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Coumarins are derivatives of benzoapyrone, or lactones of ohydroxycinnamic acid ocoumaric acid'

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Coumarins are derivatives of benzo-a-pyrone, or lactones of o-hydroxycinnamic ... colored substances and many of them are used technically as dyes e.g. alizarin. ... – PowerPoint PPT presentation

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Title: Coumarins are derivatives of benzoapyrone, or lactones of ohydroxycinnamic acid ocoumaric acid'


1
?) ??????????? Coummarins
Coumarins are derivatives of benzo-a-pyrone, or
lactones of o-hydroxycinnamic acid (o-coumaric
acid).
- ??? ???? ????? ?? ?????? ????????????? ?????
???? - ?? ???????
2
????? ??????????? ????????
1) ???? ???????? ??????? 7-hydroxy coumarine
3
2) ??????? ??????? Furanocoumarine
  • ?? ????? ????? ????? ????????? ??? Cumarinic acid
    ???????? ???? Cumaric acid.

???????? Psuralin ???????? (???????????Imperatori
ne ??????????? ?Xanthotoxine ???????? (bergaptine
They are coumarin derivatives with additional
furan ring. Ammi majus contain a group of
furanocoumarins, the parent compound is called
Psoralene. They are used for the treatment of
psoriases and leucodermia.
4
3) ????????????? Pyranocoumarins
They are benzo-?-pyrone derivatives resist
alkalis. Ammi visnaga contain furanochromones,
the major is Khellin. Khellinis a smooth muscle
relaxant used as Bronchodilator. Antispasmodic. R
enal colic. Coronary vasodilator.
Khellin.
5
????? ?? ??????????? Detection of coumarin
????? ?? ???????????
1- ??? ?????? ( ?????? ????? ??????? ) 2- ?????
????? ??? 320 ???????? 3- IR 4- CNMR
6.1-6.4 , 7.5-7.9
??????? ???????????
1- ????? 2-???????
????? ???????????
6
?) ?????????? Xanthones
????????? ?? ???????? ??? ??? ??????? ?? ???? ??
???? ???????? - ???? ??????????? ?? ????????????
?????????
- ????
??????? ?????
??????? ?????? IR ??? ?????? ??????? UV
7
?????? ??????????
1- ?????? ????????? ???? ????? ?? ?????? ???????
???????? 2- ????? ?????????? ??? ?????? ??? ????
????? ????? ????? 3- ???? ?????????? ?????? ?????
?? ??? ??????? ????????? ????? ?? ???????????? 4-
????? ??? ???? ????? ??? ?????? ?? ????
?????? 5-???? ????? ?? ??? ????? ??????
??????? Synthisis
???? ?????? ?? ????? ?????? ??? ????????? ??
?????? ??????? ?? ???? ???? ??? ??? ??? ???
????????? ?? ????? ????? ???????
8
?)???????????? ??????????? Anthraqu. Anthracene
- ???? ??? ?????? ????????? ?? ?????? ???????? -
?????? ????? ???? ???? ?????? ?????????? .
???? ??? ???????? ????? ??? ???????? ???? ,
?????? ?? ??? ????????
Anthraquinones are colored substances and many of
them are used technically as dyes e.g.
alizarin. Reduced forms of anthraquinones, which
exhibit keto-enol tautomerism, are often
encountered. The anthracene derivatives occur in
vegetable drugs in different forms at different
oxidation levels like anthraquinones, anthrones,
anthranols, or oxanthrones.
????? ???????
???????? Cascara ???????Rhubarb

?????? Aloe ????? Senna
9
?????? ?????????? Anthracene derivatives
?????? ?? / 1- ????????????Anthraquinone 2-
????????? Oxyanthrone 3 )???????? ???????
Anthranol and anthrone 4) ??? ??????
Dianthrone 5) ?????????? ?????? Aloe glycosides
The anthracene derivatives occur in vegetable
drugs in different forms at different oxidation
levels like anthraquinones, anthrones,
anthranols, or oxanthrones.
10
Interrelationship of anthraquinone derivatives
11
??????? Synthesis
12
1) ???????????? Anthraquinone
Although anthraquinone is not used extensively in
medical practice, it is the starting material for
the preparation of several synthetic laxatives
and represent the basic structure of a number of
important laxatives and dyestuffs. Borntragers
test is often used for their detection. The
derivatives of anthraquinone present in purgative
drugs may be dihydroxy phenols such as
chrysophanol, trihydroxy phenols such as emodin
or tetrahydroxy phenols such as carminic acid.
- ????? ?????? ????? - ??????? ?????? ??? .
???????? ????? ?? ????? - ???? ?????
????? ????????? ????
  • ???? ????? ????(???? ????)
  • -???????

13
Anthraquinone
Chrysophenol
Eimodine
14
2) ?????????? ?????????Anthranol and anthrone
??? ?????? ????? ????? ?????? ???????????? ?????
?? ????? ??? ?????????????? ????? ?? ???? ???????
??? ????????? Chrysarbine
These reduced anthraquinone derivatives occur
either free or combined as glycosides. They are
isomeric and one may be partially converted to
the other in solution. Anthranols are converted
upon oxidation into anthraquinones.. Schontetens
test is often used for anthranols (green
fluorescence). Anthranols and anthrones are the
main constituents of chrysarobin, a mixture of
substances.
????? ??????
???? ??? ???? ??????
15
3)????????????? Oxanthrone
These are intermediate products between
anthraquinones and anthranols. They give
anthraquinones on oxidation with hydrogen
peroxide. An oxanthrone has been reported as a
constituent of cascara bark.
??? ?????? ?????? ??? ??? ??????????? ???????????
????? ?? ???? ?????????
???? ?????????? ???????? ?? ??? ???????
16
4)??? ?????? Dianthrones
These are compounds derived from two anthrone
molecules, which may be identical or
different. One of the best known is sennoside
derived from two molecules of glucose and two
molecules of rhein-anthrone. On hydrolysis,
sennoside yields the aglycone sennidin.
??? ?????? ????? ?? ?????? ?? ????????Anthrone
????? ? ???? ???? ?????? ???????? ?? ???????
???? ????? ??? ???????? ?????????
Sennosoide ?????? ??? ?????? ????????? ??? ?????
?? ????? ?? ???????? ??????? ?? ???????????.
17
5)?????????? ?????? Aloin-type or C-glycosides
Aloin (Barbaloin) was obtained from species of
Aloe. It is strongly resistant to normal acid
hydrolysis. In aloin, the sugar is joined to
aglycone with a direct C-C linkage (a
C-glycoside). Two aloins (A and B) are known and
arise from the chiral centre at C-10.
?? ??????
??????? ???????
???? ?????? ?? ????????
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