1. Phenyl propanoids & related compounds

2. Phenolic compounds
• Phenols probably constitute the largest group pf plant
secondary metabolites.
• Phenols are utilized as Colouring agents. Flavouring agents,
aromatizers and antioxidants. E.g.
• Simple phenolic compounds
• Tannins
• Coumarins and glycosides
• Anthraquinones and glycosides
• Naphthaquinone and glycosides
• Flavones and related flavonoid glycoside
• Anthocyanidins and anthocyanins
• Lignans and lignin

4. Monomeric derivatives
• p-Coumaryl alcohol
• Coniferyl alcohol
• Sinapyl alcohol

5. Lignan: Dimeric derivatives
• Dimeric compounds formed essentially by the union of the two
molecules of a phenylpropene derivative.
• Not synthesized by lignin biosynthetic pathway.
• Unlike lignin, optically active and probably arise by stereospecific,
reductive coupling between the middle carbons of the side chain of
monomer.
• Some 300 lignans have been isolated and categorized into a number
of groups according to structural features.
• Important pharmaceutical examples are the lignans of Podophyllum
spp. which appear to be formed from two molecule of coniferyl
alcohol or the corresponding acid with subsequent modification;
apparently, a sinapic acid derivative, as might be expected by the
inspection of the podophyllotoxin molecule, is not involved.

6. Podophyllotoxin
(Podophyllum)
Macelignan
(Nutmeg)

7. Introduction-Lignan
• Lignans, cited are not however, necessarily the therapeutically
active constituents of the plant.
• Neo-lignans are also derived from the same unit as lignans but
the C6-C3 moieties are linked head to tail or head to head and
not through the beta-beta’ carbons.
• They occur in the heart wood of trees of the Mangoliaceae,
Lauraceae and Piperaceae.
• Example: Guaicum officinale resin Guaicum sanctum
• Myristica fragrans, Piper cubeba
• Magnolia officinalis Magnolia obovata:
• Magnolol: CNS Action: depressant, muscle relaxant, anti
platelet, antimicrobial, anti-tumour, anticancer, insecticidal

8. Introduction-Lignin
• It is an important polymeric substance, (C6-C3)n, laid down in a matrix of
cellulose microfibrils to strength certain cell wall.
• It is an essential component of most woody tissues and involves vessels,
tracheids, fibers and sclreids.
• Lignins from different biological sources vary in composition, depending on
the particular monomeric units in which they are composed.
• Variations in lignin constitutes also arise as a result of random
condensations of the appropriate alcohols with mesomeric free radicals
formed from them by the action of a laccase type (oxidase) enzyme.
• As there is no template for this non-enzymatic condensation the lignin
molecules formed vary in structure and so it is not possible to isolate lignin
as a compound of defined composition.

9. Introduction-Lignin
• In the wall, it appears to occur chemically combined with
hemicellulose and built up in greatest concentration in the
middle lamellae and in the primary walls.
• Lignified cell walls after treatment with Schultze’s macerating
fluid (HNO3+ Potassium chlorate) will show cellulose
reactions.
• Acid Aniline sulphate  bright yellow
• Phloroglucinol + conc. HCl  pink/red
• Chlor-zinc-iodine  yellow

10. Introduction-Phenylpropanoids
• diverse family of organic compounds that are synthesized by plants
from the amino acid Phenyl alanine.
• Their name is derived from the six-carbon, aromatic phenyl group
and the three-carbon propene tail of cinnamic acid, which is
synthesized from phenylalanine in the first step of phenyl propanoid
biosynthesis.
• Phenylpropanoids are found throughout the plant kingdom, where
they serve as essential components of a number of structural
polymers, provide protection from UV light, defend against
herbivores and pathogens, and mediate plant-pollinator interactions
as floral pigments and scent compounds.
• Concentrations of phenylpropanoids within plants are also altered
by changes in resource availability.

13. Introduction-
Phenylpropanoids
• Phenylpropanoids and other phenolics are part of the
chemical composition of sporopollenin.
• This substance found in pollen is not exactly known, due to its
unusual chemical stability and resistance to degradation by
enzymes and strong chemical reagents. Analyses have
revealed a mixture of biopolymers, containing mainly long
chain fatty acids, phenylpropanoids, phenolics and traces of
carotenoids.
• Tracer experiments have shown that phenylalanine is a major
precursor, but other carbon sources also contribute. It is likely
that sporopollenin derives from several precursors that are
chemically cross-linked to form a rigid structure

14. 1. Podophylum:
Lignan & Polyketide
• Syn: May apple, Wild mandrake
• Source: dried roots and rhizomes of American:
Podophyllum peltatum & India: Podophyllum
hexandrum (P.emodi)
• Family: Podophyllaceae (Berberidaceae)
• GS: America (US-Virginia, Kentucky, North
carolina, Tennessee, Indiana, Canada)
• Indian: Tibet, China, Afghanistan, Himalayas

15. • The rhizomes and roots are obtained from wild grown plants
growing at an altitude of 3000 to 4000 m.
• Underground rhizomes remain dormant in winter and
produce aerial shoots in April to May.
• Shoots flower during summer and die in November
• Rhizomes and roots are dug up in spring or autumn, washed,
cleaned and dried in the sun
• The drug collected in the month of may has higher resin
content than the collected in November.
• Actually the roots contain more resin than rhizomes and
hence roots are preferred.

17. • Constituents:
• P. peltatum
• 2-8% resinous material as podophyllin, Lignan dvt:
podophyllotoxin, alpha & beta peltatin, (Lignan: in form of
glycoside), Desmethyl podophyllotoxin,
desoxypodophyllotoxin, podophyllotoxone,
• Flavonoid: quercetin, kaempferol, essential oil, Starch
• P. hexandrum
• 7-15% Resin as Podophyllin
• 40% podophyllotoxin

18. • Chemical Test:
• Alcoholic ext. + strong copper acetate- brown ppt with
Indian podophyllum & green color without ppt with
American podophyllum
• USES:
• Cyto-toxic, venereal disease, Warts,
• Podophyllotoxin is semisynthetically converted to
etoposide potent anticancer agent for lung & testicular.
• Its GIT irritant, drastic purgative in moderate uses

19. Podophyllum species
• American Podophyllum
• Not so
• The CaOx crystals are fewer
and smaller (30-60-100
Micro meter)
• Less resin 2-8 %
• Contains alpha & beta
peltatin
• Podophyllotoxin is less
• Indian Podophyllum
• Vascular bundles are more
elongated radially.
• The CaOx crystals are fewer
and smaller (20-30-60 Micro
meter)
• More resin up to 7-15%
• No constituents
• Podophyllotoxin is more

20. 2. Psoralea Furanocoumarins
• Syn: Bavchi, Malaya tea
• Source: dried ripe fruits and seeds of Psoralea
corylifolia
• Family: Leguminosae
• GS: India, China, Srilanka, Nepal, Vietnam
• Constituents: coumarin like psoralen, isopsoralen,
psoralidin, isopsoralidin, carylifolean,
bavachromanol and psoralenol, Fixed oil 10%,
essential oil 0.05% and resin
• Seeds: Flavonoids: bavachalcone, bavachinin,
isobavachalcone, bavachin and isobavachin
• Seed oil: limonene, aelemene, beta-
caryophyllenoxide, 4-terpineol, linalool, geranyl
acetate, angelicin, psoralen, bakuchiol

21. • Chemical Test:
• psoralen, dissolved in alcohol + NaOH  UV light
observation yellow fluorescence
• Psoralen, dissolved in small amount of alcohol, 3 times
propylene glycol, 5 times acetic acid, 40 times water UV light
observation blue fluorescence
• Uses:
• Aphrodisiac, antibacterial, astringent, cytotoxic, diaphoretic,
diuretic, stimulant, stomachic , tonic, lower back pain, skin
disease, bed wetting, leprosy, hair loss
Psoralen
Psoralidin

22. 3. Ammi majus
• Syn: Bishop’s weed, Laceflower, Toothpick ammi, Large
bullwort
• Source: dried fruits of Ammi majus
• Family: Umbelliferae
• GS: Europe, Egypt, West africa, India
• Constituents: furanocoumarins, xanthotoxin, imperatorin,
bergapten, isopimpilin
• CT: 1) drug+ waterboilstrainfiltrate+ NaOH no rose
color  distinct from Ammi visanaga
2) Alc. Ext of fruit blue fluorescence under UV light
• Uses: furanocoumarin: stimulate pigment production in skin
when exposed to bright sunlight and hence  treatment of
vitiligo and psoriasis

23. 3. Ammi majus
• Constituents:
furanocoumarins,
xanthotoxin, imperatorin,
bergapten, isopimpilin

24. 4. Phyllanthus (Lignan)
• Syn: Bhumyamlaki, Stone breaker
• Source: dried leaves and stem of
Phyllanthus niruri
• Family: Euphorbiaceae
• GS: trophical zone
• Uses: Kidney stones treatment
Antibacterial, Anti inflammatory
Anti hepatotoxic
Antispasmodic
Anti viral
Liver tonic
Choleretic
Immuno-stimulant

26. • Constituents
• Lignans: phyllanthin, hypophyllanthine, phyltetralin,
lintetralin, niranthin, nirtetralin, nirphylline, nirurin,
niruriside.
• Terpenes: Cymene, limonene, lupeol and lupeol acetate.
• Flavonoids. Quercetin, Quercitrin, Isoquercitrin, astragalin,
rutin, physetinglucoside.
• Lipids: Ricinoleic acid, dotriancontanoic acid, linoleic acid,
linolenic acid.
• Benzenoids: Methylsalicilate.
• Alkaloids: Norsecurinine, 4 - metoxy - Norsecurinine,
entnorsecurinina, nirurine, phyllantin, phyllochrysine.
• Steroids. Beta-sitosterol.
• Alcanes: Triacontanal, Triacontanol.
• Others. Vitamin C, tanins, saponins.

27. 5. Male fern (polyketide-resin)
• Syn: Filix Mass, Rhizoma filicis Maris
• Source: dried rhizome and its
surrounding frond bases of
Dryopteris filix-mass
• Family: Polypodiaceae
• GS: Europe, England, Germany,
India: JK, HP, SK at high altitude of
5000-10000 ft.
• Use: Potent taenicide, kills worms
and expel it out, absorption from
GIT blindness, in large dose:
irritant poison

28. • Constituents:
-5% yellow resin: anthelmintic property
-Oleoresin: phloroglucinol dvt.
-Monocyclic dvt.: butyryl phloroglucinol,
aspidinol and acylfilicinic acid
-Bicyclic: albaspidin, flavaspidic acid
-Tricyclic: filicic acid