Solanocapsine

Last updated
Solanocapsine
Solanocapsine-2D-skeletal.png
Names
IUPAC name
3β-Amino-16,23-epoxy-16α,28-seco-5α-solanidan-23β-ol
Systematic IUPAC name
(2S,4aS,3bS,6aS,6bR,7S,7aR,10R,11aS,12aR,13aS,13bR,15aS)-2-Amino-4a,6a,7,10-tetramethyldocosahydronaphtho[2′′,1′′:4′,5′]indeno[1′,2′:5,6]pyrano[3,2-b]pyridin-11a(1H)-ol
Other names
3β-Amino-22,26-epimino-16α,23-epoxy-5α,22αH,25βH-cholestan-23β-ol; (3β,5α,16α,22α,23β,25β)-3-Amino-16,23-epoxy-16,28-secosolanidan-23-ol
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C27H46N2O2/c1-15-13-27(30)24(29-14-15)16(2)23-22(31-27)12-21-19-6-5-17-11-18(28)7-9-25(17,3)20(19)8-10-26(21,23)4/h15-24,29-30H,5-14,28H2,1-4H3/t15-,16+,17+,18+,19-,20+,21+,22-,23+,24-,25+,26+,27+/m1/s1 X mark.svgN
    Key: ZPTJKUUQUDRHTL-QAQRTNARSA-N X mark.svgN
  • InChI=1/C27H46N2O2/c1-15-13-27(30)24(29-14-15)16(2)23-22(31-27)12-21-19-6-5-17-11-18(28)7-9-25(17,3)20(19)8-10-26(21,23)4/h15-24,29-30H,5-14,28H2,1-4H3/t15-,16+,17+,18+,19-,20+,21+,22-,23+,24-,25+,26+,27+/m1/s1
    Key: ZPTJKUUQUDRHTL-QAQRTNARBX
  • C[C@@H]1C[C@]2([C@@H]([C@H]([C@H]3[C@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC[C@@H]6[C@@]5(CC[C@@H](C6)N)C)C)C)NC1)O
Properties
C27H46N2O2
Molar mass 430.666
Appearancelong flat colorless prisms (ethanol-H2O) [1]
Melting point 222 °C (432 °F; 495 K) [1] 216-217 °C [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Solanocapsine is a toxic steroidal alkaloid from Solanum pseudocapsicum (Jerusalem cherry).

Related Research Articles

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

Solanum is a large and diverse genus of flowering plants, which include three food crops of high economic importance: the potato, the tomato and the eggplant. It is the largest genus in the nightshade family Solanaceae, comprising around 1,500 species. It also contains the so-called horse nettles, as well as numerous plants cultivated for their ornamental flowers and fruit.

<span class="mw-page-title-main">Heinz Fraenkel-Conrat</span>

Heinz Ludwig Fraenkel-Conrat was a biochemist, famous for his research on viruses.

<i>Solanum dulcamara</i> Species of plant

Solanum dulcamara is a species of vine in the genus Solanum of the family Solanaceae. Common names include bittersweet, bittersweet nightshade, bitter nightshade, blue bindweed, Amara Dulcis, climbing nightshade, felonwort, fellenwort, felonwood, poisonberry, poisonflower, scarlet berry, snakeberry, trailing bittersweet, trailing nightshade, violet bloom, and woody nightshade.

<span class="mw-page-title-main">Solanine</span> Glycoalkaloid poison found in the nightshade family of plants

Solanine is a glycoalkaloid poison found in species of the nightshade family within the genus Solanum, such as the potato, the tomato, and the eggplant. It can occur naturally in any part of the plant, including the leaves, fruit, and tubers. Solanine has pesticidal properties, and it is one of the plant's natural defenses. Solanine was first isolated in 1820 from the berries of the European black nightshade, after which it was named. It belongs to the chemical family of saponins.

<i>Solanum pseudocapsicum</i> Species of plant

Solanum pseudocapsicum is a nightshade species with mildly poisonous fruit. It is commonly known as the Jerusalem cherry, Madeira winter cherry, or, ambiguously, "winter cherry". These perennials can be grown decoratively as house plants, but in some areas of South Africa, India, Australia and New Zealand it is regarded as a weed.

<i>Solanum americanum</i> Species of flowering plant in the nightshade family Solanaceae

Solanum americanum, commonly known as American black nightshade, small-flowered nightshade or glossy nightshade, is a herbaceous flowering plant of wide though uncertain native range. The certain native range encompasses the tropics and subtropics of the Americas, Melanesia, New Guinea, and Australia.

<i>Solanum nigrum</i> Species of flowering plant in the nightshade family Solanaceae

Solanum nigrum, the European black nightshade or simply black nightshade or blackberry nightshade, is a species of flowering plant in the family Solanaceae, native to Eurasia and introduced in the Americas, Australasia, and South Africa. Ripe berries and cooked leaves of edible strains are used as food in some locales, and plant parts are used as a traditional medicine. Some other species may also be referred to as "black nightshade".

<i>Solanum nelsonii</i> Species of shrub

Solanum nelsonii, common names pōpolo and Nelson's horsenettle, is a partially woody sprawling shrub-like perennial plant in the family Solanaceae, part of the Solanum or nightshade genus. This poisonous plant is endemic to the Pacific Islands. It grows low in coastal sites in coral rubble to pure sand.

Heterodera tabacum is a plant pathogenic nematode affecting Jerusalem cherries.

Solanum ternatum is a species of plant in the family Solanaceae. Its natural habitat is subtropical or tropical moist montane forests.

<span class="mw-page-title-main">Polyneuridine-aldehyde esterase</span>

The enzyme polyneuridine-aldehyde esterase (EC 3.1.1.78) catalyzes the following reaction:

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

Solamargine is a cytotoxic chemical compound that occurs in plants of the family Solanaceae, such as potatoes, tomatoes, and eggplants. It has been also isolated from Solanum nigrum fungal endophyte Aspergillus flavus. It is a glycoalkaloid derived from the steroidal alkaloid solasodine.

<i>Solanum erianthum</i> Species of plant

Solanum erianthum is a species of nightshade that is native to southern North America and northern South America. It has been introduced to other parts of the world and has a nearly pantropical distribution. Common names include mullein nightshade, velvet nightshade, and salvadora. The potatoes are not the fruits of the trees, they are the leaves.

<i>Solanum seaforthianum</i> Species of flowering plant

Solanum seaforthianum, the Brazilian nightshade, is a flowering evergreen vine of the family Solanaceae native to tropical South America. As a member of the Solanum genus, it is related to such plants as the tomato and potato. It is characterized by clusters of four to seven leaves and can climb to a height of 6 m (20 ft) given enough room. It blooms in the mid to late summer with clusters of star-shaped purple inflorescence followed by scarlet marble-sized berries. The plant is highly heat resistant, but cannot tolerate frost conditions. The plant contains modest amounts of various tropane alkaloids such as atropine, scopolamine and hyoscyamine and should be considered mildly toxic and inedible. Promising molluscicidal and schistosomicidal activities were displayed for the S. seaforthianum extracts and fractions which are attributed to the glycoalkaloid content.

<i>Solanum diphyllum</i> Species of flowering plant

Solanum diphyllum, commonly known as the twoleaf nightshade, is a species of nightshade native to the Americas. It is cultivated as an ornamental plant for its clusters of dark green round fruits that turn a bright yellow when ripe.

<i>Hellinsia surinamensis</i> Species of moth

Hellinsia surinamensis is a moth of the family Pterophoridae. It is found in Suriname, Argentina, Bolivia, Colombia, Ecuador, Paraguay and Uruguay.

<i>Solanum macrocarpon</i> Species of fruit and plant

Solanum macrocarpon otherwise known as the African eggplant : añara), Surinamese eggplant or Vietnamese eggplant is a plant of the family Solanaceae. S. macrocarpon is a tropical perennial plant that is closely related to the eggplant. S. macrocarpon originated from West Africa, but is now widely distributed in Central and East Africa. The plant also grows in the Caribbean, South America, and some parts of Southeast Asia. S. macrocarpon is widely cultivated for its use as a food, its medicinal purposes, and as an ornamental plant.

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

Solanidine is a poisonous steroidal alkaloid chemical compound that occurs in plants of the family Solanaceae, such as potato and Solanum americanum. Human ingestion of solanidine also occurs via the consumption of the glycoalkaloids, α-solanine and α-chaconine, present in potatoes. The sugar portion of these glycoalkaloids hydrolyses in the body, leaving the solanidine portion. Solanidine occurs in the blood serum of normal healthy people who eat potato, and serum solanidine levels fall markedly once potato consumption ceases. Solanidine from food is also stored in the human body for prolonged periods of time, and it has been suggested that it could be released during times of metabolic stress with the potential for deleterious consequences. Solanidine is responsible for neuromuscular syndromes via cholinesterase inhibition.

<span class="mw-page-title-main">Steroidal alkaloid</span> Class of chemical compounds

Steroidal alkaloids have the basic steroidal skeleton with nitrogen-based functional groups attached to the skeleton. More specifically, they are distinguished by their tetracyclic cyclopentanoperhydrophenanthrene skeleton that marks their close relationship with sterols. They fall in two major categories: Solanum alkaloids and Veratrum alkaloids. A Steroidal alkaloid has also been found in Chonemorpha fragrans, 'chonemorphine' was used to treat intestinal infections in Wistar rats..

<span class="mw-page-title-main">Solanaceae</span> Family of flowering plants that includes tomatoes, potatoes and tobacco

The Solanaceae, or the nightshades, are a family of flowering plants that ranges from annual and perennial herbs to vines, lianas, epiphytes, shrubs, and trees, and includes a number of agricultural crops, medicinal plants, spices, weeds, and ornamentals. Many members of the family contain potent alkaloids, and some are highly toxic, but many—including tomatoes, potatoes, eggplant, bell and chili peppers—are used as food. The family belongs to the order Solanales, in the asterid group and class Magnoliopsida (dicotyledons). The Solanaceae consists of about 98 genera and some 2,700 species, with a great diversity of habitats, morphology and ecology.

References

  1. 1 2 Barger, L. G.; Fraenkel-Conrat, H. L. (1936). "337. Alkaloids from Solanum pseudocapsicum, L.". Journal of the Chemical Society. 1936: 1537–1542. doi:10.1039/JR9360001537.
  2. Schlittler, E.; Uehlinger, H. (1952). "Über das Sterinalkaloid Solanocapsin". Helvetica Chimica Acta (in German). 35 (6): 2034–2044. doi:10.1002/hlca.19520350633.