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Entry
CA00898                                                            

Classification
Carotenoid Name
Crocin;
Crocin 1;
Crocetin A;
Crocin A
IUPAC name Digentiobiosyl-8,8'-diapocarotene-8,8'-dioate
Formula
C44H64O24
Molecular Weight 
976.952 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Anticarcinogenic activity (Ref.414, Ref.457).
  • Strong tyrosinase inhibitory activity (Ref.485).
  • Antihypertensive effect, antithrombotic effect (Ref.452).
  • An antioxidant - high radical scavenging activity (Ref.456).
  • Antitussive activity (Ref.458).
  • Memory and learning skills improvement (Ref.459).
  • Yellow food coloring (Ref.452, Ref.468).
  • Number of
    conjugated double bonds 
    9 including two carboxylic acid glucosylates (9 in total)
    Number of
    conjugated multiple bonds 
    9 including two carboxylic acid glucosylates (9 in total)
    Isomers 
    InChI
    InChI=1S/C44H64O24/c1-19(11-7-13-21(3)39(59)67-43-37(57)33(53)29(49)25(65-43)17-61-41-35(55)31(51)27(47)23(15-45)63-41)9-5-6-10-20(2)12-8-14-22(4)40(60)68-44-38(58)34(54)30(50)26(66-44)18-62-42-36(56)32(52)28(48)24(16-46)64-42/h5-14,23-38,41-58H,15-18H2,1-4H3/b6-5+,11-7+,12-8+,19-9+,20-10+,21-13+,22-14+/t23-,24-,25-,26-,27-,28-,29-,30-,31+,32+,33+,34+,35-,36-,37-,38-,41-,42-,43+,44+/m1/s1
    InChIKey
    SEBIKDIMAPSUBY-RTJKDTQDSA-N
    Canonical SMILES
    OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC(=O)/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C(=O)O[C@@H]3O[C@H](CO[C@@H]4O[C@H](CO)[C@H]([C@@H]([C@H]4O)O)O)[C@H]([C@@H]([C@H]3O)O)O)\C)\C)/C)/C)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
    XLogP
    -1.214
    Hydrogen Bond donors
    (Lipinski's definition)
    14
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    24
    LipinskiFailures
    3
    Complexity of molecule
    0.348
    Number of heavy atoms
    68
    TPSA
    (Topological Polar Surface Area) 
    391.200 Å2
    Source organisms
    Gardenia Jasminoides (Ref.159, Ref.383) - Land plant: gardenia
    Crocus sativus (Ref.319, Ref.485) - Land plant: saffron crocus
    Nyctanthes arbor-tristis (Ref.320) - Land plant: night jasmine
    References
  • Ref.159 : Coran, Silvia A.; Mulas, Stefano; Vasconi, Alessio, Journal of Chromatography A (2014), 1325, 221-226., "Profiling of components and validated determination of iridoids in Gardenia Jasminoides Ellis fruit by a high-​ performance-t​ hin-l​ ayer- chromatography/​ mass spectrometry approach".
  • Ref.383 : Mai Nagatoshia, Kazuyoshi Terasakaa, Miki Owakia, Makiko Sotaa, Tatsunori Inukaia, Akito Nagatsub, Hajime Mizukami, FEBS letters, Volume 586, Issue 7, 5 April 2012, Pages 1055–1061, "UGT75L6 and UGT94E5 mediate sequential glucosylation of crocetin to crocin in Gardenia jasminoides".
  • Ref.319 : Karrer, P ., and Miki, K. (1929) Pflanzenfarbstoffe XV . Der Zucker des α-Crocins, Helv. Chim. Acta 12, 985–986..
  • Ref.485 : Li CY, Wu TS, Journal of Natural Products [2002, 65(10):1452-1456], DOI: 10.1021/np020188v, "Constituents of the stigmas of Crocus sativus and their tyrosinase inhibitory activity.".
  • Ref.320 : Karrer, P., and Salomon, H. (1933) Die Bruttoformel des Crocins, Helv. Chim. Acta 16, 643–651..
  • Ref.414 : Nishino H, Murakosh M, Ii T, Takemura M, Kuchide M, Kanazawa M, Mou XY, Wada S, Masuda M, Ohsaka Y, Yogosawa S, Satomi Y, Jinno K., Cancer Metastasis Rev. 2002;21(3-4):257-64., "Carotenoids in cancer chemoprevention.".
  • Ref.457 : Julio Escribanoa, Gonzalo-Luis Alonsob, Miguel Coca-Pradosc, José-Antonio Fernández, Cancer Letters, Volume 100, Issues 1–2, 27 February 1996, Pages 23–30, "Crovin, safranal, and picrocrocin from saffron (Crocus sativus L.) inhibit the growth of human cancer cell in vitro".
  • Ref.452 : Saori Higashino, Yasuto Sasaki1, John C. Giddings, Kanae Hyodo, Shigeko Fujimoto Sakata, Koichi Matsuda, Yoko Horikawa, and Junichiro Yamamoto, Phytotherapy Research Volume 28, Issue 9, pages 1315–1319, September 2014, "Crocetin, a Carotenoid from Gardenia jasminoides Ellis, Protects against Hypertension and Cerebral Thrombogenesis in Stroke-prone Spontaneously Hypertensive Rats".
  • Ref.456 : A. N. Assimopoulou, Z. Sinakos, and V. P. Papageorgiou, Phytotherapy Research, Volume 19, Issue 11, pages 997–1000, November 2005, "Radical scavenging activity of Crocus sativus L. extract and its bioactive constituents".
  • Ref.458 : R. Srivastava, H. Ahmed, R. K. Dixit, Dharamveer, and S. A. Saraf, Pharmacogn Rev. 2010 Jul-Dec; 4(8): 200–208., doi: 10.4103/0973-7847.70919, "Crocus sativus L.: A comprehensive review".
  • Ref.459 : Abe K1, Saito H., Phytother Res. 2000 May;14(3):149-52., "Effects of saffron extract and its constituent crocin on learning behaviour and long-term potentiation.".
  • Ref.468 : Gerard P. Moss, Herbert Baxter, J.B. Harborne, Gerald P. Moss, CRC Press; 1 edition (February 15, 1993), ISBN-10: 0850667364, ISBN-13: 978-0850667363, "Phytochemical Dictionary: A Handbook of Bioactive Compounds from Plants".
  • CAS
    42553-65-1
    Links to other DB
    KNApSAcK: C00003769

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