REVISION-PHARMACOGNOSY-IV

Priyanka Goswami

Objectives

1. Bitter Glycosides drugs- Picrorrhiza, Andrographis2. Marine cyto-toxin drugs- Ara-A, Ara-C, Crassin acetate, Sinularia, Geranium

hydroquinone, Asperidol3. Phyto-toxin drugs- Abrus, Aconite, Poison ivy, Poison hemlock, Lilly of the valley,

Curare, Blighia4. Drugs used for hormone & steroid manufacturing- Dioscorea, Fenugreek, Agave, Smilax- Diosgenin, Hecogenin, Smilagenin5. Drug used for Incense stick (dhoop batti)- Benzoin

Objectives

6. Sesquiterpene lactone drug- Quassia7. Furano-coumarin glycosides drug- Ammi & Psoralea8. Steroidal saponin drugs- Dioscorea, Aspargus, Agave, Fenugreek, Smilax9. Pentacyclic triterpenoid saponin drugs- Licorice, Ginseng, Quillaia10. Lignan drugs- Phyllanthus, Podophyllum11. Amaroid lactone drug- Quassia

Objectives

12. Iridoid drug- Picrorrhiza13. Sesqui terpene glucoside & Furano diterpene drug- Tinospora14. Sesquiterpene lactone drug- Artemisia cina15. Diterpene lactone drug-Andrographis16. Polyketide drugs- Male fern & Podophyllum17. Hepatoprotective drugs- Picrorrhiza, Andrographis, Turmeric18. Anti Cancer drugs- Taxus, Podophyllum

Objectives

19. Cardio tonic & Cardia glycoside- Digitalis, Strophanthus, Thevetia, Nerium20. Rodent killer cardiac glycoside- Squill21. Expectorant drugs- Glycyrrhiza (Licorice), Tolu balsam, Benzoin, Quillaia, Eucalyptus,

Anise, Fennel22. Nervine tonic drugs- Brahmi (Hydrocotyl & Bacopa)23. Galactogogue drug- Aspargus, Fenugreek24. Rejuvenator & adaptogen (immuno modulator) increase

resistant power-drugs- Ginseng, Tinospora

Objectives

25. Treatment of Vitiligo- Ammi majus26. Treatment of Psoriasis & leucoderma- Psoralea27. Bitter stomachic drugs- Gentian, Quassia & chirata28. Anthelmintic drugs- Quassia (thread worms), Artemisia cina, Gaultheria (hook worm),

Male fern (tape worm), Kalmegh29. Sweetening agent- Licorice30. Anti malaria drug- Artemisia annua31. Sharbat preparation- Vetiver (Khus)32. Treatment of Rheumatism- Gaultheria, Palmrosa, Nutmeg, Rasna, Capsicum

Objectives

33. Skin disease drugs- Palmrosa, Peru balsam (scabies)34. Mosquito repellant cream- Citronella35. Counter irritant drugs- Eucalyptus, Turpentine, Capsicum36. Antiseptic drugs- Eucalyptus, Peppermint, Ajwon, Cinnamon, Saussurea, Myrrh,

Tolu balsam, Benzoin37. Rubefacient drugs- Turpentine38. Antispasmodic drugs- Ajwon, Dill, Hops39. Anti-epileptic drugs- Jatamansi, Valerian

Objectives

40. Anti-fungal drugs- Ajwon41. Dysuria (painful) urination drug- Sandalwood42. Dental analgesic drug- Clove43. Sedative drugs- Hops, Jatamansi44. Treatment of Asthma drugs- Saussurea45. Enteric coated tablets- Shellac46. Anti-inflammatory drugs-Turmeric, Guggul

Objectives

47. Diuretic drugs- Colophony48. Wound healing drugs- Peru balsam49. Laxative-Purgative drugs- Colocynth, Myrrh50. Veneral warts drugs- Podophyllum51. Motion sickness drug-Ginger52. Narcotic analgesic- Cannabis53. Intestinal flatulence- Asafoetida54. Oleo-gum-resin drugs- Asafoetida, Myrrh, Guggul

Objectives

55. Acid resin drugs- Colophony (abietic acid), Myrrh (commiphoric acid), Shellac (alleuritic acid)56. Ester resin drugs- Siam benzoin (coniferyl benzoate)57. Sequi terpene drugs example- Artemisia, Sandalwood, Clove, Hops, Saussurea, Valerian58. Di-terpene drugs example- Taxus59. Tetraterpenoids drug example- Carrot60. Balsam drugs (benzoic + cinnamic acid)- Tolu balsam, Peru balsam, Sumatra bezoin61. Oleo-resin drugs- Turpentine & Ginger62. Resin phenol drugs- Peruresinotannol (peru balsam), toluresinotannol (tolu balsam) & siaresinotannol (benzoin)

Alcohol volatile oil

1. Peppermint-Menthol

2. Cardamom- Borneol

3. Coriander-Coriandrol (Linalool)

4. Rose-Nerol

5. Sandalwood-Santalol

Aldehyde volatile oil

1. Cinnamon-Cinnamic aldehyde

2. Lemon peel- Citral

3. Orange peel- Citral

4. Citronella- Citronellal

5. Lemon grass- Citronellal

Ester volatile oil

1. Gaultheria (Wintergreen)-Methyl salicylate

Hydrocarbon volatile oil

1. Turpentine- pinene, carene, limonene

Ketone volatile oil

1. Caraway- Carvone

2. Spearmint – Carvone

3. Vetiver - Vetivone

4. Fennel - Fenchone

Oxide volatile oil

1. Eucalyptus- Cineole (eucalyptol)

Phenolic ether volatile oil

1. Anise-Anethol

2. Fennel- Anethol

3. Nutmeg- Myristicin

Phenol volatile oil

1. Clove- Eugenol

2. Ajwon- Thymol

Chemical test for Volatile oil

1. With alcoholic solution of Sudan red-III red color

2. With tincture alkane red color

3. With vanillin sulphuric acid yellow-orange color

(Fennel, Dill, Coriander, Cassia, Cardamom,Clove)

Chemical test for Saponinglycoside1. Foam test:

Shake with water froth formation

2. Haemolytic test:

Aq solution + drop of blood RBCs ruptured and causing hemolysis

(Licorice, Aspargus, Reetha, Shikakai)

Chemical test for Steroid & Triterpenoid saponinAlcoholic extract of drug evaporated to dryness and extract with CHCl3 (common for 1 to 3)1. Libermann buchard test-and few drops of acetic anhydride followed by conc. Sulphuric acid from side wall of test tube to the CHCl3 extract blue-violet ring at the junction steroid moiety2. Salkowaski testand add conc. H2SO4 from sidewall of test tube yellow ring at the junction steroid moiety3. SbCl3 testAdd satd solution of SbCl3 in CHCl3 containing 20% acetic anhydride pink color on heating triterpenoids & steroids4. Trichloro acetic acid test colored ppt5. Tetranitro methane test yellow color6. Zimmermann test meta dinitrobenzene solution was added to the alcoholic solution of drug containing alkali, on heating violet color (keto-steroid)

Chemical test for Cardiac glycosideTo the alc extract, add equal volume of water and 0.5 ml strong lead acetate shakedfiltered filtrate was extracted with equal volume of CHCl3 and CHCl3 extract is evaporated to dryness (common for Test 1 & 2)1. Keller-killiani testresidue dissolved in 3 ml Glacial acetic acid followed by addition of few drops of FeCl3 solution –The resultant solution transferred to test tube containing 2 ml conc. H2SO4 reddish brown layer is formed turning to bluish green after standing due to presence of digitoxose2. Legal testResidue dissolved in 2 ml pyridine and 2ml sodium nitroprusside followed by NaOH solution to make alkaline formation of pink color in presence of glycosides or aglycone moiety.3. Baljet testAddition of sodium picrate solution yellow-orange color 4. 3,5-dinitro benzoic acid testTo the alcoholic solution of drug + few drop of NaOH, followed by 2% 3,5-donitro benzoic acid pink color

Chemical test for Flavonoids

1. Ammonia testFilter paper dipped in alcoholic solution, when exposed to ammonia vapor yellow spot2. Shinoda testTo the alcoholic extract, add Mg turning and add dil. HCl red color flavonoidsTo the alcoholic extract, add Zn turning and add dil. HCl deep red to magenta color dihydro flavonoids3. Vanillin HCl testVanillin HCl added to alcoholic solution of drug pink color flavonoids

Important powder characteristics

1. Umbelliferous fruits (Dill, Fennel, Coriander)

Common: Endocarp, endosperm, yellow vittae, lignified mesocarp

Dill lignified sclreids (stone cells) & nux vomica like red nuclei like endosperm

Fennel fibers

Coriander lignified sclerenchymatous layer (spread like bed sheet) & endocarp-mesocarp combined

Important powder characteristics2. Cardamom: parallel epidermal cells like broom and if of seed coat part then having benzene type cells as well & perispermconsists of starch grain 3. Licorice: yellow fiber and lignified fibers with cal. Oxalate crystals inside or sideby & cork4. Picrorrhiza: cork5. Aspargus: lignified parenchyma6. Andrographis: diacytic stomata, covering-glandular trichome, acicular unlignified fibers7. Clove: stomata, lignified anther, aerenchyma, oil gland, polengrain8. Cassia: Cork & stone cells9. Quassia: wood: all tissue lignified, medullary rays with cal oxa & wood element, xylem vessel & fiber

Chemical test for Aloe

1. Modified bortranger’s test

The aq. Solution is treated with FeCl3, add dil. HClto bring out oxidative hydrolysis of aloe-emodin.

The hydrolysis sets free anthraquinones which are collected in organic solvent like CCl4 or ether.

The organic layer is separated and shaken with dilute ammonia

Ammonia layer shows rose-pink to cherry red color presence of C-glycoside aloe-emodin

1. CLOVE

• Syn: Lavang

• Source: dried flower buds of

Syzygium aromaticum

(Eugenia caryophyllus),

• Family: Myrtaceae

• GS: Molucca or Clove

Islands, Zanzibar, Pemba,

Madagascar, Indonesia &

Brazil.

HISTORY OF CLOVE

Cloves were used in China as earlyas 266 BC, and by the 4th

century, they were known inEurope, although veryexpensive.

Same as with nutmeg, the Dutchalso destroyed all trees fromsurrounding native islands tosecure a monopoly, andcultivated them only in a smallgroup of islands.

In 1770, the French managed tointroduce clove trees toMauritius, and startedcultivating them there, as wellas in Zanzibar, Penang andSumatra.

COLLECTION & PREPARATION

• The flower buds are collected when the lower part turns green-crimson.

• In Zanzibar & Pemba collection takes place twice yearly, between august and December.

• The inflorescence are collected from movable platforms.

• The cloves are dried in the Open air on mats & separated from their Peduncles, the later forming a separate article of commerce

known as Clove stalks.

• If left on the tree for too long, the buds open & the petals fall, leaving “brown cloves”.

• Later the fruits known as “mother cloves” are produced.

• A small portion of these, usually at a stage intermediate between that of a clove and a fully ripe fruits, are frequently found in the drug.

• Cloves are imported in bales covered with matting made from string of coconut leaves.

MACROSCOPICAL FEATURES

-Cloves are 10-17.5 mm long.

-Penang and Amboyna varieties

are the largest and plumpest.

-Zangibar variety is of good

quality and smaller and leaner

comparatively a blackish brown

rather than reddish brown color.

-The head consists of 4 slightly

projecting calyx teeth, 4

membranous petals and

numerous incurved stamens

around a large style.

-Odour: Spicy & Pungent

-Taste: Aromatic

MICROSCOPICAL FEATURES

Heavy cuticularized epidermis

Numerous oil cells (shizolysigenous)

Calcium oxalates (cluster crystals & prisms)

Stomata (epidermis of sepals)

Starch (Fruit – “mother cloves”)

Lignified sclereids

CONSTITUENTS

• 14-21% Volatile oils• 10-13% tannin• Various triterpene and esters• Glycosides of :• aliphatic and monoterpenoid alcohol,• eugenol,• isoeugenol,• farnesol, nerolidol,• sitosterol,• stigmasterol and• campestrol

USES OF CLOVE

-Stimulant aromatic

-as a Spice

-For the preparation of

volatile oil

-Sesquiterpenes:

potential anti-carcinogenic

compounds

CLOVE OIL

Oil distilled in Europe and the US normally does not need purification, while oil distilled in other areas (e.g. Madagascar) does. After purification the oil is sold with varying eugenol contents.

Oil of cloves is yellow or colourless, is slightly heavier than water.

CLOVE OIL - CONSTITUENTS

• Volatile oils – mainly eugenol & acetyleugenol

• Sesquiterpenes (α and β caryophyllenes)

• Oil of clove – like other volatile/essential oils –should be stored in a well-fitted, air-tightcontainer, & should be protected from light &heat.

CLOVE OIL - USES

Anti-septic

Aromatic

Stimulant

Flavouring Agent

2. CARDAMOM FRUIT & OIL

Syn: Ilaychi

Source: dried, nearly dried ripe

fruits of Elettaria cardamomum

Var. miniscula

Family: Zingiberaceae

PARTS USED: Seeds (should

be kept in the fruit until ready to

be used – Prevents loss of

volatile oils).

(3RD most expensive spice).

Elettaria cardamomum

• GEOGRAPHICAL SOURCES

• Sri Lanka

• Southern India-Alleppy

• Guatemala

• HISTORY

• Traditional Indian ceremonies

PRODUCTION, COLLECTION & PREPARATION

• Mainly obtained from cultivated plants (propagated by seedlings orvegetatively [problematic due to virus infection] ).

• Capsules on the same raceme ripen at different times and it is important tocollect them when nearly ripe and before that split to shed their seeds. It isbest to cutt off each fruit at the correct stage with a pair of short-bladedscissors.

• In India & Srilanka, flowering and fruiting continues for practically whole yearbut most crop is collected from October to December

• Too rapied drying is avoided, as it causes fruits to split and shed their seeds.

• Sometimes the capsules are re-moistened and further exposed to the sun-butthis sun bleaching though improving appearance, also increases the numberof split fruits.

• Bleaching may also done by placing tray of fruits over burning sulphur.

• Soaking fruits for 10min. In 2% Sod. Carbonate solution before drying.

• Capsules have the remains of the calyx at the apex and stalk at the base,removed either by hand clipping or by machines.

• Fruits then graded by means of sieves into longs, mediums and shorts andtiny.

• If sulphur bleached, are aired in the open before being packed for export.

COLLECTION & PREPARATION

• Fruits are dried slowly (outdoors or indoors).

• Too rapid drying – capsules split & shed seeds

• Calyx at the apex of the stalk and the stalk at the base may be removed.

• Fruits are graded with a sift into ‘longs’, ‘mediums’, ‘shorts’ & ‘tiny’.

• If they have been sulphur –bleached (improved colour), it will be aired outdoors before packed for transport.

MACROSCOPICAL FEATURES

• Plant is reed-like - > 4 m, with long leaves growing fromthe rhizome.

• Fruits – capsular: inferior, ovoid, 1-2 cm long.• Apex: shortly beaked & shows floral remains.• Base: rounded & shows the remain of a stalk.• Internally the capsule is 3-celled; each cell contains x2

row of seeds.• Each seed: Slightly angular, 4mm long & 3 mm broad.• Colour: dark red-brown (fully ripe seeds) paler in

unripe seeds.• Strong, pleasant, aromatic odour• Pungent taste

MICROSCOPICAL FEATURES

• Oil cells

• Predominant Parenchyma (yellow colour)

• Cells containing silica

• Starch grains

VARIETIES & ADULTERANTS

• ADULTERATION

– Powdered drug adulterated with the fruit pericarp (powdered).

• ALLIED HERBS

– Official variety – E. cardamomum var miniscula

– Other: E. cardamomum var major (more elongated & sometimes 4 cm long with dark brown pericarps)

– Amomum aromaticum (Bengal cardamom)

– Amomum subulatum (Nepal cardamom)

– Amomum cardamomum (Java cardamom)

CHEMICAL CONSTITUENTS

• 2.8 – 6.2 % volatile oil (BP-NLT 4%)

• Abundant starch (up to 50%)

• Fixed oil (1 – 10%)

• Calcium oxalate

• OIL

• Terpinyl acetate

• Cineole

• Monoterpenes (alcohol+ester)

Cineol

Elettaria: ACTIONS & USES

• Flavouring agent (curries & biscuits)

• Liqueur manufacture

• Small amount is used for pharmaceutical manufacture (Compound Tincture of Cardamom).

3. Digitalis

• Source: Dried leaves of Digitalis purpurea Linn

• Family: Scrophulariaceae

• Syn. : Purple foxglove, Lady’s glove, Finger flower

• Histroy: The word purpurea has been derived from the purple colourof flowers

• G.S.: England, Germany, France, North America, India, Iraq, Japan, Mexico, Spain, Turkey

Cultivation

• Biennial herb (a plant which blooms in its second year and then dies)

• Good quality of drug is obtained especially from cultivated plant.

• Flourish best in well drained loose soil preferably of siliceous origin with some slight shade

• Plant growing in sunny situation possesses the active qualities of herb compare to shade by trees.

• Best grown when allowed to seed itself

• Seeds should be mixed with fine sand in order to ensure even distribution.

• Before sowing soil is sterilized.

• Sown in spring, the plant is not blossom till the following year.

• In dry season, sufficient water is supplied.

• In 1st yr, long stalk with rosette of leaves is produced.

• True plant shows dull pink or magenta not pale colored or spotted externally.

Collection

• September to November by hand

• Organic matter and discolored leaves are avoided.

• After collection, leaves should be dried as soon as possible at 60°C.

• By quick drying, green color of leaves is maintained.

• Drying is carried out till moisture is NMT 5%.

• Packed under-pressure in airtight container.

Morphology

• Color: Dark grayish green

• Odour: Odourless

• Taste: bitter

• Shape: Ovate lanceolate to broadly ovate

• Size: 10-30 cm long, 4-10 cm wide

• Margin: Crenate or dentate

• Apex: Sub acute

• Base: decurrent

• Upper surface: Hairy, slightly pubescent, dark green and little wrinkled

• Lower surface: Hairy, grayish green, very pubescent

Microscopy

• Dorsiventral leaf

• Plenty of simple covering & glandular trichome on both surfaces

• Covering trichome: uniseriate, 3-4 celled long, collapsed cells, acute apex & finely warty cuticle.

• Glandular trichome: short unicellular stalk, bicellular or rarely unicellular head

• Anomocytic(ranunculaceous) stomata

• Trichome-stomata more in lower surface

• Pericycle: parenchymatous above & collechymatous below

• Calcium oxalate crystal absent

Chemical constituents:

Chemical Test

Baljet Test: thick section of leaf + Sodium picrate Yellow to orange color

Legal Test: Glycoside (dissolved in pyridine) + Sodium nitroprusside (to make alkaline)Pink to red color

Keller-killiani Test: isolate glycoside(dissolved in glacial acetic acid) + FeCl3 + H2SO4 reddish brown color between two liquids and upper layer becomes bluish green

UsesHeart complaints, internal heamorrhage, inflammatory disease,

epilepsy, acute maniaNote: it has cumulative effect in the body so the dose has to be

decided very carefully. Market preparationLanoxin tablets (Glaxo Smith Kline) Adulterants-Verbascum thapus: Mullelin leaves, covered with large woolly

branched candelabra trichomes-Primula vulgaris: long 8-9 celled covering trichomes-Symphytum officinale: comfrey leaves, multicellular trichome

forming hook at the top

4. Dioscorea

• Source: Dried tubers of Dioscorea

deltoidea, D. composita & other species of

Dioscorea

• Family: Dioscoreaceae

• Syn.: Yam, Rheumatism root

• G.S.: North western Himalaya, USA, Mexico

• Chemical Constituents:

• Non-edible as very bitter.

• Rhizome: 75% starch & phenol

• Roots: Diosgenin (4-6%) steroidal sapogenin, glycoside: smilagenin, epismilagenin, B-isomer of yammogenin,

• Enzyme: sapogenase;

• Diosgenin is hydrolytic product of saponin dioscin.

• Uses: Source of diosgenin (in manufacturing progesterone, steroidal drugs, contraceptive) & in treatment of arthritis

Phyto-toxins

CONTENT

1. Aconite

2. Curare

3. Lilly of the valley

4. Ergot

5. Poison ivy

6. Abrus

7. Belighia

8. Yew

9. Mashrooms

10. Psoralea

11. Datura

12. Poison hemlock

1. ACONITE

• Syn: wolfbane root

• Source: dried roots of Aconitum napellus (Europe)

A. Japonicum (Japan), A. carmichaelli (China), A.chasmanthum (India)

• Family: Ranunculaceae

• GS: Western Europe-spain, Himalaya

• Toxic principle: total alkaloid 0.3-1.2%

• terpene ester alkaloids: 30% aconitine, mesoaconitine,hypaconitine, neopelline, napelline, neoline

• Toxicity. All species of monkshood should be considered toxic to humans and animals. All parts of the plant are toxic, especially the roots, seeds, and new leaves. Horses have been fatally poisoned after consuming 0.075% of their body weight of the plant. The alkaloids can be absorbed through the skin and may cause poisoning in humans handling the plant.

• Mechanism of toxicologic damage. Aconitine-type diterpene alkaloids bind sodium channels, causing persistant activation.

• Diagnosis• Clinical signs. Clinical signs are similar to those caused by larkspur

poisoning. Within a few hours of ingestion, restlessness, and excessive salivation are seen. Animals develop muscle weakness and hypotension and have difficulty breathing. Eventually, affected animals will collapse in lateral recumbancy. Death may occur several hours to days post-ingestion due to either heart block and ventricular fibrillation or to respiratory failure.

• Lesions. No lesions are seen.• Treatment. No treatment has been proven effective in monkshood

poisoning. Affected animals should be stressed as little as possible. Symptomatic treatment with intravenous fluids may be helpful. Vomiting and diarrhea should be controlled. Oral activated charcoal and osmotic laxatives may be helpful to reduce absorption of alkaloids from the GI tract.

• Use: arrow poison, potent-quick acting poison

-not used internally in UK except in homeopathic doses

-formerly used for anti-neuralgic liniment

2. CURARE

• History: generic name applied to various south american arrow poisons from family menispermaceae-chondendron spp and Loganiaceae

1. Effect is too immediate that the animal can’t flee2. The muscle relaxation induced by the poison prevents

parrots3. Toxic only to parenteral route• GS: upper amazon region: brazil and peru• BS: Chondrodendron (Ch. tomentosum, Ch.

Platyphyllum, Ch. Microphyllum)• Curarea: Cu. Toxicofera, Cu. Candicans, Cu. Tecunarum,

Cu. Caurtecasasii)

2. CURARE

• Toxic principle: Tubocurarine, isochondrodendrin dimethyl ether, curine, chondrocurine, isochondrodendrine

• Use: as source of alkaloids,

• Tubocurarine chloride official in BP/EP is used to secure muscular relaxant n surgical operation and in certain neurological conditions.

• Death that kills slowly.

3. Lily of the valley

• BS: dried flower tops of Convallaria majalis• Family: Liliaceae• GS: Europe, North America, Western Asis• Compostion: complex nearly 40 glycosides

built upon about 10 aglycone and closely dependent on the geographical origin.

• Toxic principle: Chief glycoside: aglyconewith 5-beta—hydroxyl group : k-strophanthidin of convalloside, convallatoxin, desglucocheirotoxin), convallataxol & lokundjoside

3. Lily of the valley

• Convallatoxin: very active glycoside but fortunately it is very poorly absorbed in the intestine

• Although the ingestion of lily of the valley is frequently at the origin of calls to poison centers, symptoms are observed only in 10-15% cases.

• Nausea, vomiting• Toxicity even found in flower

vases containing lily.

5. Poison Ivy• Syn: sumacs, poison dogweed• BS: Toxicodendron radicans• GS: USA• Toxic Principles: Phenols: urushiols, o-diphenols substituted

by an aliphatic chain of 15-17 carbon atoms, and more or less unsaturated

• Oxidized to quinones, they formed covalent bond with proteins and yields an antigenic complex.

• Use: contact with the fresh plant results in sever and extended dermatitis with blisters.

• Hands and clothing; objects and disseminate the phenol that remain intact for months.

Chemical Constituents

10. Psoralea toxin-Furanocoumarins

• Syn: Bavchi, Malaya tea

• Source: dried ripe fruits and seeds of Psoraleacorylifolia

• Family: Leguminosae

• GS: India, China, Srilanka, Nepal, Vietnam

• Toxic principle: 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, geranylacetate, angelicin, psoralen, bakuchiol

• Chemical Test:1) psoralen, dissolved in alcohol + NaOH UV light

observation yellow fluorescence2) Psoralen, dissolved in small amount of alcohol, 3 times

propylene glycol, 5 times acetic acid, 40 times water UV light observation blue fluorescence

• USESAphrodiasic, antibacterial, astringent, cytotoxic, deobstruent, diaphoretic, diuretic, stimulant, stomachic , tonic, lower back pain, skin disease, bed wetting, leprosy, hair loss

PsoralenPsoralidin

1. Quassia• Syn: Bitter wood, Jamaica Quassia

• Source: dried wood of the stem of

Aeschrion excelsa (Picroena or Picrasma

excelsa)

• Family: Simaroubaceae

• GS: West indies, Jamaica, Guadeloupe, Martinique, Barbados, St. Vincent

• Use: Bitter tonic, Insecticide, vermicide for thread worms, slightly narcotic & acts on flies, increase appetite

Constituents & Structures1. Terpenoid : Amaroid

• quassin, an intensely bitter lactone

• Neoquassin

• Isoquassin (picrasmin)

• 18-hydroxy quassin

• Scopoletin

2. Alkaloid: Cathine-6-one

3. Volatile Oil

4. Inorganic salt: CaCl2, NaCl, sulphate of lime, oxalate, ammonical, KNO3,

Neoquassin

2. Picrorrhiza• Syn: Kutki, Yellow gentian

• Source: dried rhizomes of

Picrorrhiza kurroa

• Family: Scrophulariaceae

• GS: North-west Himalaya region at 3000-4000 m

• Use: Bitter tonic, Hepatoprotective, Immunomodulator, curing different types of jaundice, skin disease, improves eye sight, Cholagogue-stimulates gallbladder contraction to promote bile flow

Constituents & Structures1. Iridoid glycoside:

• Picroside I

• Picroside II

• Kutkoside

• Pikoroside

• Picrorhizinonhydrolysispicrorhizetin + dextrose

2. Phenolic glycoside:

• Picein

• Androsin

3. Cucurbitacin glycoside

5. Taxus• Syn: Yew

• Source & GS: dried bark of

• Taxus baccata (Europe)

• Taxus brevifolia &

T. canadensis (North america)

• Taxus cuspidata (Japan)

• Taxus wallichiana (Himalaya)

• Family: Taxaceae

Constituents & StructuresTricyclic diterpenoids:

• Taxane skeleton

• Taxusines

• Taxagifen

• Baccatin-III

• Taxine

• Taxol

• Cephalomannine

• Taxicine

USES

• Paclitaxel: mitotic spindle

poison

• M/a: it promotes assembly

of tubulin dimers into

microtubules which is stabilized

by inhibiting their

depolymerization

• Indication: Advanced ovarian

cancer, metastatic breast cancer

• S/e: neutropenia, peripheral neuropathy, CVS, alopecia

• Posology: 135-175 mg/m2

• Docetaxel:

• Indication: breast cancer

• S/e: severe neutropenia, hypersensitivity reaction, water retention, cutaneousreaction

• Posology: 100 mg/m2

7. Gentian• Syn: yellow gentian root

• Source: dried fermented roots and rhizomes of Gentiana lutea

• Family: Gentianaceae

• GS: Mountainous regions of Central and south europe, Turkey, Yugoslavia

Now: France, Italy, Germany

• Use: bitter tonic, GIT problems, anti-inflammatory, wound healing, choleretic-stimulating bile production, anti-oxidant, hepato-protective, anti-fungal

Constituents & Structures• Bitter glycoside, alkaloids, yellow

coloring agent, sugar, pectin, fixed oil

• Seco-iridoid: gentiopicroside(gentiopicrin-gentiomarine)

• Hydrolysis product: gentiogenin + glucose

• Biphenolic acid ester of gentiopicrosideamarogentinhighestbitter

• Sweroside, swertiamarine

• Yellow color is due to Xanthonegentistin or gentiamarine, isogentistin, gentioside, gentisic acid

• Alkaloid: gentianine, gentialutine

8. Chirata• Syn: Indian gentian, Indian

balmony, chirayta

• Source: entire herb of Swertiachirata

• Family: Gentianaceae

• GS: India, Nepal, Bhutan

• Use: ingredient of Mahasudrashan& Sudarashan churna, chronic fever, bitter tonic, stimulant, liver protective, promoting flow of bile, cures constipation and useful in treating dyspepsia

Constituents & Structures

Chirata:

• chiritin, gentiopicrin and amarogentin

• Amarogentin: phenol carboxylic acid ester of sweroside: related to gentiopicrin

• Ophelic acid

• Gentianine

• Gentiocrucine

9. Andrographis• Syn: Kalmegh, King of bitter, kirayet

• Source: leaves and entire aerial part of Andrographis paniculata

• Family: Acanthaceae

• GS: growing -India, Pakistan, Srilanka, Indonesia

Cultivated-China, Thailand, west indies, Mauritius

• Use: bitter tonic, febrifuge-reduce fever, anthelmintic, astringent, cholagoggue, cholera, diabetes, weakness, blood purifier, jaundice, GI disturbances, itching

Constituents & Structures

• Diterpene lactone:

kalmeghin

• Andrographolide

• Neoandrographolide

• 14-deoxy-11,12-

didehydroandrographolide

• 14-deoxy-11-oxo-

Andrographolide

• Andrographiside

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

• GS: America (US-Virginia, Kentucky, North carolina, Tennessee, Indiana, Canada)

Indian: Tibet, China, Afghanistan, Himalayas

• Collection:

The rhizome which is about 1 m in length, is dug up cut

into pieces about 10 cm in length and dried.

• 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

Starch

P. hexandrum

6-12% Resin

40% podophyllotoxin

• Chemical Test:

Alcoholic ext. + strong copper acetate- brown

ppt with Indian podophyllum & green color

without ppt with american podophyllum

• USES:

-Cyto-toxic, venereal disease

-Podophyllotoxin is semisynthetically converted to

etoposide potent anticancer agent for lung &

testicular.

-Its GIT irritant, drastic purgative in moderate

uses

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+ waterboilstrainfiltrate+ NaOH no rose

color----distinct from Ammi visanaga2) 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

• Constituents: furanocoumarins, xanthotoxin, imperatorin, bergapten, isopimpilin

4. Phyllanthus (Lignan)

• Syn: Bhumyamlaki, Stone breaker• Source: dried leaves and stem of

Phyllanthis niruri• Family: Euphorbiaceae• GS: trophical zone• Uses:

Kidney stones treatmentAntibacterialAnti inflamatoryAnti hepatotoxicAntiespasmodicAnti viralHepatotonicCholereticInmuno stimulant

• 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.

2. ASAFOETIDA

• Syn: Hing, Devil’s dung, Asant, Asafoda

• Source: Oleogum resin obtained from the incision of rhizome and root of Ferula foetida, F.rubricaulis, F.asafoetida & other species of Ferula

• Family: Umbelliferae

• GS: Iran,Pakistan, Afghanistan,

India (Kashmir)

COLLECTION

large schizogenous ducts and lysigenous cavatiescontaining milky liquid.

removal of the stem and the cutting of successive

slices in March-April.

exposed surface is covered by a dome

shaped structure made of twigs and earth.

after each slice is removed, oleo-gum-

resin exudes and when sufficiently hardened, is

collected.

The product is packed in tine lined cases for

export.

CHARACTERS

• Forms: 2 Types: Tears & Masses

• Color: golden yellowish brown

• Odor: strong

• Taste: bitter & acrid

Specification:

• NMT 15% ash

• NMT 50% matter which is insoluble in 90% alcohol

CONSTITUENTS

Resin

• Asaresinolferulate

• Ferulic acid

Volatile Oil

Sulphur containing

• C7H14S2

• C16H20S2

• C8H16S2

• C10H18S2

• C7H14S3

• C8H16S3

• Umbelliferyl ester

Gum

Flavour: R-2-butyl-1-propenyl disulphide

CT & USE

1. Powder + water trituration milky white emulsion

2. Combined umbelliferone Test: Powder+ HCl boilfilterfiltrate + NH3 blue fluorescence

3. Fractured surface+H2SO4 red color production, which changes to violet on washing with water

4. Fractured surface+HNO3green color

USE

Carminative, expectorant, flavoring curry, sauce and pickles,

nerve stimulant, intestinal flatulence, enema, sedative in

hysteria

ALLIED SPP. & ADULTERANTS

Allied spp:

Galbanum (Ferula galbaniflua and

Ammoniacum (Dorema ammoniacum)

Adulterant:

Red clay, gypsum, chalk, potato slices

4. PERU BALSAM

• Syn: China Oil, Black balsam, Peruvian balsam

• Source: Obtained from trunk of the Myroxylum balsamum var. pereirae (trunk is beaten and scorched)

• Family: Leguminosae

• GS: Central America (San Salvador, Honduras, Guatemala)

COLLECTION & PREPARATION

The balsam is collected from trees that are

around 10 years old in the month of November or

December i.e. by the end of rainy season

The trunk is beaten at an area of 30x15 cm

using the handle of the axe or a stone or a

stick.

As peru balsam is a pathological resin,

which is present only in the young twigs, a

secretion of the balsam takes place

after 5 days

A rag is placed under the bark so that it can

absorb the resin

Once the bark is exhausted the bark is

removed and the young wood is also treated in similar

manner

The resin flow for about 5-6 weeks and the fresh area on the bark are beaten and

scorched.

The rags, which are collected, are put into

strong rope bags, which are twisted at

the ends and pressed, so that balsam falls into boiling water

Balsam sinks at the bottom of water, the

water is decanted, balsam collected, packed in tins and

exported

CHARACTERS

• Color: dark brown

• Odor: aromatic vanilla like

• soluble in chloroform, chloral hydrate, in equal proportion with 90% alcohol

• sparingly soluble in petroleum ether, glacial acetic acid and insoluble in water

• Specific gravity: 1.14 to 1.17

• NLT 45% and NMT 70% of esters.

CONSTITUENTS & USES

• benzyl cinnamate (cinnamein) C6H5CH=CHCOOCH2C6H5,

• benzyl benzoate and cinnamyl cinnamate (styracin).

• 28% of resin: peruresinotannol combined with cinnamic acid, benzoic acids, alcohols (nerolidol, farnesol and benzyl alcohol) and small quantities of vanillin and free cinnamic acid.

• antiseptic dressing for wounds

• parasiticide for scabies

• internally to treat catarrh and diarrhea.

5. TOLU BALSAM

• Syn: Tolu resin, Thomas balsam, Opobalsam

• Source: Obtained by incision from the trunk of Myroxylon balsamum var. balsamum

• Family: Leguminosae

• GS: West indies, Cuba, Venezuela, Colombia

• Collection:

• V-shaped incisions in the bark

• Many such receivers are fixed on each tree, the yield per tree being 8-10kg.

• Periodically, the balsam is transferred to large containers.

CHARACTERS & CT

• Color: yellow on standing brown

• Odor & Taste: aromatic

Test

1. Alcoholic solution is acidic to Litmus

2. Powder + FeCl3 green (resinotannol)

3. Powder + Water decoction oxidation KMnO4 odor of benzaldehyde (due to oxidation of cinnamic acid)

CONSTITUENTS & USES

• 80% of resin alcohols combined with cinnamic and benzoic acids.

• 12-15% of free cinnamic and 8% of free benzoic acid.

• Benzyl benzoate, benzyl cinnamte & vanillin

• Styrene,eugenol, vanillin, ferulic acid, 1,2-diphenylethane, mono and sesqui-terpene hydrocarbon and alcohols.

• triterpenoids

• 35-50% of total balsamic acid

• USEGenuine tolu balsam is difficult to obtain

• now uses tolu flavor solution containing 5 aromatics for preparation of tolu syrup.

• antiseptic, common ingredient of cough mixture

6. SUMATRA (INDONESIA) BENZOIN

• Syn: Gum benjamin

• Source: balsamic resin obtained from the incised stem of Styrax benzoin, Styrax parallloneurus

• Family: Styracaceae

• GS: Sumatra (western Indonesia), Java, Borneo

COLLECTION Cultivation in rice plants-Tapping-Grading

Seeds are sown in rice fields, rice shading the young trees during 1st year. After

harvesting of rice the tress are allowed to grow until they are about 7 years old

Triangular wounds are made in a

vertical row about 40 cm apart, bark between

wounds being scraped

smoothly

1st secretion is very sticky and

is rejected..

After making further cuts,

each about 4 cm above the

preceding ones, harder Secretion

is obtained

Further incision, after 3 months and

secretion becomes

amorphous instead of crystalline

About 6 weeks of fresh tapping, the

product is scrapped off, outer layer (finest quality)

being kept separate from the next layer

(intermediate quality

About 2 weeks later the strip is scrapped again, giving a lower

quality darker in color and

containing fragments of

bark

Grading done mixing 3

quality: best contains most almonds and

worst contains a few almonds but abundant resin mixture

Blending done by: breaking up the drug; mixing

different proportion of 3

qualities, softening in sun

Stamping in to Tins &

commercial drug arrives in plaited container with

plastic wrapping

CHARACTERISTICS

• Occur as: brittle mass

• Color: whitish-reddish tears

• Odor: agreeable & balsamic

• Taste: slightly acrid

CONSTITUENTS

• Free balsamic acid (20% cinnamic + 10% benzoic acid)

• Triterpenoids: siaresinolic acid, sumaresinolic acid

High grade of S.paralleloneurum

3% benzoic acid

0.5% vanillin

20-30% cinnamic acid

Siaresinolic acid

Sumaresinoliac acid

ALLIED DRUGS & USES

• Internally: expectorant, antisepctic

• Ingredient: Friar’s balsam

• Externally: cosmetic lotion, food, drink, perfumary & toilet industries

• Component: Incense

Palembang, inferior quality benzoin: lighter in weight & breaking with an irregular porous fracture & as a source of natural benzoic acid

6.1 SIAM (Thailand) BENZOIN

• Source: obtained by incision of the trunk of Styrax tonkinesis

• Family: Styracaceae

• GS: Thai province of Luang prabang, Northen Laos, Northen Vietnam at altitude of 600-2500 m

• It seems that this height is necessary for resin production; not all trees are productive

METHOD OF PREPARATION

• Similar to Sumatra benzoin

• Resin, being produced at the interface of the bark and wood layers only after injury.

• Grading of tears: size, color, largest, palest

• Size: few mm to 3cm

• Color: yellowish white to reddish changes to brown due to oxidation

• Odor: agreeable & vanilla like

CONSTITUENTS

• Coniferyl benzoate, coniferyl cinnamate, coniferyl alcohol

• 10% benzoic acid, Triterpenoid acid, esters, Vanillin

CHEMICAL TEST

• Siam benzoin is expensive & liable to adulteration with the sumatrabenzoin, which can be detected by BP/EP/TLC

1. Powdered benzoin + KMnO4 warm faint odor of benzaldehyde (with sumatra benzoin due to oxidation of cinnamicacid) (NOT OBSERVED WITH SIAM)

2. Alc Ext + Alcoholic FeCl3 green color produced (with SIAM benzoin due to coniferyl benzoate-tannins) (NOT WITH SUMATRA)

3. When Sumatra benzoin is gradually heated evolves fumes of benzoic and cinnamic acid readily condensed on cool surface as a crystal sublimate

4. Petroleum ether solution of benzoin + 2-3 drops of H2SO4 in a china dish reddish brown color with SUMATRA BENZOIN and purple-red color with SIAM BENZOIN

9. SHELLACresemble cochineal insect in structure and life history

• Source: resinous substance prepared from a secretion that encrusts the bodies of a scale insect Karria Lacca (Lucifer lacca), order Hemiptera

• GS: India, Thailand, China (5% of world’s production)

• India: Leguminosae (Acacia spp., Butea frondosa), Euphorbiaceae (Aleuritis laccifera), Moraceae (Ficus spp.), Dipterocarpaceae (Cajanus indivus, Shorea talura), Rhamnaceae (Ziziphus jujuba)

• China: species of Ficus and Dalbergia (Leguminosae)

Preparation

• Lac is found on smaller branches & twigs

• Broken off and constitute stick lac

• Scraped from twigs by means of curved knives

• Usually ground in India & coloring matter is extracted with water or dilute soda solution.

• Solution evaporates to dryness constitute lac dye and exhausted lac when dried seed lac

Types of Shellac

Characters, Constituents & Uses

• Orange shellac: brownish yellow flake

• Garnet shellac: reddish brown

• 6% wax, 6.5% red water soluble coloring matter,laccaic acid, 70-85% resin, few insect remains, vegetable debris

• Resin: Hard & Soft (hydroxy fatty acid + sesqui terpene)

• Hard Resin: aleuritic acid (9,10,16-trihydroxypalmitic acid)

• Soft resin: cedrene type sesquiterpene acid, water insoluble yellow pigment –erythrolaccin (tetrahydroxy-4-methylanthraquinone

• Pharmaceutical aid, In varnishes, polish, sealing wax

Marine Cyto-toxic

• any drug that has a toxic effect on cells; commonly used in chemotherapy to inhibit the proliferation of cancerous cells

• Categorized as

– Cembranes

– Macrolide

– Depipeptides

– Miscellaneous

Cembranes

•14 membered cyclic diterpened

• Source: soft coral

• Exocyclic lactone integral part

Cembranes

• Lactone ring

– 1) Sinularine

– 2) Crassin acetate

– 3) Cytabarine = Ara-C

– 4) Fludarabine

– 5) Aplysistatin

• Non-Lactone ring

• 1) Asperidol

• 2) Geranyl hydroquinone

Sinularine

• Source: Sinularia flexibilis

• Constituents:

• Epoxide ring

• Simularin

• Dihyrdosimularin

• Simulariolide

• Application: Anti-cancer

Crassin acetate

• Source: soft coral, Caribbean gorgonian Pseudoplexaura porosa

• Use: observed to be comparatively inert to the mammalian systems but on the contrary found to be extremely cytotoxic to human leukemic as well Hella cells in vitro & mouse fibroblast.

Cytarabine = Ara-C

• Source: Cryptotethya crypta• Market preparation: Cytosar by Upjohn pharma• 1-alpha-D-arabinofuranosyl cytosine or cytosine

arabinoside• Obtained from Caribbean sponges viz. Spongosine &

Spongouridine• Synthesized from acetylation of uracil arabinoside

followed by treatment with phosphorus pentasulphideand subsequent heating with ammonia

• Application: acute myelogenous leukemia and human acute leukemia for therapeutic purpose

• Active against Erlich carcinoma, sarcoma-180 and L-1210 leukemia in mice

4) Fludarabine: Ara-A5) Aplysistatin: Aplysistatin angasi

Non-lactone

• Gorgonian coral

1) Geranyl hydroquinone: Chloroform extract of Aplydium spp.

• Cytotoxic to leukemia and mammary carcinoma & as radioprotective agent

2) Asperidol

Bryostatin

• Source: Bugula neritina• They are currently under investigation as anti-

cancer agents and as a memory enhancing agent.• Synthesis: • The low concentration in bryozoans (to extract

one gram of bryostatin, roughly one tonne of the raw bryozoans is needed.