Ergostine

Last updated
Ergostine
Ergostine.svg
Names
IUPAC name
5′α-Benzyl-2′β-ethyl-12′-hydroxyergotaman-3′,6′,18-trione
Systematic IUPAC name
(6aR,9R)-N-[(2R,5S,10aS,10bS)-5-Benzyl-2-ethyl-10b-hydroxy-3,6-dioxooctahydro-8H-[1,3]oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl]-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C34H37N5O5/c1-3-33(36-30(40)22-16-24-23-11-7-12-25-29(23)21(18-35-25)17-26(24)37(2)19-22)32(42)39-27(15-20-9-5-4-6-10-20)31(41)38-14-8-13-28(38)34(39,43)44-33/h4-7,9-12,16,18,22,26-28,35,43H,3,8,13-15,17,19H2,1-2H3,(H,36,40)/t22-,26-,27+,28+,33-,34+/m1/s1
    Key: BOLCFGMGGWCOOE-CTTKVJGISA-N
  • CC[C@@]1(C(=O)N2[C@H](C(=O)N3CCC[C@H]3[C@@]2(O1)O)Cc4ccccc4)NC(=O)[C@H]5CN([C@@H]6Cc7c[nH]c8c7c(ccc8)C6=C5)C
Properties
C34H37N5O5
Molar mass 595.700 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Ergostine is an ergoloid-like chemical compound produced by the fungus Claviceps purpurea . [1]

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Ergot or ergot fungi refers to a group of fungi of the genus Claviceps.

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Ergotism is the effect of long-term ergot poisoning, traditionally due to the ingestion of the alkaloids produced by the Claviceps purpurea fungus—from the Latin clava "club" or clavus "nail" and -ceps for "head", i.e. the purple club-headed fungus—that infects rye and other cereals, and more recently by the action of a number of ergoline-based drugs. It is also known as ergotoxicosis, ergot poisoning, and Saint Anthony's fire.

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A sclerotium, is a compact mass of hardened fungal mycelium containing food reserves. One role of sclerotia is to survive environmental extremes. In some higher fungi such as ergot, sclerotia become detached and remain dormant until favorable growth conditions return. Sclerotia initially were mistaken for individual organisms and described as separate species until Louis René Tulasne proved in 1853 that sclerotia are only a stage in the life cycle of some fungi. Further investigation showed that this stage appears in many fungi belonging to many diverse groups. Sclerotia are important in the understanding of the life cycle and reproduction of fungi, as a food source, as medicine, and in agricultural blight management.

<i>Claviceps purpurea</i> Species of fungus

Claviceps purpurea is an ergot fungus that grows on the ears of rye and related cereal and forage plants. Consumption of grains or seeds contaminated with the survival structure of this fungus, the ergot sclerotium, can cause ergotism in humans and other mammals. C. purpurea most commonly affects outcrossing species such as rye, as well as triticale, wheat and barley. It affects oats only rarely.

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Ipomoea hederacea, the ivy-leaved morning glory or Kaladana, is a flowering plant in the bindweed family. The species is native to tropical parts of the Americas, and has more recently been introduced to North America. It now occurs there from Arizona to Florida and north to Ontario and North Dakota. Like most members of the family, it is a climbing vine with alternate leaves on twining stems. The flowers are blue to rose-purple with a white inner throat and emerge in summer and continue until late fall. The leaves are typically three-lobed, but sometimes may be five-lobed or entire. Flowers occur in clusters of one to three and are 2.5–4.5 cm long and wide. The sepals taper to long, recurved tips and measure 12–24 mm long. The species shares some features with the close relative Ipomoea purpurea, and is almost identical in appearance to wild forms of I. nil.

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Purpurea, purple in Latin, may refer to:

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Secalonic acids are a group of xanthone derivatives closely related to ergoflavin and ergochrysin A that are collectively called ergochromes and belong to a class of mycotoxins initially isolated as major ergot pigments from the fungi Claviceps purpurea that grows parasitically on rye grasses. From early times and particularly in medieval Europe the consumption of grains containing ergot has repeatedly lead to mass poisonings known as ergotism which was caused by toxic ergot alkaloids and mycotoxins such as the ergochromes, due to contamination of flour by C. purpurea. A cluster of genes responsible for the synthesis of secalonic acids in C. purpurea has been identified. Secalonic acid D the enantiomer of secalonic acid A is a major environmental toxin, isolated from the fungus Penicillium oxalicum, and is a major microbial contaminant of freshly-harvested corn which causes toxicity through contamination of foodstuffs.

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Claviceps pusilla, also known as bluestem ergot, is a parasitic fungus primarily of the grass tribe Angropogoneae, particularly those in the tribe referred to as "bluestem". C. pusilla occasionally manifests characteristic triangular conidia which appear to be unique among Claviceps species.

References

  1. Crespi-Perellino, N; Guicciardi, A; Minghetti, A; Spalla, C (15 March 1981). "Incorporation of alpha-aminobutyric acid into ergostine by Claviceps purpurea". Experientia. 37 (3): 217–8. doi:10.1007/bf01991617. PMID   7238767. S2CID   5970415.