Elemene

Elemenes  |

(+)-α-Elemene

(−)-β-Elemene

|

(−)-γ-Elemene

(−)-δ-Elemene

|

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
* ((−)-β): 515-13-9 Y
* (±)-β: 33880-83-0 Y
* (−)-γ: 29873-99-2 Y
* (−)-δ: 20307-84-0 Y

3D model (JSmol)

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

ChEBI |

* ((−)-β): CHEBI:62855
* (±)-β: CHEBI:62854

ChEMBL |

* ((−)-β): ChEMBL448502

ChemSpider |

* (±)-β: 5293588
* (−)-γ: 4937571

DrugBank |

* ((−)-β): DB18097

KEGG |

* (±)-β: C17094

PubChem CID

* 80048 (α)
* ((−)-β): 6918391

UNII |

* (±)-β: 2QG8CX6LXD

CompTox Dashboard (EPA)

* DTXSID10149196
* ((−)-β): DTXSID60881211
* (±)-β: DTXSID40865690

InChI

* ((−)-β): InChI=1S/C15H24/c1-7-15(6)9-8-13(11(2)3)10-14(15)12(4)5/h7,13-14H,1-2,4,8-10H2,3,5-6H3/t13-,14+,15-/m1/s1

Key: OPFTUNCRGUEPRZ-QLFBSQMISA-N

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

Chemical compound

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

[edit]

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

[edit]

1. ^ "Floral Compound: alpha-elemene". Pherobase.com.
2. ^ "Floral Compound: delta-elemene". Pherobase.com.
3. ^ "Floral Compound: gamma-elemene". Pherobase.com.
4. ^ "Semiochemical: beta-elemene". Pherobase.com.
5. ^ Xie Q, Li F, Fang L, Liu W, Gu C (2020). "The Antitumor Efficacy of β-Elemene by Changing Tumor Inflammatory Environment and Tumor Microenvironment". BioMed Research International. 2020: 6892961. doi:10.1155/2020/6892961. PMC 7054771. PMID 32149121.
6. ^ Wang J, Li H, Yao Y, Ren Y, Lin J, Hu J, et al. (July 2018). "β-Elemene Enhances GAP-43 Expression and Neurite Outgrowth by Inhibiting RhoA Kinase Activation in Rats with Spinal Cord Injury". Neuroscience. 383: 12–21\. doi:10.1016/j.neuroscience.2018.04.045. PMID 29751054. S2CID 21735344.
7. ^ Zhu T, Xu Y, Dong B, Zhang J, Wei Z, Xu Y, Yao Y (August 2011). "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\. doi:10.3892/or.2011.1276. PMID 21519795.
8. ^ Yao YQ, Ding X, Jia YC, Huang CX, Wang YZ, Xu YH (June 2008). "Anti-tumor effect of beta-elemene in glioblastoma cells depends on p38 MAPK activation". Cancer Letters. 264 (1): 127–34\. doi:10.1016/j.canlet.2008.01.049. PMID 18442668.
9. ^ Wang G, Li X, Huang F, Zhao J, Ding H, Cunningham C, et al. (April 2005). "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\. doi:10.1007/s00018-005-5017-3. PMC 11924554. PMID 15868411. S2CID 34767648.7–8&rft.pages=881-93&rft.date=2005-04&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11924554#id-name=PMC&rft_id=https://api.semanticscholar.org/CorpusID:34767648#id-name=S2CID&rft_id=info:pmid/15868411&rft_id=info:doi/10.1007/s00018-005-5017-3&rft.aulast=Wang&rft.aufirst=G&rft.au=Li,+X&rft.au=Huang,+F&rft.au=Zhao,+J&rft.au=Ding,+H&rft.au=Cunningham,+C&rft.au=Coad,+JE&rft.au=Flynn,+DC&rft.au=Reed,+E&rft.au=Li,+QQ&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11924554&rfr_id=info:sid/en.wikipedia.org:Elemene" class="Z3988">
10. ^ Li X, Wang G, Zhao J, Ding H, Cunningham C, Chen F, et al. (April 2005). "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\. doi:10.1007/s00018-005-5027-1. PMC 11924550. PMID 15868412. S2CID 20587371.7–8&rft.pages=894-904&rft.date=2005-04&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11924550#id-name=PMC&rft_id=https://api.semanticscholar.org/CorpusID:20587371#id-name=S2CID&rft_id=info:pmid/15868412&rft_id=info:doi/10.1007/s00018-005-5027-1&rft.aulast=Li&rft.aufirst=X&rft.au=Wang,+G&rft.au=Zhao,+J&rft.au=Ding,+H&rft.au=Cunningham,+C&rft.au=Chen,+F&rft.au=Flynn,+DC&rft.au=Reed,+E&rft.au=Li,+QQ&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11924550&rfr_id=info:sid/en.wikipedia.org:Elemene" class="Z3988">
11. ^ Zhai B, Zeng Y, Zeng Z, Zhang N, Li C, Zeng Y, et al. (2018). "Drug delivery systems for elemene, its main active ingredient β-elemene, and its derivatives in cancer therapy". International Journal of Nanomedicine. 13: 6279–6296\. doi:10.2147/IJN.S174527. PMC 6186893. PMID 30349250.
12. ^ Peng X, Zhao Y, Liang X, Wu L, Cui S, Guo A, Wang W (February 2006). "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\. 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.
14. ^ Peng X, Zhao Y, Liang X, Wu L, Cui S, Guo A, Wang W (February 2006). "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\. 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

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency