Acid Rearrangement of Secoiridoids Related to Oleuropein and Secologanin

Armandodoriano Bianco; Søren Rosendal Jensen; Jens Olesen; Pietro Passacantilli; Alessia Ramunno

doi:10.1002/ejoc.200300348

Acid Rearrangement of Secoiridoids Related to Oleuropein and Secologanin

Armandodoriano Bianco
, Søren Rosendal Jensen
, Jens Olesen
, Pietro Passacantilli
, Alessia Ramunno

Department of Chemistry

University of Rome La Sapienza

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

Acid treatment of an iridoid glycoside results in the cleavage of the acetal bond between the sugar unit and the monoterpenoid aglycon. Iridoids possessing non-conjugated enol ether systems, however, undergo the hydration of the iridoid enol ether functionality in acid medium, as well as the hydrolysis of the bond. We examined the acid rearrangement of secoiridoids such as oleuropein (1) and secologanin (2) and their reduction products oleuropeinol (3) and secologaninol (4), to examine whether similar behaviour also occurs in this case.

Original language	English
Journal	European Journal of Organic Chemistry
Issue number	22
Pages (from-to)	4349-4354
ISSN	1434-193X
DOIs	https://doi.org/10.1002/ejoc.200300348
Publication status	Published - 2003

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title = "Acid Rearrangement of Secoiridoids Related to Oleuropein and Secologanin",

abstract = "Acid treatment of an iridoid glycoside results in the cleavage of the acetal bond between the sugar unit and the monoterpenoid aglycon. Iridoids possessing non-conjugated enol ether systems, however, undergo the hydration of the iridoid enol ether functionality in acid medium, as well as the hydrolysis of the bond. We examined the acid rearrangement of secoiridoids such as oleuropein (1) and secologanin (2) and their reduction products oleuropeinol (3) and secologaninol (4), to examine whether similar behaviour also occurs in this case.",

author = "Armandodoriano Bianco and Jensen, \{S{\o}ren Rosendal\} and Jens Olesen and Pietro Passacantilli and Alessia Ramunno",

year = "2003",

doi = "10.1002/ejoc.200300348",

language = "English",

pages = "4349--4354",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH",

number = "22",

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TY - JOUR

T1 - Acid Rearrangement of Secoiridoids Related to Oleuropein and Secologanin

AU - Bianco, Armandodoriano

AU - Jensen, Søren Rosendal

AU - Olesen, Jens

AU - Passacantilli, Pietro

AU - Ramunno, Alessia

PY - 2003

Y1 - 2003

N2 - Acid treatment of an iridoid glycoside results in the cleavage of the acetal bond between the sugar unit and the monoterpenoid aglycon. Iridoids possessing non-conjugated enol ether systems, however, undergo the hydration of the iridoid enol ether functionality in acid medium, as well as the hydrolysis of the bond. We examined the acid rearrangement of secoiridoids such as oleuropein (1) and secologanin (2) and their reduction products oleuropeinol (3) and secologaninol (4), to examine whether similar behaviour also occurs in this case.

AB - Acid treatment of an iridoid glycoside results in the cleavage of the acetal bond between the sugar unit and the monoterpenoid aglycon. Iridoids possessing non-conjugated enol ether systems, however, undergo the hydration of the iridoid enol ether functionality in acid medium, as well as the hydrolysis of the bond. We examined the acid rearrangement of secoiridoids such as oleuropein (1) and secologanin (2) and their reduction products oleuropeinol (3) and secologaninol (4), to examine whether similar behaviour also occurs in this case.

U2 - 10.1002/ejoc.200300348

DO - 10.1002/ejoc.200300348

M3 - Journal article

SN - 1434-193X

SP - 4349

EP - 4354

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 22

ER -

Acid Rearrangement of Secoiridoids Related to Oleuropein and Secologanin

Abstract

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