Bruceanol E

Last updated
Bruceanol E
Bruceanol E Structure.svg
Names
IUPAC name
Methyl (1β,11β,12α,15β)-15-{[(2E)-3,4-dimethyl-2-pentenoyl]oxy}-1,11,12-trihydroxy-2,16-dioxo-13,20-epoxypicrasan-21-oate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
  • InChI=1S/C28H38O11/c1-11(2)12(3)8-17(30)39-19-21-27-10-37-28(21,25(35)36-6)23(33)18(31)20(27)26(5)14(9-16(27)38-24(19)34)13(4)7-15(29)22(26)32/h8,11,13-14,16,18-23,31-33H,7,9-10H2,1-6H3/b12-8+/t13-,14+,16-,18-,19-,20-,21-,22-,23+,26+,27-,28+/m1/s1
    Key: SXRILXHNZYONKW-XZXXSJTKSA-N
  • InChI=1S/C28H38O11/c1-11(2)12(3)8-17(30)39-19-21-27-10-37-28(21,25(35)36-6)23(33)18(31)20(27)26(5)14(9-16(27)38-24(19)34)13(4)7-15(29)22(26)32/h8,11,13-14,16,18-23,31-33H,7,9-10H2,1-6H3/b12-8+/t13-,14+,16-,18-,19-,20-,21-,22-,23+,26+,27-,28+/m1/s1
    Key: SXRILXHNZYONKW-XZXXSJTKSA-N
  • CC1CC(=O)C(C2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)C=C(C)C(C)C)(OC5)C(=O)OC)O)O)C)O
Properties
C28H38O11
Molar mass 550.601 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Bruceanol E is a cytotoxic quassinoid isolated from Brucea antidysenterica with potential antitumor and antileukemic properties. [1]

See also

Related Research Articles

Brucine Chemical compound

Brucine, an alkaloid closely related to strychnine, is most commonly found in the Strychnos nux-vomica tree. Brucine poisoning is rare, since it is usually ingested with strychnine, and strychnine is more toxic than brucine. In synthetic chemistry, it can be used as a tool for stereospecific chemical syntheses.

Idarubicin

Idarubicin or 4-demethoxydaunorubicin is an anthracycline antileukemic drug. It inserts itself into DNA and prevents DNA unwinding by interfering with the enzyme topoisomerase II. It is an analog of daunorubicin, but the absence of a methoxy group increases its fat solubility and cellular uptake. Similar to other anthracyclines, it also induces histone eviction from chromatin.

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

Brucea is a genus of plant in the family Simaroubaceae. It is named for the Scottish scholar and explorer James Bruce.

Cell-cycle nonspecific antineoplastic agents (CCNS) refer to a class of pharmaceuticals that act as antitumor agents at all or any phases of the cell cycle.

Arsthinol Chemical compound

Arsthinol (INN) is an antiprotozoal agent. It was synthesized for the first time in 1949 by Ernst A.H. Friedheim by complexation of acetarsol with 2,3-dimercaptopropanol and has been demonstrated to be effective against amoebiasis and yaws. It was marketed few years later by Endo Products . Among trivalent organoarsenicals, arthinol was considered as very well tolerated. Recently, it was studied for its anticancer activity.

Romidepsin

Romidepsin, also known as Istodax, is an anticancer agent used in cutaneous T-cell lymphoma (CTCL) and other peripheral T-cell lymphomas (PTCLs). Romidepsin is a natural product obtained from the bacterium Chromobacterium violaceum, and works by blocking enzymes known as histone deacetylases, thus inducing apoptosis. It is sometimes referred to as depsipeptide, after the class of molecules to which it belongs. Romidepsin is branded and owned by Gloucester Pharmaceuticals, now a part of Celgene.

<i>Wrightia antidysenterica</i> Species of plant

Wrightia antidysenterica, the coral swirl or tellicherry bark, is a flowering plant in the genus Wrightia. Wrightia antidysenterica is sometimes confused with the species Holarrhena pubescens due to a second, taxonomically invalid publication of the name Holarrhena pubescens. It has long been known in Indian Ayurvedic tradition. It is known in Sanskrit as kuṭaja or ambikā and in Sinhala it is called වල් ඉද්ද. It is also known as "white angel" in the Philippines and in Thailand it is called "พุดพิชญา" (pudpitchaya).

<i>Simarouba</i> Family of shrubs and trees

Simarouba is a genus of trees and shrubs in the family Simaroubaceae, native to the neotropics. It has been grouped in the subtribe Simaroubina along with the Simaba and Quassia genera. They have compound leaves, with between 1 and 12 pairs of alternate pinnate leaflets. Their flowers are unisexual, relatively small and arranged in large panicles. The individual flowers have between 4 and 6 sepals and petals and between 8 and 12 stamens. The fruit is a carpophore and has up to 5 drupaceous mericarps.

Bruceanol

Bruceanols are quassinoids isolated from Brucea antidysenterica.

Steganacin Chemical compound

Steganacin is an dibenzocyclooctadiene lactone, an unusual type of lignan. It exhibits some antileukemic properties. It has been isolated from Steganotaenia araliacea. (−)-Steganacin is the natural form.

Quassinoid

Quassinoids are degraded triterpene lactones of the Simaroubaceae plant family grouped into C-18, C-19, C-20, C-22 and C-25 types. The prototypical member of the group, quassin, was first described in the 19th century from plants of the genus Quassia from which it gets its name. It was isolated in 1937 and its structure elucidated in 1961.

<i>Brucea javanica</i> Species of plant

Brucea javanica is a shrub in the family Simaroubaceae. The specific epithet javanica is from the Latin, meaning "of Java". Other common names in English include Java brucea and kosam.

EICAR (antiviral)

EICAR is a drug which acts as an inhibitor of the enzyme IMP dehydrogenase. It is a nucleoside derivative which has both anti-cancer and antiviral effects, and was originally developed for the treatment of leukemia, but was unsuccessful in human clinical trials. It has broad spectrum antiviral effects with activity against pox viruses, Semliki forest virus, Junin virus, reovirus, influenza, measles virus and respiratory syncytial virus among others, although it is not active against coronaviridae such as SARS-CoV-1. This useful spectrum of activity means that EICAR and related derivatives continue to be investigated for the treatment of viral diseases.

Bruceanol A Chemical compound

Bruceanol A is a cytotoxic quassinoid isolated from Brucea antidysenterica with potential antitumor and antileukemic properties.

Bruceanol B Chemical compound

Bruceanol B is a cytotoxic quassinoid isolated from Brucea antidysenterica with potential antitumor and antileukemic properties.

Bruceanol C Chemical compound

Bruceanol C is a cytotoxic quassinoid isolated from Brucea antidysenterica with potential antitumor and antileukemic properties.

Bruceanol D Chemical compound

Bruceanol D is a cytotoxic quassinoid isolated from Brucea antidysenterica with potential antitumor and antileukemic properties.

Bruceanol F Chemical compound

Bruceanol F is a cytotoxic quassinoid isolated from Brucea antidysenterica with potential antitumor and antileukemic properties.

Bruceanol G Chemical compound

Bruceanol G is a cytotoxic quassinoid isolated from Brucea antidysenterica with potential antitumor and antileukemic properties.

Bruceanol H Chemical compound

Bruceanol H is a cytotoxic quassinoid isolated from Brucea antidysenterica with potential antitumor and antileukemic properties.

References

  1. Okano, M; Fukamiya, N; Aratani, T; Juichi, M; Lee, KH (1985). "Antitumor agents, 74. Bruceanol-A and -B, two new antileukemic quassinoids from Brucea antidysenterica". Journal of Natural Products. 48 (6): 972–5. doi:10.1021/np50042a017. PMID   3841557.