Iridoid and phenylethanoid glycosides in the New Zealand sun hebes (Veronica; Plantaginaceae) |
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| Institution: | 1. School of Biological Sciences, Victoria University of Wellington, P.O. Box 600, Wellington 6140, New Zealand;2. Jodrell Laboratory, Royal Botanic Gardens, Kew, Richmond, Surrey TW9 3DS, UK;3. Department of Chemistry, The Technical University of Denmark, Build. 201, DK-2800 Lyngby, Denmark;1. Hebei Key Laboratory of Specialty Animal Germplasm Resources Exploration and Innovation, Hebei Normal University of Science and Technology, Qinhuangdao, Hebei 066004, People’s Republic of China;2. College of Biology Pharmacy and Food Engineering, Shangluo University, Shangluo, Shaanxi 726000, People’s Republic of China;3. Hebei Key Laboratory of Preventive Veterinary Medicine, Hebei Normal University of Science and Technology, Qinhuangdao, Hebei 066004, People’s Republic of China;4. Shandong Provincial Key Laboratory of Animal Disease Control & Breeding, Institute of Animal Science and Veterinary Medicine, Shandong Academy of Agricultural Sciences, Jinan, Shandong 250100, People’s Republic of China;1. School of Pharmaceutical Sciences, Nanjing Tech University, Nanjing 210009, People''s Republic of China;2. Department of Pharmacy, Zheng Zhou University, Zheng Zhou 450000, People''s Republic of China;3. School of Life Science & Pharmaceutical Engineering, Nanjing Tech University, Nanjing 210009, People''s Republic of China;4. School of Pharmacy, FMHS, The University of Auckland Private Bag 92019, Auckland 1142, New Zealand;1. Research Institute for Fragrance Materials, Inc., 50 Tice Boulevard, Woodcliff Lake, NJ, 07677, USA;2. Member RIFM Expert Panel, Columbia University Medical Center, Department of Dermatology, 161 Fort Washington Ave., New York, NY, 10032, USA;3. Member RIFM Expert Panel, Malmo University Hospital, Department of Occupational & Environmental Dermatology, Sodra Forstadsgatan 101, Entrance 47, Malmo, SE-20502, Sweden;4. Member RIFM Expert Panel, School of Natural Resources & Environment, University of Michigan, Dana Building G110, 440 Church St., Ann Arbor, MI, 58109, USA;5. Member RIFM Expert Panel, Fraunhofer Institute for Toxicology and Experimental Medicine, Nikolai-Fuchs-Strasse 1, 30625, Hannover, Germany;6. Member RIFM Expert Panel, University of Sao Paulo, School of Veterinary Medicine and Animal Science, Department of Pathology, Av. Prof. dr. Orlando Marques de Paiva, 87, Sao Paulo, CEP 05508-900, Brazil;7. Member RIFM Expert Panel, University of Wuerzburg, Department of Toxicology, Versbacher Str. 9, 97078, Würzburg, Germany;8. Member RIFM Expert Panel, Oregon Health Science University, 3181 SW Sam Jackson Park Rd., Portland, OR, 97239, USA;9. Member RIFM Expert Panel, Vanderbilt University School of Medicine, Department of Biochemistry, Center in Molecular Toxicology, 638 Robinson Research Building, 2200 Pierce Avenue, Nashville, TN, 37232-0146, USA;10. Member of RIFM Expert Panel, University of Pennsylvania, Perelman School of Medicine, Center of Excellence in Environmental Toxicology, 1316 Biomedical Research Building (BRB) II/III, 421 Curie Boulevard, Philadelphia, PA, 19104-3083, USA;11. Member RIFM Expert Panel, The University of Tennessee, College of Veterinary Medicine, Department of Comparative Medicine, 2407 River Dr., Knoxville, TN, 37996- 4500, USA;12. Member RIFM Expert Panel, Department of Pharmacology, University of Arizona, College of Medicine, 1501 North Campbell Avenue, P.O. Box 245050, Tucson, AZ, 85724-5050, USA;13. Member RIFM Expert Panel, Department of Dermatology, Hamamatsu University School of Medicine, 1-20-1 Handayama, Higashi-ku, Hamamatsu, 431-3192, Japan;1. Department of Pharmacognosy, School of Pharmacy, Second Military Medical University, Shanghai 200433, PR China;2. College of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 610075, PR China;3. Department of Stomatology, Changhai Hospital, Second Military Medical University, Shanghai 200433, PR China;4. Faculty of Science, School of Biomolecular Sciences, Liverpool John Moores University, Byrom Street, Liverpool, L3 3 AF England, UK;1. Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, 9 Acad. G. Bontchev Str., 1113 Sofia, Bulgaria;2. Group of Plant Cell Biotechnology and Metabolomics, The Stephan Angeloff Institute of Microbiology, Bulgarian Academy of Sciences, 139 Ruski Blvd., 4000 Plovdiv, Bulgaria;3. School of Pharmaceutical Sciences, University of Geneva, University of Lausanne, CMU – Rue Michel Servet 1, 1211 Geneva 11, Switzerland |
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| Abstract: | The sun hebes are a small clade of New Zealand Veronica formerly classified as Heliohebe. The water-soluble compounds of Veronica pentasepala, Veronica raoulii and Veronica hulkeana were studied and 30 compounds including 15 iridoid glucosides, 12 phenylethanoid glycosides, the acetophenone glucoside pungenin, the mannitol ester hebitol II and mannitol were isolated. Of these, five were previously unknown in the literature: dihydroverminoside and 3,3′,4,4′-tetrahydroxy-α-truxillic acid 6-O-catalpyl diester, named heliosepaloside, as well as three phenylethanoid glycoside esters heliosides D, E and F, all derivatives of aragoside. The esters of cinnamic acid derivatives with iridoid and phenylethanoid glycosides and an unusually high concentration of verminoside were found to be the most distinctive chemotaxonomic characters of the sun hebes. The chemical profiles of the species were compared and used to assess the phylogenetic relationships in the group. |
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