| Identification | Back Directory | [Name]
lycopodine | [CAS]
466-61-5 | [Synonyms]
lycopodine
(15R)-15-Methyllycopodan-5-one
1,9-Ethanobenzo[i]quinolizin-14-one, dodecahydro-11-methyl-, (1S,8aR,9S,11R,12aR)- | [Molecular Formula]
C16H25NO | [MDL Number]
MFCD01632777 | [MOL File]
466-61-5.mol | [Molecular Weight]
247.38 |
| Chemical Properties | Back Directory | [Melting point ]
114-115°; mp (racemate) 130-131° | [alpha ]
D -24° (alc) | [Boiling point ]
125 °C(Press: 0.2 Torr) | [density ]
1.18 g/cm3 | [storage temp. ]
Store at -20°C | [solubility ]
Soluble in DMSO | [pka]
9.36±0.40(Predicted) | [optical activity]
-24.521 (c 1.1, ethanol) |
| Hazard Information | Back Directory | [Description]
This alkaloid has, so far, been discovered in all Lycopodium species with the
exception of L. saururus Lam. It was first obtained by B6deker who assigned to
it the formula C32Hs203N2, altered to that given by Achmatowicz and Uzieblo
and confirmed by Manske and Marion. It forms colourless prisms from Et20 and
has [α]20D - 9.01 ° (Me2CO). It yields crystalline salts and derivatives: the perchlorate, m.p. 276°C; methochloride, m.p. 238-240°C, methiodide, m.p. 335-
7°C and a hydrazone, mop. 20B-2l0°C. According to Bodeker it also yields a
crystalline hydrochloride and aurichloride.
Even under pressure at 200°C in the presence of Raney Ni, the base cannot be
hydrogenated. On selenium dehydrogenation, a complex mixture of bases is
formed from which 7 -methylquinoline and 5:7 -dimethylquinoline have been
identified. 7 -methylquinoline is also stated to be formed when the base is heated
with palladium as catalyst. A stereospecific total synthesis of the (±)-form has
been described. | [Uses]
Lycopodine, a pharmacologically important bioactive component derived from Lycopodium clavatumspores, triggers apoptosis by modulating 5-lipoxygenase, and depolarizing mitochondrial membrane potential in refractory prostate cancer cells without modulating p53 activity[1]. Lycopodine inhibits proliferation of HeLa cells through induction of apoptosis via caspase-3 activation[2]. | [Definition]
ChEBI: Lycopodine is a quinolizidine alkaloid. It derives from a hydride of a lycopodane. | [IC 50]
Caspase-3; 5-Lipoxygenase | [References]
Bodeker., Annalen., 208,363 (1881)
Achmatowicz, Uzieblo., Rocz. Chern., 18,89 (1938)
Manske, Marion., Can. 1. Res., 20B, 87 (1942)
Marion, Manske., ibid, 20B, 153 (1942)
Manske, Marion., 1. Arner. Chern. Soc., 69,2126 (1947)
Anet., Tetrahedron Lett., 20, 13 (1960)
Harrison et al., Can. 1. Chern., 39,2086 (1961) |
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