Lycopodine
(Synonyms: 石松鹼) 目录号 : GC36516
Lycopodine,一种石松 (Lycopodium clavatumspores) 孢子重要的生物活性成分,通过调节难治性前列腺癌细胞中 5-脂氧合酶 (5-lipoxygenase),极化线粒体膜电位而不调节 p53 活性来诱导细胞凋亡。 Lycopodine 通过激活 caspase-3 诱导细胞凋亡来抑制 HeLa 细胞的增殖。
Cas No.:466-61-5
Sample solution is provided at 25 µL, 10mM.
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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]. Caspase-3
Lycopodine (5.22-78.3 μg/mL; 12 hours) has 50% viability at 57.62±0.086 μg/mL and 51.46±1.43 μg/mL for PC3 and LnCaP, respectively[1].Treated with Lycopodine (74-222 mM; 12 hours), the apoptotic index is with respect to the gradual increase in doses for the PC3 and LnCaP cells[1].Lycopodine (74-222 mM; 12 hours) induces cell cycle arrest at G0/G1 phase in PC3 and LnCaP cells[1].Lycopodine (0-200 µg/mL; 48 hours) shows cytotoxicity to HeLa cells in a dose and time dependent manner. However, Lycopodine shows minimal cytotoxic effects in normal peripheral blood mononuclear cells (PBMC) even at the highest dose (200 µg/mL)[2].Lycopodine (100, 200 µg/mL; 24 hours) increases level of Bax and decreases the mitochondrial cytochrome c. This is followed by an increase in expression of cytochrome c in cytosolic fraction. Lycopodine also cleaves the caspase-3 in the total cell lysate, while the expression of Bcl-2 is down regulated[2]. Cell Viability Assay[1] Cell Line: PC3 and LnCaP cells
[1]. Bishayee K, et al. Lycopodine triggers apoptosis by modulating 5-lipoxygenase, and depolarizing mitochondrial membrane potential in androgen sensitive and refractory prostate cancer cells without modulating p53 activity: signaling cascade and drug-DNA interaction. Eur J Pharmacol. 2013 Jan 5;698(1-3):110-21. [2]. Mandal SK, et al. Lycopodine from Lycopodium clavatum extract inhibits proliferation of HeLa cells through induction of apoptosis via caspase-3 activation. Eur J Pharmacol. 2010 Jan 25;626(2-3):115-22.
Cas No. | 466-61-5 | SDF | |
别名 | 石松鹼 | ||
Canonical SMILES | O=C1[C@]2([H])[C@]34[C@@](CCCN4CCC2)([H])[C@](C[C@@H](C)C3)([H])C1 | ||
分子式 | C16H25NO | 分子量 | 247.38 |
溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg |
1 mM | 4.0424 mL | 20.2118 mL | 40.4236 mL |
5 mM | 0.8085 mL | 4.0424 mL | 8.0847 mL |
10 mM | 0.4042 mL | 2.0212 mL | 4.0424 mL |
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A transannular approach toward Lycopodine synthesis
J Antibiot (Tokyo) 2019 Jun;72(6):494-497.PMID:30792516DOI:10.1038/s41429-019-0155-2.
A transannular reaction was proposed to access the Lycopodium alkaloid Lycopodine. A key bicyclic precursor was synthesized via a ring-closing metathesis reaction. Initial evaluations of the transannular aza-Prins reaction to synthesize Lycopodine were reported and discussed.
A New Lycopodine-type Alkaloid from Lycopodium japonicum
Nat Prod Res 2016 Oct;30(19):2220-4.PMID:26912449DOI:10.1080/14786419.2016.1146885.
A new lycopodine-type alkaloid, 12β-hydroxy-acetylfawcettiine N-oxide (1), together with seven known analogues, acetyllycoposerramine M (2), Lycopodine (3), lycoclavine (4), diphaladine A (5), lycoposerramine K (6), 11β-hydroxy-12-epilycodoline (7) and fawcettiine (8), were isolated from Lycopodium japonicum. Their structures were established by mass spectrometry and 1D and 2D NMR techniques. The isolated alkaloids were assayed for their inhibition activities against acetylcholinesterase, but no inhibitory activities for the compounds were detected.
Lycopodine triggers apoptosis by modulating 5-lipoxygenase, and depolarizing mitochondrial membrane potential in androgen sensitive and refractory prostate cancer cells without modulating p53 activity: signaling cascade and drug-DNA interaction
Eur J Pharmacol 2013 Jan 5;698(1-3):110-21.PMID:23142370DOI:10.1016/j.ejphar.2012.10.041.
When the prostate cancer cells become unresponsive to androgen therapy, resistance to chemotherapy becomes imminent, resulting in high mortality. To combat this situation, Lycopodine, a pharmacologically important bioactive component derived from Lycopodium clavatum spores, was tested against hormone sensitive (LnCaP) and refractory (PC3) prostate cancer cells in vitro. This study aims to check if Lycopodine has demonstrable anti-cancer effects and if it has, to find out the possible mechanism of its action. The MTT assay was performed to evaluate the cytotoxic effect. Depolarization of mitochondrial membrane potential, cell cycle, EGF receptor activity and apoptosis were recorded by FACS; profiles of different anti- and pro-apoptotic genes and their products were studied by semi-quantitative RT-PCR, indirect-ELISA, western blotting. Drug-DNA interaction was determined by CD spectroscopy. Administration of Lycopodine down-regulated the expression of 5-lipoxygenase and the 5-oxo-ETE receptor (OXE receptor1) and EGF receptor, and caused up-regulation of cytochrome c with depolarization of mitochondrial inner membrane potential, without palpable change in p53 activity, resulting in apoptosis, cell arrest at G0/G1 stage and ultimately reduced proliferation of cancer cells; concomitantly, there was externalization of phosphotidyl serine residues. CD spectroscopic analysis revealed intercalating property of Lycopodine with DNA molecule, implicating its ability to block cellular DNA synthesis. The overall results suggest that Lycopodine is a promising candidate suitable for therapeutic use as an anti-cancer drug.
Lycopodine from Lycopodium clavatum extract inhibits proliferation of HeLa cells through induction of apoptosis via caspase-3 activation
Eur J Pharmacol 2010 Jan 25;626(2-3):115-22.PMID:19786013DOI:10.1016/j.ejphar.2009.09.033.
Crude ethanolic extract of the plant Lycopodium clavatum has long been used in complementary and alternative medicine for treating various liver ailments and Alzheimer's disease. It has also been claimed to have potential anti-cancer properties in vivo in mice chronically fed liver carcinogens, p-dimethylamino azobenzene (initiator) and phenobarbital (promoter). Incidentally, crude ethanolic extract of Lycopodium clavatum is a mixture of some 201 alkaloids. In order to ascertain if any major fraction can be attributed to have pronounced anti-cancer effect, we examined this major fraction by eluting the crude extract in petroleum ether:ethyl aetate (17:3 vol/vol;) solvent and tried to understand its underlying mechanism. Studies on morphological changes, cell viability and cytotoxicity by microscopy and FACS, Western blot and immunofluorescence of Bcl-2, Bax, cytochrome c, caspase-3 were conducted. Lycopodine was found to induce chromatin condensation, inter-nucleosomal DNA fragmentation and enhanced cell population in sub-G1 region along with increase in reactive oxygen species generation and mitochondrial membrane potential depolarization, release of cytochrome c and activation of caspase-3 which are the events closely involved in apoptosis. An overall analysis of results showed that Lycopodine considerably inhibited growth of HeLa cells which indicates its potential use in chemotherapy.
Enantioselective total synthesis of Lycopodine
J Am Chem Soc 2008 Jul 23;130(29):9238-9.PMID:18582046DOI:10.1021/ja803613w.
The first enantioselective total synthesis of Lycopodine has been completed. Key steps include a highly diastereoselective organocatalyzed cyclization of a keto sulfone to establish the key C7 and C8 stereocenters and a tandem 1,3-sulfonyl shift/intramolecular Mannich cyclization to form the tricyclic core.