Clubmoss

Clubmoss (common word to refer to the Lycopodium/Huperzeria genera of plants) is a collection of plants with traditional usage in promoting memory formation, and appears to have a large collection of unique alkaloids. Its main bioactive is Huperzine-A.

This page features 16 unique references to scientific papers.

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1Sources and Composition

1.1. Sources

The Lycopodium genus (of the family Lycopodiaceae) is a genus of herbs more commonly known as Clubmoss or Toothed Clubmoss, the genus (Lycopodium) is synonymous with Huperzeria in reference to the main bioactive of clubmoss being Huperzine-A (also known as shuangyiping[1]); other less common synonyms for this plant include Devil's Ash, Devil's Claw, or Ground Pine.[2]

The related herb Lycopodium serratum appears to be a traditional chinese medicine for memory[3] and the overall genus includes the species of serratum or serrata, alpinum, annotinum, clavatum, complanatum subspecies chamaecyparissus, obscurum, and selago.[2]

The genera of Lycopodium (also known as Huperzeria) is traditionally used for memory improvement and cognition, and several species of this plant appear to have traditional usage

1.2. Composition

Plants of the Lycopodium genera tend to contain (species stated if only found in those species, otherwise the compound has been found in various species and is thought to be general):

  • Huperzine-A (shuangyiping; commonly seen as the main bioactive)

  • The C16N alkaloids lycopodane, lycopodine, alopecurane, fawcettimane, fawcettidane, serratinane and magellanane[4][5]

  • Lycoflexine and lycoposerramine[5]

  • Lobscurinol and epilobscurinol, as well as lycobscurines A-C (Lycopodium obscurum)[6][7]

  • The C16N2 alkaloids flabellidane, phlegmarane and cernuane[8][4]

  • Lycopoclavamine A (Lycopodium clavatum)[9]

  • Lycoposquarrosamine-A[9]

  • Lycospidine A[10] as well as Lyconadins D and E (from Lycopodium complanatum)[11]

  • Complanadine alkaloids, including Complanadine A,[12] B,[13], C.[14] D,[14] and E[11]

  • Ferulic Acid (0.443% dry weight)[15]

There appears to be a large amount of structurally unique alkaloids in this plant. Although their bioactivity is not completely elucidated right now, they are unique to the genera of Lycopodium/Huperzeria and there is more than just Huperzine-A


2Neurology

2.1. Cholinergic Neurotransmission

2.2. Neurogenesis

Complanadine structures from lycopodium complanatum have been found to induce mRNA for NGF at a concentration of 100μM by 3.9 (complanadine A), 2.3 (complanadine B), 2.4 (complanadine D), and 2.8-fold (complanadine E).[11] This has been reported previously with complanadines C and D.[14]

Complanadine structures (unique to lycopodium complanatum) may increase NGF levels, but this occurs at quite a high concentration and may not be practically relevant for supplementation of the plant


3Inflammation and Immunology

3.1. Interventions

A study using fractions of Lycopodium clavatum in a mouse model of acetic-acid induced capillary permeability increases, it was found that the most active fragment (500mg/kg chloroform extract causing 32.1% inhibition) was less potent than the reference drug of indomethacin at 10mg/kg (44.6% inhibition).[2] This fraction was mostly (84.5%) lycopodine.[2]

Potential anti-inflammatory effects, but seems pretty weak relative to reference drugs and requires quite a high dosage as well


4Interactions with Aesthetics

4.1. Skin

Lycopodium clavatum appears to have traditional usage in Turkey for wound healing properties[2] and has usage for burn healing as well.[16]

Scientific Support & Reference Citations

References

  1. Tang XC Huperzine A (shuangyiping): a promising drug for Alzheimer's disease. Zhongguo Yao Li Xue Bao. (1996)
  2. Orhan I, et al. Appraisal of anti-inflammatory potential of the clubmoss, Lycopodium clavatum L. J Ethnopharmacol. (2007)
  3. Traditional Chinese medicines and new drug development.
  4. Ayer WA The lycopodium alkaloids. Nat Prod Rep. (1991)
  5. Itoh N, et al. Total syntheses of (±)-fawcettimine, (±)-fawcettidine, (±)-lycoflexine, and (±)-lycoposerramine-q. Chemistry. (2013)
  6. Pan K, Luo JG, Kong LY Three new Lycopodium alkaloids from Lycopodium obscurum. J Asian Nat Prod Res. (2013)
  7. Some new Lycopodium alkaloids.
  8. New phlegmarane-type, cernuane-type, and quinolizidine alkaloids from two species of Lycopodium.
  9. Ten new fawcettimine-related alkaloids from three species of Lycopodium.
  10. Cheng JT, et al. Lycospidine A, a New Type of Lycopodium Alkaloid from Lycopodium complanatum. Org Lett. (2013)
  11. Ishiuchi K, et al. Lyconadins D and E, and complanadine E, new Lycopodium alkaloids from Lycopodium complanatum. Bioorg Med Chem. (2011)
  12. Total Synthesis of (+)-Complanadine A Using an Iridium-Catalyzed Pyridine C-H Functionalization.
  13. Complanadine B, obscurumines A and B, new alkaloids from two species of Lycopodium.
  14. Ishiuchi K, et al. Complanadines C and D, new dimeric alkaloids from Lycopodium complanatum. Bioorg Med Chem. (2007)
  15. A HPTLC method for the identification of ferulic acid from Lycopodium clavatum.
  16. A preliminary survey of traditional medicinal plants in the west coast and interior of Saba.