Loganin

Last updated
Loganin
Loganin structure.svg
Loganin 3D BS.png
Names
IUPAC name
Methyl (1S,4aS,6S,7R,7aS)-1-(β-D-glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Systematic IUPAC name
Methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Other names
Loganoside
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.038.529 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 242-398-0
KEGG
PubChem CID
UNII
  • InChI=1S/C17H26O10/c1-6-9(19)3-7-8(15(23)24-2)5-25-16(11(6)7)27-17-14(22)13(21)12(20)10(4-18)26-17/h5-7,9-14,16-22H,3-4H2,1-2H3/t6-,7+,9-,10+,11+,12+,13-,14+,16-,17-/m0/s1
    Key: AMBQHHVBBHTQBF-UOUCRYGSSA-N
  • InChI=1/C17H26O10/c1-6-9(19)3-7-8(15(23)24-2)5-25-16(11(6)7)27-17-14(22)13(21)12(20)10(4-18)26-17/h5-7,9-14,16-22H,3-4H2,1-2H3/t6-,7+,9-,10+,11+,12+,13-,14+,16-,17-/m0/s1
    Key: AMBQHHVBBHTQBF-UOUCRYGSBL
  • C[C@H]1[C@H](C[C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
Properties
C17H26O10
Molar mass 390.385 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Loganin is one of the best-known of the iridoid glycosides. It is named for the Loganiaceae, having first been isolated from the seeds of a member of that plant family, namely those of Strychnos nux-vomica . It also occurs in Alstonia boonei (Apocynaceae), [1] a medicinal tree of West Africa and in the medicinal/entheogenic shrub Desfontainia spinosa (Columelliaceae) native to Central America and South America.

Biosynthesis

Loganin is formed from loganic acid by the enzyme loganic acid O-methyltransferase (LAMT). Loganin then becomes a substrate for the enzyme secologanin synthase (SLS) to form secologanin, a secoiridoid monoterpene found as part of ipecac and terpene indole alkaloids.

Related Research Articles

<span class="mw-page-title-main">Apocynaceae</span> Dogbane and oleander family of flowering plants

Apocynaceae is a family of flowering plants that includes trees, shrubs, herbs, stem succulents, and vines, commonly known as the dogbane family, because some taxa were used as dog poison Members of the family are native to the European, Asian, African, Australian, and American tropics or subtropics, with some temperate members. The former family Asclepiadaceae is considered a subfamily of Apocynaceae and contains 348 genera. A list of Apocynaceae genera may be found here.

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

Alstonia is a widespread genus of evergreen trees and shrubs, of the family Apocynaceae. It was named by Robert Brown in 1811, after Charles Alston (1685–1760), professor of botany at Edinburgh from 1716 to 1760.

<i>Triosteum</i> Genus of flowering plants in the honeysuckle family Caprifoliaceae

Triosteum, commonly known in American English as horse-gentian or, less commonly, feverwort, and, in Standard Chinese as 莛子藨属, is a genus of flowering plants belonging to the family Caprifoliaceae. A genus of six species in total, it has three species native to North America, and three more in eastern Asia.

<span class="mw-page-title-main">Indole alkaloid</span> Class of alkaloids

Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known different compounds, it is one of the largest classes of alkaloids. Many of them possess significant physiological activity and some of them are used in medicine. The amino acid tryptophan is the biochemical precursor of indole alkaloids.

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

Iridoids are a type of monoterpenoids in the general form of cyclopentanopyran, found in a wide variety of plants and some animals. They are biosynthetically derived from 8-oxogeranial. Iridoids are typically found in plants as glycosides, most often bound to glucose.

In enzymology, a loganate O-methyltransferase is an enzyme that catalyzes the chemical reaction

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

Camptothecin (CPT) is a topoisomerase inhibitor. It was discovered in 1966 by M. E. Wall and M. C. Wani in systematic screening of natural products for anticancer drugs. It was isolated from the bark and stem of Camptotheca acuminata, a tree native to China used in traditional Chinese medicine. It has been used clinically more recently in China for the treatment of gastrointestinal tumors. CPT showed anticancer activity in preliminary clinical trials, especially against breast, ovarian, colon, lung, and stomach cancers. However, it has low solubility and adverse effects have been reported when used therapeutically, so synthetic and medicinal chemists have developed numerous syntheses of camptothecin and various derivatives to increase the benefits of the chemical, with good results. Four CPT analogues have been approved and are used in cancer chemotherapy today, topotecan, irinotecan, belotecan, and trastuzumab deruxtecan. Camptothecin has also been found in other plants including Chonemorpha fragrans.

<i>Alstonia constricta</i> Species of tree

Alstonia constricta, commonly known as quinine bush or bitterbark, is an endemic Australian endemic shrub or small tree of the family Apocynaceae.

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

Boonein is an iridoid isolated from Alstonia boonei, a medicinal tree of West Africa.

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

Nareline is a bio-active alkaloid isolated from Alstonia boonei, a medicinal tree of West Africa.

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

Picrinine is a bio-active alkaloid from Alstonia boonei, a medicinal tree of West Africa.

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

Scholarine is an alkaloid isolated initially from Alstonia scholaris by Banerji and Siddhanta. Subsequently, it was obtained from the West African tree Alstonia boonei. The derivative N-Formylscholarine has been isolated from the fruit pods of Alstonia scholaris.

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

Pseudoakuammigine is a bio-active alkaloid from Alstonia boonei, a medicinal tree from West Africa.

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

Picralinal is a bio-active alkaloid from Alstonia scholaris, a medicinal tree of West Africa.

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

Scholaricine is an alkaloid that has been isolated from Alstonia boonei, a tree of West Africa.

Alstonia boonei is a very large, deciduous, tropical-forest tree belonging to the Dogbane Family (Apocynaceae). It is native to tropical West Africa, with a range extending into Ethiopia and Tanzania. Its common name in the English timber trade is cheese wood, pattern wood or stool wood while its common name in the French timber trade is emien.

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

Tabersonine is a terpene indole alkaloid found in the medicinal plant Catharanthus roseus and also in the genus Voacanga. Tabersonine is hydroxylated at the 16 position by the enzyme tabersonine 16-hydroxylase (T16H) to form 16-hydroxytabersonine. The enzyme leading to its formation is currently unknown. Tabersonine is the first intermediate leading to the formation of vindoline one of the two precursors required for vinblastine biosynthesis.

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

Loganic acid is an iridoid. Loganic acid is synthesized from 7-deoxyloganic acid by the enzyme 7-deoxyloganic acid hydroxylase (7-DLH). It is a substrate for the enzyme loganate O-methyltransferase for the production of loganin.

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

Harpagoside is a natural product found in the plant Harpagophytum procumbens, also known as devil's claw. It is the active chemical constituent responsible for the medicinal properties of the plant, which have been used for centuries by the Khoisan people of southern Africa to treat diverse health disorders, including fever, diabetes, hypertension, and various blood related diseases.

<i>Alstonia congensis</i> Species of plant

Alstonia congensis, is a tree within the Apocynaceae family and one of two African species within the Alstonia genus, the other being the Alstonia boonei De Wild. Both have similar morphological characteristics.

References

  1. Adotey, J. P.; Adukpo, G. E.; Opoku-Boahen, Y.; Armah, F. A. (2012). "A Review of the Ethnobotany and Pharmacological Importance of Alstonia boonei De Wild (Apocynaceae)". ISRN Pharmacology. 2012: 587160. doi:10.5402/2012/587160. PMC   3413980 . PMID   22900200.