Tulipanin Names IUPAC name 3′,4′,5,5′,7-Pentahydroxy-3-[α-L -rhamnopyranosyl-(1→6)-β-D -glucopyranosyloxy]flavylium
Systematic IUPAC name (42 S ,43 R ,44 S ,45 S ,46 R ,72 R ,73 R ,74 R ,75 R ,76 S )-13 ,14 ,15 ,25 ,27 ,43 ,44 ,45 ,73 ,74 ,75 -Undecahydroxy-76 -methyl-21 λ4 -3,6-dioxa-2(2,3)-[1]benzopyrana-4(2,6),7(2)-bis(oxana)-1(1)-benzenaheptaphan-21 -ylium
Other names Delphinidin-3-rutinosideO -rutinoside
Identifiers ChemSpider KEGG UNII InChI=1S/C27H30O16/c1-8-18(32)21(35)23(37)26(40-8)39-7-17-20(34)22(36)24(38)27(43-17)42-16-6-11-12(29)4-10(28)5-15(11)41-25(16)9-2-13(30)19(33)14(31)3-9/h2-6,8,17-18,20-24,26-27,32,34-38H,7H2,1H3,(H4-,28,29,30,31,33)/p+1/t8-,17+,18-,20+,21+,22-,23+,24+,26+,27+/m0/s1
N Key: PLKUTZNSKRWCCA-LTSKFBHWSA-O
N O(C[C@H]4O[C@@H](Oc2cc3c(O)cc(O)cc3[o+]c2c1cc(O)c(O)c(O)c1)[C@H](O)[C@@H](O)[C@@H]4O)[C@@H]5O[C@H]([C@H](O)[C@@H](O)[C@H]5O)C
Properties C27 H31 ClO16 27 H31 O16 + Molar mass 611.52 g/mol Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tulipanin is an anthocyanin . It is the 3-O-rutinoside of delphinidin . It can be found in Alstroemeria spp.Berberis spp.Cissus sicyoides Hymenocallis spp.Manihot utilissima Meliosma tenuis , Musa acuminata Ophiopogon japonicus Petunia exserta Petunia reitzii , blackcurrant (Ribes nigrum ), Schismatoglottis concinna , Secale cereale Solanum betaceum Thaumatococcus daniellii Tulipa spp[ 1] [ 2] eggplants .[ 3]
References ^ Harborne, The Handbook of Natural Flavonoids, 2, (1999), 1, Anthocyanins ^ Tulipanin on kanaya.naist.jp ^ Structures and Antioxidant Activity of Anthocyanins in Many Accessions of Eggplant and Its Related Species. Keiko Azuma, Akio Ohyama, Katsunari Ippoushi, Takashi Ichiyanagi, Atsuko Takeuchi, Takeo Saito and Hiroyuki Fukuoka, J. Agric. Food Chem., 2008, 56 (21), pp 10154–10159, doi :10.1021/jf801322m
3-Hydroxyanthocyanidins 3-Deoxyanthocyanidins O -Methylated anthocyanidinsAnthocyanins Glucosides: Diglucosides:
Cyanin (Cyanidin 3,5-O -diglucoside ) Delphin (Delphinidin 3,5-O -diglucoside) Malvin (Malvidin 3,5-diglucoside)Pelargonin (Pelargonidin 3,5-O -diglucoside)Peonin (Peonidin 3,5-O -diglucoside) Petunin (Petunidin 3,5-O -diglucoside) Others glycosides:
Antirrhinin (Cyanidin 3-O -rutinoside)Idaein (Cyanidin 3-O -galactoside)Delphinidin 3-O -rhamnoside Petunidin 3-O -arabinoside Petunidin 3-O -galactoside Petunidin 3-O -rhamnoside Petunidin 3-O -rutinoside Primulin (Malvidin 3-O -galactoside)Pulchellidin 3-rhamnoside (Delphinidin 3-O -rutinoside) Acylated anthocyanins
Acetylated anthocyanins
Cyanidin 3-O -(6-acetyl)glucoside Delphinidin 3-O -(6-acetyl)glucoside Malvidin 3-O -(6-acetyl)glucoside Petunidin 3-O -(6-acetyl)galactoside Petunidin 3-O -(6-acetyl)glucoside Peonidin 3-O -(6-acetyl)glucoside Coumaroylated anthocyaninscis - and trans -) Caffeoylated anthocyanins Malvidin 3-O -(6-p -caffeoyl)glucoside Peonidin 3-O -(6-p -caffeoyl)glucoside Malonylated anthocyanins Malonylmalvin (malvidin 3-(6″-malonylglucoside)-5-glucoside) Acylated anthocyanin diglycosides Cyanidin 3-O -(di-p -coumarylglucoside)-5-glucoside Gentiodelphin (delphinidin 3-''O''-glucosyl-5-''O''-(6-''O''-caffeoyl-glucosyl)-3′-''O''-(6-''O''-caffeoyl-glucoside)) Nasunin (Delphinidin 3-(p -coumaroylrutinoside)-5-glucoside)Petanin (petunidin 3-[6-O -(4-O -(E )-p -coumaroyl-O -α-l-rhamnopyranosyl)-β-D -glucopyranoside]-5-O -β-D -glucopyranoside) Violdelphin (Delphinidin 3-rutinoside-7-O -(6-O -(4-(6-O -(4-hydroxybenzoyl)-β-D -glucosyl)oxybenzoyl)-β-D -glucoside)
Flavanol-anthocyanin adducts Malvidin glucoside-ethyl-catechin Catechin(4α→8)pelargonidin 3-O -β-glucopyranoside Epicatechin(4α→8)pelargonidin 3-O -β-glucopyranoside Afzelechin(4α→8)pelargonidin 3-O -β-glucopyranoside Epiafzelechin(4α→8)pelargonidin 3-O -β-glucopyranoside Miscellaneous
