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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

(benzoquinones)

  • P-quinone

  • O-quinone


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Q10


Naphthoquinones

(naphthoquinones)

  • -(1,4) -(1,2) amphi-(2,6)


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  • juglon


Phenanthraquinones

(phenanthraquinones)


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I


Anthraquinones

(anthraquinones)


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  • 1.

  • -OH

  • -OH

  • -OH


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  • 2.


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  • 3.


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A


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  • Bornatragers0.1g2-3ml


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a-

b-


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  • PPCTLC


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  • a-Pb+Mg2+

  • Pb+pH

  • 1a-1b-OH-

  • 1a-OHOH---

  • 0.5%905


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~

~

~

~


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  • C77-


Furocoumarins

(furocoumarins) ()

  • 7-

6,7-

7,8-


Pyranocoumarins

(pyranocoumarins) ()

  • C-6C-82,2---

6,7-

7,8-


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  • (psolalen)

  • (osthole)(HBsAg)

  • (scoparon)

  • (callophylloide)


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  • (365nm)


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  • (flavonoids) 2-2-phenyl-chromone


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  • C6-C3-C6

2-C6-C3-C6


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  • 2000-OH-OCH3


B 2 3

B-2-3-

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

-3-

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


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  • CCCOC


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  • (-OH-CH3)

  • ;

  • ;


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  • (hesperidin)P

  • (ginkgetin)(puerarin)(rutin)

  • (kaempferol)


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  • (baicalin)(silybin)

  • (isoliquiritigenin)daidzein


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


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verbenachalcone


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  • 1.-

    ~


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  • 2


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


1 monoterpenes

1. (monoterpenes)

  • C10H162


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l- l-


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  • N-(N-hydroxycantharidimide)


2 sesquiterpenes

2. (sesquiterpenes)

  • C15H243


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a-


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

  • (dihydroqinghaosu)(artemether)(artesunate)

  • Artemisiacina Berg.-(-santonin)


3 diterpenes

3.(diterpenes)

  • C20H324

  • (camphorene)


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A

  • (taxol)


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  • (volatile oils)(essential oils)


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56 136 300

56136300


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  • 0.8501.070

  • +97-1171.4301.610


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  • 10%-

  • -GC-MS


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:


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(lignans)


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  • (podophyllotoxin)

  • (schisantherin A)(schisanhenol)

  • (magnolol)(honokiol)

  • (arctiin)


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R=CH3

R=H


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  • (iridoids)10(iridoid)(secoiridoid)


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  • (gentiopicrin)

  • (gardenoside)(geniposide)


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  • Azulenoids

  • Saussurea involucrate(involucratolactone)Eupatorium rotundifolium(euparotin)


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  • (amino acids)

  • (peptides)22020

  • (proteins) 20


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56


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  • Taxusbrevifolia


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15

2090


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


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  • ,

  • 1994

    10-DABBaccatin


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  • :

    10


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  • (building block)(precursor)


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  • (bigenesis):,

  • (biosynthesis):


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  • WallachRuzicka

  • WintersteinTrier

    -


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  • biomimeticsynthesis


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  • 14C3H13C15N18O2H


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  • 3H14C


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  • 13C1.12H0.01515N0.3618O0.2


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  • :

    ,


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:

  • C2(),,

  • C5()

  • C6


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  • (shikimicacid)

  • (polyketides)

  • (mevalonicacid, MVA)


Shikimicacid

(shikimicacid)


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4-

7-

5-

5-

-


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-

-

-

b-

-


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A


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56


Polyketides

(polyketides)

  • AA


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A

A


Mevalonicacid mva

(mevalonicacid, MVA)


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(mevalonicacid pathway)


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:


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(amino acid pathway)


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  • 1.

  • 2.


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  • 3.

  • 4.


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