PHARM.

D
Chemical Pharmacognosy- I
Lecture 28
May 11th, 2011

LACTONE
GLYCOSIDES

M. Ahsan Khalid, B.Pharm

B.Pharm,, Pharm. D
M.Phil Scholar (RIPS/RIU)
HIPS--HUKIC
HIPS
 Lactone glycosides
• Coumarin
• Classified as a simple phenylpropanoid
• occurs in Tonka Beans, sweet vanila grass
( Anthoxanthum odoratum; Fam Poaceae),
sweet clover (Melilotus albus/officinalis;
Fabaceae) etc.
• Formerly used as flavoring agent, FDA
banned the use of coumarin and coumarin
containing materials as flavoring agent
(con’t)
 Lactone glycosides

– Bishydroxycoumarin (Dicumarol) is obtained

from improperly cured leaves and
flowering tops of Melilotus officinalis
(Fabaceae)
– Anti - Coagulant property (determine by
APTT) as prophylaxis and treatment of venous
thrombosis and pulmonary embolism
– Interfere with Vit K action
 Lactone glycosides
• Aside from coumarin (lactone of o-hydroxy
cinnamic acid), other hydroxylated coumarin
derivatives occurring in plants are:
1. Skimmin - Japanese star anise
2. Aesculin - horse chestnut tree
3. Daphnin - Mezereum
4. Scopolin - Belladonna
5. Limettin - Citrus trees
 Santonica USP VIII (1905)
Synonym: Levant, Aleppo, Alexandria
Wormseed, Semen Cinae, sea
wormseed

Origin: dried unexpanded flower heads of

Artemisia cina (Asteraceae)
Constituent:
chief: β - santonin(sesquiterpene lactone),
artemisin(crystalline lactone)
Use: Anthelmintic (roundworm e.g. ascaris)
little effect on threadworm,
 no effect on Taenia
Santonica
- action is due to spasmodic contraction of the GIT
rendering worm incapable of movement -- excreted
in bowel; should not be followed by a purgative

Allied drug in the Phillipines

Seeds of Quisqualis indica (Combretaceae)
known as niog - niogan
used as anthelmintic agent
Cantharides NF X (1955)

Synonym: Spanish flies, Russian flies,

Blistering Flies
Origin: dried insects of Cantharis vesicatoria
(Meloidae)
Constituent: Cantharidin (lactone or
anhydride of cantharidic acid)
Use: Irritant, Vesicant, Rubefacient removes
warts (topically)
Internally: excreted by kidney, irritating to
urinary tract --- resulting in priapism
Cantharides
Note:
Popular as Aphrodisiac - Dangerous and
reported can cause death

Insect found in shrubs of Caprifoliaceae and

Oleaceae
Mature insect - brilliant green with metallic
luster
 Psoralens
• Photosensitizing furocoumarin
• Common cause of phototoxicity
1. Methoxsalen (8-methoxypsoralen,
Xanthotoxin)
- Present in the cremocarp of Ammi majus
(Apiaceae)
- Used to facilitate repigmentation in
idiopathic vitiligo (Leukoderma)
- Symptomatic control of severe,
disabling psoriasis
CAUTION: Therapy is carcinogenic, cataract
development, Actinic degeneration of
skin(Photochemical degeneration)
Psoralens
2. Trioxsalen (4,5’,8 - trimethoxypsoralen)
- synthetic furocoumarin
- treatment of vitiligo
3. Khellin (Visnaga, khella)
- furochrome found in fruits of Ammi
visnaga (toothpickweed; Apiaceae)
- Vasodilator (bronchial asthma and
angina pectoris,
- Visnadin mild inotropic – dilate coronary
vessels
- used as urethral spasm and renal colic
Psoralens

• Interactions
– Hepatotoxic herbs - additive
– St. John wort -photosensitivity
– Lifestyle – alcohol leads to hepatotoxicity