Foeniculoside I

Foeniculoside I
Names

IUPAC name 2-(3-hydroxy-5-{6-hydroxy-4-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl}phenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
Other names cis-miyabenol C 11a-O-β-D-glucopyranoside
Identifiers
CAS Registry Number	168010-10-4
Jmol-3D images	Image
SMILES OCC1OC(OC2=CC(=CC(O)=C2)C2C(OC3=CC(O)=CC(C4C(OC5=C4C(\C=C\C4=CC=C(O)C=C4)=CC(O)=C5)C4=CC=C(O)C=C4)=C23)C2=CC=C(O)C=C2)C(O)C(O)C1O
Properties
Chemical formula	C₄₈H₄₂O₁₄
Molar mass	842.83 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Foeniculoside I is a stilbenoid. It is a glucoside of the stilbene trimer cis-miyabenol C. It can be found in Foeniculi fructus (fruit of Foeniculum vulgare).^[1]

References

↑ Four new glycosides of stilbene trimer from Foeniculi fructus (fruit of Foeniculum vulgare MILLER). Ono M, Ito Y, Kinjo J, Yahara S, Nohara T and Niiho Y, Chemical and pharmaceutical bulletin, 1995, vol. 43, no 5, pages 868-871 INIST:3610745

External links

Foeniculoside I at the Human Metabolome Database

Oligostilbenoids and their glycosides

Diptoindonesin C
Diptoindonesin F
Gnetin H
Hemsleyanol D
Isohopeaphenol
Laetevirenol A, B, C, D and E
Suffruticosol A and B
Viniferal
E-ω-viniferin
Z-ω-viniferin

Dimers

Diptoindonesin G
Jezonodione
B
Scirpusin A
Tibeticanol (piceatannol dimer)

Trimers

Amurensin B
Gnetin E
Gneyulin A
Johorenol A
Ampelopsin E
Vaticanol G

Tetramers:

Dibalanocarpol
Gnetin J (3"-hydroxygnetin E)
Gnetin K (3"-methoxygnetin E)
Gnetuhainin R (isorhapontigenin tetramer)
Laetevirenol F and G

Higher polymers
(five units or more)

Vaticanol D, H, I and J

Oligomeric forms
of resveratrol

Dimers	Amurensin A and H Ampelopsin A B D and F Balanocarpol Cyphostemmin A and B δ-viniferin ε-viniferin Gnetin A and C Leachinol F Malibatol A Pallidol Parthenocissin A Quadrangularin A Restrytisol A, B and C Vitisinol D

Trimers	α-viniferin Ampelopsin C Amurensin C, D and G Hopeanolin Malaysianol A Miyabenol C Resviniferin A and B trans-diptoindonesin B

Tetramers	Ampelopsin H Amurensin K Caraphenol B Carasinol B Flexuosol A Hopeaphenol Kobophenol A Miyabenol A Vaticanol B and C Vaticaphenol A Vitisin A B and C β-viniferin (cyclic resveratrol tetramer)

Pentamers	Amurensin E and F

Hexamers	Chunganenol

Higher polymers	γ-viniferin Valeriaphenol A

Glycosides or conjugates

Diptoindonesin A (C-glucoside of ε-viniferin)
Foeniculoside I (glucoside of miyabenol C), II, III and IV
Laevifonol (an ε-viniferin-ascorbic acid hybrid compound)
Laevifoside (O-glucoside of ampelopsin A)