Beta-elemene

Beta-elemene
Compound Structure:
Synonyms: BETA-ELEMENE;(-)-beta-Elemene;beta-Elemen;Levo-beta-elemene;Elemene;(1S,2S,4R)-1-methyl-2,4-di(prop-1-en-2-yl)-1-vinylcyclohexane;2,4-Diisopropenyl-1-methyl-1-vinylcyclohexane;b-elemene;beta-Elemene, (-)-;CHEBI:62855;Levo-b-elemene
Compound ID: NMPC-661
PubChem ID:

6918391

Molecular Formula: C15H24
Canonical SMILES: CC(=C)C1CCC(C(C1)C(=C)C)(C)C=C
InChIKey: OPFTUNCRGUEPRZ-QLFBSQMISA-N
About the compound:

Beta-elemene, a compound predominantly found in plants such as celery, mint, and various others used in traditional medicine, has garnered attention for its potential therapeutic applications, especially in cancer treatment. While not typically used as a dietary supplement in its pure form, some cancer patients turn to herbs high in beta-elemene as part of their treatment regimen. Laboratory studies have shown that beta-elemene can inhibit the growth of cancer cells through various mechanisms. However, human studies conducted so far have been poorly designed and provide insufficient evidence to conclusively determine its effectiveness. Some studies suggest an improvement in the quality of life for cancer patients, but more research is required to confirm these findings. In addition to its potential anti-cancer properties, beta-elemene has also been found to inhibit human sperm function in vitro, affecting sperm vitality. The clinical significance of this effect remains unknown. Beta-elemene has particularly piqued scientific interest due to its presence in numerous medicinal plants, including the Chinese medicinal herb Yu Jin (Curcuma wenyujin). In vitro experiments have demonstrated that beta-elemene acts as a Rho kinase inhibitor and exhibits anti-proliferative effects on certain cancer cell types. This suggests potential applications in chemotherapy. In China, clinical trials have reported benefits for cancer treatment, leading to the approval of beta-elemene in forms like liposome injection and oral emulsion by the China Food and Drug Administration (CFDA) for adjunct therapy in various cancers. However, there is skepticism among Western experts regarding the safety and efficacy of beta-elemene, largely due to the small scale of these trials. Institutions like the Memorial Sloan–Kettering Cancer Center have commented on the poor quality of the human trials conducted so far. Furthermore, a Cochrane Review evaluating the available literature concluded that there is no definitive evidence from randomized controlled trials to support or refute the effectiveness of elemene as a treatment for lung cancer.

1. Peng X, Zhao Y, Liang X, et al. Assessing the quality of RCTs on the effect of beta-elemene, one ingredient of a Chinese herb, against malignant tumors. Contemp Clin Trials. Feb 2006;27(1):70-82.

2. Zheng S, Yang H, Zhang S, et al. Initial study on naturally occurring products from traditional Chinese herbs and vegetables for chemoprevention. J Cell Biochem Suppl. 1997;27:106-112.

3. Yao YQ, Ding X, Jia YC, et al. Anti-tumor effect of beta-elemene in glioblastoma cells depends on p38 MAPK activation. Cancer Lett. Jun 8 2008;264(1):127-134.

https://en.wikipedia.org/wiki/Elemene


Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

204.35 g/mol

XLogP3-AA

6.1

Hydrogen Bond Donor Count

0

Hydrogen Bond Acceptor Count

0

Rotatable Bond Count

3

Exact Mass

204.187800766 g/mol

Monoisotopic Mass

204.187800766 g/mol

Topological Polar Surface Area

0Ų

Heavy Atom Count

15

Formal Charge

0

Complexity

284

Isotope Atom Count

0

Defined Atom Stereocenter Count

3

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Source: PubChem

Source Species: Gmelina arborea
Pachira glabra
Senna podocarpa
Solanum nigrum
Synedrella nodiflora
Tithonia diversifolia
Cymbopogon citratus
Zingiber officinale
Araucaria cunninghamii
Brachystegia eurycoma
Hyparrhenia rufa
Eugenia uniflora
Centratherum punctatum
Morinda lucida
Murraya Koenigii
Plumeria alba
Pteris togoensis
Pyrenacantha staudtii
Tecoma stans
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