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23 Biogynth.ticPrthxay! > Iropre& R!1. rtrd T..!Eroid! Seondaly neubolites with i$prrc e thc b6ic uils md wiih m hpiical fmula (Cillji e boadly classificd 6 t rFnd or tdF@idg Moy natunt p@dwrs tub 6 terFrcr steoids, ctc- @ e fod.d by difidt cmbimlion of iepEre uiis in he.d- T.rF@i& play a vital rcI. in thc lirs ofhmy orgaisG by cxertine hehbolic cont ol .d by m.diariq in int6- sld int r-!p.ci6 irardion!, such s poliDt@ ald d.fcG i, plets. Teipenoids re biosynthsized in i& difeMr pathwys, bded on th Min buildirg bl@ts, isp.nr.ryt diphosphar. Cpr) (sch€Dcz,t) &d din Oyt attyt diph6Dlt i t!. Dcrhyldrduirotphospba& (MEp) p{hwy or I n6xy-D-xytutc (DOX) ?s 26
Flhsy ir th. chloDpLst fo@ IPP for ooto- ed diGrpemrds, .nd ih. ncldotic &id OrvA) pd{rw.y in th€ cylosl, prdus I}P for sesquil€rpooid. Pu! A., .t 4/.,20011 A-_^-\-\- E *.,1 S.h@-2.r: Biost bsb ofr.rpcmids ir pt.&tr slowirg the maslodc &id (MVA) (A) dd lnoxy,Drrlul@ (DOX) (B) pothmys fo. rh. prcduclion of tpp. > Md.lo!.t Prthrry I ""-l.z'." i.-; EI Th. qtac in pl€rts is oNat d io ..dyt{oA aad @nd65ed *ith mI[a uit of 4.tyl-CoA 10 8.nerar€ a@toa.ctyl-CoA (Sch.m€-2.l). Th. addnion of. third ac4yl-CoA yiclds (,t!3,hyd.oxy-l-n.ibylstutdyt-CoA GrMccoA), *.rich is $t6.qEnily Gdu..d by dr. €.zyn HMc-CoA Eduq4sc io (n)-Devalonic acid (MvA) fDubey, v. S., ./ at., 20031. MvA fien uodcrgG . ei6 of ptssdoryrarioG, tN of CO, ed imry&i. tl a-r^_i_ 9" " ^..^"-l-; 2l
Page 1 and 2: Irohtion rnd StructE!'e Elrcidrdotr
Page 3 and 4: Th.si! C€dficate Ttir b to oltry
Page 5 and 6: ta-----i.at--*Lt*-tt-A rt-rcr-#a.ll
Page 7 and 8: 3.0.I.ibtior ud ChDclelation of Sso
Page 9 and 10: 32313 t.231.4 3,23j5 3,23.4,6 3,23!
Page 11 and 12: FiRt &d fom6l I oFq bJ' sim.6t Snd
Page 13 and 14: I.tFd&dor of Ph. D. R.6EL Sctlohr I
Page 15 and 16: Thc ct]@tedarior ad stu.nr! .lucidd
Page 17 and 18: 2) Klom Cl.dd.n6lt?. Funrodit r!.n.
Page 19 and 20: S.ction-B A higbly dliv. ed sel4til
Page 21 and 22: GENER.AL INTRODUCTION
Page 23 and 24: ag6ts [&on' 1992; VeL, D. J.H-,4 aL
Page 25 and 26: fic. 1.1 MediciBlly imPodrnt Mlural
Page 27 and 28: cfcds. chin* tiditio!.I mdiciB mill
Page 29 and 30: iui@ for wic.s plsvid.d by rft@dirc
Page 31 and 32: @nrodds, including el.ven n w aad a
Page 33 and 34: 2.0 INTRODUCTION z.l 2.1.1 Itrloduc
Page 35 and 36: Ti6pda baeigi F@ has b@ u$d 6 4 4ti
Page 37 and 38: .l. Ird@si!: bFtlvaq ed.{tli, putiq
Page 39 and 40: 2,2.0 secondaryMet bolites of Tinos
Page 41 and 42: :i I a rl t 3 a' t I ax '^z :t F 9
Page 43 and 44: 2 i c I F 6 c B { t E 6' "o I b E s
Page 45 and 46: lt 1|'
Page 47: -48 r1l .b 'i-{tr 62 63 64 ADrL.prr
Page 51 and 52: T I (3P4 c"i I l'+P4 I l-- ]_".*"'
Page 53 and 54: A c'19 mehyl sltift to C-5 in ?E (r
Page 55 and 56: CHAPTER.3 R.ESUIL]IS AND DISCUSSION
Page 57 and 58: Nays were also pdfom.d on najd coin
Page 59 and 60: CoDpound I ha rhe dol@ule fomuro Cl
Page 61 and 62: s d.dE d rt r c.l3 (& 82.0) 5nd C-l
Page 63 and 64: tr'\ ) c6Hi -8 )a coHto" r|.. 3.4!
Page 65 and 66: !.1.1.12 2-lydnryhonP.i@l& c (2) IU
Page 67 and 68: 1.65 (H-l lb) sho*.d CosY creePct}l
Page 69 and 70: f + I t ri \\ Sc!@e3} MN tugncltiti
Page 71 and 72: 3.1.1.1, IUPAC: (2r,5r,6X,8S,9S,1 O
Page 73 and 74: al rc 140.7 ws due ro c-3 ol.finic
Page 75 and 76: T.brF3-3: '3C- &d 'H-NMR'ch@i.d sbi
Page 77 and 78: $-nMrumr.d dbonyl sysrstr. Thc 'H-N
Page 79 and 80: 6 (& 4.39) snd C-8 (dH 33E) nldhiE
Page 81 and 82: T.bF!,a: I'c'- dd I H-NMR' ch.oical
Page 83 and 84: IL, ru), 3.80 (d4 .r6,a 6!= I 1.8 H
Page 85 and 86: The st rcochedsrry in conpoud s B d
Page 87 and 88: a.r,l.l.6 Ti!@rnDoridc D (6) IUPAC:
Page 89 and 90: Trblr3J: 't^' ald 'H"NMR' chdic.l l
Page 91 and 92: (orqlrp, Hl lb) *a ai8tr.d to rh. C
Page 93 and 94: Thc HMBC s!6um of cmpoud 7 supPoncd
Page 95 and 96: J.l,l.l.8 Bonp.l6id. r (E) IUPAC: M
Page 97 and 98: .tC{e.I a{naterl wbjle M620. H-5. H
Page 99 and 100:
t 1.1.1,9 IUFACT Mlrhyl (21,6s.54x,
Page 101 and 102:
T.btF!J| rrc'- &d 'H-1,\4R'chmiol 3
Page 103 and 104:
.dboro. ft. do*nfi€ld signals a1
Page 105 and 106:
and 2D spetFl .lrL with th€ Epork
Page 107 and 108:
speiru, th. preton sigtrd .t ,x l2l
Page 109 and 110:
-*v*L Puilicat on of ii&tion Bwl (5
Page 111 and 112:
d6tu .n Th. h! Eoidi.. h lh. rt$.dd
Page 113 and 114:
3.12.2 4.12,2.1 Krown Col3liluera!
Page 115 and 116:
J.IJ,2J rv-rodtbomucif.ri!.09) Comp
Page 117 and 118:
3.1.2.2,5 M.s!ododrc(21) compound 2
Page 119 and 120:
signars for rwo doubr€ doubters a
Page 121 and 122:
3.1.3.1.4 Cylidi!.(25) Conpoutrd 25
Page 123 and 124:
J.l.a.l3 Cy.h.!€L!ol(2t) Conlound
Page 125 and 126:
CHAP:TER. 3 E)GERIMENTAI
Page 127 and 128:
3.2.1.2J Collm chnbltogbpny vs Frfo
Page 129 and 130:
Lol.rio! ol Pon constit!.llt fmd t-
Page 131 and 132:
3 .? a a 3 t : t t ! .4 ? I F € E
Page 133 and 134:
f, -" 3i ii IF ls tt t; ! 3 I iI !E
Page 135 and 136:
S.[cne!.|rr Isolation of compounds
Page 137 and 138:
t-Hydotybonpct6irlG c o) IUPAC, (2x
Page 139 and 140:
ldlD'r -35-d (c 0.056, cHroH) IR (K
Page 141 and 142:
tdlD I'r +135.1./ (. 0.0?a, Cs3otD
Page 143 and 144:
FA&MS Cvc) ,,/r: 519 [M - tt]- EFMS
Page 145 and 146:
313.,1.0 sub-6*tion Fry2 (900 ms) f
Page 147 and 148:
'&Nre (cDclr, 300 MH2) ,, 2.21 (lH,
Page 149 and 150:
sa Hib), 3.80 0 H, dd J6! trr= I l-
Page 151 and 152:
P€rcenb8. yl.ld: l4,Ox l0' Strr.:
Page 153 and 154:
'H-NMR (CDrOD, l0O MH') t: 1.73 (lH
Page 155 and 156:
atrord @mDoDd 16 (1.4 6& 2.1 x l0r%
Page 157 and 158:
323.4$.2 (zlN-FomyL0on.b. (U-z) 'H-
Page 159 and 160:
Elryana W @eorD r-. m (log r): 310
Page 161 and 162:
Itc.Nlm (cDct3, l m mL,) d: t 46.0
Page 163 and 164:
106). InErpidation of spetd .rd phy
Page 165 and 166:
AIMS Cvc) a'zi 242 tM- Hl EI-MS r'l
Page 167 and 168:
prcduced conpobd 2E (13.6 h8,8.5 cn
Page 169 and 170:
CFIAPTER. 4 BIOLOGICAI ASSAYS
Page 171 and 172:
2002; Yotodq 'r., .t al, 2OOlt Csvi
Page 173 and 174:
I oourobodubrorr rctivir' dilb rhol
Page 175 and 176:
q@ us€d s d.ndards for II3 rd !C'
Page 177 and 178:
. Chitri.lw, G.; Jai., Al sip6hin l
Page 179 and 180:
. M4.iakd, P. N; Joly, C I iN@!@4s
Page 181 and 182:
. Sk4 Y. C.; ChoS; Y. B.: Aln d, A
Page 183 and 184:
Chrpt r 5 Applic.tion of NucLophili
Page 185 and 186:
MuuSe in 2o0l md steSlich in 1969 E
Page 187 and 188:
5.13 Cbirrl Nucleophilic Acyl Trrff
Page 189 and 190:
'nr€ chihl vc$ion of DMAP catalys
Page 191 and 192:
Tl@tuE, ii E NuD.d thal a gcrad 6Pi
Page 193 and 194:
11! R- h.ix, (-R-qqjrcct$r !1&R'p q
Page 195 and 196:
Recr)6t llialio! of r19. (4E% ec) n
Page 197 and 198:
|he cidut elvc sisral (CDCL), whil.
Page 199 and 200:
i3.r.2,4 At wEi. Srnth.s6 Sy I6i. o
Page 201 and 202:
coniimB stirins bcf@ t!'@ling tl -7
Page 203 and 204:
To a $lurion of KHMDS in THF (1.2
Page 205 and 206:
yeuow sorid. |E-NMR (400 MIIZ, CDCb
Page 207 and 208:
visoE liquid. wde obhined. fte cry3
Page 209 and 210:
A elution of €ialyst 93 (1.5 ns,
Page 211 and 212:
5.6 GLOSSARY . 'I|-NMR SlstrD: A on
Page 213 and 214:
Elcrntr lDp.ct Ma Spetnu (EI-MS): A
Page 215 and 216:
Org.non.t Uic: Orgdic ohpoo!& onlai
Page 217 and 218:
EI Er-i,{s- Ert|r FAB Fis. H HMBC c
Page 219 and 220:
N ROESY RP RT SN -siE rot fng t@ Ot
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