Eurycomanone

Eurycomanone
Names
	Other names Pasakbumin-A
Identifiers
CAS Number	84633-29-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	24742022Stereo differ;
PubChem CID	3069398;
UNII	X7F43HL2HB ;
CompTox Dashboard (EPA)	DTXSID101004921 ;
	InChI InChI=1S/C20H24O9/c1-7-4-10(21)13(23)17(3)9(7)5-11-18-6-28-20(27,16(17)18)12(22)8(2)19(18,26)14(24)15(25)29-11/h4,9,11-14,16,22-24,26-27H,2,5-6H2,1,3H3/t9-,11+,12+,13+,14-,16+,17+,18?,19-,20+/m0/s1 Key: UCUWZJWAQQRCOR-HVKQXNTCSA-N;
	SMILES CC1=CC(=O)[C@H]([C@]2([C@H]1C[C@@H]3C45[C@@H]2[C@@]([C@@H](C(=C)[C@@]4([C@H](C(=O)O3)O)O)O)(OC5)O)C)O;
Properties
Chemical formula	C20H24O9
Molar mass	408.403 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

Eurycomanone is a chemical compound that has been isolated from Eurycoma longifolia, also known as the longjack plant or tongkat ali.^[1] Eurycomanone is distributed throughout the plant, with the highest concentration in leaves. Researchers measured 6.0568 μg/mL in leaves, and only 0.3533 μg/mL in roots. ^[2]

Mechanism of action

Eurycomanone is thought to be central to the sex-hormone increasing effects of Eurycoma longifolia supplementation. In vitro, eurycomanone has been shown to enhance testosterone steroidogenesis through its inhibitory effects on aromatase, presumably causing testosterone production to increase to restore downstream estrogen homeostasis.^[1]

As of November 2022, there are no studies investigating the effects of isolated Eurycomanone in human subjects. However, studies investigating the effects supplementation with Eurycoma longifolia in human subjects have observed increases in free and total testosterone, with some studies showing increases or no changes in estradiol, luteinizing hormone, sex binding hormone globulin and follicle-stimulating hormone in both healthy and hypogonadism-affected men.^[3]^[4]^[5]

References

^ ^a ^b Low, Bin-Seng; Choi, Sy-Bing; Abdul Wahab, Habibah; Kumar Das, Prashanta; Chan, Kit-Lam (August 2013). "Eurycomanone, the major quassinoid in Eurycoma longifolia root extract increases spermatogenesis by inhibiting the activity of phosphodiesterase and aromatase in steroidogenesis". Journal of Ethnopharmacology. 149 (1): 201–207. doi:10.1016/j.jep.2013.06.023. PMID 23810842.
^ Jusoh, Samsiah; Ghani, Rosnani Abd.; Kadir, Wan Rasidah W Ab; Ishak, Mohamad Fakhri (October 2015). "Phytochemical Assessment of Multi-Locational Tongkat Ali (Eurycoma longifolia) in Peninsular Malaysia". Jurnal Teknologi. 77 (3). doi:10.11113/jt.v77.6011.
^ Chan, Kai Quin; Stewart, Claire; Chester, Neil; Hamzah, Sareena H.; Yusof, Ashril (May 2021). "The effect of Eurycoma Longifolia on the regulation of reproductive hormones in young males". Andrologia. 53 (4): e14001. doi:10.1111/and.14001. ISSN 1439-0272. PMID 33559971. S2CID 231868035.
^ Leisegang, Kristian; Finelli, Renata; Sikka, Suresh C.; Panner Selvam, Manesh Kumar (2022-08-04). "Eurycoma longifolia (Jack) Improves Serum Total Testosterone in Men: A Systematic Review and Meta-Analysis of Clinical Trials". Medicina (Kaunas, Lithuania). 58 (8): 1047. doi:10.3390/medicina58081047. ISSN 1648-9144. PMC 9415500. PMID 36013514.
^ Talbott, Shawn M; Talbott, Julie A; George, Annie; Pugh, Mike (2013-05-26). "Effect of Tongkat Ali on stress hormones and psychological mood state in moderately stressed subjects". Journal of the International Society of Sports Nutrition. 10 (1): 28. doi:10.1186/1550-2783-10-28. ISSN 1550-2783. PMC 3669033. PMID 23705671.

[Low_2013-1] Low, Bin-Seng; Choi, Sy-Bing; Abdul Wahab, Habibah; Kumar Das, Prashanta; Chan, Kit-Lam (August 2013). "Eurycomanone, the major quassinoid in Eurycoma longifolia root extract increases spermatogenesis by inhibiting the activity of phosphodiesterase and aromatase in steroidogenesis". Journal of Ethnopharmacology. 149 (1): 201–207. doi:10.1016/j.jep.2013.06.023. PMID 23810842.

[Jusoh_2013-2] Jusoh, Samsiah; Ghani, Rosnani Abd.; Kadir, Wan Rasidah W Ab; Ishak, Mohamad Fakhri (October 2015). "Phytochemical Assessment of Multi-Locational Tongkat Ali (Eurycoma longifolia) in Peninsular Malaysia". Jurnal Teknologi. 77 (3). doi:10.11113/jt.v77.6011.

[3] Chan, Kai Quin; Stewart, Claire; Chester, Neil; Hamzah, Sareena H.; Yusof, Ashril (May 2021). "The effect of Eurycoma Longifolia on the regulation of reproductive hormones in young males". Andrologia. 53 (4): e14001. doi:10.1111/and.14001. ISSN 1439-0272. PMID 33559971. S2CID 231868035.

[4] Leisegang, Kristian; Finelli, Renata; Sikka, Suresh C.; Panner Selvam, Manesh Kumar (2022-08-04). "Eurycoma longifolia (Jack) Improves Serum Total Testosterone in Men: A Systematic Review and Meta-Analysis of Clinical Trials". Medicina (Kaunas, Lithuania). 58 (8): 1047. doi:10.3390/medicina58081047. ISSN 1648-9144. PMC 9415500. PMID 36013514.

[5] Talbott, Shawn M; Talbott, Julie A; George, Annie; Pugh, Mike (2013-05-26). "Effect of Tongkat Ali on stress hormones and psychological mood state in moderately stressed subjects". Journal of the International Society of Sports Nutrition. 10 (1): 28. doi:10.1186/1550-2783-10-28. ISSN 1550-2783. PMC 3669033. PMID 23705671.

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