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Elemene

From Wikipedia, the free encyclopedia
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
KEGG
UNII
  • ((−)-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
  • (+)-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
C15H24
Molar mass204.357 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Elemenes are a group of closely related naturalchemical compounds found in a variety of plants. The elemenes, which include α-, β-, γ-, and δ-elemene, arestructural isomers of each other and are classified assesquiterpenes. 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 theChinese medicinal herb Yu Jin (郁金,Curcuma wenyujin).[5] Experiments performedin vitro show that β-elemene acts as aRho kinase inhibitor,[6] and hasanti-proliferative effects toward somecancer cell types,[7][8][9][10] indicating the possibility of its use inchemotherapy.Clinical trials in China have been conducted in which benefits for cancer treatment have been reported, and bothliposome injection and oralemulsion forms of β-elemene have been approved by theChina Food and Drug Administration (CFDA) as anadjuvant 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 theMemorial Sloan–Kettering Cancer Center stating that "human trials conducted so far are of poor quality".[13] ACochrane 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 ofβ-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.PMID 15868411.S2CID 34767648.
  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.PMID 15868412.S2CID 20587371.
  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
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