Tulipanin
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-rutinoside Delphinidin 3-O -rutinoside Delphinidin-3-glucorhamnoside
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 C27 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).
Chemical compound
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] and in 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 (anthocyaninidin glycosides)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)
Ideain (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
Tulipanin (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 anthocyanins (cis - 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
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