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Venenatine
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Names
IUPAC name
methyl (1R,15S,18R,19S,20S)-18-hydroxy-8-methoxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C22H28N2O4/c1-27-18-5-3-4-15-19(18)13-8-9-24-11-12-6-7-17(25)20(22(26)28-2)14(12)10-16(24)21(13)23-15/h3-5,12,14,16-17,20,23,25H,6-11H2,1-2H3/t12-,14+,16-,17-,20+/m1/s1
    Key: WMMZYEBFJWWUJX-YCSGKXEJSA-N
  • COC1=CC=CC2=C1C3=C(N2)[C@H]4C[C@H]5[C@H](CC[C@H]([C@H]5C(=O)OC)O)CN4CC3
Properties
C22H28N2O4
Molar mass 384.5
Hazards
Lethal dose or concentration (LD, LC):
176 mg/kg (mouse, intraperitoneal)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Venenatine is an indole alkaloid that was first isolated from Alstonia venenata in 1964.[1] It is also found in A. macrophylla and A. scholaris.[2] It appears to have antifungal properties[3] and has been synthesized.[4][5] Venenatine inhibits the p300 histone acetyltransferase enzyme.[6]

References

[edit]
  1. ^ Govindachari TR, Viswanathan N, Pai BR, Savitri TS (January 1964). "Chemical constituents of Alstonia venenata R.Br". Tetrahedron Letters. 5 (16): 901–906. doi:10.1016/S0040-4039(00)90405-2.
  2. ^ Tan MC, Carranza MS, Linis VC, Malabed RS, Oyong GG (31 May 2019). "Antioxidant, Cytotoxicity, and Antiophidian Potential of Alstonia macrophylla Bark". ACS Omega. 4 (5): 9488–9496. doi:10.1021/acsomega.9b00082. PMC 6648722. PMID 31460040.
  3. ^ Singh UP, Sarma BK, Mishra PK, Ray AB (2000). "Antifungal activity of venenatine, an indole alkaloid isolated from Alstonia venenata". Folia Microbiologica. 45 (2): 173–176. doi:10.1007/BF02817419. PMID 11271828.
  4. ^ Lebold TP, Wood JL, Deitch J, Lodewyk MW, Tantillo DJ, Sarpong R (2013). "A divergent approach to the synthesis of the yohimbinoid alkaloids venenatine and alstovenine". Nature Chemistry. 5 (2): 126–131. Bibcode:2013NatCh...5..126L. doi:10.1038/nchem.1528. PMC 3556932. PMID 23344433.
  5. ^ Tang M, Lu H, Zu L (2024). "Collective total synthesis of stereoisomeric yohimbine alkaloids". Nature Communications. 15 (1) 941. Bibcode:2024NatCo..15..941T. doi:10.1038/s41467-024-45140-2. PMC 10830567. PMID 38296955.
  6. ^ Magudeeswaran S, Poomani K (2020). "Binding mechanism of spinosine and venenatine molecules with p300 HAT enzyme: Molecular screening, molecular dynamics and free-energy analysis". Journal of Cellular Biochemistry. 121 (2): 1759–1777. doi:10.1002/jcb.29412. ISSN 0730-2312. PMID 31633226. Retrieved 22 May 2026.

Further reading

[edit]
  • Bhattacharya SK, Ray AB, Dutta SC (1975). "Psychopharmacological investigations of the 4-methoxyindole alkaloids of Alstonia venenata". Planta Medica. 27 (2): 164–170. Bibcode:1975PlMed..27..164B. doi:10.1055/s-0028-1097779. PMID 1121530.
  • Dhawan BN (25 January 1995). "Research properties in natural products having CNS effects". Current Science. 68 (2): 202–204. JSTOR 24096503.
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