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五、醌类化合物 PowerPoint PPT Presentation


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五、醌类化合物. 醌类化合物 — 具有不饱和酮结构 分布 — 分子中连接助色团,作为色素而存在。 应用 — 抗菌抗癌等生理活性; -- 染料和指示剂的母体。. 结构类型 : 四种类型基母核. 主要有 苯醌 萘醌 菲醌 蒽醌 。. 苯醌类 (benzoquinones). 对苯醌 P-quinone 邻苯醌 O-quinone. 辅酶 Q 10. 信筒子醌. 萘醌类(naphthoquinones). α -(1,4) 萘醌 β -(1,2) 萘醌 amphi-(2,6) 萘醌.

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五、醌类化合物

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  • --


:


(benzoquinones)

  • P-quinone

  • O-quinone


Q10


(naphthoquinones)

  • -(1,4) -(1,2) amphi-(2,6)


  • juglon


(phenanthraquinones)


I


(anthraquinones)


  • 1.

  • -OH

  • -OH

  • -OH


  • 2.


  • 3.


A


  • Bornatragers0.1g2-3ml


a-

b-


  • PPCTLC


  • a-Pb+Mg2+

  • Pb+pH

  • 1a-1b-OH-

  • 1a-OHOH---

  • 0.5%905


~

~

~

~




  • C77-


(furocoumarins) ()

  • 7-

6,7-

7,8-


(pyranocoumarins) ()

  • C-6C-82,2---

6,7-

7,8-


  • (psolalen)

  • (osthole)(HBsAg)

  • (scoparon)

  • (callophylloide)



  • (365nm)


  • (flavonoids) 2-2-phenyl-chromone


  • C6-C3-C6

2-C6-C3-C6


  • 2000-OH-OCH3


B-2-3-

(flavones) (flavonol) (flavanones) (flavanonols) (anthocyanidins) (xanthones)

-3-

(flavan-3-ols) (isoflavones) (isoflavanones) (chalcones) (dihydrochalcones) (aurones)


  • CCCOC


  • (-OH-CH3)

  • ;

  • ;



  • (hesperidin)P

  • (ginkgetin)(puerarin)(rutin)

  • (kaempferol)


  • (baicalin)(silybin)

  • (isoliquiritigenin)daidzein


  • Verbena littoralis H. B. K. verbenachalconeC-O-C(NGF)


verbenachalcone


  • 1.-

    ~


  • 2


  • (terpenoids)(isoprene)(mevalonic acid)(C5H8)n22000


1. (monoterpenes)

  • C10H162


l- l-


  • N-(N-hydroxycantharidimide)


2. (sesquiterpenes)

  • C15H243


a-


  • Artemisia annua L.(qinghaosu, arteannin, artemisinin)

  • (dihydroqinghaosu)(artemether)(artesunate)

  • Artemisiacina Berg.-(-santonin)


3.(diterpenes)

  • C20H324

  • (camphorene)


A

  • (taxol)


  • (volatile oils)(essential oils)




56136300


  • 0.8501.070

  • +97-1171.4301.610


  • 10%-

  • -GC-MS


:


(lignans)


  • (podophyllotoxin)

  • (schisantherin A)(schisanhenol)

  • (magnolol)(honokiol)

  • (arctiin)


R=CH3

R=H


  • (iridoids)10(iridoid)(secoiridoid)


  • (gentiopicrin)

  • (gardenoside)(geniposide)


  • Azulenoids

  • Saussurea involucrate(involucratolactone)Eupatorium rotundifolium(euparotin)


  • (amino acids)

  • (peptides)22020

  • (proteins) 20



56



  • Taxusbrevifolia


15

2090


  • TaxolTaxol:0.00001-0.069% 3000=10=1kg Taxol=500


  • ,

  • 1994

    10-DABBaccatin


  • :

    10


  • (building block)(precursor)


  • (bigenesis):,

  • (biosynthesis):



  • WallachRuzicka

  • WintersteinTrier

    -


  • biomimeticsynthesis





  • 14C3H13C15N18O2H


  • 3H14C


  • 13C1.12H0.01515N0.3618O0.2



  • :

    ,



:

  • C2(),,

  • C5()

  • C6


  • (shikimicacid)

  • (polyketides)

  • (mevalonicacid, MVA)


(shikimicacid)


4-

7-

5-

5-

-


-

-

-

b-

-




A


56


(polyketides)

  • AA


A

A


(mevalonicacid, MVA)


(mevalonicacid pathway)



:




(amino acid pathway)



  • 1.

  • 2.


  • 3.

  • 4.


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