The document discusses various phenylpropanoids and related compounds that are derived from plants, including their chemical structures, biological sources, constituents, and some uses. It provides details on specific phenylpropanoid-containing plants like podophyllum, psoralea, ammi majus, phyllanthus, and male fern, outlining their constituents like lignans, furanocoumarins, polyketides, and resins. The document also gives background on phenolic compounds, monomeric and dimeric derivatives, lignans, lignin, and their roles in plant biology and chemistry.

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