Chemistry:Apiin
Apiin is a natural flavonoid, a diglycoside of the flavone apigenin found in the winter-hardy plants parsley[1] and celery,[2] and in banana leaf.[3] The glycoside moiety at carbon-7 of apigenin, O-β-D-apiofuranosyl(→)2-β-D-glucosyl, is carried by several other flavones in parsley plant and seed.[4] The sugar apiose possibly play a role in winter hardiness of celery, duckweed and parsley.[5]
Biosynthesis
Apiin is a diglycoside of the flavone, apigenin. Its biosynthesis in plants involves a sequence of enzymes, with chalcone synthase being the one that forms the ring system of the natural product naringenin. Naringenin is then oxidised to apigenin:[6][7]
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Next, the enzyme flavone 7-O-beta-glucosyltransferase transfers a glucose sugar fragment from UDP-glucose, giving apigetrin, with uridine diphosphate (UDP) as byproduct:[6][8]
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Finally, apigetrin is converted to apiin when a second apiose sugar is added by the enzyme flavone apiosyltransferase:[7]
- REDIRECT Template:Chemical reaction
References
- ↑ H. Meyer; A. Bolarinwa; G. Wolfram; J. Linseisen (2006). "Bioavailability of Apigenin from Apiin-Rich Parsley in Humans". Ann Nutr Metab 50 (3): 167–172. doi:10.1159/000090736. PMID 16407641. https://opus.bibliothek.uni-augsburg.de/opus4/frontdoor/index/index/docId/85767.
- ↑ S. R. Gupta (1952). "A study of apiin from the parsley seeds and plant". Proceedings of the Indian Academy of Sciences, Section A 35 (5). doi:10.1007/BF03172503.
- ↑ Sayadi, Khali; Akbarzadeh, Fatemeh; Pourmardan, Vahid; Saravani-Aval, Mehdi; Sayadi, Jalis; Chauhan, Narendra Pal Singh; Sargazi, Ghasem (2021). "Methods of green synthesis of Au NCs with emphasis on their morphology: A mini-review". Heliyon (Cell Press) 7 (6). doi:10.1016/j.heliyon.2021.e07250. ISSN 2405-8440. PMID 34189304. Bibcode: 2021Heliy...707250S.
- ↑ "Methods in plant biochemistry". Carbohydrates. 2. Academic Press. 2 December 2012. p. 245. ISBN 978-0-08-098420-9.
- ↑ Advances in Carbohydrate Chemistry and Biochemistry. 31. Academic Press. 5 November 1975. p. 136. ISBN 0-08-056290-6.
- ↑ 6.0 6.1 Ververidis Filippos, F; Trantas Emmanouil; Douglas Carl; Vollmer Guenter; Kretzschmar Georg; Panopoulos Nickolas (October 2007). "Biotechnology of flavonoids and other phenylpropanoid-derived natural products. Part I: Chemical diversity, impacts on plant biology and human health". Biotechnology Journal 2 (10): 1214–34. doi:10.1002/biot.200700084. PMID 17935117.
- ↑ 7.0 7.1 Hădărugă, Daniel-Ioan; Hădărugă, Nicoleta-Gabriela (2023). "Flavones: Structure, Properties, Sources and Food Applications". Handbook of Food Bioactive Ingredients. pp. 111–158. doi:10.1007/978-3-031-28109-9_4. ISBN 978-3-031-28108-2.
- ↑ Sutter, Arne; Ortmann, Rainer; Grisebach, Hans (1972). "Purification and properties of an enzyme from cell suspension cultures of parsley catalyzing the transfer of d-glucose from UDP-d-glucose to flavonoids". Biochimica et Biophysica Acta (BBA) - Enzymology 258 (1): 71–87. doi:10.1016/0005-2744(72)90967-9. PMID 5058406.
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