??? ????Phenylpropanoids

1
??? ????Phenylpropanoids
2
8.1 Introduction
3

• ???????????????????(Glucosinolates)??????,????????
  ?
• ???????????,?????????????,??????????????(Plant
  phenolics)?

4
Classification

• Hydroxycinnamic acids - p-Coumaric acid, caffeic
  acid
• Phenylpropenes - anethole, eugenol,
• Coumarins -cylized by o-Coumaric acid
• Chromone -isomer of coumarin or may be by
  polyketide pathway

5

• Abridged phenylpropanoids -catechol, methyl
  salicylate, gallic acid, Phenylethanol
• Flavonoids - Cinnamic acids conjugated with
  polyketides (triketides)
• Lignans Neolignans -dimers of phenylpropanoids
  linked by the propane side chain
• Lignins -polymers of phenylpropane (Coniferyl
  alcohol)
• Tannins -hydrolysable (Galloylated Glucose)
  condensed (proanthocyanidins, also polymers of
  flavonoids)

6

• Phenylpropanes ? highmolecular weight polymers,
  e.g. Lignins Tannins
• Lignins?????(Cellulose)???????????,??Lignins??????
  ?????????????(Hemicellulose)??????
• Tannins(??) ????????????? ?????(Condensed
  tannins),?????????(Proanthocyanidins),???????(Hydr
  olyzable tannins)?

7
(No Transcript)
8
8.2 ???????????
9
(No Transcript)
10
(No Transcript)
11
8.3 ????????? Simple Phenylpropanoids

• Simple Phenylpropanoids - phenyl propenes eg.
  Anethole?Eugenol?Myristicin

12

• Abridged phenylpropanoids -Benzoic acid?Methyl
  salicylate?Salicin?Vanillin?Capsaicin

13

• ???????? -p-Coumaric acid?Caffeic acid?Ferulic
  acid?Sinapic acid
• ???(Coumarin)-warfarin, dicumarol
• ???(Chromones) -Khellin

14
(No Transcript)
15
Capsicum-Cayenne pepper

• ??-?????(Capsicum)?????????
• ??-
• 1. ????? C. frutecens Linné
• 2. Tabasco pepper? C. annuum Linné var. conoides
  Irish
• 3. ????????(Louisiana long pepper)? C. annum
  Linné var. longum Sendt
• 4. Louisiana short pepper???Honka????Louisiana????
  ????
• ??-Garden pepper?Paprika?Pimento?Mexican
  chillies?Tabasco pepper

16
C. frutescens
C. annuun
17

• ??-Capsaicin 0.02 ?1.5??????????????????0.2????
  ?
• ??-???????(Rheumatoid arthritis)?????(Osteoarthrit
  is)???????(Post herpetic neuragia)?????????(Diabet
  ic neuropathy)???????(Post mastectomy)????????(Pos
  t amputation of neuroma,?????)?

18

• ????-????????C-Type??????????P??(Substance P)
  (PPain)
• ??-????45???????,?????
• ??-
• C. frutescens -???????????,??????????????????????
  
• C. annuum -??,?????????????????????????????

19
8.3-1 ???Coumarins

• ???????????(o-Hydroxycinnamic acid)???,Coumarin???
  ???????????Coumarou??????????????????????,???????
  ??????,?????

20
? ?

• ???? -
• ????(Tonka bean) Dipteryx odorata?D.
  oppostifolia
• ???(Sweet clover) Melilotus albus ?M.
  officinalis
• ???(Red clover ) Trifolium pratense
• ???-
• ???(Sweet vernal grass, Anthoxanthum odoratum )
• ???-
• ?????(Sweet scented bedstraw,Galium triflorum )

21
(No Transcript)
22
Melilotus albus
23
M. officinalis
24
Trifolium pratense
25
Anthoxanthum odoratum
26
Galium triflorum
27
? ?

• ?????????????????????,?????????????????
  ,??FDA??????????????????????
• ???(Black haw,Viburnum prunifolium Linné?V.
  opulus Linné,Caprifoliaceae)???????,?????????Scopo
  letin(6-Methoxy-7-hydroxycoumarin)????????

28
Bishydroxycoumarin or dicumarol

• Suorce-M. officinalis (Fabaceae),?????(curing)????
  ??????????,?????????,????????????
• ??-????????K???,??????????????,????????(Heparin)??
  ????????????

29
Psoralens

• Source -???(Apiaceae)????(Rutaceae)????(Apium
  graveolens)??Sclerotina sclerotiorum??????,???????
  ????(Phytoalexin)
• Activity -Photosensitizing effect
• ??-Methoxsalen(Methoxypsoralen or
  Xanthotoxin),?Ammi majus ?????,??????Vitiligo(??)?
  ?????????????(Psoriasis)?????,Methoxsalen?????????
  ,??????????????(???)???
• Trioxalen?4,5,8-Trimethoxypsoralen????????????????
  ?Vitiligo

30
(No Transcript)
31

• ??-??(???)????(Cataract)???????(Actinic
  degeneration),??????????????????

Vitiligo
32
Echinaceae(???)

• ??-Cone flower?Purple cone flower
• ??-Echinaceae angustifolia D. Candolle?E. pallida
  Nutt.??(Asteraceae)???????
• ??-??????????????,??????E. purpurea (Linné)Moench
  ?????????????,???????????

33
Echinaceae purpurea
34
E. pallida
E. angustifolia
35

• ??-???????????????
• 1. ?????(Heteroxylan)???????
• 2. ??????????(Arabinogalactan)????????????,?????
• 3. Alkamides???????Chicoric acid????????

36

• ??-Echinaceae?1885??????(Dr. H.C.F.
  Meyer)?????????(Blood purifier)???????????,???????
  ??????????????????????????????????????

37

• ??- ???,??????????????????,????????????????????,??
  ???(Lotions)???????,????????,?????????????????????
  ?

38
????-

• ???????????????,?????????,???????????????????????,
  ????????(Tumor necrosis factor)???,????????,??????
  Properdin????(Interferon)????

39
Tumor necrosis factor??????

• ??????a-???????????????cytokine???????????????????
  ??,?interleukin 1??????????????????,?????????endot
  oxins??????????????????????(Cytotoxicity)?
• ??????ß-???T-Cell???,?????????

40
Khellin

• ??-Ammi visnaga Lam.(Apiaceae)
• ??-??????????
• ??-??????????????(Renal colic)Khellin??????????,?
  ??????????,????????(Coronary insufficiency)????(An
  gina pectoris)???(Bronchial asthma),??????????????
  ????????
• Khellin????????????????Cromolyn sodium
  ?????,?????????????,?????????????????????????

41
(No Transcript)
42
(No Transcript)
43
8.4 Lignans and Neolignans????????

• ???????????,???????????????,?????????????
• Lignans??????????Ferulic acid(???)???Coniferyl
  alcohol,??????????(Oxidative Dimerization)???C3???
  b?????
• Neolignans??????????-?(C-C)?????
• ??????????????????????(Antifeedant)?????????????,?
  ???????????????????,???????????????

44
Podophyllum????

• ??-Mayapple?American mandrake
• ??-Podophyllum peltatum Linné(Berberidaceae???)???
  ??????Podophyllum????,?????,?peltatum???????????
  ???,????????????,????????????????????
• ??-?????????????????(Virginia)???????(North
  Carolina)

45
(No Transcript)
46
(No Transcript)
47

• ??-??3.56???,???????????,????20?Podophyllotoxin
  ?10?a-Peltatin?5?b-Peltatin??,Podophyllum???????
  ??????????????,????????????????

48

• Podophyllin??????(Antimitotic)?????
• Podophyllin??????trans????????,??????,??Epimerizat
  ion???????????????cis???????,???Picropodophyllin
• Podophyllum??????5??,??????????,?????????????????
  ?(???????????????????(Wart)-Condyloma
  acuminata,?????????)

49
????

• ??Podophyllum,????????????????P. emodi
  Wallich,??????????,???????????,??11.412,??Podoph
  yllotoxin????????P. peltatum?
• ??????????Dysosma pleiantha??????

50
P. Emodi P. hexaandrum
51
???
Dysosma pleiantha
52
Preparation of Podophyllin

• ??????(Percolation)???????
• ???
• ?????????????
• ????????
• ???????
• Podophyllum????????,????????,?????25??????????????
  ?,???????????,??????????????

53
Usage-

• Podophyllum?????????(Papilloma)??????,????????25?
  ???????(??????,?????70?96?????,Podophyllum???????
  ????????
• a-Peltatin?b-Peltatin????????????????

54
Podophyllotoxin Derived Clinical Therapeutic
Agents- Etoposide

• Etoposide?Podophyllotoxin???????,??????????,?Podop
  hyllotoxin????????????
• C-1????????Ethylidene glucoside
• C-4?Podophyllotoxin??????
• C-4OCH3 ? OH
• C-4 OH?Etoposide???DNA???????
• Ethylidene glucoside??????Podophyllotoxin???

55
(No Transcript)
56
????-

• ????????????????????????????????(Non-small cell
  lung cancer)????????,?????????????(Non-lymphocytic
  leukemia)??????(Hodgkins disease)????????(Non-Ho
  dgkins lymphoma)???????(Kaposis
  sarcoma)???????(Neuroblastoma)????

57
????-

• ????????,?????
• ??DNA,?????????DNA???,?????????-????(Phase
  specific),??G2??????????G2??S????
• ?????Endonuclease??????DNA???
• ?????????Topoisomerase (II)???
• ????C-4OH???????????,???????????????????
• Etophos?Etoposide?C-4??????,???????????

58
Teniposide

• ??????????????????????????????????(Acute
  lymphoblastic leukemia)
• Teniposide???????????Etoposide????

59
8.5 ???Flavonoids

• ????C6-C3-C6????????,??????(Chromane
  ring)????2?3?4?????????
• ?????Flavones?Flavanones?flavonols?Anthocyanidins?
  Isoflavones?Isoflavanone,Aurone,??????????????Chal
  cone,???????

60
(No Transcript)
61
(No Transcript)
62

• ??????
• ?????????????????????

63
??????????

• ????p-Coumaroyl CoA?3???Malonyl
  CoA???,?????????????,?A???????Chalcone,??B??????Fl
  avanone?,???????????????????????

64
(No Transcript)
65
(No Transcript)
66
(No Transcript)
67
???Rutin

• ???????????????????Hesperidin(???)???????P(Vitamin
  P)??????(Permeability factor)
• ?????????Hesperidin??????????????? (?????????)

68
???Milk thistle

• ??-Silybum marianum (Linné) Gaertn(Asteraceae)????
  ???????
• ??-Silymarin Silybin?Isosilybin?Silydianin?silych
  ristin?Dehydrosilybin?

69
????

• ?????????? ? ?????????? ???????????? ?
  ??????????????
• Silybin???????????,?????DNA?RNA???I?(DNA-dependent
  RNA polymerase I)??????,???????,??????????RNA????
  ?,???????????????????????

70
??-

• ????????????????(Supportive treatment)
• ???????????,??Silymarin?????140mg?

71
8.6 ??Tannins

• ?? -?????????,?????????????
• ?? -
• ???????(Hydrolyzable Tannins),?????(Gallic
  acid)????????(Hexahydroxydiphenic
  acid)?????????????????

72
(No Transcript)
73
????????(Nonhydrolyzable Tannins)??????(Condensed
tannins)

• ????(Proanthocyanidin)???????????,????????????,???
  ???-?????????????(Anthocyanidin)
• ???????????????????????????????2????Flavan-3-ol?,
  ?Catechin(???),?Flavan-3,4-diol?,?leucocyanidin??
  ???????,????????????????Phlobaphanes???????

74
?? -

• ??????????,??????
• ???????????????????
• ????????????????????
• ?K3 Fe(CN)6?NH3????????
• ?????????????,???????1???????
• ??????,????????????

75
??-

• ????????????????,??????????Ellagic
  acid??????"Bloom",???(Phlobaphene)?????"??(Tanner'
  s red)"?
• ?????
• ???????????????
• ?????????????tannate????
• ??????????????????????,?????,?????????
• ??????????

76
???(Astringent)???

• ?????????,????????,??????????????????????

77
?????

• ??????Leucoanthocyanidin????????Oligomeric
  proanthocyanidin??Pycnogenols
• ????(Antioxidant),?????????????????(Free radical
  scavengers)

78
What are Free radicals?

• Singlet oxygen, superoxide anion, hydrogen
  peroxide, hydroperoxide, hydroxide radical,any
  species that contain unpaired electron(s) even
  the element or metal ions (such as Fe2, Cu,)

79
????

• ???(Vitis vinifera Linné)
• ??(Pinnus pinaster Soland.)???????????
• ??(Camellia sinensis)??30
• ????-?????????????????????????????

80
??????Hamamelis Leaf

• ??-Witch Hazel Leaves
• ??-?????????,???(Hamamelis virginiana)?????Hamamel
  is?Hama?????????????,melis????,???????????,???????
  ????????Virginiana??????????,??????Blue Ridge
  Mountain?????????????????????????,????????

81
(No Transcript)
82
??-

• 1. Pyrogallol TanninHamamelitannin(???)?Gallotann
  in?Gallic acid?
• 2. Hamamelose?
• 3. ???2-hexen-1-al (9.7)?acetaldehyde
  (3.2)?a-ionone (3.5)?b-ionone (1.0)?safrole
  (0.2)?

83
??-

• ???Hamamelis water ?Distilled Hamamelis
  extract???1415???????,???????,?????,????????????
  ???????

84
???Nutgall

• ??-Turkey gall?Galla halephenesis?
• ??-????????,Quercus lusitanica?Q.
  infectoria(Fagaceae)?????????(Cynipidae)??,????(Cy
  nips tinctoria)?????????????,?????,?????
• ??-???????????????

85
??-????????????

1. ??????????????,????????????????
2. ??????,???????????,?????????????????
3. ????,???????????????????????,???????(Blue
   gall),??,???
4. ???????,??????,??,??????????????????????,???????,?
   ???????(White gall),??,???

86
(No Transcript)
87
??-

• 1. Pyrogallol Tannin
• (1) Turkish Tannin?5070 Gallotannic
  acid?67?Gallic acid??Glucose????Hexa?Heptagalloy
  l glucose,????Methyl gallate?1,2,3,6-
  Tetragalloylglucose?1,3,4,6-Tetragalloylglucose?
• (2) Gallic acid?
• (3) Ellagic acid?
• 2. ???
• ??-???????Tannin???????????????Tannin??????

88
???Chinense gall?Japanese gall

• ??-???????,???(Rhus chinensis Mill.)??????????????
  ??(Aphididae)??,?????(Schlechtendalia
  chinensis)??????????,?????,?????
• ??-???????????
• ??-???
• ????????
• ????????(??)?

89
??-?Pyrogallol Tannin

1. Chinese-Tannin?7080 Gallotannin?89?Gallic
   acid?????b-Glucose????Octa-?Nonagalloyl
   glucose?????1,2,3,4,6-Penta- galloyl glucose
   ?Methyl gallate?
2. Gallic Acid

90
(No Transcript)
91
????Gallic acid

• ??-???????,????????????
• ??-?3,4,5-??????(3,4,5-Trihydroxybenzoic
  acid),????????
• ??-???????(Bismuth subgallate)?????n-Propyl
  gallate????????,??????????