Protopanaxatriol

Last updated
Protopanaxatriol
Protopanaxatriol.svg
Names
IUPAC name
(20R)-Dammar-24-ene-3β,6α,12β,20-tetrol
Systematic IUPAC name
(1S,3aR,3bR,5S,5aR,7S,9aR,9bR,11R,11aR)-1-[(2R)-2-Hydroxy-6-methylhept-5-en-2-yl]-3a,3b,6,6,9a-pentamethylhexadecahydro-1H-cyclopenta[a]phenanthrene-5,7,11-triol
Identifiers
3D model (JSmol)
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C30H52O4/c1-18(2)10-9-13-30(8,34)19-11-15-28(6)24(19)20(31)16-22-27(5)14-12-23(33)26(3,4)25(27)21(32)17-29(22,28)7/h10,19-25,31-34H,9,11-17H2,1-8H3/t19-,20+,21-,22+,23-,24-,25-,27+,28+,29+,30+/m0/s1 X mark.svgN
    Key: SHCBCKBYTHZQGZ-DLHMIPLTSA-N X mark.svgN
  • InChI=1/C30H52O4/c1-18(2)10-9-13-30(8,34)19-11-15-28(6)24(19)20(31)16-22-27(5)14-12-23(33)26(3,4)25(27)21(32)17-29(22,28)7/h10,19-25,31-34H,9,11-17H2,1-8H3/t19-,20+,21-,22+,23-,24-,25-,27+,28+,29+,30+/m0/s1
    Key: SHCBCKBYTHZQGZ-DLHMIPLTBT
  • O[C@H]4[C@@H]1[C@H](CC[C@]1([C@]2([C@@H]([C@]3(C)[C@@H]([C@@H](O)C2)C(C)(C)[C@@H](O)CC3)C4)C)C)[C@@](O)(C)CC\C=C(/C)C
Properties
C30H52O4
Molar mass 476.742 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  verify  (what is  Yes check.svgYX mark.svgN ?)

Protopanaxatriol (PPT) is an organic compound that is an aglycone of ginsenosides, a group of steroid glycosides. [1] It is a dammarane-type tetracyclic triterpene sapogenins found in ginseng (Panax ginseng) and in notoginseng (Panax pseudoginseng).

See also

Related Research Articles

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

The Araliaceae are a family of flowering plants composed of about 43 genera and around 1500 species consisting of primarily woody plants and some herbaceous plants commonly called the ginseng family. The morphology of Araliaceae varies widely, but it is predominantly distinguishable based on its woody habit, tropical distribution, and the presence of simple umbels.

<span class="mw-page-title-main">Ginseng</span> Root of a plant used in herbal preparations

Ginseng is the root of plants in the genus Panax, such as Korean ginseng (P. ginseng), South China ginseng (P. notoginseng), and American ginseng (P. quinquefolius), characterized by the presence of ginsenosides and gintonin. Ginseng is common in the cuisines and medicines of China and Korea.

<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.

<i>Panax</i> Genus of plants

The Panax (ginseng) genus belongs to the Araliaceae (ivy) family. Panax species are characterized by the presence of ginsenosides and gintonin. Panax is one of approximately 60 plant genera with a classical disjunct east Asian and east North American distribution. Furthermore, this disjunct distribution is asymmetric as only two of the ~18 species in genus are native to North America.

<i>Panax ginseng</i> Species of flowering plant

Panax ginseng, ginseng, also known as Asian ginseng, Chinese ginseng or Korean ginseng, is a species of plant whose root is the original source of ginseng. It is a perennial plant that grows in the mountains of East Asia.

<i>Withania somnifera</i> Species of plant

Withania somnifera, known commonly as ashwagandha or winter cherry, is an evergreen shrub in the Solanaceae or nightshade family that grows in India, the Middle East, and parts of Africa. Several other species in the genus Withania are morphologically similar.

<i>Gynostemma pentaphyllum</i> Species of flowering plant

Gynostemma pentaphyllum, also called jiaogulan, is a dioecious, herbaceous climbing vine of the family Cucurbitaceae widely distributed in South and East Asia as well as New Guinea. Jiaogulan has recently been incorporated into traditional medicine.

<i>Panax pseudoginseng</i> Species of flowering plant

Panax pseudoginseng is a species of plant in the family Araliaceae, native to Nepal and Tibet. Common names include pseudoginseng, Nepal ginseng and Himalayan ginseng. Pseudoginseng belongs to the same scientific genus as ginseng. In Latin, the word panax means "cure-all", and the family of ginseng plants is one of the best-known herbs.

<i>Panax notoginseng</i> Species of flowering plant

Panax notoginseng is a species of the genus Panax, and it is commonly referred to in English as Chinese ginseng or notoginseng. In Chinese it is called tiánqī, tienchi ginseng, sānqī or sanchi, three-seven root, and mountain plant. P. notoginseng belongs to the same scientific genus as Panax ginseng. In Latin, the word panax means "cure-all", and the family of ginseng plants is one of the best-known herbs.

Nectria radicicola is a plant pathogen that is the causal agent of root rot and rusty root. Substrates include ginseng and Narcissus. It is also implicated in the black foot disease of grapevine. It is of the genus Nectria and the family Nectriaceae. N. radicicola is recognizable due to its unique anatomy, morphology, and the formation of its anamorph Cylindrocarpon desructans.

<span class="mw-page-title-main">Ginsenoside</span> Class of steroids

Ginsenosides or panaxosides are a class of natural product steroid glycosides and triterpene saponins. Compounds in this family are found almost exclusively in the plant genus Panax (ginseng), which has a long history of use in traditional medicine that has led to the study of pharmacological effects of ginseng compounds. As a class, ginsenosides exhibit a large variety of subtle and difficult-to-characterize biological effects when studied in isolation.

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

Panaxatriol is an organic compound that is an aglycone of ginsenosides, a group of steroid glycosides. It is a dammarane-type tetracyclic triterpene sapogenin found in ginseng and in notoginseng. It is formed by the dehydration of protopanaxatriol.

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

Protopanaxadiol (PPD) is an organic compound that is an aglycone of ginsenosides, a group of steroid glycosides. It is a dammarane-type tetracyclic terpene sapogenin found in ginseng and in notoginseng.

<span class="mw-page-title-main">American ginseng</span> Species of flowering plant

American ginseng is a species of flowering plant in the ivy family Araliaceae. It is native to eastern North America and introduced in China. The specific epithet quinquefolius means "five-leaved", which refers to the typical number of leaflets per leaf. It is one of a group of taxa known as "ginseng".

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

The amyrins are three closely related natural chemical compounds of the triterpene class. They are designated α-amyrin (ursane skeleton), β-amyrin (oleanane skeleton) and δ-amyrin. Each is a pentacyclic triterpenol with the chemical formula C30H50O. They are widely distributed in nature and have been isolated from a variety of plant sources such as epicuticular wax. In plant biosynthesis, α-amyrin is the precursor of ursolic acid and β-amyrin is the precursor of oleanolic acid. All three amyrins occur in the surface wax of tomato fruit. α-Amyrin is found in dandelion coffee.

Dammarenediol II synthase (EC 4.2.1.125, dammarenediol synthase, 2,3-oxidosqualene (20S)-dammarenediol cyclase, DDS, (S)-squalene-2,3-epoxide hydro-lyase (dammarenediol-II forming)) is an enzyme with systematic name (3S)-2,3-epoxy-2,3-dihydrosqualene hydro-lyase (dammarenediol-II forming). This enzyme catalyses the following chemical reaction

<i>Panax trifolius</i> Species of plant

Panax trifolius, commonly called dwarf ginseng, is a plant native to the Northeastern and Appalachian regions of North America. It is found in low mesic woods with acidic soils.

<span class="mw-page-title-main">Pseudoginsenoside F11</span> Chemical compound

Pseudoginsenoside F11 is a chemical natural product found in American ginseng but not in Asian ginseng, although it has similar properties to the Asian ginseng compound ginsenoside Rf. The molecule is a triterpenoid saponin member of the dammarane family and contains a four-ring rigid skeleton. Compounds in the ginsenoside family are found almost exclusively in plants of the genus Panax. A wide variety of difficult-to-characterize in vitro effects have been reported for the compounds in isolation. Pseudoginsenoside F11 and its derivatives are sometimes referred to as having an ocotillol-type skeleton structure.

Chinese ginseng may refer to:

<span class="mw-page-title-main">Ginsenoside Rb1</span> Chemical compound

Ginsenoside Rb1 (or Ginsenoside Rb1 or GRb1 or GRb1) is a chemical compound belonging to the ginsenoside family.

References

  1. Kang, Soo Yeon; Schini-Kerth, Valérie B.; Kim, Nak Doo (1995). "Ginsenosides of the protopanaxatriol group cause endothelium-dependent relaxation in the rat aorta". Life Sciences. 56 (19): 1577–1586. doi:10.1016/0024-3205(95)00124-o. PMID   7723586.