Cinchonain-Ib

Names
IUPAC name

(2R,3R,4′′S)-4′′-(3,4-Dihydroxyphenyl)-3,3′,4′,5-tetrahydroxy-6′′H-pyrano[2′′,3′′:7,8]flavan-6′′-one

Systematic IUPAC name

(2R,3R,10S)-2,10-Bis(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4,9,10-tetrahydro-2H,8H-(benzo[1,2-b:3,4-b′]dipyran)-8-one

Identifiers

CAS Number

* 85022-69-1 Y

3D model (JSmol)

* Interactive image

ChEMBL |

* ChEMBL401058 Y

ChemSpider |

* 8631931 Y

PubChem CID

* 442675

UNII |

* F742N63ATR Y

InChI

* InChI=1S/C24H20O9/c25-14-3-1-10(5-17(14)28)12-8-21(31)32-20-9-16(27)13-7-19(30)23(33-24(13)22(12)20)11-2-4-15(26)18(29)6-11/h1-6,9,12,19,23,25-30H,7-8H2/t12-,19+,23+/m0/s1 Y

Key: LKCOZWLUAKSRQM-IBUUURQNSA-N Y

SMILES

* O=C5Oc3c(c2O[C@H](c1ccc(O)c(O)c1)[C@H](O)Cc2c(O)c3)[C@H](c4ccc(O)c(O)c4)C5

Properties

Chemical formula

| C24H20O9
Molar mass | 452.415 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

Cinchonain-Ib is a flavonolignan found in the bark of Trichilia catigua used as catuaba.[1] A 2009 study revealed that Cinchonian-Ib derived from boiled Eriobotrya japonica leaves has a glucose-lowering effect in rats, and could possibly be used to manage diabetes mellitus in humans.[2]

## References

1. ↑ Beltrame, F. L.; Filho, E. R.; Barros, F. A. P.; Cortez, D. A. G.; Casset, Q. B. (2006). "A validated higher-performance liquid chromatography method for quantification of cinchonain Ib in bark and phytopharmaceuticals of Trichilia catigua used as Catuaba". Journal of Chromatography A 1119 (1–2): 257–263. doi:10.1016/j.chroma.2005.10.050. PMID 16360665.
2. ↑ Qa’dan, Fadi; Verspohl, Eugen. J.; Nahrstedt, Adolf; Petereit, Frank; Matalka, Khalid Z. (15 July 2009). "Cinchonain Ib isolated from Eriobotrya japonica induces insulin secretion in vitro and in vivo" (in en). Journal of Ethnopharmacology 124 (2): 224–227. doi:10.1016/j.jep.2009.04.023. ISSN 0378-8741. PMID 19397981. https://www.sciencedirect.com/science/article/abs/pii/S0378874109002657. Retrieved 19 October 2022.

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*[CID]: Compound ID