
Ghamkhar K, Revell C, Erskine W (2012) Biserrula pelecinus L. – genetic diversity in a promising pasture legume for the future. Crop & Pasture Science 63, 833–839.
| Biserrula pelecinus L. – genetic diversity in a promising pasture legume for the future.Crossref | GoogleScholarGoogle Scholar |
Ginn PE, Mansell JEKL, Rakich PM (2007) Skin and appendages. In ‘Jubb, Kennedy and Palmer’s pathology of domestic animals’. 5th edn. (Ed. M Grant Maxie) pp. 553–781. (Saunders Elsevier: Philadelphia)
Howieson JG, Loi A, Carr SJ (1995) Biserrula pelecinus L. – a legume pasture species with potential for acid, duplex soils which is nodulated by unique root-nodule bacteria. Australian Journal of Agricultural Research 46, 997–1009.
| Biserrula pelecinus L. – a legume pasture species with potential for acid, duplex soils which is nodulated by unique root-nodule bacteria.Crossref | GoogleScholarGoogle Scholar |
Jones WP, Kinghorn AD (2006) Extraction of plant secondary metabolites. In ‘Natural products isolation’. 2nd edn. (Eds SD Sarker, Z Latif, AI Gray) pp. 323–351. (Humana Press: Totowa, New Jersey)
Loi A, Howieson JG, Nutt BJ, Carr SJ (2005) A second generation of annual pasture legumes and their potential for inclusion in Mediterranean type farming systems. Australian Journal of Experimental Agriculture 45, 289–299.
| A second generation of annual pasture legumes and their potential for inclusion in Mediterranean type farming systems.Crossref | GoogleScholarGoogle Scholar |
Loi A, Hogg N, Nutt B, Revell C and Fedorenko D (2010) Growing biserrula to improve grain and livestock production. Department of Agriculture and Food Western Australia Bulletin 4805.
López-Lázaro M (2009) Distribution and biological activities of the flavonoid luteolin. Mini-Reviews in Medicinal Chemistry 9, 31–59.
| Distribution and biological activities of the flavonoid luteolin.Crossref | GoogleScholarGoogle Scholar | 19149659PubMed |
McKenzie R (2012) ‘Australia’s poisonous plants, fungi and cyanobacteria; a guide to species of medical and veterinary importance.’ pp. 50–52. (CSIRO Publishing: Melbourne)
Merck Veterinary Manual (2014) Merck veterinary manual. Available at: www.merckmanuals.com/vet/integumentary_system/photosensitization/overview_of_photosensitization.html (accessed 24 April 2014).
Nichols P, Loi A, Revell C, Ewing M, Nutt B, Snowball R, Pei You M, Howieson J, Carr S, Foster K, Skinner P, McClements D, Barbetti M, Craig A, Howie J, Nair R, Hughes S, Auricht G, De Koning C, Dear B, Sandral G, Hackney B, Croker G, Evans P, Lloyd D, Hall E (2007) Annual pasture legume improvement in southern Australia – 15 years of change. Field Crops Research 104, 10–23.
| Annual pasture legume improvement in southern Australia – 15 years of change.Crossref | GoogleScholarGoogle Scholar |
Niknam V, Ebrahimzadeh H, Maasoumi AA (2003) Toxic nitro compounds in Astragalus species. Biochemical Systematics and Ecology 31, 557–562.
| Toxic nitro compounds in Astragalus species.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXit1KntLc%3D&md5=08811a012b915b9053d6f02f59d2d64bCAS |
Ojala T, Vuorela P, Kiviranta J, Vuorela H, Hiltunen R (1999) A bioassay using Artemia salina for detecting phototoxicity of plant coumarins. Planta Medica 65, 715–718.
| A bioassay using Artemia salina for detecting phototoxicity of plant coumarins.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXotF2ltbk%3D&md5=0fa200fd2c42b73a73030ce47b8ea5baCAS | 10630112PubMed |
Pape WJW, Brandt M, Pfannenbecker U (1994) Combined in vitro assay for photohaemolysis and haemoglobin oxidation as part of a phototoxicity test system assessed with various phototoxic substances. Toxicology In Vitro 8, 755–757.
| Combined in vitro assay for photohaemolysis and haemoglobin oxidation as part of a phototoxicity test system assessed with various phototoxic substances.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXmslGgs70%3D&md5=a48fad42e62dfc79dbd1efe68fc9ebccCAS |
Quinn JC, Kessell A, Weston LA (2014) Secondary plant products causing photosensitization in grazing herbivores: their structure, activity and regulation. International Journal of Molecular Sciences 15, 1441–1465.
| Secondary plant products causing photosensitization in grazing herbivores: their structure, activity and regulation.Crossref | GoogleScholarGoogle Scholar | 24451131PubMed |
Revell CK, Revell DK (2007) Meeting ‘duty of care’ obligations when developing new pasture species. Field Crops Research 104, 95–102.
| Meeting ‘duty of care’ obligations when developing new pasture species.Crossref | GoogleScholarGoogle Scholar |
Rios JL, Waterman PG (1997) A review of the pharmacology and toxicology of Astragalus. Phytotherapy Research 11, 411–418.
| A review of the pharmacology and toxicology of Astragalus.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXmslChsb4%3D&md5=36d92e7dcbd0e9b78a69841b9fd128a3CAS |
Tapper BA, Lohrey E, Hove EL, Allison RM (1975) Photosensitivity from chlorophyll-derived pigments. Journal of the Science of Food and Agriculture 26, 277–284.
| Photosensitivity from chlorophyll-derived pigments.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE2MXlsVaktr0%3D&md5=32c92f02d8897f1d482c429e27174ee9CAS | 1134066PubMed |
Tavčar Benković ET, Zigon D, Friedrich M, Plavec J, Kreft S (2014) Isolation, analysis and structures of phototoxic fagopyrins from buckwheat. Food Chemistry 143, 432–439.
| Isolation, analysis and structures of phototoxic fagopyrins from buckwheat.Crossref | GoogleScholarGoogle Scholar |
Thomas DT, Milton JTB, Revell CK, Ewing MA, Dynes RA, Murray K, Lindsay DR (2010) Preference of sheep among annual legumes is more closely related to plant nutritive characteristics as plants mature. Animal Production Science 50, 114–123.
| Preference of sheep among annual legumes is more closely related to plant nutritive characteristics as plants mature.Crossref | GoogleScholarGoogle Scholar |
Yamauchi N, Watada AE (1991) Regulated chlorophyll degradation in spinach leaves during storage. Journal of the American Society for Horticultural Science 116, 58–62.
