Triterpenes are classified based on the number of isoprene units they contain. Squalene is a 30-carbon triterpene containing six double bonds. Its structure was elucidated through reactions showing the presence of double bonds and the absence of conjugated double bonds. Oxidation and ozonolysis reactions provided further insight into its structure. Carotenoids are tetraterpenoids containing 9-11 double bonds that may terminate in rings. Alpha and beta carotene are prominent carotenoids, with beta carotene being the most well-known and a provitamin A.
Introduction, classification, isolation, purification, biological activity of alkaloids, general methods of structural determination of alkaloids, structural elucidation of Morphine, Reserpine and Emetine
Alkaloids are a group of naturally occurring chemical compounds that mostly contain basic nitrogen atoms.
The term alkaloid was coined by Meissner, a German pharmacist, in 1819.
Alkaloids are cyclic organic compounds containing nitrogen in a negative state of oxidation with limited distribution among living organisms.
Most alkaloids contain oxygen in their molecular structure; those compounds are usually colorless crystals at ambient conditions.
Some alkaloids are colored, like berberine (yellow) and sanguinarine (orange).
Most alkaloids are weak bases, but some, such as theobromine and theophylline, are amphoteric.
Many alkaloids dissolve poorly in water but readily dissolve in organic solvents.
Most alkaloids have a bitter taste or are poisonous when ingested.
Introduction, classification, isolation, purification, biological activity of alkaloids, general methods of structural determination of alkaloids, structural elucidation of Morphine, Reserpine and Emetine
Alkaloids are a group of naturally occurring chemical compounds that mostly contain basic nitrogen atoms.
The term alkaloid was coined by Meissner, a German pharmacist, in 1819.
Alkaloids are cyclic organic compounds containing nitrogen in a negative state of oxidation with limited distribution among living organisms.
Most alkaloids contain oxygen in their molecular structure; those compounds are usually colorless crystals at ambient conditions.
Some alkaloids are colored, like berberine (yellow) and sanguinarine (orange).
Most alkaloids are weak bases, but some, such as theobromine and theophylline, are amphoteric.
Many alkaloids dissolve poorly in water but readily dissolve in organic solvents.
Most alkaloids have a bitter taste or are poisonous when ingested.
Contents includes at least three strategies of synthesis for each of three, four, five and six membered heterocylic ring with one or two heteroatoms. One mechanism described out of the three strategies. Few name reactions are described and the other are simple synthetic methods. This presentation was prepared for the partial fulfillment of Master of Pharmacy. The content was taken from the various books, mentioned in slide with the title of references.
Chemistry of Natural Products
Alkaloids
• Introduction; classification; isolation; general methods for structure elucidation; discussion with particular reference to structure and synthesis of ephedrine, nicotine, atropine, quinine, papaverine and morphine.
• Terpenoids
• Introduction; classification; isolation; general methods for structure elucidation; discussion with particular reference to structure and synthesis of citral, α-terpineol, α-pinene, camphor and α-cadinene.
• Steroids
• Introduction; nomenclature and stereochemistry of steroids; structure determination of cholesterol and bile acids; introduction to steroidal hormones with particular reference to adrenal cortical hormones.
Chemsitry of Natural Products-Flavonoids and quercetinSurendraKumar338
# Quercetin is the most abundant dietary flavonoid. It has been linked to improved exercise performance and reduced inflammation, blood pressure, and blood sugar level.
# Flavonoids any of large class of plant pigments having a structure based on or similar to that of flavone.
When there are two functional groups of unequal reactivity within a molecule, the more reactive group can be made to react alone, but it may not be possible to react the less reactive functional group selectively.
A group the use of which makes possible to react a less reactive functional group selectively in presence of a more reactive group is known as protecting group.
A protecting group blocks the reactivity of a functional group by converting it into a different group which is inert to the conditions of some reaction(s) that is to be carried out as part of a synthetic route
Active constituent of drugs used in diabetic therapyAkshay Kank
In this slide the active constituents which is isolated from herbal sources used for to treat the type 1 and type 2 diabetes is covered. 'Gymnema' and 'swerita chirata' herbal plant is also covered in the slide.This work help in to focus the herbal emphasis on diabetes.
Contents includes at least three strategies of synthesis for each of three, four, five and six membered heterocylic ring with one or two heteroatoms. One mechanism described out of the three strategies. Few name reactions are described and the other are simple synthetic methods. This presentation was prepared for the partial fulfillment of Master of Pharmacy. The content was taken from the various books, mentioned in slide with the title of references.
Chemistry of Natural Products
Alkaloids
• Introduction; classification; isolation; general methods for structure elucidation; discussion with particular reference to structure and synthesis of ephedrine, nicotine, atropine, quinine, papaverine and morphine.
• Terpenoids
• Introduction; classification; isolation; general methods for structure elucidation; discussion with particular reference to structure and synthesis of citral, α-terpineol, α-pinene, camphor and α-cadinene.
• Steroids
• Introduction; nomenclature and stereochemistry of steroids; structure determination of cholesterol and bile acids; introduction to steroidal hormones with particular reference to adrenal cortical hormones.
Chemsitry of Natural Products-Flavonoids and quercetinSurendraKumar338
# Quercetin is the most abundant dietary flavonoid. It has been linked to improved exercise performance and reduced inflammation, blood pressure, and blood sugar level.
# Flavonoids any of large class of plant pigments having a structure based on or similar to that of flavone.
When there are two functional groups of unequal reactivity within a molecule, the more reactive group can be made to react alone, but it may not be possible to react the less reactive functional group selectively.
A group the use of which makes possible to react a less reactive functional group selectively in presence of a more reactive group is known as protecting group.
A protecting group blocks the reactivity of a functional group by converting it into a different group which is inert to the conditions of some reaction(s) that is to be carried out as part of a synthetic route
Active constituent of drugs used in diabetic therapyAkshay Kank
In this slide the active constituents which is isolated from herbal sources used for to treat the type 1 and type 2 diabetes is covered. 'Gymnema' and 'swerita chirata' herbal plant is also covered in the slide.This work help in to focus the herbal emphasis on diabetes.
Vitamin A or Retinol
It is monocyclic diterpenoid.
Molecular formula of retinol is C20H30O.
It is optically inactive and sensitive to light and air. It is destroyed by UV light.
Vitamin A has multiple functions: It is important for growth and development, for the maintenance of the immune system and good vision.
The deficiency of vitamin A causes night blindness, as well as dry eye and skin.
CONSTITUTION OF RETINOL
Molecular formula of Retinol
Presence of primary alcoholic group
Presence of five double bonds
Presence of β ionone nucleus
Presence of group
Position of c-methyl groups
Number of isoprene unit
Structure of Retinol
Confirmation of structure
Synthesis of Retinol
Molecular formula of Retinol
The molecular formula of retinol has been found to be C20H30O.
Presence of primary alcoholic group
As vitamin A forms an ester with p- nitrobenzoic acid, it follows that vitamin A contains a hydroxyl group.
C20H30O
Moreover ,the oxidation of vitamin A yields an aldehyde indicating that the hydroxyl group is primary alcoholic one.
Presence of five double bonds and one ring
When Vitamin A catalytically reduced in the presence of platinum or aluminum amalgam, Vitamin A react with five moles of hydrogen forming perhydroretinol (C20H40O).
The reaction indicates the presence of five double bonds in vitamin A.
Vitamin A forms adduct with maleic anhydride it indicating that vitamin A contains conjugated double bonds.
The formula of deoxygenated parent saturated hydrocarbon of Vitamin A is C20H40 which corresponds to CnH2n molecular formula which is the general formula for compounds having one ring. Hence, Vitamin A is a monocyclic compound.
Presence of β -ionone nucleus
Ozonolysis of vitamin A yields geronic acid per molecule of the vitamin.
Therefor vitamin A may contain one β ionone unit, since β –ionone also gives geronic acid on oxidation.
Presence of 2-methyl propene groups
Retinol is oxidized with alkaline KMnO4 at high temperature yields two molecules of acetic acid per molecule of Vitamin.
It indicates the presence of two 2-methyl propene groups in the side chain.
Position of C-Methyl group
The position of C-methyl group in the side chain has been assumed from the fact that most of the carotenoids contain isoprene units.
Number of Isoprene units
Treatment of vitamin A with alcoholic hydrogen chloride yields an anhydro form which on selenium dehydrogenation yields 1,6-dimethyl naphthalene. The formation of this product can only be explained if there are two isoprene units in the vitamin A.
When vitamin A is oxidized with alkaline KMnO4 at high temperature, it yields two moles of CH3COOH indicating the presence of two isoprene units.
Structure of Retinol
Confirmation of structure
Structure of Vitamin A was confirmed by the synthesis of per hydro retinol A from β-ionone that had been found to be identical with the product obtained by the reduction of vitamin A.
Van dorp and Tishler’s synthesis
Study material for chemistry UG and PG students
Chapter No 05 Terpenoids, Study of natural product Chemistry of natural products, Pharmaceutical chemistry.
Deep Behavioral Phenotyping in Systems Neuroscience for Functional Atlasing a...Ana Luísa Pinho
Functional Magnetic Resonance Imaging (fMRI) provides means to characterize brain activations in response to behavior. However, cognitive neuroscience has been limited to group-level effects referring to the performance of specific tasks. To obtain the functional profile of elementary cognitive mechanisms, the combination of brain responses to many tasks is required. Yet, to date, both structural atlases and parcellation-based activations do not fully account for cognitive function and still present several limitations. Further, they do not adapt overall to individual characteristics. In this talk, I will give an account of deep-behavioral phenotyping strategies, namely data-driven methods in large task-fMRI datasets, to optimize functional brain-data collection and improve inference of effects-of-interest related to mental processes. Key to this approach is the employment of fast multi-functional paradigms rich on features that can be well parametrized and, consequently, facilitate the creation of psycho-physiological constructs to be modelled with imaging data. Particular emphasis will be given to music stimuli when studying high-order cognitive mechanisms, due to their ecological nature and quality to enable complex behavior compounded by discrete entities. I will also discuss how deep-behavioral phenotyping and individualized models applied to neuroimaging data can better account for the subject-specific organization of domain-general cognitive systems in the human brain. Finally, the accumulation of functional brain signatures brings the possibility to clarify relationships among tasks and create a univocal link between brain systems and mental functions through: (1) the development of ontologies proposing an organization of cognitive processes; and (2) brain-network taxonomies describing functional specialization. To this end, tools to improve commensurability in cognitive science are necessary, such as public repositories, ontology-based platforms and automated meta-analysis tools. I will thus discuss some brain-atlasing resources currently under development, and their applicability in cognitive as well as clinical neuroscience.
ISI 2024: Application Form (Extended), Exam Date (Out), EligibilitySciAstra
The Indian Statistical Institute (ISI) has extended its application deadline for 2024 admissions to April 2. Known for its excellence in statistics and related fields, ISI offers a range of programs from Bachelor's to Junior Research Fellowships. The admission test is scheduled for May 12, 2024. Eligibility varies by program, generally requiring a background in Mathematics and English for undergraduate courses and specific degrees for postgraduate and research positions. Application fees are ₹1500 for male general category applicants and ₹1000 for females. Applications are open to Indian and OCI candidates.
Phenomics assisted breeding in crop improvementIshaGoswami9
As the population is increasing and will reach about 9 billion upto 2050. Also due to climate change, it is difficult to meet the food requirement of such a large population. Facing the challenges presented by resource shortages, climate
change, and increasing global population, crop yield and quality need to be improved in a sustainable way over the coming decades. Genetic improvement by breeding is the best way to increase crop productivity. With the rapid progression of functional
genomics, an increasing number of crop genomes have been sequenced and dozens of genes influencing key agronomic traits have been identified. However, current genome sequence information has not been adequately exploited for understanding
the complex characteristics of multiple gene, owing to a lack of crop phenotypic data. Efficient, automatic, and accurate technologies and platforms that can capture phenotypic data that can
be linked to genomics information for crop improvement at all growth stages have become as important as genotyping. Thus,
high-throughput phenotyping has become the major bottleneck restricting crop breeding. Plant phenomics has been defined as the high-throughput, accurate acquisition and analysis of multi-dimensional phenotypes
during crop growing stages at the organism level, including the cell, tissue, organ, individual plant, plot, and field levels. With the rapid development of novel sensors, imaging technology,
and analysis methods, numerous infrastructure platforms have been developed for phenotyping.
Observation of Io’s Resurfacing via Plume Deposition Using Ground-based Adapt...Sérgio Sacani
Since volcanic activity was first discovered on Io from Voyager images in 1979, changes
on Io’s surface have been monitored from both spacecraft and ground-based telescopes.
Here, we present the highest spatial resolution images of Io ever obtained from a groundbased telescope. These images, acquired by the SHARK-VIS instrument on the Large
Binocular Telescope, show evidence of a major resurfacing event on Io’s trailing hemisphere. When compared to the most recent spacecraft images, the SHARK-VIS images
show that a plume deposit from a powerful eruption at Pillan Patera has covered part
of the long-lived Pele plume deposit. Although this type of resurfacing event may be common on Io, few have been detected due to the rarity of spacecraft visits and the previously low spatial resolution available from Earth-based telescopes. The SHARK-VIS instrument ushers in a new era of high resolution imaging of Io’s surface using adaptive
optics at visible wavelengths.
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.
hematic appreciation test is a psychological assessment tool used to measure an individual's appreciation and understanding of specific themes or topics. This test helps to evaluate an individual's ability to connect different ideas and concepts within a given theme, as well as their overall comprehension and interpretation skills. The results of the test can provide valuable insights into an individual's cognitive abilities, creativity, and critical thinking skills
This presentation explores a brief idea about the structural and functional attributes of nucleotides, the structure and function of genetic materials along with the impact of UV rays and pH upon them.
2. TERPENOIDS
• DEFINITION: Originally, the term “terpene” was employed to describe
a mixture of isomeric hydrocarbons of the molecular formula C10H16
occurring in the terpentine and many essential oils which are
obtained from the sap and tissues of certain plant and trees. The
oxygenated derivatives like alcohols, aldehydes, ketones, etc. at that
time called camphor.
• CLASSIFICATIONS: Class No. of isoprene
units
Molecular
formula
1. Isoprene 1 C5H8
2. Monoterpene 2 C10H16
3. Sesquiterpenes 3 C15H24
4. Diterpenes 4 C20H32
5. Triterpenes 6 C30H48
6. Tetraterpenes 8 C40H64
7. Polyterpenes n (C5H8)n
3. MONOTERPENOIDS
• The monoterpenoids are composed of two isoprene units. These are the simplest natural
occurring terpenoids which are isolated from essential oils obtains from the leaves, roots and
barks of various plant.
• These compounds have pleasant odours and are largely used as perfumery industry.
• Monoterpenoids may be divided into three groups:
1. Acyclic monoterpenes. Example- citral.
2. Monocyclic monoterpenes. Example- menthol
3. Bicyclic monoterpenes. Example- camphor
A. CITRAL
• It is considered to be the most important member of the acyclic monoterpenes because the
structure of remaining terpenoids in this group are based on the structure of citral.
• It is optically inactive oil with lemon like smell.
• Pale yellow in colour, b.p. 228.C
4. • ISOLATION
lemon grass oil, citral is obtained by its fractional distillation under reduced pressure. This is then
purified by forming the bisulphite compounds the latter compounds further decomposed with sodium
bicarbonate yields, pure citral
• CONSTITUTION OF CITRAL
• Molecular formula- C10H16O.
• Presence of 2 double bond -
As citral adds on two moles of bromine or hydrogen, this shows that it contain 2 double bond
C10H20O C10H16O C10H16OBr4
tertrahydrocitral citral citral tetrabromide
Citral on ozonolysis yields acetone, laevuladehyde and glyoxal. This shows that citral is an acyclic
compounds containing 2 double bond.
5. • PRESENCE OF ALDEHYDE GROUP –
citral forms oximes & reduces Fehling solution therefore O-atom is aldehyde group
Presence of carbonyl group as aldehyde is further confirmed by -
7. B. MENTHOL
• Menthol is an optically active compound.
• Only its (-) form occurs naturally in peppermint oils.
• It’s a saturated compound having melting point 43.C.
• It is used as an antiseptic and an aesthetic.
CONSTITUTION OF MENTHOL -
• Molecular formula- C10H20O
• Presence of alcoholic group - as menthol forms esters readily with acids, this means
that it must posses an alcoholic group.
• Presence of secondary alcohol
The oxidation of menthol yields ketone, indicating that the hydroxyl group in menthol is
secondary in nature.
8. • Presence of p-menthane skeleton-
menthol on dehydration and dehydrohalogention form p-cymene
• Explaining the structure of menthol
9. C. CAMPHOR
• It is the most important constituent of the oil of the camphor.
• Occur in the Cinnamonum camphora.
• It is solid having melting point 180.C and it is optically active
• Uses - as an insect repellent.
- as an mild disinfectant and stimulant for heart muscles.
- for the production of smokeless powders and explosives.
CONSTITUTION OF CAMPHOR-
• Molecular formula - C10H16O.
• Presence of keto group
It form oxime with hydroxylamine
When camphor is distilled with iodine it yields cavacrol.
I2 +
10. • Presence of –CH2CO group.
When camphor is treated with amyl nitrite and hydrochloric acid, it yields iso nitroso camphor
• Presence of six membered ring
11. • 6. Nature of carbon frame in camphor.
when camphor is oxidized with nitric acid, it yields a crystalline dibasic acid , camphoric acid C10H16O4.
as a camphoric acid possesses the same number of carbon atom as camphor , it means that the keto
group must be present in one of the ring of camphor. Further camphoric acid is dicarboxlic acid and its
molecular refraction reveals that it is also saturated. Thus during the conversion camphor into
camphoric acid , there occur the opening of ring containing the keto group and therefore camphoric
acid must be monocyclic compound.
When camphoric acid is further oxidized with nitric acid , camphoric acid is obtained.
12. DITERPENOIDS
Definition:-
• Diterpenes are a class of chemical compounds composed of two terpene units, often with the
molecular formula C20H32.
• Diterpenes consist of four isoprene subunits.
• They are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway,
with geranylgeranyl pyrophosphate being a primary intermediate.
• Diterpenes form the basis for biologically important compounds such as retinol, retinal, phytol and
taxanes.
• Diterpenes can be classified as linear, bicyclic, tricyclic or tetracyclic, pentacyclic, and macrocyclic
diterpenes depending on their skeletal core.
• In nature, they are commonly found in a polyoxygenated form with keto and hydroxyl groups, these
last often esterified by small-sized aliphatic or aromatic acids.
Acyclic: Phytol
Monocyclic: Vitamin A(retinol)
Bicyclic: Manool
Tricyclic: Abietic acid, Podocarpic acid
Tetracyclic: Gibberellic acid
13. PHYTOL
• Introduction:-
• It is a kind of diterpene which comes under the “acyclic diterpene” category.
• Phytol is an acyclic diterpene alcohol and a constituent of chlorophyll.
• It is obtained from alkaline hydrolysis of chlorophyll, which is then converted to phytanic acid and
stored in fats.
• It is commonly used as a precursor for the manufacture of synthetic forms of vitamin E and vitamin K1.
• It is an optically active compound which boils at 145°C at 0.03mm pressure.
• Molecular Formula: C20H40O
• Melting Point: < 25 °C
PHYTOL
14. STRUCTURAL ELUCIDATION-
• Molecular formula: C20H40O
• Presence of double bond :
When it is catalytically hydrogenated, it adds on one mole of hydrogen to form dihydrophytol indicating
that phytol contains one double bond.
• Presence of primary alcoholic group :
Phytol on oxidation with chromic acid yields monocarboxylic acid called phytenic acid which has same
no. of C- atom indicating the presence of primary alcoholic group.
• Ozonolysis of phytol :
on ozonolysis it yields glycoaldehyde and a saturated ketone
15. • Structure of saturated ketone may be written as follows :
Structure of saturated ketone is confirmed by its synthesis from ketone(I):
16. RETINOL
• It is a kind of diterpene which comes under the “Monocyclic diterpene” category.
• It is also called Vitamin A
• Vitamin A is the fat soluble vitamin, is a group of unsaturated nutritional organic compounds that
includes retinol, retinal, retinoic acid, and several provitamin A carotenoids (most notably beta-
carotene).
• All forms of vitamin A have a beta-ionone ring to which an isoprenoid chain is attached, called a retinyl
group.
• Molecular Formula: C20H30O
17.
18. • Molecular formulae : C20H30O
• Double bond present:
It consumes 5 hydrogen molecules during hydrogenation in presence of Pd catalyst, that means 5 double
bonds are present in the structure.
STRUCTURAL ELUCIDATION
19. • Isoprene Units Confirmation: The oxidation of Vit.A with Pot. Permagnate gives 2 molecules of Acetic
acid which indicates 2 Isoprene units are present in structure.
• Methyl group: The oxidation of Vit.A in the presen e of CrO3 which gives 3 molecules of Acetic acid. It
means, 3 methyl groups are present.
20. • Hydroxy(–OH) group:
presence of –OH group can be determined by the formation of acetates with acetic anhydride.
Upon Oxidation, Retinol converts to Retinal(aldehyde) and then converts to Retinoic acid. It means, there
is primary alchohol present in structure.
21. • Beta-Ionone Nucleus:
Ozonolysis of retinol gives geronic acid which can directly obtained by ozonolysis of beta-Ionone.It
confirms the basic nucleus of beta-Ionone is present in structure.
22. TAXOL
• It is a type of Complex diterpene.
• Taxol, a diterpenoid natural product first isolated from Taxus brevifolia, is one of today’s better known
anticancer drugs.
• The paclitaxel molecule consists of a tetracyclic core called baccatin III and an amide tail.
• The core rings are conveniently called (from left to right) ring A (a cyclohexene), ring B (a cyclooctane),
ring C (a cyclohexane) and ring D (an oxetane).
• MOLECULAR FORMULAE – C47H51NO14
27. SQUALENE
• Squalene is a natural 30-carbon organic compound originally obtained for commercial purposes
primarily from shark liver oil (hence its name, as Squalus is a genus of sharks), although plant sources
(primarily vegetable oils) are now used as well, including amaranth seed, rice bran, wheat germ, and
olives. Yeast cells have been genetically engineered to produce commercially useful quantities of
"synthetic" squalane, which is similar to squalene.
28. STRUCTURAL ELUCIDATION
• Molecular formulae: C30H50
• Presence of double bonds :
The molecular formulae of fully saturated squalene was found to be perhydrosqualene with 6H₂
molecule.
• Absence of conjugated double bonds in squalene:
Squalene fails to undergo reduction whwn treated with Na – metal amd amyl alcohol which indicates
absence of conjugated double bonds
• Oxidation of squalene with chromyl chloride:
On oxidation with CrO₂Cl₂ in CCl₄ gives Formaldehyde , Acetaldehyde ,Succinic acid
• Ozonolysis of squalene :
29. CAROTENOIDS
• Carotenoids are the group of non-nitrogenous , yellow , red or orange pigments that are universally
distributed in living things.
• These are also called tetraterpenoids , that are produced by plants and algae as well as several
bacteria and fungi.
• There are over 600 known carotenoids
• They split into 2 classes xanthophyll and carotenes
• Tetraterpenoids contain 40 C atoms
• General structure of carotenoid is a polyene chain consisting of 9-11 double bonds and possibly
terminating in rings
30. ALPHA & BETA CAROTENOIDS
• About 600- 700 different carotenoids are known of which α & β carotene are the most prominent
• Β carotene is the most known carotenoid and the most often naturally occurring carotene also known
as provitamin A