Is the separation of medicinally active portions of plant (and animal) tissues using selective solvents through standard procedures.
The products so obtained from plants are relatively complex mixtures of metabolites, in liquid or semisolid state or in dry powder form (after removing the solvent), & are intended for oral or external use
The Medicinal plants constitute an effective source of both traditional and modern medicines, herbal medicine has been shown to have genuine utility and about 80% of rural population depends on it as primary health care. [WHO, (2005)]
AN INTRODUCTION TOPLANT SECONDARY METABOLITES :ITS APPLICATIONSSupriya Sankranthi
This presentation is about different types of secondary metabolites produced by the plants and thier applications in different fields like medicine,drugs,cosmetics and perfumery,plant defense,role in ecological balance,textile industries.
drug metabolism, phase I metabolism, biotransformation, Xenobiotics- substances foreign to body
Non polar lipid soluble compounds are made polar lipid insoluble, so that they are easily excreted.
Advantages of metabolism
Termination of drug action
↓ toxicity
Reduced lipophilicity.
Renal / biliary excretion ↑
↑ water solubility
↑ polarity
↑ excretion
Loss of phsiological activity
Active drug → more active drug
Non Active drug → active drug
Active drug → inactive drug
BIOTRANSFORMATION REACTIONS - 2 TYPES
Phase I / Non synthetic / Functionalization
A functional group is generated
Metabolite – active or inactive
Phase II / Synthetic / Conjugation
Metabolite is usually inactive
BIOTRANSFORMATION REACTIONS - 2 TYPES
Phase I / Non synthetic / Functionalization
A functional group is generated
Metabolite – active or inactive
Phase II / Synthetic / Conjugation
Metabolite is usually inactive
Depending upon nature and localisation of enzymes which catalyse reaction –
Microsomal enzymes
Non- Microsomal enzymes
Oxidation of alcohol
ethanol→ acetaldehyde → acetic acid →TCA cycle → CO₂
Eg.
chloral hydrate → trichloroacetic acid
mefenamic acid → hydroxy methyl derivative
ALIPHATIC HYDROXYLATION
Hydroxyl group added to drug
RCH2CH3 O RCHOHCH3
Salicylic acid to Gentisic acid
Ibuprofen
Tolbutamide, Chlorpropamide,
alkaloids -General methods of structural elucidation of Alkaloids. Structura...ramiah valliappan
General methods of structural
elucidation of Alkaloids. Structural
Elucidation and synthesis of
Papaverine, Quinine and Morphine.
Stereoselective synthesis of
Reserpine. Biosynthesis of Alkaloids.
Sem II, Paper III, Unit II……
Plants produce a vast and diverse organic compounds, which do not appear to participate directly in growth and development.These substances traditionally referred to as secondary metabolites which terpenes are one of them.
Phytochemical screening and antioxidant activity of clove mistletoe leaf extr...iosrphr_editor
Clove mistletoe (Dendrophthoe pentandra (L.) Miq) is one of the semi-parasitic plants belonging to the Loranthaceae family. Clove mistletoe leaf extracts have many biological activities such as antibacterial, antioxidant and antidiabetes. The purpose of this study was to determine the content of secondary metabolites in clove mistletoe leaf extracts through phytochemical screening and determine its antioxidant activity through DPPH free radical scavenging. Samples were tested include water and ethanol 70 % extracts, as well as n-hexane, ethyl acetate and ethanol fractions. Phytochemical screening showed that all samples containing tannins and flavonoids but no alkaloids. The highest total phenol contents was ethyl acetate fraction namely 358.4 mg GAE/ g. The best antioxidant activity was water extract, ethanol 70 % extract and ethyl acetate fraction. Therefore, clove mistletoe leaf extracts are potential source for antioxidant.
Phytochemical screening and antioxidant activity of clove mistletoe leaf extr...iosrphr_editor
Clove mistletoe (Dendrophthoe pentandra (L.) Miq) is one of the semi-parasitic plants belonging to the Loranthaceae family. Clove mistletoe leaf extracts have many biological activities such as antibacterial, antioxidant and antidiabetes. The purpose of this study was to determine the content of secondary metabolites in clove mistletoe leaf extracts through phytochemical screening and determine its antioxidant activity through DPPH free radical scavenging. Samples were tested include water and ethanol 70 % extracts, as well as n-hexane, ethyl acetate and ethanol fractions. Phytochemical screening showed that all samples containing tannins and flavonoids but no alkaloids. The highest total phenol contents was ethyl acetate fraction namely 358.4 mg GAE/ g. The best antioxidant activity was water extract, ethanol 70 % extract and ethyl acetate fraction. Therefore, clove mistletoe leaf extracts are potential source for antioxidant.
Chemical conversion of a substance mediated by living organisms or enzymes
Can result in DETOXIFICATION and BIOACTIVATION
Vital to survive
Key in defense mechanism
Natural products and chemical products differ in several ways, including their origin, composition, production methods, and potential applications. Here are some key differences between the two:
Origin:
Natural Products: These are derived from natural sources, such as plants, animals, microorganisms, or minerals. Examples include herbal remedies, essential oils, and food products.
Chemical Products: These are synthesized in laboratories or chemical factories. They are typically created through chemical reactions and processes.
Composition:
Natural Products: They often contain a complex mixture of naturally occurring compounds, and their composition can vary based on the source and environmental factors. These products may contain a combination of chemicals produced by living organisms.
Chemical Products: They are typically composed of pure or well-defined chemical compounds. Their composition is consistent and can be precisely controlled.
Production Methods:
Natural Products: Obtained through extraction, purification, or isolation processes from natural sources. The methods may involve techniques like distillation, solvent extraction, or fermentation.
Chemical Products: Synthesized through chemical reactions involving various reagents and catalysts in controlled laboratory conditions. These reactions are typically reproducible.
Purity:
Natural Products: May contain impurities or variations in composition due to the natural source. Purity levels can vary significantly.
Chemical Products: Can be highly purified, with known and consistent chemical compositions.
Safety and Regulation:
Natural Products: May be subject to fewer regulations, leading to potential variability in safety and efficacy. Some natural products may also have potential side effects or interactions with medications.
Chemical Products: Typically subject to rigorous safety testing and regulatory oversight, which helps ensure a certain level of safety and efficacy.
Environmental Impact:
Natural Products: May have a lower environmental impact if sourced sustainably, but overharvesting or unsustainable practices can lead to ecological harm.
Chemical Products: The production of chemicals can have environmental consequences, including the generation of waste and pollution. However, sustainable and green chemistry practices aim to mitigate these impacts.
Applications:
Natural Products: Often used in traditional medicine, cosmetics, food, and some pharmaceuticals. They are favored for their perceived natural and holistic qualities.
Chemical Products: Widely used in various industries, including pharmaceuticals, plastics, agriculture, and electronics. They can be designed for specific purposes and are essential in modern manufacturing and technology.
It's important to note that both natural and chemical products have their own advantages and disadvantages, and the choice between them often depends on factors like safety, efficacy, cost, sustainability,
AN INTRODUCTION TOPLANT SECONDARY METABOLITES :ITS APPLICATIONSSupriya Sankranthi
This presentation is about different types of secondary metabolites produced by the plants and thier applications in different fields like medicine,drugs,cosmetics and perfumery,plant defense,role in ecological balance,textile industries.
drug metabolism, phase I metabolism, biotransformation, Xenobiotics- substances foreign to body
Non polar lipid soluble compounds are made polar lipid insoluble, so that they are easily excreted.
Advantages of metabolism
Termination of drug action
↓ toxicity
Reduced lipophilicity.
Renal / biliary excretion ↑
↑ water solubility
↑ polarity
↑ excretion
Loss of phsiological activity
Active drug → more active drug
Non Active drug → active drug
Active drug → inactive drug
BIOTRANSFORMATION REACTIONS - 2 TYPES
Phase I / Non synthetic / Functionalization
A functional group is generated
Metabolite – active or inactive
Phase II / Synthetic / Conjugation
Metabolite is usually inactive
BIOTRANSFORMATION REACTIONS - 2 TYPES
Phase I / Non synthetic / Functionalization
A functional group is generated
Metabolite – active or inactive
Phase II / Synthetic / Conjugation
Metabolite is usually inactive
Depending upon nature and localisation of enzymes which catalyse reaction –
Microsomal enzymes
Non- Microsomal enzymes
Oxidation of alcohol
ethanol→ acetaldehyde → acetic acid →TCA cycle → CO₂
Eg.
chloral hydrate → trichloroacetic acid
mefenamic acid → hydroxy methyl derivative
ALIPHATIC HYDROXYLATION
Hydroxyl group added to drug
RCH2CH3 O RCHOHCH3
Salicylic acid to Gentisic acid
Ibuprofen
Tolbutamide, Chlorpropamide,
alkaloids -General methods of structural elucidation of Alkaloids. Structura...ramiah valliappan
General methods of structural
elucidation of Alkaloids. Structural
Elucidation and synthesis of
Papaverine, Quinine and Morphine.
Stereoselective synthesis of
Reserpine. Biosynthesis of Alkaloids.
Sem II, Paper III, Unit II……
Plants produce a vast and diverse organic compounds, which do not appear to participate directly in growth and development.These substances traditionally referred to as secondary metabolites which terpenes are one of them.
Phytochemical screening and antioxidant activity of clove mistletoe leaf extr...iosrphr_editor
Clove mistletoe (Dendrophthoe pentandra (L.) Miq) is one of the semi-parasitic plants belonging to the Loranthaceae family. Clove mistletoe leaf extracts have many biological activities such as antibacterial, antioxidant and antidiabetes. The purpose of this study was to determine the content of secondary metabolites in clove mistletoe leaf extracts through phytochemical screening and determine its antioxidant activity through DPPH free radical scavenging. Samples were tested include water and ethanol 70 % extracts, as well as n-hexane, ethyl acetate and ethanol fractions. Phytochemical screening showed that all samples containing tannins and flavonoids but no alkaloids. The highest total phenol contents was ethyl acetate fraction namely 358.4 mg GAE/ g. The best antioxidant activity was water extract, ethanol 70 % extract and ethyl acetate fraction. Therefore, clove mistletoe leaf extracts are potential source for antioxidant.
Phytochemical screening and antioxidant activity of clove mistletoe leaf extr...iosrphr_editor
Clove mistletoe (Dendrophthoe pentandra (L.) Miq) is one of the semi-parasitic plants belonging to the Loranthaceae family. Clove mistletoe leaf extracts have many biological activities such as antibacterial, antioxidant and antidiabetes. The purpose of this study was to determine the content of secondary metabolites in clove mistletoe leaf extracts through phytochemical screening and determine its antioxidant activity through DPPH free radical scavenging. Samples were tested include water and ethanol 70 % extracts, as well as n-hexane, ethyl acetate and ethanol fractions. Phytochemical screening showed that all samples containing tannins and flavonoids but no alkaloids. The highest total phenol contents was ethyl acetate fraction namely 358.4 mg GAE/ g. The best antioxidant activity was water extract, ethanol 70 % extract and ethyl acetate fraction. Therefore, clove mistletoe leaf extracts are potential source for antioxidant.
Chemical conversion of a substance mediated by living organisms or enzymes
Can result in DETOXIFICATION and BIOACTIVATION
Vital to survive
Key in defense mechanism
Natural products and chemical products differ in several ways, including their origin, composition, production methods, and potential applications. Here are some key differences between the two:
Origin:
Natural Products: These are derived from natural sources, such as plants, animals, microorganisms, or minerals. Examples include herbal remedies, essential oils, and food products.
Chemical Products: These are synthesized in laboratories or chemical factories. They are typically created through chemical reactions and processes.
Composition:
Natural Products: They often contain a complex mixture of naturally occurring compounds, and their composition can vary based on the source and environmental factors. These products may contain a combination of chemicals produced by living organisms.
Chemical Products: They are typically composed of pure or well-defined chemical compounds. Their composition is consistent and can be precisely controlled.
Production Methods:
Natural Products: Obtained through extraction, purification, or isolation processes from natural sources. The methods may involve techniques like distillation, solvent extraction, or fermentation.
Chemical Products: Synthesized through chemical reactions involving various reagents and catalysts in controlled laboratory conditions. These reactions are typically reproducible.
Purity:
Natural Products: May contain impurities or variations in composition due to the natural source. Purity levels can vary significantly.
Chemical Products: Can be highly purified, with known and consistent chemical compositions.
Safety and Regulation:
Natural Products: May be subject to fewer regulations, leading to potential variability in safety and efficacy. Some natural products may also have potential side effects or interactions with medications.
Chemical Products: Typically subject to rigorous safety testing and regulatory oversight, which helps ensure a certain level of safety and efficacy.
Environmental Impact:
Natural Products: May have a lower environmental impact if sourced sustainably, but overharvesting or unsustainable practices can lead to ecological harm.
Chemical Products: The production of chemicals can have environmental consequences, including the generation of waste and pollution. However, sustainable and green chemistry practices aim to mitigate these impacts.
Applications:
Natural Products: Often used in traditional medicine, cosmetics, food, and some pharmaceuticals. They are favored for their perceived natural and holistic qualities.
Chemical Products: Widely used in various industries, including pharmaceuticals, plastics, agriculture, and electronics. They can be designed for specific purposes and are essential in modern manufacturing and technology.
It's important to note that both natural and chemical products have their own advantages and disadvantages, and the choice between them often depends on factors like safety, efficacy, cost, sustainability,
Professional air quality monitoring systems provide immediate, on-site data for analysis, compliance, and decision-making.
Monitor common gases, weather parameters, particulates.
The increased availability of biomedical data, particularly in the public domain, offers the opportunity to better understand human health and to develop effective therapeutics for a wide range of unmet medical needs. However, data scientists remain stymied by the fact that data remain hard to find and to productively reuse because data and their metadata i) are wholly inaccessible, ii) are in non-standard or incompatible representations, iii) do not conform to community standards, and iv) have unclear or highly restricted terms and conditions that preclude legitimate reuse. These limitations require a rethink on data can be made machine and AI-ready - the key motivation behind the FAIR Guiding Principles. Concurrently, while recent efforts have explored the use of deep learning to fuse disparate data into predictive models for a wide range of biomedical applications, these models often fail even when the correct answer is already known, and fail to explain individual predictions in terms that data scientists can appreciate. These limitations suggest that new methods to produce practical artificial intelligence are still needed.
In this talk, I will discuss our work in (1) building an integrative knowledge infrastructure to prepare FAIR and "AI-ready" data and services along with (2) neurosymbolic AI methods to improve the quality of predictions and to generate plausible explanations. Attention is given to standards, platforms, and methods to wrangle knowledge into simple, but effective semantic and latent representations, and to make these available into standards-compliant and discoverable interfaces that can be used in model building, validation, and explanation. Our work, and those of others in the field, creates a baseline for building trustworthy and easy to deploy AI models in biomedicine.
Bio
Dr. Michel Dumontier is the Distinguished Professor of Data Science at Maastricht University, founder and executive director of the Institute of Data Science, and co-founder of the FAIR (Findable, Accessible, Interoperable and Reusable) data principles. His research explores socio-technological approaches for responsible discovery science, which includes collaborative multi-modal knowledge graphs, privacy-preserving distributed data mining, and AI methods for drug discovery and personalized medicine. His work is supported through the Dutch National Research Agenda, the Netherlands Organisation for Scientific Research, Horizon Europe, the European Open Science Cloud, the US National Institutes of Health, and a Marie-Curie Innovative Training Network. He is the editor-in-chief for the journal Data Science and is internationally recognized for his contributions in bioinformatics, biomedical informatics, and semantic technologies including ontologies and linked data.
Earliest Galaxies in the JADES Origins Field: Luminosity Function and Cosmic ...Sérgio Sacani
We characterize the earliest galaxy population in the JADES Origins Field (JOF), the deepest
imaging field observed with JWST. We make use of the ancillary Hubble optical images (5 filters
spanning 0.4−0.9µm) and novel JWST images with 14 filters spanning 0.8−5µm, including 7 mediumband filters, and reaching total exposure times of up to 46 hours per filter. We combine all our data
at > 2.3µm to construct an ultradeep image, reaching as deep as ≈ 31.4 AB mag in the stack and
30.3-31.0 AB mag (5σ, r = 0.1” circular aperture) in individual filters. We measure photometric
redshifts and use robust selection criteria to identify a sample of eight galaxy candidates at redshifts
z = 11.5 − 15. These objects show compact half-light radii of R1/2 ∼ 50 − 200pc, stellar masses of
M⋆ ∼ 107−108M⊙, and star-formation rates of SFR ∼ 0.1−1 M⊙ yr−1
. Our search finds no candidates
at 15 < z < 20, placing upper limits at these redshifts. We develop a forward modeling approach to
infer the properties of the evolving luminosity function without binning in redshift or luminosity that
marginalizes over the photometric redshift uncertainty of our candidate galaxies and incorporates the
impact of non-detections. We find a z = 12 luminosity function in good agreement with prior results,
and that the luminosity function normalization and UV luminosity density decline by a factor of ∼ 2.5
from z = 12 to z = 14. We discuss the possible implications of our results in the context of theoretical
models for evolution of the dark matter halo mass function.
Introduction:
RNA interference (RNAi) or Post-Transcriptional Gene Silencing (PTGS) is an important biological process for modulating eukaryotic gene expression.
It is highly conserved process of posttranscriptional gene silencing by which double stranded RNA (dsRNA) causes sequence-specific degradation of mRNA sequences.
dsRNA-induced gene silencing (RNAi) is reported in a wide range of eukaryotes ranging from worms, insects, mammals and plants.
This process mediates resistance to both endogenous parasitic and exogenous pathogenic nucleic acids, and regulates the expression of protein-coding genes.
What are small ncRNAs?
micro RNA (miRNA)
short interfering RNA (siRNA)
Properties of small non-coding RNA:
Involved in silencing mRNA transcripts.
Called “small” because they are usually only about 21-24 nucleotides long.
Synthesized by first cutting up longer precursor sequences (like the 61nt one that Lee discovered).
Silence an mRNA by base pairing with some sequence on the mRNA.
Discovery of siRNA?
The first small RNA:
In 1993 Rosalind Lee (Victor Ambros lab) was studying a non- coding gene in C. elegans, lin-4, that was involved in silencing of another gene, lin-14, at the appropriate time in the
development of the worm C. elegans.
Two small transcripts of lin-4 (22nt and 61nt) were found to be complementary to a sequence in the 3' UTR of lin-14.
Because lin-4 encoded no protein, she deduced that it must be these transcripts that are causing the silencing by RNA-RNA interactions.
Types of RNAi ( non coding RNA)
MiRNA
Length (23-25 nt)
Trans acting
Binds with target MRNA in mismatch
Translation inhibition
Si RNA
Length 21 nt.
Cis acting
Bind with target Mrna in perfect complementary sequence
Piwi-RNA
Length ; 25 to 36 nt.
Expressed in Germ Cells
Regulates trnasposomes activity
MECHANISM OF RNAI:
First the double-stranded RNA teams up with a protein complex named Dicer, which cuts the long RNA into short pieces.
Then another protein complex called RISC (RNA-induced silencing complex) discards one of the two RNA strands.
The RISC-docked, single-stranded RNA then pairs with the homologous mRNA and destroys it.
THE RISC COMPLEX:
RISC is large(>500kD) RNA multi- protein Binding complex which triggers MRNA degradation in response to MRNA
Unwinding of double stranded Si RNA by ATP independent Helicase
Active component of RISC is Ago proteins( ENDONUCLEASE) which cleave target MRNA.
DICER: endonuclease (RNase Family III)
Argonaute: Central Component of the RNA-Induced Silencing Complex (RISC)
One strand of the dsRNA produced by Dicer is retained in the RISC complex in association with Argonaute
ARGONAUTE PROTEIN :
1.PAZ(PIWI/Argonaute/ Zwille)- Recognition of target MRNA
2.PIWI (p-element induced wimpy Testis)- breaks Phosphodiester bond of mRNA.)RNAse H activity.
MiRNA:
The Double-stranded RNAs are naturally produced in eukaryotic cells during development, and they have a key role in regulating gene expression .
This pdf is about the Schizophrenia.
For more details visit on YouTube; @SELF-EXPLANATORY;
https://www.youtube.com/channel/UCAiarMZDNhe1A3Rnpr_WkzA/videos
Thanks...!
THE IMPORTANCE OF MARTIAN ATMOSPHERE SAMPLE RETURN.Sérgio Sacani
The return of a sample of near-surface atmosphere from Mars would facilitate answers to several first-order science questions surrounding the formation and evolution of the planet. One of the important aspects of terrestrial planet formation in general is the role that primary atmospheres played in influencing the chemistry and structure of the planets and their antecedents. Studies of the martian atmosphere can be used to investigate the role of a primary atmosphere in its history. Atmosphere samples would also inform our understanding of the near-surface chemistry of the planet, and ultimately the prospects for life. High-precision isotopic analyses of constituent gases are needed to address these questions, requiring that the analyses are made on returned samples rather than in situ.
Nutraceutical market, scope and growth: Herbal drug technologyLokesh Patil
As consumer awareness of health and wellness rises, the nutraceutical market—which includes goods like functional meals, drinks, and dietary supplements that provide health advantages beyond basic nutrition—is growing significantly. As healthcare expenses rise, the population ages, and people want natural and preventative health solutions more and more, this industry is increasing quickly. Further driving market expansion are product formulation innovations and the use of cutting-edge technology for customized nutrition. With its worldwide reach, the nutraceutical industry is expected to keep growing and provide significant chances for research and investment in a number of categories, including vitamins, minerals, probiotics, and herbal supplements.
2. Aims
1. What is the natural product chemistry.
2. The important of natural product chemistry.
3. The distinction between primary and secondary
metabolites.
4. The structural characteristics of the major
classes of natural product and recognize their
biosynthetic building blocks.
5. The chemistry underlying the methods of
isolating natural products.
6. Structure elucidation of the natural product.
3. Introductio
n
Natural products are organic compounds that are
formed by living systems.
Naturally occurring compounds may be divided
into three broad categories:
Firstly: compounds which occur in all cells and
play a central role in the metabolism and
reproduction of those cells. These compounds
include the nucleic acids and the common amino
acids and sugars. “primary metabolites”
4. Introduction
Secondly, there are the high-molecular-weight
polymeric materials such as cellulose, the lignins
and the proteins which form the cellular structures.
Finally, compounds that are characteristic of a
limited range of species. “secondary metabolites”.
Most primary metabolites exert their biological
effect within the cell or organism that is responsible
for their production.
Secondary metabolites, on the other hand, have
often
attracted interest because of their biological effect
on other organisms.
5. Introduction
Many of the biologically active constituents of the
medicinal plants are secondary metabolites.
A number of screening programmes for bioactive
compounds exist and have led to new drugs, for
example taxol, which is used for the treatment of
various cancers.
They can be defensive substances, antifeedants,
attractants and pheromones.
Chemotaxonomy provides another reason for
examining the constituents of plants.
6. Introduction
A pheromone is a substance released by one
individual of a species which causes a change in
behaviour by another member of the same species.
Chemotaxonomy involves the use of natural
products in the classification of species.
A phytochemical is a natural product produced by
a plant.
20. Natural Products wich are slightly modified in order to improve their
activities or decrease the side-effects.
- 400 BC Use of the bark and leaves of willow
tree to releave pain and fever (Greece).
- 1758 Edward Stone (England) chew the
bark of a willow tree Þ bitter ÞÞ discovery of
Salicin and Salicilic acid (side effect: stomach
pain)
- 1897 Felix Hoffmann (BAYER, Germany)
synthesise
Aspirin.
23. Methods used in structure of
Compounds
1. Classical Methods
a. double bond
The compound should be pure
Br2/ CCl4
Br
Br
Br
Br
O
O
O
O
O
O
+
Diene Dienophile Adduct
Diels- Alder Reaction
26. Carbonyl: CO
O NH2OH NOH
Spectroscopic tools
1. MS, FABMS, ESIMS, HPLCMS, GCMS: Molecular formula
2. IR: Function groups.
3. UV: Chromophore.
4. NMR: 1H-NMR, 13C-NMR.
5. Optical rotation.
27. Terpenoids
Terpenoids are secondary metabolites synthesized by plants,
marine organisms, fungi by head to tail joining of isoprene
units.
1
2
3
4
Head
Tail
5
methylbuta-1,3-diene
Isopentenyl pyrophosphate
C C C C C C C C
C C
C C C C C C C C
C C
C C C C
C
head tail head tail
28. Terpenids
Terpenoids originate through the condensation of the universal
phosphorylated derivative of hemiterpene, isopentenyl
diphosphate (IPP) and dimethylallyl diphosphate (DMAPP)
giving geranyl pyrophosphate (GPP).
32. Terpenoids
Mono-, sesqui-, di-, and sesterpenes contain the
isoprene units linked in a head to tail fashion. The
triterpenes and carotenoids (tetraterpenes) contain two
C15 and C20 units respectively linked head to head.
Many terpenes are hydrocarbons, but oxygen-
containing compounds such as alcohols, aldehydes or
ketones are also found.
Mono- and sesquiterpenes are the chief constituents
of the essential oils while the other terpenes are
constituents of balsams, resins, waxes, and rubber.
33. A number of inducible terpenoid defensive compounds
(phytoalexins) from angiosperm species are well known
(Stoessl et al., Phytochemistry 1976, 15, 855).
Isoprenoid units are also found within the framework of other
natural molecules.
Thus, indole alkaloids, several quinones (vitamin K), alcohols
(vitamin E, vitamin A formed from β-carotene), phenols,
isoprenoid alcohols (also known as terpenols or polyprenols)
also contain terpenoid fragments.
According to Bohlmann J et al. (PNAS 1998, 95, 4126), there
are in excess of 1000 monoterpenes, more than 7000
sesquiterpenes and more than 3000 diterpenes.
34. Monoterpenes
Monoterpenes are major components of the aromas of
plants, obtained from leaves, flowers and fruits. These volatile
natural products, known as essential oils, form the basis of
the perfumery and flavouring industries.
GPP as the basic substance for Monoterpenes
36. Acyclic Monoterpenes
Defensive role of simple terpenes have been demonstrated as for more
complex compounds.
Experimentally, a study of Arabidopsis thaliana engineered to overexpress a
terpene synthase leading to the emition of large amounts of linalool, which is
normally produced only in trace levels.
37. Linalool has been the subject of numerous studies investigating its anxiolytic
(anti-stress) effects. Inhalation of Linalool, extracted from natural essential
oils, leads to decreased aggressive behavior, lessens stress response.
Linalool
Ruzicka
Synthesis of Linalool
38. 2.Thermal reaction
Acid catalysis convert Linalool into geraniol and nerol.
Geraniol
It is the primary part of rose oil,
palmarosa oil, and citronella oil.
50. 2. Synthesis from Myrcene
1. Allylic amine from myrcene, 2. asymmetric isomerisation in the presence of a
BINAP rhodium complex, 3. R-citronellal after hydrolysis, 4. cyclised by a
carbonyl-ene-reaction initiated by zinc bromide to isopulegol, 5.
hydrogenation .
54. BICYCLIC MONOTERPENES
Plants containing thujone are used in herbal medicine, mainly for their immune-system
stimulating effects.
Pinene is, as limonene, an allelochemichal emitted by the roots of Quercus ilex.
Camphor and pinene are allelochemicals emitted by Salvia leucophylla (Nishida N et al.,
J Chem Ecol , 2005, 31, 1187).
55. Camphor
O
Dried rosemary leaves, (Rosmarinus officinalis), in the mint family,
contain up to 20% camphor.
It is used for its scent, as an ingredient in cooking (mainly in
India), as an embalming fluid, for medicinal purposes, and in
religious ceremonies.
57. Iridoids
Iridoids are a class of bicyclic monoterpenes found in a wide variety of
plants and in some animals.
Chemically, iridoids usually consist of a cyclopentane ring fused to a six-
membered oxygen heterocycle, as exemplified by nepetalactone.
Nepetalactone
Iridoids are typically found in plants as glycosides,
most often bound to glucose.
Iridodial is in equilibrium with its hemiacetal.
iridoids exhibit a wide range of bioactivities including cardiovascular, hypoglycemic,
anti-inflammatory, antispasmodic, antitumor, antiviral, immunomodulator and purgative
activities (Didna B et al., Chem Pharm Bull 2007, 55, 159).
58. sesquiterpene
Some sesquiterpenes are found in the higher boiling
portions of essential oils.
The Conipositae are the largest family Of flowering plants Their flowers have characteristically a large number of petals Typical
examples are the daisy and the sunflower
Acyclic Sesquiterpene
HO
Farnesol
OH
Nerolidol
60. The function of zingiberene and curcumene as insecticides,
repellents, and insect feeding deterrents.
The plant hormone abscisic acid, which stimulates leaf fall and
dormancy in plants.
Abscisic acid
61. Synthesis of β-Santalene
The asymmetric synthesis of Diels Alder reaction of Allene ester 18 with
cyclopentadiene, then selective reduction to yield 20 followed by oxidation”
Pyridinium chlorochromate” and Wolf-Kischner reduction.
62. Bicyclic Sesquiterpene
The classic bicyclic sesquiterpene is caryophyllene, from the
oil of cloves, which has a nine-membered ring and
cyclobutane ring.
Accumulation of rishitin as one of a major phytoalexin synthesis in tomato
plant was measured in leaves and stems after elicited by 1% of silver nitrate
at different plant ages.
63. Tricyclic Sesquiterpene
α-Santalol is an organic chemical compound and is a
principal constituent of oil of sandalwood.
α-cedren and β-cedrene and cedrol was detected in
Juniperus virginiana .
Juniperus virginiana
64. Sesquiterpenlactone
Santonin is a drug which was widely used in the past as an
anthelminthic a drug that expels parasitic worms.
Artemisinin
Artemisinin, obtained from Artemisia annua, have recently been
recommended by the World Health Organization for the treatment of resistant
strains of malaria.
65. Dry plant
Ethanol
39 g extract,
H2O/MeOH (7:3).
CHCl3/BuOH
CHCl3
CC
Hexane/ethyl acetate
1 2
Sesquiterpenes and a Phenylpropanoid from Cordia trichotoma
Z. Naturforsch, 59c, 19-22 (2004). , L. Pessoa et-al
66. IR (KBr): νmax = 3415, 2935, 2870, 1461, 1376, 1074, 1026.
EIMS: m/z (rel. int.) = 256 ([M]+, < 1), 241 ([M-CH3]+, 3.5), 223
([241- H2O]+, 3.8), 205 ([241D2H2O]+, 2.1).
Sesquiterpenes and a Phenylpropanoid from Cordia trichotoma
Z. Naturforsch, 59c, 19-22 (2004).
67. HO
OH
H
OH
3.18, dd, 10.7, 4.1
1.97, dt, 10.7, 10.7, 3.1
1.56, m
1.68, 1.58, m 1.07, d, 10.3
3.9, t, 10.3
1.33, m
1.52, 1.37, m
1.91, 1.04, m
2.35, m
0.98, d, 7.1
0.91, d, 6.9
1.02, s
1.46,s
HO
OH
H
OH
80.0
27.9
42.7
58.1 53.3
19.7
39.5
27.3
21.9
16.4
14.2
34.8
73.1 70.3
42.4
1H and 13C-NMR of (+)-1,4,6α-trihydroxyeudesmane
68. 2D 1H,1H – Homocorrelation NMR Spectra
Both F1 and F2 frequency axes denote 1H chemical shifts which are correlated
through spin-spin-coupling homonuclear shift-correlation experiment.
1H,1H-COSY ("COrrelation SpectroscopY")
H
C
H
2JH-H
geminal
H
C C
H
vicininal
3JH-H
4JH-H
w-conformation
H H
C
C C
8.63, d, 2 Hz
8.87, d, 2 Hz
ppm
7.5
8.0
8.5
9.0 ppm
7.5
8.0
8.5
9.0
HO H
H
H
H
H
H
H
H
H
O
OH
H
K.S
69. HMQC (“Heteromolecular Multiple Quantum Coherence") and
HSQC (“Heteromolecular Single Quantum Coherence")
2D 1H,13C – Heterocorrelation NMR Spectra
H
C
H
C
H
H C
H
H
• Indirect detection of 13C through magnetisation transfer
from 1H to 13C enhanced sensitivity in comparison with 13C NMR
• Correlation between 1H and 13C through 1 bond (1JCH).
ppm
3
4
5
6
7
8 ppm
50
100
OH
O
O
OH
HO
1J1H-13C
3.90, s
56.9, s
3.90, s
56.9, s
23.3
3.23, d
Xanthohumol
K.S
73. They have 20 carbon atoms and are derived from
geranylgeraniol pyrophosphate
Diterpene
They are found in the resinous high-boiling fractions
remaining after distillation of essential oils.
The rosin remaining after distilling pine turpentine, for
instance, is rich in diterpenoids
74. Diterpenoid groups that are physiologically active include:
Vitamin A activity (retinol)
Phytohormones that regulate plant growth and germination,
e.g. gibberellin, fungal hormones that stimulate the switch from
asexual to sexual reproduction.
Disease resistance agents (phytoalexins) e.g. trisporic acid;
the anticancer drug, taxol, from the bark of the yew tree.
Phytol is a partially saturated diterpene, a monounsaturated
derivative of geranylgeraniol which is part of the chlorophyll
molecule.
75. Acyclic Diterpene
Plaunotol is the active ingredient of a commercial drug named
Kelnac®, is a mucosal protective factorenhancing antiulcer agent.
Science Asia 32 (2006): 17-20, Wanchai De-Eknamkul et-al
Furanoditerpenes are found in Compositea family.
77. β-Ionon react with acetylene in base, partial hydrogenation and
Grinard reaction with vinyl metal organometallic, then Wittig
reaction with 3-formylcrotylacetate to afford Vitamine A acetate.
Syntheis of Viatmine A from β-Ionon
79. The steviol glycosides are responsible for the sweet taste of the leaves of the
stevia plant (Stevia rebaudiana, Asteraceae). These compounds are 40 to 300
times sweeter than sucrose.
Phorbol ester is phorbol-12-myristate-13-acetate (PMA), which is used as a
research tool in models of carcinogenesis.
Tetrahydrocannabinol, also known as Δ9-THC or Δ9-tetrahydrocannabinol, is the
main psychoactive substance found in the plant.
Tetrahydrocannabinol
PMA
Steviol
82. Sesterterpenes
Variously unsaturated and branched sesterpenes, known as
Haslenes, were found in species of diatomaceous algae.
They are derived from geranylfarnesol pyrophosphate and have
25 carbon atoms.
83. Triterpenes
They form a large group of natural substances which includes
steroids and consequently sterols. Squalene is the immediate
biological precursor of all triterpenoids.
84. Squalane is a completely saturated derivative of squalene. it is largely used as
a component in many cosmetic products. It is obtained by hydrogenation of
squalene extracted from olive oil.
The common tetracyclic triterpene lanosterol is a major constituent of wool
fat and its esters are found in lanolin cream.
Other triterpenes,such as the α- and β-amyrins are found in wood resin and
the bark of many trees.
HO
18
19
20 21
22
23
24 25
26
27
28
29
30
1
3
5
7
9
11
13
15
17
β-amyrins
α- amyrins
lanosterol
Olean
Ursane
85. Lupane
Pentacyclic triterpenoids based on the lupane skeleton are found vegetables
and fruit.
Lupeol was shown to have various pharmacological properties, inducing anti-
inflammatory and anti-arthritic responses and inhibition of tumor growth
(Saleem M et al., Cancer Res 2005, 65, 11203) in animal cells.
The traditional medicine ginseng (Panax ginseng) contains glycosides of
triterpenes such as protopanaxadiol Chinese.
O
H
HO
H
HO
H
H
OH
H
O
OH
Saponins: Glycosidic compounds which could be triterpenes or steroidal or
steroidal alkaloids.
OH
HO
H
OH
H
H
protopanaxadiol Saponins
86. Ursolic acid is found at high concentration in coffee seeds and in apple fruit.
It is used in cosmetics as an anti-inflammatory, antibacterial and antifungal
drug. Ursolic acid is also able to inhibit some form of cancer, particularly
multiple myeloma (Pathak AK et al, Mol Cancer Res 2007, 5, 943).
Although limonin was first isolated by Bernay in 1841, Its
structure was finally established in 1987 by the work of three
groups, those of Ley, Nakanishi and Kraus.
87. Tetraterpenes
It consist of eight isoprenoid units “Carotenoids “
Carotenoids can be considered derivatives of lycopene, found in
tomatoes, fruits and flowers.
Lycopene is a bioactive red colored pigment naturally occurring in
plants.
Interest in lycopene is increasing due to increasing evidence proving its
antioxidant activities and its preventive properties toward numerous
diseases.
In vitro, in vivo and ex vivo studies have demonstrated that lycopene-
rich foods are inversely associated to diseases such as cancers,
cardiovascular diseases, diabetes, and others. A review of all these
aspects may be consulted (Kong KW et al., Molecules 2010, 15, 959).
88. Carotenoids may be acyclic (seco-carotenoids) or cyclic (mono- or bi-,
alicyclic or aryl). Oxyfunctionalization of various carotenoids leads to a
large number of xanthophylls in which the function may be a hydroxyl,
methoxyl, carbonyl, oxo, formyl or epoxy group.
89. Dietary phytoene is accumulated in human skin where it can
potentially protect the skin (UV absorber, antioxidant, anti
inflammatory).
β-carotene is probably the most important as a precursor of
vitamin A.
In human serum several carotenes and xanthophylls have been
detected “(lutein, zeaxanthin, cantaxanthin and β-cryptoxanthin”.
Fucoxanthin, as an allenic carotenoid with a 5,6-monoepoxide
group, is one of the most abundant carotenoid in brown algae and
diatoms.
Fucoxanthin
90. Steroids
Steroids form an important group of compounds based on the
fundamental saturated tetracyclic hydrocarbon : 1,2-
cyclopentanoperhydrophenanthrene (sterane or gonane).
This nucleus, partially or completely hydrogenated, is generally
substituted by methyl groups at C10 and C13. A chemical group
(ketone, hydroxyl...) or an alkyl side-chain may also be present at
C17.
91. According to their chemical structure, the wide array of steroid
molecules may be divided into several groups:
Sterols, Bufadienolides, Cardenolides, Cucurbitacins,
Sapogenins, Steroidal alkaloids, Bile acids, Hormonal steroids.
92. In 5 α-cholstane, all rings are trans and substituted groups are in β-position.
in 5 β- (A/B cis-, B/C und C/D trans). The presence of OH group at C-3 in β-
position is common while the configuration of substituent at positon 5,10 / 8,9 /
13,14 is different .
α- and β- cholstane
93. Sterols may be found either as free sterols, acylated (sterol esters), alkylated
(steryl alkyl ethers), sulfated (sterol sulfate), or linked to a glycoside moiety
(steryl glycosides) .
Sterols
Cholesterol is found in high concentrations in animal cell
membranes.
Cholesterol has numerous functions, as a precursor to hormones
and vitamins, to providing mechanical strength and a control of
the behavior of membranes (Rog T et al., Biochim Biophys Acta
2009, 1788, 97).
94. Sulfated sterols isolated from the sponge Pseudoaxinissa digitata
(Demospongia, order Axinellida) and showing anti-HIV activity.
95. Bufadienolides
They are typically polyhydroxy C24
steroids with a pentadienolide ring at
C-17. They are important for their
cardiotonic activity..
Cardenolides
Their structure is closely related to
bufadienolides but these C23 steroids
possess a butenolide ring located at C-17.
They are widely distributed in plants mainly
as glycosides and are either toxic or insect
deterrents.
96. Sapogenins
They form the aglycon part of saponins which have well known
detergent properties. They are oxygenated C27 steroids with an
hydroxyl group in C-3.
These steroids can regulate steroid hormones.
Thus, diosgenin can be chemically converted into corticosteroids,
estrogens and progesterone.
97. They form a large group of molecules where a nitrogen atom is
integrated into a ring or in a substituent.
The steroid nucleus can contain double bonds and hydroxyls in
various positions.
Steroid alkaloids
These alkaloids are only distributed in Solanaceae (potato,
tomato, eggplant ...). Fortunately, their toxic properties disappear
by structural transformation during ripening.
98. Bile acids
Bile acids are the end products of cholesterol utilization,
synthesized in the liver.
The most common bile acids are C24 steroids with a carboxyl
group at C-24 and up to three hydroxyl groups on the steroid
nucleus, one being at C-3.
99. Bile acids have long been known to be essential in dietary lipid
absorption and cholesterol catabolism.
Bile acids have been discovered to activate specific nuclear
receptors.
They regulate the increase in energy expenditure in adipose
tissue, preventing obesity and resistance to insulin (Watanabe M
et al., Nature 2006, 439, 484).
النبات طريق عن الربو مرض تثبيط في دولية اختراع براءة يحققان سعوديان
,
بروقيري فغونيا
102. Total Synthesis of steroid
Vinyl allylether undergo γ-δ rearrangement to afford aldehyde. Reaction with
propargylmagnesium bromide then reaction with methyl lithium and bromide reagent in
acid medium to afford triene diketone, followed by intraldol-condensation to give tetra-en
then oxidation with osmium oxide and finally aldol cyclization .
105. The initial isopropylidene unit of the GGPP chain leads to two perhydronaphtalene
bicyclic intermediates resulting in the two enantiomeric series that differ from each other
in their inverted configurations of the carbons C-5, C-9 and C-10.
Molecules 2007, 12, 456