Hederagenin

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Hederagenin
Hederagenin.svg
Names
IUPAC name
3β,23-Dihydroxyolean-12-en-28-oic acid
Systematic IUPAC name
(4aS,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-9-Hydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.701 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C30H48O4/c1-25(2)13-15-30(24(33)34)16-14-28(5)19(20(30)17-25)7-8-22-26(3)11-10-23(32)27(4,18-31)21(26)9-12-29(22,28)6/h7,20-23,31-32H,8-18H2,1-6H3,(H,33,34)/t20-,21+,22+,23-,26-,27-,28+,29+,30-/m0/s1 Yes check.svgY
    Key: PGOYMURMZNDHNS-MYPRUECHSA-N Yes check.svgY
  • InChI=1/C30H48O4/c1-25(2)13-15-30(24(33)34)16-14-28(5)19(20(30)17-25)7-8-22-26(3)11-10-23(32)27(4,18-31)21(26)9-12-29(22,28)6/h7,20-23,31-32H,8-18H2,1-6H3,(H,33,34)/t20-,21+,22+,23-,26-,27-,28+,29+,30-/m0/s1
    Key: PGOYMURMZNDHNS-MYPRUECHBG
  • O=C(O)[C@]35[C@H](C\2=C\C[C@@H]1[C@@]4([C@@H](CC[C@]1([C@]/2(C)CC3)C)[C@](C)(CO)[C@@H](O)CC4)C)CC(C)(C)CC5
Properties
C30H48O4
Molar mass 472.710 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Hederagenin is a triterpenoid which is a chemical constituent of the Hedera helix plant.

Contents

Hederagenin is the aglycone part of numerous saponins found in Hedera helix (common ivy), the most prevalent of these being hederacoside C and alpha-hederin. It is also one of three primary triterpenoids extracted from the Chenopodium quinoa plant categorized by the EPA as a biopesticide. [1] HeadsUp Plant Protectant is made up of approximately equal ratios of the saponin aglycones oleanolic acid, hederagenin, and phytolaccagenic acid and is intended for use as a seed treatment on tuber (e.g. potato seed pieces), legume, and cereal seeds or as a pre-plant root dip for roots of transplants, at planting, to prevent fungal growth, bacterial growth, and viral plant diseases.

Hederagenin has been found to have antidepressant-like effects in a rodent models. [2]

History

Hederagenin was discovered by L. Posselt in 1849 and named hederic acid. [3] However, Posselt was not able to isolate a pure substance or obtain an exact formula: his hederic acid was hederagenin mixed with some tannin impurity. [4]

All of these compounds share the same pentacyclic framework:

Related Research Articles

<span class="mw-page-title-main">Quinoa</span> Edible plant in the family Amaranthaceae

Quinoa is a flowering plant in the amaranth family. It is a herbaceous annual plant grown as a crop primarily for its edible seeds; the seeds are rich in protein, dietary fiber, B vitamins and dietary minerals in amounts greater than in many grains. Quinoa is not a grass but rather a pseudocereal botanically related to spinach and amaranth, and originated in the Andean region of northwestern South America. It was first used to feed livestock 5,200–7,000 years ago, and for human consumption 3,000–4,000 years ago in the Lake Titicaca basin of Peru and Bolivia.

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

Amaranthaceae is a family of flowering plants commonly known as the amaranth family, in reference to its type genus Amaranthus. It includes the former goosefoot family Chenopodiaceae and contains about 165 genera and 2,040 species, making it the most species-rich lineage within its parent order, Caryophyllales.

<i>Hedera</i> Genus of flowering plants in the family Araliaceae

Hedera, commonly called ivy, is a genus of 12–15 species of evergreen climbing or ground-creeping woody plants in the family Araliaceae, native to Western Europe, Central Europe, Southern Europe, Macaronesia, northwestern Africa and across central-southern Asia east to Japan and Taiwan.

<span class="mw-page-title-main">Glycoside</span> Molecule in which a sugar is bound to another functional group

In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of Heliconius butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body.

Saponins, also selectively referred to as triterpene glycosides, are bitter-tasting usually toxic plant-derived organic chemicals that have a foamy quality when agitated in water. They are widely distributed but found particularly in soapwort, a flowering plant, the soapbark tree and soybeans. They are used in soaps, medicines, fire extinguishers, speciously as dietary supplements, for synthesis of steroids, and in carbonated beverages. Structurally, they are glycosides, sugars bonded to another organic molecule, usually a steroid or triterpene, a steroid building block. Saponins are both water and fat soluble, which gives them their useful soap properties. Some examples of these chemicals are glycyrrhizin and quillaia, a bark extract used in beverages.

<i>Chenopodium pallidicaule</i> Species of plant

Chenopodium pallidicaule, known as cañihua, canihua or cañahua and also kaniwa, is a species of goosefoot, similar in character and uses to the closely related quinoa(Chenopodium quinoa).

<i>Stellaria media</i> Species of flowering plant (chickweed)

Stellaria media, chickweed, is an annual flowering plant in the family Caryophyllaceae. It is native to Eurasia and naturalized throughout the world, where it is a weed of waste ground, farmland and gardens. It is sometimes grown as a salad crop or for poultry consumption.

<i>Hedera helix</i> Species of flowering plant

Hedera helix, the common ivy, English ivy, European ivy, or just ivy, is a species of flowering plant of the ivy genus in the family Araliaceae, native to most of Europe and western Asia. A rampant, clinging evergreen vine, it is a familiar sight in gardens, waste spaces, and wild areas, where it grows on walls, fences, tree trunks, etc. across its native and introduced habitats. As a result of its hardy nature, and its tendency to grow readily without human assistance, ivy attained popularity as an ornamental plant, but escaped plants have become naturalised outside its native range and grow unchecked in myriad wild and cultivated areas.

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

Triterpenes are a class of terpenes composed of six isoprene units with the molecular formula C30H48; they may also be thought of as consisting of three terpene units. Animals, plants and fungi all produce triterpenes, including squalene, the precursor to all steroids.

<i>Chenopodium nuttalliae</i> Species of edible plant native to Mexico

Chenopodium nuttalliae is a species of edible plant native to Mexico. It is known by the common names huauzontle and Aztec broccoli. Other variations of the name include huauhzontle, huazontle, huanzontle, and guausoncle. It is related to other commonly-consumed plants such as quinoa, amaranth, and epazote, as well as the common American weeds goosefoot and lambsquarters. The plant grows upright branches with red tinted green leafy stems. Huauzontle stems superficially resemble baby broccoli, although the stems are much thinner, and support fewer of the leaves.

<i>Chenopodium berlandieri</i> Species of edible flowering plant

Chenopodium berlandieri, also known by the common names pitseed goosefoot, lamb's quarters, and huauzontle (Nahuatl) is an annual herbaceous plant in the family Amaranthaceae.

<i>Barringtonia acutangula</i> Species of plant

Barringtonia acutangula is a species of Barringtonia native to coastal wetlands in southern Asia and northern Australasia, from Afghanistan east to the Philippines, Queensland and the Northern Territory. Common names include freshwater mangrove, itchytree and mango-pine.

<span class="mw-page-title-main">Oleanolic acid</span> Pentacyclic chemical compound in plant leaves and fruit

Oleanolic acid or oleanic acid is a naturally occurring pentacyclic triterpenoid related to betulinic acid. It is widely distributed in food and plants where it exists as a free acid or as an aglycone of triterpenoid saponins.

<span class="mw-page-title-main">Polyscias fruticosa</span> Species of shrub

Polyscias fruticosa, or Ming aralia, is a perennial plant, dicot evergreen shrub or dwarf tree native to India. The plant grows fairly slowly but can reach up to 1 to 2 meters in height. The leaves are of a dark green pigment, glossy in texture, and are tripinnate and appear divided. Individual leaves vary from narrowly ovate to lanceolate and are about 10 cm long.

<i>Bobgunnia madagascariensis</i> Species of legume

Bobgunnia madagascariensis, also called the snake bean plant, is a species of legume in the family Fabaceae.

<i>Hedera nepalensis</i> Species of vine

Hedera nepalensis is a species of perennial Ivy native to Nepal and Bhutan, as well as Afghanistan, Pakistan, India, China, Laos, Myanmar, Thailand, and Vietnam, at altitudes of about 1000–3000 m. Plants grow up to 30 m in height, with simple leaves ranging from 2–15 cm long, and yellow flowers.

<i>Chenopodium giganteum</i> Species of flowering plant

Chenopodium giganteum, also known as tree spinach, is an annual, upright many-branched shrub with a stem diameter of up to 5 cm at the base, that can grow to a height of up to 3 m.

<i>Achyranthes aspera</i> Species of plant

Achyranthes aspera is a species of plant in the family Amaranthaceae. It is distributed throughout the tropical world. It can be found in many places growing as an introduced species and a common weed. It is an invasive species in some areas, including many Pacific Islands environments.

Momordin is one of several saponins derived from oleanolic acid, a triterpenoid. These chemical compounds are found in some plants of the genus Momordica, which includes the bitter melon and the balsam apple, as well as in other Asian herbal medicine plants such as Kochia scoparia and Ampelopsis radix.

α-Hederin Chemical compound

α-Hederin (alpha-hederin) is a water-soluble pentacyclic triterpenoid saponin found in the seeds of Nigella sativa and leaves of Hedera helix.

References

  1. BIOPESTICIDES REGISTRATION ACTION DOCUMENT, Saponins of Chenopodium quinoa.
  2. Zhou, D; Jin, H; Lin, HB; Yang, XM; Cheng, YF; Deng, FJ; Xu, JP (2010). "Antidepressant effect of the extracts from Fructus Akebiae". Pharmacology Biochemistry and Behavior. 94 (3): 488–95. doi:10.1016/j.pbb.2009.11.003. PMID   19931301.
  3. L. Posselt, "On the constituents of the seeds of ivy", Liebig's Annalen der Chemie, January 1849.
  4. John Lionel Simonsen, The Terpenes, p. 174, Cambridge University Press, 1947 OCLC   309782.