Elemene

Elemenes  |

(+)-α-Elemene

(−)-β-Elemene

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(−)-γ-Elemene

(−)-δ-Elemene

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Names
IUPAC names

(+)-α: (S)-1-Isopropyl-6-methyl-3-(propan-2-ylidene)-6-vinylcyclohex-1-ene
(−)-β: (1S,2S,4R)-1-Methyl-2,4-di(prop-1-en-2-yl)-1-vinylcyclohexane
(−)-γ: (3R,4R)-1-Isopropyl-4-methyl-3-(prop-1-en-2-yl)-4-vinylcyclohex-1-ene
(−)-δ: (3R,4R)-1-Isopropyl-4-methyl-3-(prop-1-en-2-yl)-4-vinylcyclohex-1-ene

Identifiers

CAS Number

* 11029-06-4 (unspecified isomer) Y
* 5951-67-7 ((+)-α) Y
* 33880-83-0 ((±)-β) Y
* 515-13-9 ((−)-β) Y
* 29873-99-2 ((−)-γ) Y
* 20307-84-0 ((−)-δ) Y

3D model (JSmol)

* (+)-α: Interactive image
* (−)-β: Interactive image
* (−)-γ: Interactive image
* (−)-δ: Interactive image

PubChem CID

* 80048 (α)
* 6918391 (β)

SMILES

* (+)-α: C[C@]1(C=C)C(C(C)C)=C/C(CC1)=C(C)/C

* (−)-β: C[C@]1(C=C)[C@H](C(C)=C)C[C@H](C(C)=C)CC1

* (−)-γ: C[C@@]1(C=C)[C@@H](C(C)=C)C=C(C(C)C)CC1

* (−)-δ: CC(C)C1=C[C@H](C(C)=C)[C@@](C)(C=C)CC1

Properties

Chemical formula

| C15H24
Molar mass | 204.357 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

Elemenes are a group of closely related natural chemical compounds found in a variety of plants. The elemenes, which include α-, β-, γ-, and δ-elemene, are structural isomers of each other and are classified as sesquiterpenes. The elemenes contribute to the floral aromas of some plants,[1][2][3] and are used as pheromones by some insects.[4]

## Applications

β-Elemene in particular has attracted scientific interest because of its prevalence in a variety of medicinal plants, such as the Chinese medicinal herb Yu Jin (郁金, Curcuma wenyujin).[5] Experiments performed in vitro show that β-elemene acts as a Rho kinase inhibitor,[6] and has anti-proliferative effects toward some cancer cell types,[7][8][9][10] indicating the possibility of its use in chemotherapy. Clinical trials in China have been conducted in which benefits for cancer treatment have been reported, and both liposome injection and oral emulsion forms of β-elemene have been approved by the China Food and Drug Administration (CFDA) as an adjuvant therapy for use in the treatment of various cancers.[11] However, Western experts have been skeptical of claims for the safety and efficacy of β-elemene, with the trials being relatively small scale,[12] and the Memorial Sloan–Kettering Cancer Center stating that "human trials conducted so far are of poor quality".[13] A Cochrane Review of the available literature concluded that "there is no evidence from randomised controlled trials to confirm or refute the effectiveness of elemene as a treatment for lung cancer".[14] A general review on beta elemene.[15]

## References

1. ↑ "Floral Compound: alpha-elemene". Pherobase.com. http://www.pherobase.com/database/floral-compounds/floral-taxa-compounds-detail-alpha-elemene.php.
2. ↑ "Floral Compound: delta-elemene". Pherobase.com. http://www.pherobase.com/database/floral-compounds/floral-taxa-compounds-detail-delta-elemene.php.
3. ↑ "Floral Compound: gamma-elemene". Pherobase.com. http://www.pherobase.com/database/floral-compounds/floral-taxa-compounds-detail-gamma-elemene.php.
4. ↑ "Semiochemical: beta-elemene". Pherobase.com. http://www.pherobase.com/database/compound/compounds-detail-beta-elemene.php.
5. ↑ "The Antitumor Efficacy of β-Elemene by Changing Tumor Inflammatory Environment and Tumor Microenvironment". BioMed Research International 2020: 6892961. 2020. doi:10.1155/2020/6892961. PMID 32149121.
6. ↑ "β-Elemene Enhances GAP-43 Expression and Neurite Outgrowth by Inhibiting RhoA Kinase Activation in Rats with Spinal Cord Injury". Neuroscience 383: 12–21. July 2018. doi:10.1016/j.neuroscience.2018.04.045. PMID 29751054.
7. ↑ "β-elemene inhibits proliferation of human glioblastoma cells through the activation of glia maturation factor β and induces sensitization to cisplatin". Oncology Reports 26 (2): 405–13. August 2011. doi:10.3892/or.2011.1276. PMID 21519795.
8. ↑ "Anti-tumor effect of beta-elemene in glioblastoma cells depends on p38 MAPK activation". Cancer Letters 264 (1): 127–34. June 2008. doi:10.1016/j.canlet.2008.01.049. PMID 18442668.
9. ↑ "Antitumor effect of beta-elemene in non-small-cell lung cancer cells is mediated via induction of cell cycle arrest and apoptotic cell death". Cellular and Molecular Life Sciences 62 (7–8): 881–93. April 2005. doi:10.1007/s00018-005-5017-3. PMID 15868411.
10. ↑ "Antiproliferative effect of beta-elemene in chemoresistant ovarian carcinoma cells is mediated through arrest of the cell cycle at the G2-M phase". Cellular and Molecular Life Sciences 62 (7–8): 894–904. April 2005. doi:10.1007/s00018-005-5027-1. PMID 15868412.
11. ↑ "Drug delivery systems for elemene, its main active ingredient β-elemene, and its derivatives in cancer therapy". International Journal of Nanomedicine 13: 6279–6296. 2018. doi:10.2147/IJN.S174527. PMID 30349250.
12. ↑ "Assessing the quality of RCTs on the effect of beta-elemene, one ingredient of a Chinese herb, against malignant tumors". Contemporary Clinical Trials 27 (1): 70–82. February 2006. doi:10.1016/j.cct.2005.07.002. PMID 16243588.
13. ↑ "About Herbs, Botanicals & Other Products: Beta-elemene". Memorial Sloan–Kettering Cancer Center. 9 August 2023. http://www.mskcc.org/cancer-care/herb/beta-elemene.
14. ↑ "Assessing the quality of RCTs on the effect of beta-elemene, one ingredient of a Chinese herb, against malignant tumors". Contemporary Clinical Trials 27 (1): 70–82. February 2006. doi:10.1016/j.cct.2005.07.002. PMID 16243588.
15. ↑ Adio, A. M. (2009), (-)-trans-B-Elemene and related compounds: occurrence, synthesis, and anticancer activity,Tetrahedron, volume 65, issue 27, 5145-5159 | https://doi.org/10.1016/j.tet.2009.04.062

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*[CID]: Compound ID