New compounds from Rhodiola kirilowii - Scientia Pharmaceutica

01-07.qxp

22.03.2007

11:16

Seite 29

Scientia Pharmaceutica (Sci. Pharm.) 75, 29-34 (2007) © Österreichische Apotheker-Verlagsgesellschaft m. b. H., Wien, Printed in Austria

29

1HZ FRPSRXQGV IURP 5KRGLROD NLULORZLL +HOPXW :LHGHQIHOG  0RQLND =\FK :DOGHPDU %XFKZDOG 0LURVáDZD )XUPDQRZD 

3KDUPDFHXWLFDO ,QVWLWXWH 8QLYHUVLW\ RI %RQQ $Q GHU ,PPHQEXUJ  ' %RQQ *HUPDQ\



'HSDUWPHQW RI %LRORJ\ DQG 3KDUPDFHXWLFDO %RWDQ\ 0HGLFDO 8QLYHUVLW\ RI :DUVDZ  :DUVDZ 3RODQG 

5HVHDUFK ,QVWLWXWH RI 0HGLFLQDO 3ODQWV  3R]QDĔ 3RODQG

$EVWUDFW )LYH FRPSRXQGV ZHUH LVRODWHG IURP URRW H[WUDFWV RI 5KRGLROD NLULORZLL DUEXWLQ HSLJDOORFDWHFKLQ JDOODWH UKRGLRF\DQRVLGH $ IUXFWRS\UDQR JOXFRS\UDQRVH DQG ORWDXVWUDOLQ 7KH ILUVW IRXU FRPSRXQGV ZHUH IRXQG LQ WKLV SODQW IRU WKH ILUVW WLPH /RWDXVWUDOLQ VDOLGURVLGH GDXFRVWHURO DQG W\URVRO ZHUH DOUHDG\ GHVFULEHG WR EH FRQWDLQHG (VSHFLDOO\ VDOLGURVLGH DV D 5KRGLROD PDUNHU FRPSRXQG FRXOG QRW EH GHWHFWHG LQ RXU VDPSOHV 7KH VWUXFWXUHV ZHUH HVWDEOLVKHG E\ 105 VWXGLHV

.H\ZRUGV 5KRGLROD NLULORZLL DUEXWLQ HSLJDOORFDWHFKLQ JDOODWH UKRGLRF\DQRVLGH $ ORWDXVWUDOLQ IUXFWRS\UDQR JOXFRS\UDQRVH

,QWURGXFWLRQ 5KRGLROD NLULORZLL 5HJ 5HJ &UDVVXODFHDH LV XVHG LQ WKH &KLQHVH WUDGLWLRQDO PHGLFLQH IRU WKH HQKDQFHPHQW RI WKH DELOLW\ RI DQWLDQR[LD LW VKRZV DQWLFRDJXODWLYH SURSHUWLHV DQG GHFUHDVHV WKH OHYHO RI EORRG VXJDU 5K NLULORZLL LV DOVR VDLG WR SURWHFW SHRSOH HIILFLHQWO\ DJDLQVW FDUGLRSXOPRQDU\ IXQFWLRQ SUREOHPV ZKHQ PRYLQJ WR KLJK DOWLWXGH  P >@ 7KH SODQW ZDV UHSRUWHG WR FRQWDLQ VDOLGURVLGH W\URVRO GDXFRVWHURO ORWDXVWUDOLQ VXFURVH EHWDVLWRVWHURO >@ 2XU UHLQYHVWLJDWLRQ RI

01-07.qxp

22.03.2007

11:16

Seite 30

30

Helmut Wiedenfeld et al.:

FXOWLYDWHG 5K NULORZLL OHG WR WKH LVRODWLRQ RI  FRPSRXQGV ZKLFK ZHUH LGHQWLILHG E\ 105VWXGLHV DV DUEXWLQ   HSLJDOORFDWHFKLQ JDOODWH   UKRGLRF\DQRVLGH $   ORWDXVWUDOLQ   IUXFWRS\UDQR JOXFRS\UDQRVH  

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

([SHULPHQWDO 3ODQW PDWHULDO 5RRWV DQG UKL]RPHV RI 5K NLULORZLL ZHUH FROOHFWHG LQ 6HSWHPEHU  DQG LGHQWLILHG LQ WKH 5HVHDUFK ,QVWLWXWH RI 0HGLFLQDO 3ODQWV 3R]QDĔ 7KH SODQW JURZWK ZDV FRQWUROOHG 7KH UHDFWLRQ DQG PLQHUDO FRPSRQHQWV RI WKH VRLO WKH DLU WHPSHUD WXUH WKH DYHUDJH VXP RI KXPLGLW\ DQG UDLQ DV ZHOO DV WKH VXQ SHULRGV ZHUH PRQLWRUHG SHUPDQHQWO\ ,QVWUXPHQWV +3/& 'LRQH[ V\VWHP SXPS  *LQD  DXWRVDPSOHU '$' V ZLWK D &&  1XFOHRGXU & 3\UDPLG  — FROXPQ 0DFKHUH\1DJHO *HUPDQ\  GDWD

01-07.qxp

22.03.2007

11:16

Seite 31

New compounds from Rhodiola kirilowii

31

DFTXLVLWLRQ &KURPHOHRQ 9  EXLOG  105 %UXNHU $& '062' FKHPLFDO VKLIWV Q SSP ZHUH UHIHUHQFHG WR '062  DQG  SSP UHVSHFWLYHO\  FRXSOLQJ FRQVWDQWV LQ +] )ODVK OLTXLG FKURPDWRJUDSK\ )/&   [  FP FROXPQ 3RO\JRSUHS &  0DFKHUH\1DJHO *HUPDQ\  ([WUDFWLRQ DQG LVRODWLRQ

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   +G-   &   P  &   P  &   P  &   P  &   P  (SLJDOORFDWHFKLQ JDOODWH  105 Q SSP ->+]@  &   +G-   &   + GG   &   + GG - +]   &  &   + G -   &  &   + G -   &  &  &  &   + G -   &  &  &   &   + G -   &  &  &  5KRGLRF\DQRVLG $  105 Q SSP ->+]@  &   +G-    +G-   &   +W-   &  &   +V  &  &

01-07.qxp

22.03.2007

11:16

32

Seite 32

Helmut Wiedenfeld et al.:

  +G-   &C   +GG-  +]  &   + GG -   &   + P  &   + P  &   +$ G -     +% G -   /RWDXVWUDOLQ  105 Q SSP ->+]@  &  &   +T-   &   +W-   &   +V  &  &   +G-   &   +GG-   &   +GG-   &   +P  &   +P  &   +$G-    +%G-   )UXFWRS\UDQR JOXFRS\UDQRVH  105 Q SSP ->+]@  &   + G -   &   ±  + P  &   ±  + P  &   ±  + P  &   ±  + P  &   ±  + P  &   ±  + P  &   ±  + P  &   ±  + P  &   ±  + P  &   ±  + P  &   ±  + P 

01-07.qxp

22.03.2007

11:16

Seite 33

New compounds from Rhodiola kirilowii

 

+  +  2+ +2  +

+







+2



2



+

 2+



 



2 2 

+



  2+





2+ 

+

 +2

+

 2

+ +

2+

 2+

 +

2  



2 2+

2+

+

 +

 2+

2+

2+





+ 

2+ 



+

 2+

2+





&1 

2+

2+



 +

&1

2+ 

 &+

2 2

 +

+

+

2



 +  +  2+ +2  +







 &+

+





2



2+

2+









2+







2 2 

2+

2+ 

2+



+ 

2+





&+ 

+



+



)LJXUHV RI FRPSRXQGV  ± 

5HIHUHQFHV >@ =KDQJ =+ )HQJ 6+ +X *' &DR =. :DQJ /@ %URZQ 53 *HUEDUJ 3/ 5DPD]DQRY = 5KRGLROD URVHD $ 3K\WRPHGLFLQDO 2YHUYLHZ +HUEDO*UDP   >@ %\NRY 9$ =DSHVRFKQD\D ** .XUNLQ 9$ 0HGLFLQDO 3ODQWV 7UDGLWLRQDO DQG %LRWHFKQLFRORJLFDO $VSHFWV RI 2EWDLQLQJ 0HGLFLQDO 3UHSDUDWLRQV IURP 5KRGLROD 5RVHD / $ 5HYLHZ  3KDUP &KHP -   >@ =KDQJ + =KDQJ 6 :DQJ - &KHQ @ 3HQJ -1 0D &@