PRESENTED BY :

AYESHA BIBI
M.PHIL STUDENT

PRESENTED TO:
Respected
teacher: Dr.Firdos
2

Contents:

Introduction
How derived?
Structure
Occurrence
Classification
Biosynthesis
Extraction
Spectral analysis by Ms/Ms
Charecteristics
Biological properties
Objectives

IRIDOIDS

INTRODUCTION: IRIDOIDS
Class

of secondary metabolites .
Monoterpenes biosynthesized from isoprene.
Intermediates in the biosynthesis of alkaloids.
More than 2500 Iridoids compounds isolated.
Found in nature as Secroiridoids.

Ref. http://en.wikipedia.org/wiki/Iridoid
http://dx.doi.org/10.5772/55784

IRIDOIDS : HOW DERIVED?

Compounds like iridomyrmecine, iridolacotne and
iridoidal involved in Insects defensive mechanism
isolated from the ant Iridomirmex genus, for which
iridoids are named.

iridomyrmecin
e

INTRODUCTION: IRIDOIDS
Class

of secondary metabolites .
Monoterpenes biosynthesized from isoprene.
Intermediates in the biosynthesis of alkaloids.
More than 2500 Iridoids compounds isolated.
Found in nature as Secroiridoids.

Ref. http://en.wikipedia.org/wiki/Iridoid
http://dx.doi.org/10.5772/55784

Iridoid was first isolated in the latter period of the

nineteenth century.
However, the basic skeleton of iridoid was not
identified until 1958.
O. Halpern and H. Schmid proposed what iridoid
looks like while investigating Plumieride structure.

STRUCTURE: IRIDOIDS
Methylcyclopentan-[C]-Pyran Skeleton
Iridane + Six member Oxygen ring
Iridane skeleton cis-2-oxa-bicyclo-[4,3,0]-nonane
Iridane: Cyclopentane ring
Generally consist of 10, 9, or rarely 8 carbon
atoms.
C11 is more frequently missing than C10.
May have more or multiple variation up to
polycyclic
Structures.

Ref: http://dx.doi.org/10.5772/55784

GENERAL IRIDOID
SKELETON

IRRIDOIDS : OCCURRENCE
Insects s: Ants
Plants: Dicotyledon: Angiosperm
Plants family: Dipsacales, Genitianales,
Scrophulariales,
Lamiales
Aucubin and Catalpol --- Most common iridoids in
the plant kingdom

Ref: http://www.slideshare.net/priyankagoswami/terpenoid-iridoid?
related=1

IRIDOIDS - CLASSIFICATION
1. Iridoids 10 carbon atoms bicyclic
a. Glycosides iridoids (Accubin, catapol)
b. Non- glycosides iridoids (alkaloids, skytantine)
2.SecoiridoidsOxidative cleavage at 7,8 bond of
cylopentane

a. Glycosidic secoiridoids
b. Non-glycosidic secoiridoids
Glycosides glycosidic linkage between -OH group
on
anomeric carbon of D-glucose and theOH
inof the
1-position
of aglycone
Journal
the Brazilian
Chemical Society
PrintversionISSN 0103-5053 J. Braz. Chem.
Soc.vol.12no.2So PauloMar./Apr.2001 .http://dx.doi.org/10.1590/S0103-

Different classes of iridoids

1.Iridoids

2.Secoiridoid

IRIDOIDS: BIOSYNTHESIS
Iridoids are formed from geraniol by the
mevalonate pathway.
Geraniol is the major ingredient in rose
essential oils (40-60%), and smells rose-like
odor.

http://iridoid.org/?page_id=42

The iridoid ring synthesized by the enzyme

iridoids synthase .
Iridoid synthase uses 10-Oxogeranial as a
substrate.
Two-step mechanism,
i. Reduction step NADPH-dependent
ii. Cyclization step that occurs through either
a Diels-Alder reaction or an intramolecular
Michael addition

Total bio synthesis of iridoids:

Secologanin

Extraction: Iridoids
Extractio
n
Polar solvents, alcohols of
diff. concentration for
extraction

Initial
separationi.re- dissolving extraction residue in H2O
ii. Re-extracting with immiscible solvent of increasing
polarity

Fractionatio
n
Chromatography (on alumina ,charcoal)
Porous polymers with polar eluents and by polar
RP HPLC
Purificatio

TLC,HPL
C

Detectio
n
Trim and Hill Color reagent (dilute sol. CuSO4
and HCl

Detection
spray
Vanillin H2SO4, hot
HCl

Spectral Analysis
In MS, formate adduct ion [M+HCOO]- diagnostic ion having methyl ester,
lactone, or carboxyl group at their C-4 positions.
Neutral losses of H2O, CO2, CH3OH, CH3COOH, and a glucosidic unit helps
to identify functional substituent are in the MS/MS spectra.

Structural information of basic skeleton and its substituents

by 1,4F, 2,6F,and 2,7F fragments.
By the he relative abundances of the fragment ions 1,4F
and 2,7F,
7,8-cyclopentene-type
andSPECTROMETRY
cyclopentane-type
IGs, can
be
RAPID
COMMUNICATIONS IN MASS
Rapid Common.
Mass
Spectrom.
2008;
22: 19411954 Published online in Wiley InterScience (www.interscience.wiley.com)
differentiated
DOI: 10.1002/rcm.3579

Characteristics of iridoids
Iridoids are also refer as Pseudoindicans .
Bitter taste.
Easily dissolve in H2O.
Some iridoids upon hydrolysis develop Blue coloration.
Delicate show great Instability , iridoids plants species darkens soon
after collecting.
Leticia J. El-Naggar , Jack L. Beal J. Nat. Prod., 1980, 43 (6), pp 649707 DOI:
10.1021/np50012a001 Publication Date: November 1980

Biological Properties
Shows wide spectrum of Biological
Activity
Defensive Function in ants
Anti- Inflammatory
Anti bacterial
Anti Fungal
Anti Tumoral
Anti Oxidative
Anti Protozoal

Thank you..!
Question is guaranteed but answers
are not.