Narciclasine

Last updated
Narciclasine
Narciclasine.svg
Names
Preferred IUPAC name
(2S,3R,4S,4aR)-2,3,4,7-Tetrahydroxy-3,4,4a,5-tetrahydro-9H-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one
Other names
BRN 1087400, Lycoricidin-A, Lycoricidinol, NSC 266535
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.214.093 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
  • InChI=1S/C14H13NO7/c16-6-1-5-4-2-7-13(22-3-21-7)11(18)8(4)14(20)15-9(5)12(19)10(6)17/h1-2,6,9-10,12,16-19H,3H2,(H,15,20)/t6-,9+,10+,12-/m0/s1
    Key: LZAZURSABQIKGB-AEKGRLRDSA-N
  • InChI=1/C14H13NO7/c16-6-1-5-4-2-7-13(22-3-21-7)11(18)8(4)14(20)15-9(5)12(19)10(6)17/h1-2,6,9-10,12,16-19H,3H2,(H,15,20)/t6-,9+,10+,12-/m0/s1
    Key: LZAZURSABQIKGB-AEKGRLRDBO
  • C1OC2=C(O1)C(=C3C(=C2)C4=C[C@@H]([C@H]([C@H]([C@@H]4NC3=O)O)O)O)O
Properties
C14H13NO7
Molar mass 307.258 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN (what is  Yes check.svgYX mark.svgN ?)

Narciclasine is a toxic alkaloid found in various Amaryllidaceae species. [1]

Related Research Articles

<span class="mw-page-title-main">Asparagales</span> Order of monocot flowering plants

Asparagales is an order of plants in modern classification systems such as the Angiosperm Phylogeny Group (APG) and the Angiosperm Phylogeny Web. The order takes its name from the type family Asparagaceae and is placed in the monocots amongst the lilioid monocots. The order has only recently been recognized in classification systems. It was first put forward by Huber in 1977 and later taken up in the Dahlgren system of 1985 and then the APG in 1998, 2003 and 2009. Before this, many of its families were assigned to the old order Liliales, a very large order containing almost all monocots with colorful tepals and lacking starch in their endosperm. DNA sequence analysis indicated that many of the taxa previously included in Liliales should actually be redistributed over three orders, Liliales, Asparagales, and Dioscoreales. The boundaries of the Asparagales and of its families have undergone a series of changes in recent years; future research may lead to further changes and ultimately greater stability. In the APG circumscription, Asparagales is the largest order of monocots with 14 families, 1,122 genera, and about 36,000 species.

<i>Narcissus</i> (plant) Genus of plants in the Amaryllis (Amaryllidaceae)

Narcissus is a genus of predominantly spring flowering perennial plants of the amaryllis family, Amaryllidaceae. Various common names including daffodil, narcissus, and jonquil are used to describe all or some members of the genus. Narcissus has conspicuous flowers with six petal-like tepals surmounted by a cup- or trumpet-shaped corona. The flowers are generally white and yellow, with either uniform or contrasting coloured tepals and corona.

<span class="mw-page-title-main">Asphodelaceae</span> Family of flowering plants in the order Asparagales

Asphodelaceae is a family of flowering plants in the order Asparagales. Such a family has been recognized by most taxonomists, but the circumscription has varied widely. In its current circumscription in the APG IV system, it includes about 40 genera and 900 known species. The type genus is Asphodelus.

<span class="mw-page-title-main">Asparagaceae</span> Family of plants

Asparagaceae, known as the asparagus family, is a family of flowering plants, placed in the order Asparagales of the monocots. The family name is based on the edible garden asparagus, Asparagus officinalis. Those who live in the temperate climates may be surprised to learn that this family includes both common garden plants as well as common houseplants. The garden plants include asparagus, yucca, bluebell, and hosta, and the houseplants include snake plant, corn cane, spider plant and plumosus fern.

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

Lycorine is a toxic crystalline alkaloid found in various Amaryllidaceae species, such as the cultivated bush lily, surprise lilies (Lycoris), and daffodils (Narcissus). It may be highly poisonous, or even lethal, when ingested in certain quantities. Regardless, it is sometimes used medicinally, a reason why some groups may harvest the very popular Clivia miniata.

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

Piribedil (trade names Pronoran, Trivastal Retard, Trastal, Trivastan, Clarium and others) is an antiparkinsonian agent and piperazine derivative which acts as a D2 and D3 receptor agonist. It also has α2-adrenergic antagonist properties.

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

Pancratistatin (PST) is a natural compound initially extracted from spider lily, a Hawaiian native plant of the family Amaryllidaceae (AMD).

<i>Boophone</i> Genus of plants

Boophone is a small genus of herbaceous, perennial and bulbous plants in the Amaryllis family It consists of two confirmed species distributed across South Africa to Kenya and Uganda. It is closely related to Crossyne, a genus whose species have prostrate leaves. They are drought tolerant but not cold-hardy, and are very poisonous to livestock.

Alan W. Meerow is an American botanist, born in New York City in 1952. He specializes in the taxonomy of the family Amaryllidaceae and the horticulture of palms and tropical ornamental plants. He also works on the population genetics and molecular systematics of cycads and palms.

<span class="mw-page-title-main">Amaryllidaceae</span> Family of flowering plants comprising members popular for horticulture and vegetable production

The Amaryllidaceae are a family of herbaceous, mainly perennial and bulbous flowering plants in the monocot order Asparagales. The family takes its name from the genus Amaryllis and is commonly known as the amaryllis family. The leaves are usually linear, and the flowers are usually bisexual and symmetrical, arranged in umbels on the stem. The petals and sepals are undifferentiated as tepals, which may be fused at the base into a floral tube. Some also display a corona. Allyl sulfide compounds produce the characteristic odour of the onion subfamily (Allioideae).

<span class="mw-page-title-main">Hippeastreae</span> Tribe of flowering plants

Hippeastreae is a tribe of plants belonging to the subfamily Amaryllidoideae of the Amaryllis family (Amaryllidaceae). Species in this tribe are distributed in South America. Flowers are large and showy, zygomorphic, with the stamens in varying lengths, inflorescence bracts are often fused basally. The seeds are flattened, winged or D-shaped. Reported basic chromosome numbers are x= 8-13, 17, and higher. All the species in this tribe present a remarkable aesthetic interest and horticultural value.

<span class="mw-page-title-main">Amaryllidoideae</span> Subfamily of flowering plants

Amaryllidoideae is a subfamily of monocot flowering plants in the family Amaryllidaceae, order Asparagales. The most recent APG classification, APG III, takes a broad view of the Amaryllidaceae, which then has three subfamilies, one of which is Amaryllidoideae, and the others are Allioideae and Agapanthoideae. The subfamily consists of about seventy genera, with over eight hundred species, and a worldwide distribution.

<span class="mw-page-title-main">Narcisseae</span> Tribe of flowering plants

Narcisseae is a small tribe of plants belonging to the subfamily Amaryllidoideae of the Amaryllis family (Amaryllidaceae), where it forms part of the Eurasian clade, and is one of three tribes in the European (Mediterranean) clade. It contains two genera and approximately 58 species, but probably also Lapiedra. The two genera are distinguished from each other by the presence of a paraperigonium in the former.

<span class="mw-page-title-main">Galantheae</span> Tribe of flowering plants

Galantheae is a tribe of plants belonging to the subfamily Amaryllidoideae of the Amaryllis family (Amaryllidaceae). As of 2017, it contains three genera, although more were included previously. The position of the ovary is inferior.

Nina Rønsted is a Danish botanist, who is Director of Science and Conservation at The National Tropical Botanical Garden, Hawaii.

<span class="mw-page-title-main">Allioideae</span> Large subfamily of flowering plants in the family Amaryllidaceae

Allioideae is a subfamily of monocot flowering plants in the family Amaryllidaceae, order Asparagales. It was formerly treated as a separate family, Alliaceae. The subfamily name is derived from the generic name of the type genus, Allium. It is composed of about 18 genera.

<i>Allium</i> Genus of flowering plants in the family Amaryllidaceae

Allium is a genus of monocotyledonous flowering plants with hundreds of species, including the cultivated onion, garlic, scallion, shallot, leek, and chives. The generic name Allium is the Latin word for garlic, and the type species for the genus is Allium sativum which means "cultivated garlic".

<span class="mw-page-title-main">Traubiinae</span> Subtribe of flowering plants

Traubiinae is a subtribe of plants classified under the tribe Hippeastreae. It belongs to the subfamily Amaryllidoideae of the Amaryllis family (Amaryllidaceae).

<span class="mw-page-title-main">Eustephieae</span> Tribe of flowering plants

Eustephieae is a tribe, where it forms part of the Andean clade, one of two American clades.

<span class="mw-page-title-main">Crininae</span> Subtribe of flowering plants

Crininae is one of four subtribes within the tribe Amaryllideae, with a pantropical distribution (Crinum) and also sub-Saharan Africa.

References

  1. Kornienko A, Evidente A (2008). "Chemistry, biology, and medicinal potential of narciclasine and its congeners". Chem Rev. 108 (6): 1982–2014. doi:10.1021/cr078198u. PMC   2856661 . PMID   18489166.

Bibliography