Kuliah Alkaloid
Kuliah Alkaloid
Kuliah Alkaloid
h ht tm ml l 1
A|ka|o|d
Pendahu|uan
Turourar yarg rergardurg a||a|o|d le|ar
d|gura|ar o|er rarus|a urlu| oeroaga|
|eper|uar sererja| adarya peradaoar
(1000 3V).
Ter dar Epredra d| Cr|ra
Kop| dar cardu d| T|rur Tergar
Ko|a dar K|ra d| daerar Ardes (Arer||a)
Looe||a d| Yurar| elc.
wa|aupur pada Wa|lu |lu yarg d|gura|ar
rarya s|rp||s|a alau a|r reousar dar oe|ur
d||elaru| seryaWa apa yarg oer|as|al
atasan
0u|urya |sl||ar a||a|o|d d|gura|ar |arera
|e|orpo| seryaWa yarg d||era| ler|eo|r
daru|u ada|ar |e|orpo| seryaWa orgar||
yarg oers|lal oasa |erar.
a||a|| = oasa
o|d = reryerupa|
0eWasa |r| d||elaru| oarya| seryaWa
a||a|o|d yarg l|da| oers|lal seoaga| oasa
|erar lap| relra| oar|ar ada yarg oers|lal
asar
8ejarah
Te|ar d|gura|ar urlu| oeroaga| |eper|uar
seperl| ooal perargsarg, r|prol||/sedal|l,
r|rurar, racur d||.
Pergguraar da|ar oerlu| e|slra| a||oro|
(elaro|) d|pe|opor| o|er 0a|er d| Yurar| (00
sr)
0||eroarg|ar |eo|r |arjul o|er lao|o-lao|o
ls|ar. ( a|. loru 3|ra)
3lor| seorarg Apole|er dar| Auslr|a ru|a|
rerdororg pergguraar e|slra|/l|r|lur
da|ar pergooalar 'roderr.
Terdapatnya a|ka|o|d
ururrya dar| lurourar oerourga.
Juga d|leru|ar pada
oa|ler| (p|os|rar|r dar| Pseudororas
aerug|rosa)
jarur (|||opod|r dar| C|av|seps purpurea),
serargga (sa|s|lo|s|r )
8|ola |aul,
rara||a (rus|op|r|d|r dar| oerarg2 Karada)
8|sa lerdapal pada se|urur oarag|ar
lurourar lap| dergar |oserlras| pada
oarag|ar2 lerlerlu
N||ol|r pada daur, K|r|r pada |u||l oalarg,
erel|r pada a|ar,
8|j| leroa|au l|da| rergardurg r||ol|r,
r||ol|r d|leru|ar pada saal o|j| ru|a|
oer|ecaroar.
Ada yarg lerdapal da|ar oerlu| |orp|e|s
dergar seryaWa |a|r ser|rgga oaru o|sa
d|dele|s| sele|ar |orp|e|s lerseoul lerura|.
Terdapalrya a||a|o|d leroesar pada
Arg|osperrae lerulara pada lar|||
Apocyraceae (RauWo|l|a, Calrararlrus)
Ruo|aceae (K|ra, garo|r, |pecac) Rulaceae
Logar|aceae Legur|rosae 3o|araceae
(Alropa, 0alura, N|col|ara) Papaveraceae
(Papaver) Corpos|lae
Pene||t|an a|ka|o|d dar| oarar ooal a|ar
0erosere (1803) rerdapal|ar seryaWa
ser| rurr| ulara a|l|l dar| cardu |asar
yarg d|oer| rara rar|ol|r.
3erlurrer (1805) oerras|| rerdapal|ar
a||a|o|d rurr| perlara dar| cardu yarg
d|oer| rara rorl|r (Vorpreus = 0eWa T|dur
Yurar|)
Pe||el|er dar Caverlou (Fa|u|las Farras|
Par|s) oerras|| rerg|so|as| oarar ooal
perl|rg (3lr||r|r, erel|r, orus|r,p|per|r,
|ole|r, ||r|r, co|||s|r dar |or||r (dar| racur
re|r|oc| yarg d|gura|ar urlu| rerourur
3ocrales)
Kor||r |r| rerupa|ar a||a|o|d perlara yarg
d||ara|ler|sas| (18Z0) dar d|s|rles|s (188)
Kaj|ar K|r|a/a|l|l|las oaru ru|a|
rerper||ral|ar ras|| pada aoad |e XX
(slr||r|r d||so|as| 1819, slru|lur oaru
d||elaru| pasl| larur 191)
0ergar oer|eroargrya le|r|| |so|as|
|roralogral| (1910-ar) dar e|us|das| slru|lur
secara spe|lros|op| (190-ar)
per|eroargar lPTEK a||a|o|d oer|eroarg
pesal.
P Pr ro of f. .D Da ay ya ar r A Ar rb ba ai in n/ /S SE EM ME ES ST T~ ~5 5/ /a al lk ka al lo oi id d. .h ht tm ml l 2
0eWasa |r| le|ar d||era| |eo|r dar| 5000
a||a|o|d
dergar o|oa|l|l|las yarg sargal oeragar.
K|as|l||as|
Para ar|| oerusara urlu| reroer||ar
oalasar dar ||as|l||as| a||a|o|d lap| l|da| ada
yarg oerar2 reruas|ar.
KLA8|F|KA8|
Yarg pa||rg oarya| d|ler|ra ada|ar
||as|l||as| dar| legrauer yarg reroag|
a||a|o|d oerdasar|ar pre|ursor o|os|rles|s
seryaWa |r|.
True a||a|o|d : -rerper||ral|ar oeroaga|
o|oa|l|l|las
-Vergardurg N- releros|||||
-0|o|os|rles|s dar| asar ar|ro
-0|a|ar lerdapal da|ar oerlu| garar dg
asar orgar|| (r|s. K|r|r, alrop|r d||)
Proloa||a|o|d : -8eroerlu| ar|ra sederrara,
N l|da| da|ar oerlu|
||alar releros|||||
-0|o|os|rles|s dar| asar ar|ro, oers|lal
oasa.
-d|seoul juga ar|ra o|o|og|s (r|s: eledr|r,
res|a||r)
Pseudoa||a|o|d : l|da| d|o|os|rles|s dergar
pre|ursor asar ar|ro|
-oers|lal oasa (Kole|r)
8|fat F|s|ka K|m|a A|ka|o|d
0|a|ar ururrya lerdapal da|ar oerlu|
garar.
ururrya oeroerlu| |r|sla| l|da| oeWarra,
alau da|ar oerlu| gararrya oeroerlu|
|r|sla|.
ururya l|da| |arul da|ar a|r dar |arul
da|ar pe|arul orgar||, sedarg|ar oerlu|
gararrya |arul da|ar a|r.
A||a|o|d |ualerrer dar g|||os|da l|da| |arul
da|ar pe|arul orgar|| lap| |arul da|ar a|r
8|fat K|m|a A|ka|o|d
ururrya oers|lal oasa |erar. T|rg|al
|eoasar lerl|rgg| d|oer||ar o|er |e|orpo|
ursur yarg ler||al dergar N yarg oers|lal
seoaga| pero|a| e|e|lror. Ar|ra se|urder,
lers|er a||lal|| , ar|ra aroral||, dar ar|da.
A||a|o|d |ualerrer ra|ar oers|lal seoaga|
asar.
Karera adarya ursur N yarg rudar
lero|s|das| reroerlu| seryaWa r-o|s|d,
|eslao||ar lerl|rgg| d|oer||ar o|er garar
asar |ual dar| a||a|o|d dergar |eoasaar
yarg re|al|l oesar.
0ele|s| a||a|o|d
A||a|o|d |arera o|oa|l|l|lasrya dar slru|lus
||r|arya yarg oeragar reroer||ar
larlargar lerserd|r| oag| ar|| K8A.
0ele|s| :
Cara wa|| :
20 g d|rel|u|s dergar El0l, d|uap|ar,
d|laroar|ar lC| 1, |arular d|p|sar|ar,
d|dele|s| dergar perea|s| Vayer.
Cara K|arg 0oug|as :
3arpe| d|oasa|ar dergar arror|a,
d|e|slra| dergar eler, d|lar|| dergar asar
d|dele|s| dergar perea|s| Vayer.
Cara Cu|veror-F|lzgera|d :
3arpe| segar (2 g), d|polorg ra|us, d|gerus
dergar oarluar pas|r, d|oasar|ar dergar
10 r| ClC|3, d|laroar|ar 10 r| K|orolorr
Arror|a (0.05N), |ap|sar ||orolorr d|sar|rg,
d|laroar|ar 1 r| l2301 2N, d||oco|,
|ap|sar asar d|aro|| dar d|le|s| dergar
peraroarar perea|s| a||a|o|da.
Calalar
Cara-cara d|alas rer||||| |eurgu|ar dar
|e|erarar
T|da| serua a||a|o|d |arul da|ar
eler/||orolorr
T|da| serua yarg () dergar
Vayer/0ragerdorll ada|ar a||a|o|d
oeoerapa jer|s |urar|r, lerpero|d, asar
ar|ro juga () dergar pere|as| a||a|o|d
(rea|s| () pa|su), dar oarya| juga a||a|o|d
yarg regal|l dergar perea|s| d|alas .
3arpe| |er|rg a|ar (-) dergar relode
Cu|veror-F|lzgera|d
|arera l|da| |arul da|ar ||orolorr.
P Pr ro of f. .D Da ay ya ar r A Ar rb ba ai in n/ /S SE EM ME ES ST T~ ~5 5/ /a al lk ka al lo oi id d. .h ht tm ml l 3
urlu| d| |apargar Veloda Cu|veror-
F|lzgera|d re|al|l |eo|r pra|l|s
dar rurg||r ul| d||a|sara|ar.
Perea|s| pergerdap a| : Vayer, wagrer,
3||||oW|lraral d||
Perea|s| Warra a| : 0ragerdorll
Ekstraks|
oeradasar|ar s|lal ||r|a dar l|s||arya
reloda e|slra|s| a||a|o|d |r| sargal
oeragar.
syaralrya :
Ka|au rurg||r l|da| rara|
8|sa rerge|slra| dergar oa|| dergar
cepal.
Veroer||ar per|sarar perdaru|uar
(lra|s|oras|) yarg oa||
T|da| rerusa| seryaWa yarg a|ar
d||so|as|
Ekstraks|
8|asarya d|gura|ar pe|arul po|ar (Ve0l
alau El0l)
Ka|au seryaWa oe|ur d||era| o|asarya
d|gura|ar reloda raseras| alau
Ka|au a||a|o|drya slao|| o|sa juga d||a|u|ar
dergar rerggura|ar 3o|r|el
Fraks|onas|
urlu| reryederrara|ar carpurar
o|asarya d||a|u|ar lra|s|oras|. (oerdasar|ar
|easarar, |e|arular, |epo|arar d||.)
|so|as|
Per|sarar dergar |roralogral|.
Perurr|ar dergar |r|sla||sas|/peroualar
lururar/|roralogral| d||
C Co on nt to o
Heksan
Ekstrak heksan
(cek
Mar
MeOH
Pekatkan
Partisi EtoAc-2% Asam Tartrat
EtOAc (fraksi netral/basa sgt
lemah)
2% Asam Tartrat
Basakan
(NH3/Na2CO3)
Ekstrak dengan
Alkaloid basa
lemah
Larutan air basa
(boleh jadi
mengandung
Sampel
P Pr ro of f. .D Da ay ya ar r A Ar rb ba ai in n/ /S SE EM ME ES ST T~ ~5 5/ /a al lk ka al lo oi id d. .h ht tm ml l 4
Perurr|ar
Kr|sla||sas| |argsurg
Kr|sla||sas|-der|val|sas|
0rad|erl pl exlracl|or
Kroralogral| (serapar, parl|s|)
F||lras| (sepradex)
Kara|ler|sas| / E|us|das| 3lru|lur
TL
sp (3eryaWa |a|ra|, sudul pular opl||)
uv, (seryaWa Aroral||/||alar |oryugas|)
lR (ul| gugus lurgs|)
V3 (8V)
1l RVl (ul| pos|s| dar ||alar l)
13C RVl (ul| pos|s| dar ||alar C)
8eoerapa pe|arul ul| s|sl|r KLT
ClC|3/Ve0l (9:1; 19:1)
ClC|3/Tr|el||ar|r (9:1)
EloAc
El0Ac - Ve0l (19:1), (9:1), (1:1)
Perggo|orgar a||a|o|d oerdasar|ar precursor
8|os|rles|s a||a|o|d
8|os|rles|s oeoerapa pre|ursor relaoo||l se|urder dar relaoo||l pr|rer ulara
A|ka|o|d turunan L|s|n
8eoerapa A||a|o|d lururar ||s|r
Pur|ca graralur : lsope||el|er|r, pe||el|er|r, pseudope||el|er|r.
A||a|o|d P|per sp.: P|per|r.
Tr|lo||ur pralerse : 3|alrar|r ('sa||val|or laclor pada lerra|.
Cyl|sus |aourrur : cyl|s|r (racur lrd lerra|)
P Pr ro of f. .D Da ay ya ar r A Ar rb ba ai in n/ /S SE EM ME ES ST T~ ~5 5/ /a al lk ka al lo oi id d. .h ht tm ml l 5
|os|ntesa A|ka|o|d turunan ||s|n
A||a|o|d
lururar po||aselal
|os|ntesa A|ka|o|d Turunan Po||asetat (kon||n}
8eoerapa a|a|o|d lururar po||aselal
Pinus sp (P|naceae} : p|n|d|n
Conium maculatum : kon||n, N-met||kon||n, konh|dr|n
Carica papaya : karpa|n,
8emut 3olenopsis saevisima : 8o|enops|n A dan |soso|enops|n A
Kumbang Coccinella septempunctata :Koks|ne|||n
Elaeocarpus sp : e|a|okarp|n, e|a|okarp|d|n
P Pr ro of f. .D Da ay ya ar r A Ar rb ba ai in n/ /S SE EM ME ES ST T~ ~5 5/ /a al lk ka al lo oi id d. .h ht tm ml l 6
Turunan Po||asetat
|os|ntesa asam antra|n||at
P Pr ro of f. .D Da ay ya ar r A Ar rb ba ai in n/ /S SE EM ME ES ST T~ ~5 5/ /a al lk ka al lo oi id d. .h ht tm ml l 7
eberapa a|ka|o|d turunan asam antran||at
Fen||aa|an|n-t|ros|n
P Pr ro of f. .D Da ay ya ar r A Ar rb ba ai in n/ /S SE EM ME ES ST T~ ~5 5/ /a al lk ka al lo oi id d. .h ht tm ml l 8
8eoerapa A||a|o|da lururar PA dar TY
Lopoprora W||||ars|| : Ves|a||r
Epredra sp : Eledr|r
Vargar|lar|a |rd|ca : l|||o|r|s|r, se|ur|r|re, P|grer : re|ar|r
Papaver sorr|lerur : papaver|r, rorl|r
Varus|a : adrera||r, roradrera||r, 0opa
Crordroderdror sp : Tuoocurar|re
Alkaloid
1. Meskalin
2. Adrenalin
3. Efedrin
4. Papaverin
5. Tubokurarin
6. Kodein
7. Morfin
8.Kolkisin
9. Emetin
Asal
1. Lopophora williamsii
2. Manusia/hewan
3. Ephedra sp
4. Papaver somniferun
5. Chondrodendron sp
6. Papaver somniferum
7. Papaver somniferum
8. Coilchicum autumnale
9. Cephaelis ipecacuanha
Kasiat
1. Halusinogen
2. Neurotransmitter
3. Simfatomimetik
4. Vasodilator
5. Relaksasi otot rangka
6. Antitussif
7. Narkotik-analgetik
8. Gout suppression
9. antiemetik
P Pr ro of f. .D Da ay ya ar r A Ar rb ba ai in n/ /S SE EM ME ES ST T~ ~5 5/ /a al lk ka al lo oi id d. .h ht tm ml l 9
eberapa a|ka|o|d sederhana turunan tryptophan
P Pr ro of f. .D Da ay ya ar r A Ar rb ba ai in n/ /S SE EM ME ES ST T~ ~5 5/ /a al lk ka al lo oi id d. .h ht tm ml l 10
A A| || |a a| |o o| |d d | |r rd do o| | r ro or ro ol le er rp pe er ro o| |d da a| |: :
A A| || |a a| |o o| |d d A As sa a| | a a| |l l| |l l| |l la as s l la ar rr ra a| |o o| |o og g| |s s
1 1. .A Aj jr ra a| || |c c| |r re e C Ca al lr ra ar ra ar rl lr ru us s r ro os se eu us s l ly yp po ol le er rs s| |v ve e
2 2. .A Aj jr ra a| || |r r R Ru uW Wo o| |l l| |a a s sp p A Ar rl l| |a ar rr ry yl lr rr r| |c c
3 3. .C Ca ar rp pl lo ol lr re ec c| |r re e C Ca ar rp pl lo ol lr re ec ca a a ac cu ur r| |r ra al la a A Ar rl l| |c ca ar rc ce er r
1 1. .0 0e es se er rp p| |d d| |r re e R Ra au uW Wo o| |l l| |a a c ca ar re es sc ce er rs s l ly yp po ol le er rs s| |v ve es s
5 5. .l lo oo og ga a| |r re e T Ta ao oe er rr ra ar rl lr re e | |o oo og ga a P Ps sy yc cr ro ol lo or r| |r re el l| |c c
. .L Le eu ur ro oc cr ry ys sl l| |r re e C Ca al lr ra ar ra ar rl lr ru us s r ro os se eu us s A Ar rl l| |c ca ar rc ce er r
Z Z. . 0 0u u| |r r| |d d| |r re e R Re er r| |j ja a s sp p C Ca ar rd d| |a ac c d de ep pp pr re es ss sa ar rl l
8 8. . R Re es se er rp p| |r r R Ra au uW Wo o| |l l| |a a v vo or r| |l lo or r| |a a r ry yp po ol le er rs s| |v ve e
9 9. . 3 3l lr ry yc cr rr r| |r re e 3 3l lr ry yc cr rr ro os s r ru ux x l lo or r| |c ca a C CN N3 3 d de ep pr re es ss sa ar rl l
1 10 0. .v v| |r rc ca a| |e eu uc co oo o| |a as sl l| |r re e C Ca al lr ra ar ra ar rl lr ru us s r ro os se eu us s A Ar rl l| |c ca ar rc ce er r
1 11 1. .v v| |r rc ca ar r| |r re e v v| |r rc ca a r ra aj jo or r l ly yp po ol le er rs s| |v ve es s
Alkaloid indol monoterpenoid
P Pr ro of f. .D Da ay ya ar r A Ar rb ba ai in n/ /S SE EM ME ES ST T~ ~5 5/ /a al lk ka al lo oi id d. .h ht tm ml l 11
P Pr ro of f. .D Da ay ya ar r A Ar rb ba ai in n/ /S SE EM ME ES ST T~ ~5 5/ /a al lk ka al lo oi id d. .h ht tm ml l 12
a|kao|da catharantus
le|ar oerras|| d||derl|l||as| |eo|r dar| 90 jer|s
v|rca|eucoo|asl|re (vL8), R = Cl3 (1 g/lor)
Leurocrysl|re (vCR), R = Cl0 (20 rg/lor)
A|ka|o|d Co|ongan s|sa
A|ka|o|d pur|n
A||a|o|d 0o|. s|sa
Vacrocyc||c pepl|de a||a|o|ds
Vusrroors pepl|de a||a|o|ds
3ax|lo|s|r