Cheilanthifoline

Last updated
Cheilanthifoline
(-)-(S)-Cheilanthifoline.svg
Names
IUPAC name
2-Methoxy-2′H-[1,3]dioxolo[4′,5′:9,10]berbin-3-ol
Systematic IUPAC name
(6aS)-9-Methoxy-6,6a,11,14-tetrahydro-2H,12H-[1,3]dioxolo[4,5-h]isoquinolino[2,1-b]isoquinolin-8-ol
Other names
(S)-Cheilanthifoline
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
  • rac:InChI=1S/C19H19NO4/c1-22-18-8-13-12(7-16(18)21)4-5-20-9-14-11(6-15(13)20)2-3-17-19(14)24-10-23-17/h2-3,7-8,15,21H,4-6,9-10H2,1H3
    Key: MKRKFSHHTKVRAR-UHFFFAOYSA-N
  • (S)-:InChI=1S/C19H19NO4/c1-22-18-8-13-12(7-16(18)21)4-5-20-9-14-11(6-15(13)20)2-3-17-19(14)24-10-23-17/h2-3,7-8,15,21H,4-6,9-10H2,1H3/t15-/m0/s1
    Key: MKRKFSHHTKVRAR-HNNXBMFYSA-N
  • rac:COc1cc2c(cc1O)CCN3C2Cc4ccc5c(c4C3)OCO5
  • (S)-:COC1=C(C=C2[C@@H]3CC4=C(CN3CCC2=C1)C5=C(C=C4)OCO5)O
Properties
C19H19NO4
Molar mass 325.364 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(S)-Cheilanthifoline is a benzylisoquinoline alkaloid (BIA) which has been isolated from Corydalis dubia [1] and Argemone mexicana .[ citation needed ] (S)-Cheilanthifoline is metabolically derived from (S)-reticuline, a pivotal intermediate in the biosynthesis of numerous BIAs. (S)-Cheilanthifoline is the immediate precursor of the BIA (S)-stylopine ((S)-stylopine synthase/CYP719A20), which is the precursor for the alkaloids protopine and sanguinarine. [2]

Related Research Articles

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Noscapine is a benzylisoquinoline alkaloid, of the phthalideisoquinoline structural subgroup, which has been isolated from numerous species of the family Papaveraceae. It lacks significant hypnotic, euphoric, or analgesic effects affording it with very low addictive potential. This agent is primarily used for its antitussive (cough-suppressing) effects.

<span class="mw-page-title-main">Scoulerine</span> Chemical compound

Scoulerine, also known as discretamine and aequaline, is a benzylisoquinoline alkaloid (BIA) that is derived directly from (S)-reticuline through the action of berberine bridge enzyme. It is a precursor of other BIAs, notably berberine, noscapine, (S)-tetrahydropalmatine, and (S)-stylopine, as well as the alkaloids protopine, and sanguinarine. It is found in many plants, including opium poppy, Croton flavens, and certain plants in the genus Erythrina.

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The enzyme (S)-norcoclaurine synthase (EC 4.2.1.78) catalyzes the chemical reaction

<i>Corydalis ambigua</i> Species of flowering plants in the poppy family Papaveraceae

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<span class="mw-page-title-main">Pukateine</span> Chemical compound

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<span class="mw-page-title-main">Higenamine</span> Chemical compound

Higenamine (norcoclaurine) is a chemical compound found in a variety of plants including Nandina domestica (fruit), Aconitum carmichaelii (root), Asarum heterotropioides, Galium divaricatum, Annona squamosa, and Nelumbo nucifera.

<span class="mw-page-title-main">Benzylisoquinoline</span> Chemical compound

Substitution of the heterocycle isoquinoline at the C1 position by a benzyl group provides 1‑benzylisoquinoline, the most widely examined of the numerous benzylisoquinoline structural isomers. The 1-benzylisoquinoline moiety can be identified within numerous compounds of pharmaceutical interest, such as moxaverine; but most notably it is found within the structures of a wide variety of plant natural products, collectively referred to as benzylisoquinoline alkaloids. This class is exemplified in part by the following compounds: papaverine, noscapine, codeine, morphine, apomorphine, berberine, tubocurarine.

<span class="mw-page-title-main">Tetrandrine</span> Chemical compound

Tetrandrine, a bis-benzylisoquinoline alkaloid, is a calcium channel blocker. It is isolated from the plant Stephania tetrandra, and other Chinese and Japanese herbs.

<span class="mw-page-title-main">Canadine</span> Chemical compound

(S)-Canadine, also known as (S)-tetrahydroberberine and xanthopuccine, is a benzylisoquinoline alkaloid (BIA), of the protoberberine structural subgroup, and is present in many plants from the family Papaveraceae, such as Corydalis yanhusuo and C. turtschaninovii.

<span class="mw-page-title-main">Nantenine</span> Chemical compound

Nantenine is an alkaloid found in the plant Nandina domestica as well as some Corydalis species. It is an antagonist of both the α1-adrenergic receptor and the serotonin 5-HT2A receptor, and blocks both the behavioral and physiological effects of MDMA in animals.

<span class="mw-page-title-main">Protopine</span> Chemical compound

Protopine is an alkaloid occurring in opium poppy, Corydalis tubers and other plants of the family papaveraceae, like Fumaria officinalis. Protopine is metabolically derived from the benzylisoquinoline alkaloid (S)-Reticuline through a progressive series of five enzymatic transformations: 1) berberine bridge enzyme to (S)-Scoulerine; 2) (S)-cheilanthifoline synthase/CYP719A25 to (S)-Cheilanthifoline; 3) (S)-stylopine synthase/CYP719A20 to (S)-Stylopine; 4) (S)-tetrahydroprotoberberine N-methyltransferase to (S)-cis-N-Methylstylopine; and ultimately, 5) N-methylstylopine hydroxylase to protopine.

<span class="mw-page-title-main">Reticuline</span> Chemical compound

Reticuline is a chemical compound found in a variety of plants including Lindera aggregata, Annona squamosa, and Ocotea fasciculata. It is based on the benzylisoquinoline structure.

<span class="mw-page-title-main">Sibiricine</span> Chemical compound

Sibiricine is a bioactive isoquinoline alkaloid isolated from Corydalis crispa (Fumariaceae), which is a Bhutanese medicinal plant from the Himalayas.

<span class="mw-page-title-main">Tetrahydrocoptisine</span> Chemical compound

Tetrahydrocoptisine is an alkaloid isolated from Corydalis impatiens.

<span class="mw-page-title-main">Corydaline</span> Chemical compound

Corydaline is an acetylcholinesterase inhibitor isolated from Corydalis yanhusuo.

<span class="mw-page-title-main">Chelidonine</span> Chemical compound

Chelidonine is an isolate of Papaveraceae with acetylcholinesterase and butyrylcholinesterase inhibitory activity.

<span class="mw-page-title-main">Magnoflorine</span> Chemical compound

(S)-Magnoflorine is a quaternary benzylisoquinoline alkaloid (BIA) of the aporphine structural subgroup which has been isolated from various species of the family Menispermaceae, such as Pachygone ovata,Sinomenium acutum, and Cissampelos pareira. 

<span class="mw-page-title-main">Aporphine alkaloids</span>

Aporphine alkaloids are naturally occurring chemical compounds from the group of alkaloids. After the benzylisoquinoline alkaloids they are the second largest group of isoquinoline alkaloids.

<span class="mw-page-title-main">Corydalis Alkaloids</span>

Corydalis Alkaloids are categorized as natural products of the isoquinoline alkaloid type.

References

  1. Wangchuk, P; Keller, PA; Pyne, SG; Willis, AC; Kamchonwongpaisan, S (2012). "Antimalarial alkaloids from a Bhutanese traditional medicinal plant Corydalis dubia". Journal of Ethnopharmacology. 143 (1): 310–3. doi:10.1016/j.jep.2012.06.037. PMID   22796506.
  2. Hagel, Jillian; Morris, Jeremy S; Lee, Eun-Jeong; Desgagne-Penix, Isabel; Bross, Crystal D; Chang, Limei; Chen, Xue; Farrow, Scott C; Zhang, Te (2015). "Transcriptome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants". BMC Plant Biology. 15: 227. doi: 10.1186/s12870-015-0596-0 . PMC   4575454 . PMID   26384972.