全 文 :2016
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Vol41,No.6 March,2016
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!ÆÇ 1, NÈ 1, ¶À 2, 3É 2, )ÊË 1 (1. V£WZXZY `a0|WZY z]^_ ~z1Õ 2°34£bcd¼ ,` a 100050; 2. 5677Xk¡¢£¤ £b8³9:»k«]^äVv ®z³9»Ý]^Vv , 5 350002) [ lm ]
j¢Þß Ganodermatheaecolum Lkd 。 j¢Þß²Êpq?wF 、ODS¨ PreHPLC öKL() Z_ , @òzLúVv_=<^ 。 j¢Þß=r
15
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(7),3β,7β8·Ô11,15,23LÔß8,168à26]à³(8),ganolucidicacidB(9),ganolucidateF(10),Þ
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C2à³(11),Þß]ζ(12),Þß]AP3(13),Þß]Bà³(14),ÞßÊB(15)。_=1~15:ò!]ñX1 =r 。 [ nop ] Þß ; j¢Þß ; Lkd TriterpenoidsfromGanodermatheaecolum LIULiying1,KANGJie1,WUChanghui2,LIYe2,CHENRuoyun1 (1.StateKeyLaboratoryofBioactiveSubstanceandFunctionofNaturalMedicines,InstituteofMateria Medica,ChineseAcademyofMedicalSciencesandPekingUnionMedicalColege,Beijing100050,China; 2.NationalEdibleFungiprocesingTechnologicalResearchSubCenter,MedicinalFungiCultivationandDeepProcesingofNational Local,JointEngineeringResearchCenter,FujianXianzhilouBiologicalScienceandTechnologyCo.,Ltd.,Fuzhou350002,China) [Abstract] FifteenlanostanetriterpenoidswereisolatedfromtheethanolextractofGanodermatheaecolumbymeansofpreparative HPLC,columnchromatographyoversilicagel,ODSandwereidentifiedaslucidoneC(1),lucidoneD(2),7oxoganodericacidZ2 (3),7oxoganodericacidZ(4),ganoderenicacidH(5),ganoderenicacidB(6),3β,7βdihydroyl11,15,23trioxolanost8,16dien 26oicacid(7),3β,7βdihydroyl11,15,23trioxolanost8,16dien26oicacidmethylester(8),ganolucidicacidB(9),ganolucidate F(10),methylganoderateC2(11),ganodericacidζ(12),ganodericacidAP3(13),methylganoderateB(14),andganoderolB(15) Compounds115wereisolatedfromthisspecieforthefirsttime [Keywords] Ganoderma;Ganodermatheaecolum;triterpenoids doi:10.4268/cjcmm20160617 3%ÞßX1B 98 ? ,《 %,m
》2015
y
(VeÞßÔÐ?òß Ganodermalucidum(Ley ssexFr.)Karst. e¸ß GranodermasinenseZhaoXu etZhang 9±3 。 j¢Þß Gtheaecolum ò Þß&ÞßX1 , ÖüÆ°H9 , 4shòÞßX i , ?5-^Þ , ªNEù 2014 ymÜú[ÉB ·5701· 2016 y 3 z à 41 áà 6 } Vol41,No.6 March,2016 ôj¢Þß_^D, , j¢Þß_ ¨,hi:bBòk. 。 ëP&
Ì{ , ÞßÖü_ò>Åd 、 Lkd 、 ° ºd 、 {d 、 Ñ ´ 、 >ü 、 Ô]d_= , DB e/0 、 %% 、 et_ 、 eÎÏhi ; Síh i ; ÐÑVÊhi ; e¢& 、 ±ùÄ1hiö 。 Þß Lkd_=B±ù3+- [12]、 e HIV1 ¢& e HIV1 Ñ Ó [34]、 ±ù/0ÄÅ°± [5] ö hi 。 N(î}j¢Þß²Êpqnú° §¨ , $ÊKÊ1XDBÃÑ T] ÒÓ±ù , ² 100mg·L-1 O , ±ù¬Ýr 88%, ²Êpqnúõâ_
, = rú 5 &Lkd_= ,5 w¶_= , , §¨<Äãÿ$ 6 _= DL |zÅ3 æç HL7702 %ÄÅDB[vh i [6]。 N^0Ìk.j¢Þß²Êpqb ?¹W 50% ²Êß±1X¨ 70% ²Êß±1X =r 15 Lkd_= , _Vvò$ß7 C(1), $ß7 D(2),7 Ô Þß] Z2(3),7Ô Þß] Z(4), Þßà] H(5), Þßà] B(6),3β, 7β8·Ô11,15,23LÔß8,168à26 ] (7),3β,7β8·Ô11,15,23LÔß8, 16 8à 26 ]à³ (8),ganolucidicacidB(9), ganolucidateF(10), Þß] C2à³(11),Þß] ζ (12), Þß] AP3(13),Þß]Bà³(14),ÞßÊ B(15)。 _= 1~15 :ò!]ñX1$ =r 。 1 ʸ VNS600,Bruker400,BrukerAV500 åçatÁ uv NMR L ;Agilent1100 õT LC/MSDTrapSL ¢´iÁuv ESIMS;Agilent ¢²KLÁ , YMCC18(20mm×250mm,5μm)KLN;LC3000 $ïKLÁ ; Ò²NKLwF RP18(50μm)ò YMC DE°Æ ; pòKLwF GF254NKLwF (200~300 í ) òQH·_gj°Æ ; MÅEF SephadexLH20 ò GEPharmacia DE°Æ ; ³i¥ 1:òZeKLZ 。 j¢Þß° 2012 y 7 zµ°H9)AÙ4 , 7 $%&%X°
³!:Q
Vvòj¢ Þß Gtheaecolum, ËÌBN (NoS2421) ý° $%A&%,
³BN¸ 。 2 pq 20kg j¢Þß3§Ç~ , i 95% ²Ê ï®pq , µïËÖl9 , =raH 1kg。 aH? D101 ?¹W , ²Ê ªÂß±~=r 50% ²Ê 1 360g,70% ²Ê1 110g。50% ²Ê1@ òwFNKL , µi»H àÊ (100∶1~1∶ 1) ß± , =r FrsA~J a 10 1 。 $ FrB 1 (10g) ?wFNKL , iÙö ®7 (9∶1~ 1∶1) ß± ,Frs1~25 a 25 ® 。FrB8 ?wF NKL , iÙö ®7ö (4∶1) ß± , =r_= 2(45mg)。FrB9 ?wFNKL , iÙö ®7 ö (7∶3) ß± , =r_= 7(25mg),FrB25 ? wFNKL , iÙö ®7ö (6∶4) ß± , =r_ = 8(10mg)。FrC 1 (35g) ?wFNKL , i Ùö ®7 (9∶1~1∶1) ß± ,Frs1~36 a 36 ® 。FrC5 ?wFNKL , iÙö ®7ö (9∶1) ß± , =r_= 1(4mg),5(56mg),FrC9 ?wFNKL , iÙö ®7ö (4∶1) ß± , =r _= 11(3mg),9(2mg),10(5mg),FrC21 ? wFNKL , iÙö ®7ö (6∶4) ß± , =r_ = 6(2mg),13(15mg)。FrD 1 (84g) ?w FNKL , i»H àÊ (30∶1~1∶1) ß± , Frs1~55 a 55 ® 。FrD11 ?wFNKL , iÙö ®7ö (2∶1) ß± , =r_= 14(1 mg),FrD32 ?wFNKL , i»H àÊö (9∶ 1) ß± , =r_= 12(2mg)。70% ²Ê1@ò wFNKL , i»H àÊ (20∶1~1∶1) ß ± , =r FrsA~G a 10 1 。 $ FrA 1 (21g) ?wFNKL , i»H àÊ (10∶1~1∶ 1) ß± ,Frs1~10 a 10 ® 。FrA2 ?wFN KL , i»H àÊö (10∶1) ß± , =r_= 3 (135mg),FrA8 ?wFNKL , i»H àÊö (7∶3) ß± , =r_= 4(210mg),FrE 1 (15 g) ?wFNKL , i»H àÊ (7∶3~1∶1) ß ± ,Frs1~8 a 8 ® 。FrE7 ?wFNKL , i »H àÊö (6∶4) ß± , =r_= 15(5mg)。 3 <^Vv _= 1 Kxv§w 。ESIMSm/z 4052[M+H]+。1HNMR(pyridined5,600MHz)δ: 105(3H,s,H18),109(3H,s,H19),127(3H,s, H29),149(3H,s,H30),157(3H,s,H28),208 (3H,s,H21),350(1H,dd,J=48,66Hz,H3), ·6701· ûóö : j¢Þß$Lkd
496(1H,m,H7),532(1H,dd,J=12,78Hz,H 15);13CNMR(pyridined5,150MHz)Ü1。b$ =.^Þ [7] k. 3β,7β,15αtrihydroxy4,4, 14αtrimethyl11,20dioxo5αpregn8ene[÷,IV v_= 1 ò$ß7 C(lucidoneC)。 Ü 1 _= 1~8 13CNMR =. Table1 13CNMRdataofcompounds18 No 1 2 3 4 5 6 7 8 1 354 336 339 348 361 356 347 347 2 288 274 275 274 344 287 276 276 3 775 775 776 779 770 777 783 783 4 391 391 388 389 460 395 387 387 5 499 510 501 498 486 501 497 497 6 290 362 189 366 369 284 260 260 7 6931990202219911999 667 672 672 8 15991463150613891478159115811581 9 14191517151816491521142814201420 10 393 406 398 397 399 394 391 391 11 199019842023 2361995198119821982 12 515 482 516 301 491 498 444 444 13 475 440 473 449 494 466 516 516 14 548 565 489 477 572 583 587 587 15 7242056 321 3192074215121102110 16 307 348 273 287 374 38712341234 17 567 528 489 489 514 50218891889 18 191 179 168 158 180 193 313 313 19 198 178 175 183 181 187 185 185 20 20762054 360 36215381538 283 283 21 311 312 183 186 214 211 209 209 22 - - 345 34712571254 493 493 23 - - 257 2581992197220622062 24 - - 14501455 413 485 454 454 25 - - 12701266 285 356 347 347 26 - - 172917291812180017981798 27 - - 120 120 164 179 169 169 28 288 279 278 250 284 253 282 282 29 166 155 154 274 224 166 156 156 30 204 219 258 153 181 288 329 329 OMe - - - - - - - 520 _= 2 ËÓKxv§w 。ESIMSm/z 4012[M+H]+。1HNMR(CDCl3,500MHz)δ: 073(3H,s,H18),088(3H,s,H19),102(3H,s, H29),126(3H,s,H30),158(3H,s,H28),219 (3H,s,H21),305(1H,d,J=160Hz,H12α), 277(1H,d,J=160Hz,H12β),334(1H,t,J= 175,175Hz,H17),325(1H,dd,J=50,200 Hz,H3);13CNMR(CDCl3,125MHz)Ü1。ìb =.^Þ [8] k. 3βhydroxy4,4,14αtrimeth yl7,11,15,20tetraoxo5αpregn8ene÷,IVv_ = 2 ò$ß7 D(lucidoneD)。 _= 3 K§w ( àÊ )。ESIMSm/z 5292[M-H]-。1HNMR(CDCl3,400MHz)δ:080 (3H,s,H18),087(3H,s,H29),092(3H,d,J= 64Hz,H21),100(3H,s,H28),116(3H,s,H 30),129(3H,s,H19),182(3H,s,H27),327 (1H,dd,J=52,112Hz,H3);13CNMR(CDCl3, 100MHz) Ü 1。 @òzL=.`^Þ [8] =., IVvñ_=ò 7oxoganoderic acidZ2。 _= 4 K § w ( à Ê )。ESIMS m/z5292[M-H]-。1HNMR(CDCl3,400MHz)δ: 065(3H,s,H18),088(3H,s,H29),091(3H,s, H28),094(3H,d,J=56Hz,H21),099(3H,s, H30),117(3H,s,H19),183(3H,s,H27),328 (1H,dd,J=44,116Hz,H3);13CNMR(CDCl3, 100MHz) Ü 1。 @òzL=.`^Þ [9] =., Vvñ_=ò 7oxoganodericacidZ。 _= 5 Kxv§w 。ESIMSm/z 5113[M-H]-。1HNMR(CDCl3,500MHz)δ:328 (1H,dd,J=50,105Hz,H3),315(1H,dd,J= 70Hz,H25),214(3H,s,H21),155(3H,s,H 30),125(3H,s,H19),120(3H,d,J=70Hz,H 27),104(3H,s,H28),089(3H,s,H29),071 (3H,s,H18);13CNMR(CDCl3,125MHz)Ü 1。 ìb=.^Þ [10] k. ganoderenicacidH [ ÷ , IVv_= 5 òÞßà] H。 _= 6 K 。ESIMSm/z5153[M+ H]+。1HNMR(CDC13,600MHz)δ:106(3H,s,H 18),109(3H,s,H29),125(3H,s,H30),138 (3H,d,J=72Hz,H27),141(3H,s,H19),146 (3H,s,H28),226(3H,s,H21),349(1H,dd,J= 59,102Hz,H3),484(1H,dd,J=87,87Hz,H 7),632(1H,s,H22);13CNMR(CDC13,150MHz) Ü 1。 ^Þ [11] k.=.[÷ , IVv_= 6 ò ganoderenicacidB =.²z 。 _= 7 ¹ËK ( àÊ )。ESIMSm/z 5153[M+H]+。1HNMR(CDCl3,400MHz)δ: 084(3H,s,H29),101(3H,s,H28),110(3H,d, J=68Hz,H21),118(3H,s,H19),120(3H,d, ·7701· 2016 y 3 z à 41 áà 6 } Vol41,No.6 March,2016 J=64Hz,H27),121(3H,s,H18),152(3H,s, H30),322(1H,dd,J=56,108Hz,H3),478 (1H,dd,J=99,77Hz,H7),573(1H,s,H 16);13CNMR(CDCl3,100MHz)Ü1。@òzL =.`^Þ [12] =., Vvñ_=ò 3β,7βdihydroxy11,15,23trioxolanost8,16dien 26oicacid。 _= 8 K§w ( àÊ )。ESIMSm/z 5273[M-H]-。1HNMR(CDCl3,500MHz)δ:084 (3H,s),102(3H,s),110(3H,d,J=72Hz), 119(3H,s),118(3H,d,J=64Hz),121(3H, s),150(3H,s),320(1H,dd,J=56,110Hz), 364(3H,s),478(1H,dd,J=96,80Hz),573 (1H,s)。13CNMR(CDCl3,125MHz)=.Ü 1。 ² 1HNMR ëú³àÔv< δ364(3H,s);13C
NMR
ëδ520tàÔv<。@òzL=. `^Þ [12] =., Vvñ_=ò 3β, 7βdihydroxy11,15,23trioxolanost8,16dien26oic acidmethylester。 _= 9 K§w ( àÊ )。ESIMSm/z 5013[M-H]-。1HNMR(pyridined5,600MHz)δ: 095(3H,d,J=60Hz,H21),097(3H,s,H29), 109(3H,s,H18),134(3H,d,J=72Hz,H27), 136(3H,s,H30),147(3H,s,H19),184(3H,s, H28),351(1H,dd,J=48,66Hz,H3),464 (1H,dd,J=60,36Hz,H15);13CNMR(pyridine d5,150MHz)δ:2083(C23),1973(C11),1761 (C26),1636(C8),1388(C9),769(C3),710 (C15),531(C14),517(C12),513(C5),489 (C22),481(C17),464(C13),460(C24), 387(C4),382(C16),373(C10),348(C25), 342(C1),320(C20),298(C7),279(C2), 279(C30),187(C21),185(C28),184(C 19),169(C6),167(C27),161(C18),157(C 29)。 @òzL=.`^Þ [13] =., Vvñ_=ò ganolucidicacidB。 _= 10 K§w ( àÊ )。ESIMSm/z 5013[M-H]-。1HNMR(pyridined5,500MHz)δ: 093(3H,s,H18),109(3H,s,H29),110(3H,d, J=62Hz,H21),124(3H,s,H28),136(3H,s, H19),147(3H,s,H30),215(3H,s,H27),351 (1H,m,H3),460(1H,dd,J=92,59Hz,H15), 499(1H,dt,J=81,60Hz,H23);13CNMR(pyri dined5,125MHz)δ:1983(C11),1706(C26), 1645(C8),1452(C24),1396(C9),1285(C 25),777(C3),719(C15),667(C23),539(C 14),527(C12),522(C5),497(C17),472(C 13),442(C22),395(C4),394(C16),381(C 10),351(C1),342(C20),307(C6),288(C 2),287(C28),197(C21),195(C30),192(C 19),177(C7),168(C18),165(C29),133(C 27)。 @òzL=.`^Þ [14] =., Vvñ_=ò 3β,15α,23trihydroxy11oxo5αla nosta8,24dien26oicacid(ganolucidateF)。 _= 11 K ( àÊ )。ESIMSm/z 5333[M+H]+。1HNMR(CDCl3,400MHz)δ: 088(3H,s,H18),102(3H,s,H30),085(3H,d, J=60Hz,H21),118(3H,d,J=70Hz,H27), 102(3H,s,H28),085(3H,s,H29),127(3H,s, H19),332(1H,m,H3),455(1H,dd,J=102, 72Hz,H7),469(1H,m,H15),239(1H,m,H 22α),224(1H,m,H22β);13CNMR(CDCl3,100 MHz)δ:2098(C23),1995(C11),1740(C26), 1575(C8),1421(C9),782(C3),725(C15), 696(C7),539(C14),524(C12),519(C31), 491(C5),481(C17),471(C13),454(C24), 420(C22),386(C4),386(C10),364(C16), 346(C1),346(C25),323(C20),284(C6), 282(C28),278(C2),198(C19),195(C21), 194(C30),171(C27),157(C18),97(C29)。 ² 1HNMR ëú³àÔv< δ376(3H,s);13C
NMR
ëδ519tàÔv<。ìb=.^ Þ [15] k. methylganoderateC2[÷,IVv_ = 11 òÞß] C2à³。 _= 12 K 。ESIMSm/z5153 [M+H]+。1HNMR(pyridined5,600MHz)δ:091 (3H,s,H18),104(3H,s,H29),113(3H,s,H 28),115(3H,d,J=54Hz,H21),136(3H,s,H 19),174(3H,s,H30),215(3H,s,H27),343 (1H,dd,J=48,66Hz,H3),484(1H,dd,J= 87,87Hz,H23),737(1H,d,J=84Hz,H 24);13CNMR(pyridined5,150MHz)δ:2081(C 15),2004(C11),1999(C7),1708(C26), 1518(C9),1472(C8),1428(C24),1288(C ·8701· ûóö : j¢ÞßLkd
25),768(C3),667(C23),577(C14),517(C
5),499(C12),461(C16),447(C13),438(C
17),410(C10),410(C22),398(C4),370(C
6),342(C1),340(C20),284(C28),282(C
2),215(C30),201(C21),181(C19),163(C
18),162(C29),135(C27)。
^Þ
[16]
k.
ganodericacidζ=.²z。
_=
13
K§w
(
àÊ
)。ESIMSm/z
5292[M-H]-。1HNMR(pyridined5,600MHz)δ:
101(3H,s,H18),112(3H,s,H29),131(3H,d,
J=72Hz,H27),135(3H,s,H28),139(3H,s,
H30),178(3H,s,H19),184(3H,s,H21),435
(1H,dd,J=96,66Hz,H15);13CNMR(pyridine
d5,150MHz)δ:2154(C3),2112(C23),2046
(C7),2012(C11),1778(C26),1523(C9),
1504(C8),733(C20),720(C15),528(C
14),525(C22),521(C12),509(C17),490
(C5),478(C13),477(C24),464(C4),391
(C10),368(C6),350(C1),345(C25),339
(C2),302(C16),272(C28),266(C21),206
(C30),202(C29),189(C18),175(C19),
170(C27)。
@òzL=.`^Þ
[17]
=
.,
Vvñ_=ò
ganodericacidAP3。
_=
14
K~
。EIMSm/z530[M]+·,
512[M-H2O]
+。1HNMR(CDCl3,600MHz)δ:086
(3H,s,H18),102(3H,d,J=60Hz,H21),109
(3H,d,J=72Hz,H27),122(3H,s,H29),125
(3H,s,H19),135(3H,s,H21),217(3H,s,H
28),321(1H,dd,J=48,66Hz,H3),481(1H,
dd,J=60,84Hz,H7);13CNMR(CDCl3,150
MHz)δ:2172(C23),2094(C15),1977(C11),
1743(C27),1568(C8),1427(C9),783(C
3),668(C7),585(C14),519(C31),503(C
12),491(C22),490(C17),467(C24),456
(C5),450(C10),409(C16),388(C13),386
(C4),348(C1),347(C25),315(C20),281
(C2),277(C6),266(C26),244(C29),198
(C21),184(C28),174(C19),170(C18),
154(C30)。
²
1HNMR
qL$$ëú³àÔv<
δ376(3H,s);13CNMR$ë δ519tàÔv
<
,
^Þk
[18]
.
methylganoderateB
=.²
z
,
IVv_=
14
òÞß]
B
à³
。
_=
15
K§w
(
àÊ
)。ESIMSm/z
5292[M-H]-。1HNMR(CDCl3,400MHz)δ:057
(3H,s,H18),088(6H,s,H28
¨
H30),092
(3H,d,J=64Hz,H21),098(3H,s,H29),101
(3H,s,H19),167(3H,s,H27),324(1H,dd,J=
44,108Hz,H3),399(2H,s,H26),532(1H,
d,J=60Hz,H7),540(1H,d,J=64Hz,H24),
547(1H,d,J=60Hz,H11)。13CNMR(CDCl3,
150MHz)δ:1459(C9),1427(C8),1343(C
25),1270(C24),1202(C7),1163(C11),789
(C3),691(C26),509(C17),503(C5),491
(C14),438(C13),387(C4),378(C12),374
(C10),361(C20),359(C22),357(C1),315
(C16),281(C2),279(C15),278(C29),256
(C28),245(C23),230(C6),227(C19),184
(C21),158(C30),157(C18),136(C27)。
@
òzL=.`^Þ
[19]
=.,
Vvñ_
=òÞßÊ
B。
4
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/_=¨
PTK
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ATP,37℃
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âª
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TMB
ãK¢¸-¢
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;
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,
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450nm
u
A。
±ù¬
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(A
ʸ
-A
³
)/(A
ʸ
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ö
)×100%[20]。
u¥<Äãÿj¢Þß²Êpq
50%
²Ê
1XDB[vÑ T]ÒÓ±ù
,IC50ò
787μmol·L-1,_=1~15Ñ T]ÒÓ
:B±ùhi
(IC50>10μmol·L
-1)。
5
<Äõã
N
j¢Þß²Êpqb?¹W
50%
²Ê1X¨
70%
²Ê1X=r
15
Lk
d_=
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,
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。
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HepG2
ÄÅ
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