Ergocornine → Ergocryptine

HRID 543873Notes

Reaction equation

[CH3:1][CH:2]([C@@H:4]1[N:13]2[C:14]([C@@:16]([NH:21][C:22]([C@@H:24]3[CH:39]=[C:38]4[C@@H:27]([CH2:28][C:29]5[C:33]6[C:34]4=[CH:35][CH:36]=[CH:37][C:32]=6[NH:31][CH:30]=5)[N:26]([CH3:40])[CH2:25]3)=[O:23])([CH:18]([CH3:20])[CH3:19])[O:17][C@@:12]2([OH:41])[C@H:11]2[N:7]([CH2:8][CH2:9][CH2:10]2)[C:5]1=[O:6])=[O:15])[CH3:3].[CH3:42][CH:43]([CH2:45][C@@H:46]1[N:55]2[C:56]([C@@:58]([NH:63][C:64]([C@@H:66]3[CH:81]=[C:80]4[C@@H:69]([CH2:70][C:71]5[C:75]6[C:76]4=[CH:77][CH:78]=[CH:79][C:74]=6[NH:73][CH:72]=5)[N:68]([CH3:82])[CH2:67]3)=[O:65])([CH:60]([CH3:62])[CH3:61])[O:59][C@@:54]2([OH:83])[C@H:53]2[N:49]([CH2:50][CH2:51][CH2:52]2)[C:47]1=[O:48])=[O:57])[CH3:44].[CH3:84]C([C@@H]1N2C([C@@](NC([C@@H]3C=C4[C@@H](CC5C6C4=CC=CC=6NC=5)N(C)C3)=O)(C(C)C)O[C@@]2(O)[C@H]2N(CCC2)C1=O)=O)C.CC(C[C@@H]1N2C([C@@](NC([C@@H]3C=C4[C@@H](CC5C6C4=CC=CC=6NC=5)N(C)C3)=O)(C(C)C)O[C@@]2(O)[C@H]2N(CCC2)C1=O)=O)C>>[CH3:44][CH:43]([CH2:45][C@@H:46]1[N:55]2[C:56]([C@@:58]([NH:63][C:64]([C@@H:66]3[CH:81]=[C:80]4[C@@H:69]([CH2:70][C:71]5[C:75]6[C:76]4=[CH:77][CH:78]=[CH:79][C:74]=6[NH:73][CH:72]=5)[N:68]([CH3:82])[CH2:67]3)=[O:65])([CH:60]([CH3:61])[CH3:62])[O:59][C@@:54]2([OH:83])[C@H:53]2[N:49]([CH2:50][CH2:51][CH2:52]2)[C:47]1=[O:48])=[O:57])[CH3:42].[CH3:84][CH2:3][C@@H:2]([C@H:4]1[N:13]2[C:14]([C@@:16]([NH:21][C:22]([C@@H:24]3[CH:39]=[C:38]4[C@@H:27]([CH2:28][C:29]5[C:33]6[C:32](=[CH:37][CH:36]=[CH:35][C:34]=64)[NH:31][CH:30]=5)[N:26]([CH3:40])[CH2:25]3)=[O:23])([CH:18]([CH3:19])[CH3:20])[O:17][C@@:12]2([OH:41])[C@H:11]2[N:7]([CH2:8][CH2:9][CH2:10]2)[C:5]1=[O:6])=[O:15])[CH3:1]

Participants

Reactant 3

HCID 73453Ergocornine

HCID 134551Ergocryptine

HCID 86739404HCID 86739404, compound

Product 2

HCID 134551Ergocryptine

HCID 161309HCID 161309, compound

Procedure

According to the spectrum of the produced alkaloids, the new strain belongs to the chemical rage ergocornine-ergocryptine. Ergocornine and ergocryptine in the weight ratio of approximately 1:1 are the main alkaloids contained in both the parasitic ergot sclerotia and the mycelium of saprophytic culture. The ergocryptine component is formed by α-ergocryptine and β-ergocryptine in parasitic sclerotia in a weight ratio of approximately 2:1 to 1:1, and in saprophytic mycelium without precursoring in a weight ratio of approximately 5:1. Customary ergometrine and futher a small amount of ergosine and traces of ergocristine, ergotamine, lysergylvaline amide, ergoxine (ergostine, ergonine, ergoptine) and of further three nonidentified alkaloids are the components of the alkaloid spectrum besides the above set forth main alkaloids.

Sources & evidence

ORD record: ord-7d01866ab236460f9cbd20f9c8406a4d
Source dataset: uspto-grants-1984_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04447540

Reaction notes

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