ligstroside (Q27269447)

chemical structure

Ligstroside.svg
1,020 × 470; 25 KB

0 references

mass

524.189±0 dalton

1 reference

ligstroside (English)

methyl (4S,6S)-5-ethylidene-4-[2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate

14 October 2016

stereoisomer of

2 references

methyl (4S,5E,6S)-5-ethylidene-4-[2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl]-6-[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate

2 references

methyl (4S,5E,6R)-5-ethylidene-4-[2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate

2 references

methyl (4R,5E,6S)-5-ethylidene-4-[2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate

2 references

methyl (4S,5Z,6S)-5-ethylidene-4-[2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl]-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate

1 reference

1 reference

methyl (4S,5E,6S)-5-ethylidene-4-[2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl]-6-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate

1 reference

chemical formula

C₂₅H₃₂O₁₂

1 reference

ligstroside (English)

14 October 2016

canonical SMILES

CC=C1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)OC)CC(=O)OCCC3=CC=C(C=C3)O

1 reference

ligstroside (English)

14 October 2016

isomeric SMILES

C/C=C/1\[C@@H](C(=CO[C@H]1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)OC)CC(=O)OCCC3=CC=C(C=C3)O

1 reference

Secoiridoids and hydroxycoumarins in Bulgarian Fraxinus species

ligstroside (English)

14 October 2016

6 references

A secoiridoid glucoside and a phenolic compound from Fraxinus ornus bark

Secoiridoid glucosides from fraxinus ornus bark

Secoiridoid and Phenolic Compounds fromFraxinus ornus

Secoiridoid glucosides from fraxinus ornus bark

Complement-Mediated Antiinflammatory Action of Extracts and Pure Secoiridoids Isolated from Fraxinus Species

Fraxinus excelsior

6 references

Secoiridoids and hydroxycoumarins in Bulgarian Fraxinus species

Iridoids from Fraxinus excelsior with adipocyte differentiation-inhibitory and PPARalpha activation activity.

Biosynthesis of secoiridoid glucosides in oleaceae

Biosynthesis of iridoids in Syringa and Fraxinus: Carbocyclic iridoid precursors

Excelsioside, a secoiridoid glucoside from Fraxinus excelsior

Fraxinus excelsior seed extract FraxiPure™ limits weight gains and hyperglycemia in high-fat diet-induced obese mice.

Olea europaea

7 references

Direct Identification of Phenolic Glucosides from Olive Leaf Extracts by Atmospheric Pressure Ionization Tandem Mass Spectrometry

Secoiridoids from Olea europaea

A secoiridoid glucoside from Olea europaea

Liquid chromatography with electrospray ionisation mass spectrometric detection of phenolic compounds from Olea europaea

Isolation of cornoside from Olea europaea and its transformation into halleridone

Molluscicides from olive Olea europaea and their efficient isolation by counter-current chromatographies

A secoiridoid glucoside from Olea europaea

Fraxinus americana

1 reference

Secoiridoid glucosides from Fraxinus americana

Fraxinus formosana

1 reference

A secoiridoid glucoside from Fraxinus formosana

Fraxinus insularis

1 reference

Four secoiridoid glucosides from fraxinus insularis

Fraxinus pallisiae

1 reference

Secoiridoids and hydroxycoumarins in Bulgarian Fraxinus species

Jasminum officinale

1 reference

Structure Elucidation of Two Secoiridoid Glucosides from Jasminum officinale L. var. grandiflorum (L.) KOBUSKI.

Jasminum polyanthum

3 references

Two dimeric secoiridoid glucosides from Jasminum polyanthum

Jaspolyside, a secoiridoid glycoside from Jasminum polyanthum

Secoiridoid Glycosides fromJasminum Polyanthum

Ligustrum japonicum

2 references

A secoiridoid glucoside from Ligustrum japonicum

Three secoiridoid glucosides from Ligustrum japonicum

Phillyrea latifolia

3 references

Biosynthesis of secoiridoid glucosides in oleaceae

In Vitro Anti-Inflammatory Activity of Iridoids and Triterpenoid Compounds Isolated from Phillyrea latifolia L

Phytochemical analysis of Phillyrea latifolia L., a new source of oleuropeoside

Picconia excelsa

1 reference

Iridoid glucosides from Picconia excelsa

Syringa josikaea

3 references

Biosynthesis of secoiridoid glucosides in oleaceae

Biosynthesis of iridoids in Syringa and Fraxinus: Carbocyclic iridoid precursors

Biosynthesis of iridoids in Syringa and Fraxinus: Carbocyclic iridoid precursors

Syringa vulgaris

4 references

Biosynthesis of iridoids in Syringa and Fraxinus: Carbocyclic iridoid precursors

Two new phenolic glycosides from Syringa reticulata

Iridoids of the bark of Syringa vulgaris

TLC and HPLC analysis of syringin in Syringa vulgaris

Fraxinus chinensis

1 reference

Isolation and structure elucidation of secoiridoid glucosides from Fraxinus rhynchophylla leaves

Fraxinus uhdei

1 reference

Additional secoiridoid glucosides from Fraxinus uhdei

Ligustrum lucidum

6 references

Secoiridoid constituents from the fruits of Ligustrum lucidum

[Studies on the constituents of Ligustrum species. XIX. Structures of iridoid glucosides from the leaves of Ligustrum lucidum AIT]

Antioxidative glucosides from the fruits of Ligustrum lucidum

In vitro evaluation of secoiridoid glucosides from the fruits of Ligustrum lucidum as antiviral agents

Three secoiridoid glucosides from Ligustrum japonicum

A secoiridoid glucoside from Ligustrum japonicum

Ligustrum vulgare

2 references

HPLC analysis of flavonoids and secoiridoids in leaves of Ligustrum vulgare L. (Oleaceae)

Secoiridoid glucosides and unusual recyclized secoiridoid aglycones from Ligustrum vulgare

Osmanthus heterophyllus

2 references

Secoiridoid Di-glycosides from Osmanthus ilicifolius

Studies on the Constituents of Osmanthus Species. III. On the Components of the Leaves of Osmanthus ilicifolius (HASSK.) MOUILLEFERT

Osmanthus ilicifolius

2 references

Secoiridoid Di-glycosides from Osmanthus ilicifolius

Studies on the Constituents of Osmanthus Species. III. On the Components of the Leaves of Osmanthus ilicifolius (HASSK.) MOUILLEFERT

Inga feuillei

1 reference

Secoiridoid glucosides and related compounds from Syringa reticulata and their antioxidant activities

Ligustrum obtusifolium

1 reference

Studies on the Constituents of Ligustrum Species. IX. On the Components of the Fruits of Ligustrum obtusifolium SIEB. et ZUCC. (3)

Osmanthus × fortunei

1 reference

Studies on the Constituents of Osmanthus Species. IV. On the Components of the Leaves of Osmanthus fortunei CARR.

Osmanthus fragrans

1 reference

Studies on the Constituents of Osmanthus Species. I. On the Components of the Leaves of Osmanthus fragrans LOUR. var. aurantiacus MAKINO (1)

Inga feuilleei

1 reference

Secoiridoid glucosides and related compounds from Syringa reticulata and their antioxidant activities

Fraxinus angustifolia

1 reference

Secoiridoids from Fraxinus angustifolia

Fraxinus griffithii

1 reference

A secoiridoid glucoside from Fraxinus formosana

Identifiers

InChI

InChI=1S/C25H32O12/c1-3-15-16(10-19(28)34-9-8-13-4-6-14(27)7-5-13)17(23(32)33-2)12-35-24(15)37-25-22(31)21(30)20(29)18(11-26)36-25/h3-7,12,16,18,20-22,24-27,29-31H,8-11H2,1-2H3/b15-3+/t16-,18+,20+,21-,22+,24-,25-/m0/s1

1 reference

ligstroside (English)

14 October 2016

1 reference

Global Substance Registration System

ligstroside (English)

14 October 2016

2 references

UNII

83S9SA69C5

ligstroside (English)

14 October 2016

https://commonchemistry.cas.org/detail?cas_rn=35897-92-8

8 April 2021

1 reference

Methyl (2S,3E,4S)-3-ethylidene-2-(beta-D-glucopyranosyloxy)-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-3,4-dihydro-2H-pyran-5-carboxylate (English)

14 October 2016

2 references

ligstroside (English)

14 October 2016

ChEBI ID

149585

mapping relation type

exact match

2 references

ChEBI release 2021-03-01

International Chemical Identifier

1 reference

LIGSTROSIDE (English)

14 October 2016

1 reference

1 reference

UNII

83S9SA69C5

2 references

Global Substance Registration System

UNII

83S9SA69C5

ligstroside (English)

14 October 2016