Libiguin A

Libiguin A

Libiguin A
Clinical data
Drug classPro-sexual agent
ATC code
  • None
Identifiers
  • [(1S,4R,5R,9S,10R,12R,14R,15S,16S,17R,18S,19S)-4-(furan-3-carbonyl)-18-(2-methoxy-2-oxoethyl)-4,12,17,19-tetramethyl-15-(2-methylpropanoyloxy)-7-oxo-8,11,13,20-tetraoxaheptacyclo[10.7.1.114,17.01,10.05,10.09,15.014,19]henicosan-16-yl] 2-methylpropanoate
CAS Number
PubChem CID
Chemical and physical data
FormulaC37H46O13
Molar mass698.762 g·mol−1
3D model (JSmol)
  • CC(C)C(=O)O[C@H]1[C@@]2(C[C@]34[C@]1([C@@H]5[C@]67[C@H](CC(=O)O5)[C@](CC[C@@]6([C@@]3([C@H]2CC(=O)OC)C)O[C@](O4)(O7)C)(C)C(=O)C8=COC=C8)OC(=O)C(C)C)C
  • InChI=1S/C37H46O13/c1-18(2)26(41)46-28-31(6)17-35-32(7,21(31)14-23(38)43-9)34-12-11-30(5,25(40)20-10-13-44-16-20)22-15-24(39)45-29(37(28,35)47-27(42)19(3)4)36(22,34)50-33(8,48-34)49-35/h10,13,16,18-19,21-22,28-29H,11-12,14-15,17H2,1-9H3/t21-,22+,28-,29-,30+,31+,32-,33+,34-,35+,36+,37-/m0/s1
  • Key:BFLOIRXWKQQOAJ-LDRQOQGOSA-N

Libiguin A is a naturally occurring limonoid found in Neobeguea mahafalensis, a flowering plant found in Madagascar with a long history of traditional medical use.[1][2][3][4][5] It is a derivative of phragmalin.[1] The compound has been reported to produce highly potent, strong, and long-lasting pro-sexual effects in rodents.[1][5] The semisynthesis of libiguin A from phragmalin has been described.[2] An analogue also found in Neobeguea mahafalensis, libiguin B, has similar pro-sexual effects but is far less potent in comparison.[1][2][5] Another analogue, a synthetic compound known as volufralin (LIB-01; DIC-2024), is under development for the treatment of erectile dysfunction and premature ejaculation.[6][7] Libiguin A was first described in the scientific literature by 2014.[1][2]

See also

References

  1. ^ a b c d e Razafimahefa S, Mutulis F, Mutule I, Liepinsh E, Dambrova M, Cirule H, et al. (March 2014). "Libiguins A and B: novel phragmalin limonoids isolated from Neobeguea mahafalensis causing profound enhancement of sexual activity". Planta Medica. 80 (4): 306–314. doi:10.1055/s-0033-1360390. PMID 24549927.
  2. ^ a b c d Grigorjeva L, Liepinsh E, Razafimahefa S, Yahorau A, Yahorava S, Rasoanaivo P, et al. (May 2014). "Semisynthesis of libiguin A and its analogues by trans-lactonization of phragmalin". The Journal of Organic Chemistry. 79 (9): 4148–4153. doi:10.1021/jo500318w. PMID 24716657.
  3. ^ Fossen T, Yahorau A, Yahorava S, Raharinjato F, Razafimahefa S, Rasoanaivo P, et al. (July 2016). "New Polyfunctional Phragmalin Limonoids from Neobeguea mahafalensis". Planta Medica. 82 (11–12): 1087–1095. doi:10.1055/s-0042-108741. PMID 27340794.
  4. ^ Zhang Y, Xu H (2017). "Recent progress in the chemistry and biology of limonoids". RSC Advances. 7 (56): 35191–35220. doi:10.1039/c7ra04715k. ISSN 2046-2069. 3.1.14. Neobeguea. As described in Fig. 15, 11 new limonoids, namely, dodoguin 313, dormir A–G 314–320, 108 libiguins A 321, libiguins B (a) 322 and libiguins B (b) 323, 109 were isolated from the root barks of Neobeguea mahafalensis, a medicinal plant in Madagascar. Interestingly, compounds 318, and 321–323 contained a C-16/30 d-lactone ring, which was the rst time reported in this species. [...] compound 322 exhibited a potent sexual enhancing activity.
  5. ^ a b c Hill RA, Connolly JD (December 2018). "Triterpenoids". Natural Product Reports. 35 (12): 1294–1329. doi:10.1039/c8np00029h. PMID 29993074. Neobeguea mahafalensis is the source of the phragmalin derivatives libiguin A 560 and libiguin B 561 (in equilibrium with its keto tautomer).202 These compounds are reported to have aphrodisiac properties.
  6. ^ "LIB 01". AdisInsight. 26 December 2025. Retrieved 27 January 2026.
  7. ^ Foster B (12 January 2026). "A new approach could radically change erectile dysfunction treatment". Drug Discovery News. Retrieved 27 January 2026.

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