Sinococuline

Last updated
Sinococuline
Sinococuline Structure.svg
Names
Preferred IUPAC name
(2S,3S,4aS,10S)-2,3,4-Trihydroxy-1,5-dimethoxy-3,4,9,10-tetrahydro-2H-10,4a-(azanoethano)phenanthrene
Identifiers
3D model (JSmol)
PubChem CID
UNII
  • InChI=1S/C18H23NO5/c1-23-12-4-3-9-7-10-14-17(24-2)15(21)11(20)8-18(14,5-6-19-10)13(9)16(12)22/h3-4,10-11,15,19-22H,5-8H2,1-2H3/t10-,11-,15-,18-/m0/s1
    Key: MFKPWBJXKCSPGK-KNORBDTNSA-N
  • COC1=C(C2=C(C[C@H]3C4=C([C@H]([C@H](C[C@]42CCN3)O)O)OC)C=C1)O
Properties
C18H23NO5
Molar mass 333.384 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Sinococuline is a bioactive alkaloid found in Cocculus trilobus . [1]

Related Research Articles

Alkaloid Class of naturally occurring chemical compounds

Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure may also be termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and, more rarely, other elements such as chlorine, bromine, and phosphorus.

Quinoline Chemical compound

Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N. It is a colorless hygroscopic liquid with a strong odor. Aged samples, especially if exposed to light, become yellow and later brown. Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. Quinoline itself has few applications, but many of its derivatives are useful in diverse applications. A prominent example is quinine, an alkaloid found in plants. Over 200 biologically active quinoline and quinazoline alkaloids are identified. 4-Hydroxy-2-alkylquinolines (HAQs) are involved in antibiotic resistance.

<i>Menispermum</i> Genus of flowering plants

Menispermum (moonseed) is a small genus of deciduous climbing woody vines in the moonseed family (Menispermaceae). Plants in this genus have small dioecious flowers, and clusters of small grape-like drupes. The name, moonseed, comes from the shape of the seed, which resembles a crescent moon. The word Menispermum is derived from the Greek words μήν (mēn), meaning (crescent) moon, and σπέρμα (sperma) meaning seed. The common name moonseed is also applied to some other species in the related genus Cocculus.

Ergoline Chemical compound

Ergoline is a chemical compound whose structural skeleton is contained in a variety of alkaloids, referred to as ergoline derivatives or ergoline alkaloids. Ergoline alkaloids, one being ergine, were initially characterized in ergot. Some of these are implicated in the condition ergotism, which can take a convulsive form or a gangrenous form. Even so, many ergoline alkaloids have been found to be clinically useful. Annual world production of ergot alkaloids has been estimated at 5,000–8,000 kg of all ergopeptines and 10,000–15,000 kg of lysergic acid, used primarily in the manufacture of semi-synthetic derivatives.

Picrotoxin Chemical compound

Picrotoxin, also known as cocculin, is a poisonous crystalline plant compound. It was first isolated by the French pharmacist and chemist Pierre François Guillaume Boullay (1777–1869) in 1812. The name "picrotoxin" is a combination of the Greek words "picros" (bitter) and "toxicon" (poison). A mixture of two different compounds, picrotoxin occurs naturally in the fruit of the Anamirta cocculus plant, although it can also be synthesized chemically.

Menispermaceae Family of flowering plants

Menispermaceae is a family of flowering plants. The alkaloid tubocurarine, a neuromuscular blocker and the active ingredient in the 'tube curare' form of the dart poison curare, is derived from the South American liana Chondrodendron tomentosum. Several other South American genera belonging to the family have been used to prepare the 'pot' and 'calabash' forms of curare. The family contains 68 genera with some 440 species, which are distributed throughout low-lying tropical areas with some species present in temperate and arid regions.

<i>Cocculus</i> Genus of flowering plants

Cocculus is a genus of 11 species of woody vines and shrubs, native to warm temperate to tropical regions of North America, Asia and Africa. The common name moonseed is also used for the closely related genus Menispermum.

<i>Anamirta cocculus</i> Climbing plant

Anamirta cocculus is a Southeast Asian and Indian climbing plant. Its fruit is the source of picrotoxin, a poisonous compound with stimulant properties.

<i>Stephania</i> Genus of plants

Stephania is a genus of flowering plants in the family Menispermaceae, native to eastern and southern Asia and Australia. They are herbaceous perennial vines growing to around four metres tall, with a large, woody caudex. The leaves are arranged spirally on the stem, and are peltate, with the leaf petiole attached near the centre of the leaf. The name Stephania comes from the Greek, "a crown". This refers to the anthers being arranged in a crown like manner.

Sparteine

Sparteine is a class 1a antiarrhythmic agent; a sodium channel blocker. It is an alkaloid and can be extracted from scotch broom. It is the predominant alkaloid in Lupinus mutabilis, and is thought to chelate the bivalent cations calcium and magnesium. It is not FDA approved for human use as an antiarrhythmic agent, and it is not included in the Vaughan Williams classification of antiarrhythmic drugs.

Berberine Quaternary ammonium cation

Berberine is a quaternary ammonium salt from the protoberberine group of benzylisoquinoline alkaloids found in such plants as Berberis, such as Berberis vulgaris (barberry), Berberis aristata, Mahonia aquifolium, Hydrastis canadensis (goldenseal), Xanthorhiza simplicissima (yellowroot), Phellodendron amurense, Coptis chinensis, Tinospora cordifolia, Argemone mexicana, and Eschscholzia californica. Berberine is usually found in the roots, rhizomes, stems, and bark.

Stephania tetrandra is a herbaceous perennial vine of the family Menispermaceae native to China and Taiwan. It grows from a short, woody caudex, climbing to a height of around three meters. The leaves are arranged spirally on the stem, and are peltate, i.e. with the leaf petiole attached near the centre of the leaf. Its root is used in traditional Chinese medicine (TCM).

<i>Conium maculatum</i> Poisonous herbaceous plant in the carrot family

Conium maculatum, colloquially known as hemlock, poison hemlock or wild hemlock, is a highly poisonous biennial herbaceous flowering plant in the carrot family Apiaceae, native to Europe and North Africa. A hardy plant capable of living in a variety of environments, hemlock is widely naturalized in locations outside its native range, such as parts of Australia, West Asia, and North and South America, to which it has been introduced. It is capable of spreading and thereby becoming an invasive weed.

C. indicus may refer to:

<i>Byasa alcinous</i> Species of butterfly

Byasa alcinous, the Chinese windmill, is a butterfly of the family Papilionidae.

<i>Cocculus carolinus</i> Species of flowering plant

Cocculus carolinus, commonly called the Carolina coralbead, or snailseed, is a perennial vine of the moonseed family (Cocculus). It is native to North America, where it is found in Mexico and in several states in the United States from the Southeast to the Midwest.

Elymoclavine Chemical compound

Elymoclavine is an ergot alkaloid. It can be produced from C. fusiformis from Pennisetum typhoideum. It is a precursor in the biosynthesis of D-(+)-lysergic acid. Ergot alkaloids are natural products derived from L-tryptophan. They are often toxic for humans and animals. Despite that they are also well known for their pharmacological activities.

Coclaurine Chemical compound

Coclaurine is a nicotinic acetylcholine receptor antagonist which has been isolated from a variety of plant sources including Nelumbo nucifera, Sarcopetalum harveyanum, Ocotea duckei, and others. It belongs to the class of tetrahydroisoquinoline alkaloids. Dimerization of coclaurine leads to the biscoclaurine alkaloids such as cepharanthine.

Muhammad Iqbal Choudhary is a scientist in the field of organic chemistry from Pakistan. He is known for his research in various areas relating to natural product chemistry. He has more than 800 research publications. In 2015 he was recognised as the second most productive scientist in Pakistan.

<i>Hemihegetotherium</i> Extinct genus of mammals

Hemihegetotherium is an extinct genus of Notoungulate, from the suborder Typotheria. It lived from the Middle to the Late Miocene, and its fossilized remains were discovered in South America.

References

  1. Itokawa, H; Tsuruoka, S; Takeya, K; Mori, N; Sonobe, T; Kosemura, S; Hamanaka, T (1987). "An antitumor morphinane alkaloid, sinococuline, from Cocculus trilobus". Chemical & Pharmaceutical Bulletin. 35 (4): 1660–2. doi: 10.1248/cpb.35.1660 . PMID   3652302.