EFSA Compendium of Botanicals

Draft - work in progress

Huperzia serrata (Thunb.) Trevis. // Lycopodium serratum Thunb.

Family:: Lycopodiaceae
Approval state:: Approved
Number of articles retrieved:: 974
Number of processed references:: 7

Compositions

#1: Alkaloids (1-methyllycodine, 6 beta-Hydroxyhuperzine A, 8 alpha-Hydroxy-15,16-dehydro-des-N-methyl-alpha-obscurine, N-Methyl-16-hydroxyhuperzine B, N-Methylhuperzine A) in aerial parts #2: Huperzine A (dried herb) #3: Huperzine B (dried herb) #4: Huperzine A (stems) #5: quinolizidine alkaloid derivative: 6 alpha,11alpha-dihydroxylycopodine, lycoposerramine K (Stems) #6: Huperzine A (dried herb) #7: Huperzine B (dried herb) #8: lycopodine derivatives: lycopodine, huperserramines A, B, C, lycopodine-6a,11a-diol, lycopodine-6a-ol, lycoposerramine H, -I -M, -K, -W, -R, phlegmariuine, diphaladine, luciduline (whole plant) #9: huperzine B (whole plant) #10: huperzine M (whole plant) #11: huperzine A (whole plant) #12: Lycodine (unspecified) #13: Lycopodium alkaloids derivative: phlegmarine, fawcettimine (unspecified)

Endpoint Studies

#1: fever, nausea, fatigue and elevated liver enzymes #2: huperzine A displayed potent α-glucosidase inhibitory activity (IC50 20 μM) in S. cerevisiae #3: huperzine B displayed potent α-glucosidase inhibitory activity (IC50 20 μM) in S. cerevisiae #4: lycopodine-6a,11a-diol displayed potent α-glucosidase inhibitory activity (IC50 148.1 μM) in S. cerevisiae

Genotoxicity

Composition #1: Liu, Yu-Chen., Zhang, Zhi-Jun., Su, Jia., Peng, Li-Yan., Pan, Lu-Tai., Wu, Xing-De., Zhao, Qin-Shi. Lycodine-Type Lycopodium Alkaloids from the Whole Plants of Huperzia serrata. . natural products and bioprospecting, 2017 . DOI: 10.1007/s13659-017-0140-z. [DOI link]

Language:

English (en)
Plant part:

Aerial part of plants (as part-nature) (A166F)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

EtOH (60%)
Substance:

Alkaloids (RF-00004360-PAR)
Additional substance description:

1-methyllycodine,
Analytical method code:

Nuclear Magnetic Resonance (NMR) (F061A)
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

Alkaloids (1-methyllycodine, 6 beta-Hydroxyhuperzine A, 8 alpha-Hydroxy-15,16-dehydro-des-N-methyl-alpha-obscurine, N-Methyl-16-hydroxyhuperzine B, N-Methylhuperzine A) in aerial parts

Composition #2: Li, XN., Ma, RY., Su, HH., Sun, HH., Ma, GH., Su, ZG., Zha, SH. Rapid purification of huperzine A and B with two polystyrene based resins by preparative low-pressure liquid chromatography . journal of liquid chromatography & related technologies, 2006, vol. 29, no. 4, p. 569–582. DOI: 10.1080/10826070500479302. [DOI link]

Language:

English (en)
Plant part:

Unspecified (A07XD)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

1% H2SO4
Substance:

huperzine A (RF-00003428-PAR)
Analytical method code:

High Performance Liquid Chromatography (HPLC)/Liquid Chromatography (LC) (F018A)
Result unit:

Milligram/litre (G062A)
Result expression:

Dry matter (B002A)
Result type:

Numerical Value (VAL)
Value (concentration, content):

12.46
Internal remarks:

Huperzine A (dried herb)

Composition #3: Li, XN., Ma, RY., Su, HH., Sun, HH., Ma, GH., Su, ZG., Zha, SH. Rapid purification of huperzine A and B with two polystyrene based resins by preparative low-pressure liquid chromatography . journal of liquid chromatography & related technologies, 2006, vol. 29, no. 4, p. 569–582. DOI: 10.1080/10826070500479302. [DOI link]

Language:

English (en)
Plant part:

Unspecified (A07XD)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

1% H2SO4
Substance:

huperzine B (RF-00003429-PAR)
Analytical method code:

High Performance Liquid Chromatography (HPLC)/Liquid Chromatography (LC) (F018A)
Result unit:

Milligram/litre (G062A)
Result expression:

Dry matter (B002A)
Result type:

Numerical Value (VAL)
Value (concentration, content):

5.66
Internal remarks:

Huperzine B (dried herb)

Composition #4: Shan, Wei-Guang., Ren, Feng-Yun., Ying, You-Min., Tong, Cui-Ping., Zhan, Zha-Jun. A new lycopodine alkaloid from Huperzia serrata. journal of chemical research, 2012, no. 1, p. 15–16. DOI: 10.3184/174751912X13249872110014. [DOI link]

Language:

English (en)
Plant part:

Stem / stalk (as part-nature) (A067S)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Substance:

huperzine A (RF-00003428-PAR)
Analytical method code:

Nuclear Magnetic Resonance (NMR) (F061A)
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

Huperzine A (stems)

Composition #5: Shan, Wei-Guang., Ren, Feng-Yun., Ying, You-Min., Tong, Cui-Ping., Zhan, Zha-Jun. A new lycopodine alkaloid from Huperzia serrata. journal of chemical research, 2012, no. 1, p. 15–16. DOI: 10.3184/174751912X13249872110014. [DOI link]

Language:

English (en)
Plant part:

Stem / stalk (as part-nature) (A067S)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Substance:

Quinolizidine alkaloids (RF-00004327-PAR)
Additional substance description:

lycopodine derivative: 6 alpha,11alpha-dihydroxylycopodine, lycoposerramine K
Analytical method code:

Nuclear Magnetic Resonance (NMR) (F061A)
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

quinolizidine alkaloid derivative: 6 alpha,11alpha-dihydroxylycopodine, lycoposerramine K (Stems)

Composition #6: Zhang, Hongchao., Liang, Hao., Kuang, Pengqun., Yuan, Qipeng., Wang, Yan. Simultaneously preparative purification of Huperzine A and Huperzine B from Huperzia serrata by macroporous resin and preparative high performance liquid chromatography . journal of chromatography b-analytical technologies in the biomedical and life sciences, 2012, vol. 904, p. 65–72. DOI: 10.1016/j.jchromb.2012.07.019. [DOI link]

Language:

English (en)
Plant part:

Unspecified (A07XD)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

1.0 N HCl
Substance:

huperzine A (RF-00003428-PAR)
Analytical method code:

High Performance Liquid Chromatography (HPLC)/Liquid Chromatography (LC) (F018A)
Result unit:

Percent (G138A)
Result expression:

Dry matter (B002A)
Result type:

Numerical Value (VAL)
Value (concentration, content):

1.66-2.03
Internal remarks:

Huperzine A (dried herb)

Composition #7: Zhang, Hongchao., Liang, Hao., Kuang, Pengqun., Yuan, Qipeng., Wang, Yan. Simultaneously preparative purification of Huperzine A and Huperzine B from Huperzia serrata by macroporous resin and preparative high performance liquid chromatography . journal of chromatography b-analytical technologies in the biomedical and life sciences, 2012, vol. 904, p. 65–72. DOI: 10.1016/j.jchromb.2012.07.019. [DOI link]

Language:

English (en)
Plant part:

Unspecified (A07XD)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

1.0 N HCl
Substance:

huperzine B (RF-00003429-PAR)
Analytical method code:

High Performance Liquid Chromatography (HPLC)/Liquid Chromatography (LC) (F018A)
Result unit:

Percent (G138A)
Result expression:

Dry matter (B002A)
Result type:

Numerical Value (VAL)
Value (concentration, content):

0.80-0.91
Internal remarks:

Huperzine B (dried herb)

Composition #8: Ying, You-Min., Liu, Xiao-Sa., Tong, Cui-Ping., Wang, Jian-Wei., Zhan, Zha-Jun., Shan, Wei-Guang. Lycopodium Alkaloids from Huperzia serrata. helvetica chimica acta, 2014, vol. 97, no. 10, p. 1433–1439. DOI: 10.1002/hlca.201400015. [DOI link]

Language:

English (en)
Plant part:

Live plants (as part-nature) (A0BA0)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

EtOH (95%)
Substance:

lycopodine (RF-00003475-PAR)
Additional substance description:

lycopodine derrivatives: lycopodine, huperserramines A, -B, -C, lycopodine-6a,11a-diol, lycopodine-6a-ol, lycoposerramine H, -I -M, -K, -W, -R, phlegmariuine, diphaladine, luciduline
Analytical method code:

Standard Chromatographic tests (paper- thin layer- and column chromatography) (F016A)
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

lycopodine derivatives: lycopodine, huperserramines A, B, C, lycopodine-6a,11a-diol, lycopodine-6a-ol, lycoposerramine H, -I -M, -K, -W, -R, phlegmariuine, diphaladine, luciduline (whole plant)

Composition #9: Ying, You-Min., Liu, Xiao-Sa., Tong, Cui-Ping., Wang, Jian-Wei., Zhan, Zha-Jun., Shan, Wei-Guang. Lycopodium Alkaloids from Huperzia serrata. helvetica chimica acta, 2014, vol. 97, no. 10, p. 1433–1439. DOI: 10.1002/hlca.201400015. [DOI link]

Language:

English (en)
Plant part:

Live plants (as part-nature) (A0BA0)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

EtOH (95%)
Substance:

huperzine B (RF-00003429-PAR)
Analytical method code:

Standard Chromatographic tests (paper- thin layer- and column chromatography) (F016A)
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

huperzine B (whole plant)

Composition #10: Ying, You-Min., Liu, Xiao-Sa., Tong, Cui-Ping., Wang, Jian-Wei., Zhan, Zha-Jun., Shan, Wei-Guang. Lycopodium Alkaloids from Huperzia serrata. helvetica chimica acta, 2014, vol. 97, no. 10, p. 1433–1439. DOI: 10.1002/hlca.201400015. [DOI link]

Language:

English (en)
Plant part:

Live plants (as part-nature) (A0BA0)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

EtOH (95%)
Substance:

Alkaloids (RF-00004360-PAR)
Additional substance description:

Huperzine M
Analytical method code:

Standard Chromatographic tests (paper- thin layer- and column chromatography) (F016A)
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

huperzine M (whole plant)

Composition #11: Ying, You-Min., Liu, Xiao-Sa., Tong, Cui-Ping., Wang, Jian-Wei., Zhan, Zha-Jun., Shan, Wei-Guang. Lycopodium Alkaloids from Huperzia serrata. helvetica chimica acta, 2014, vol. 97, no. 10, p. 1433–1439. DOI: 10.1002/hlca.201400015. [DOI link]

Language:

English (en)
Plant part:

Live plants (as part-nature) (A0BA0)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

EtOH (95%)
Substance:

huperzine A (RF-00003428-PAR)
Analytical method code:

Standard Chromatographic tests (paper- thin layer- and column chromatography) (F016A)
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

huperzine A (whole plant)

Composition #12: Ferreira, Ana., Rodrigues, Marcio., Fortuna, Ana., Falcao, Amilcar., Alves, Gilberto. Huperzine A from Huperzia serrata: a review of its sources, chemistry, pharmacology and toxicology . phytochemistry reviews, 2016, vol. 15, no. 1, p. 51–85. DOI: 10.1007/s11101-014-9384-y. [DOI link]

Language:

English (en)
Plant part:

Unspecified (A07XD)
Additional extraction description:

unspecified
Substance:

lycodine (RF-00003474-PAR)
Analytical method code:

Unspecified (F598A)
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

Lycodine (unspecified)

Composition #13: Ferreira, Ana., Rodrigues, Marcio., Fortuna, Ana., Falcao, Amilcar., Alves, Gilberto. Huperzine A from Huperzia serrata: a review of its sources, chemistry, pharmacology and toxicology . phytochemistry reviews, 2016, vol. 15, no. 1, p. 51–85. DOI: 10.1007/s11101-014-9384-y. [DOI link]

Language:

English (en)
Plant part:

Unspecified (A07XD)
Additional extraction description:

unspecified
Substance:

Alkaloids (RF-00004360-PAR)
Additional substance description:

Lycopodium alkaloids derivative: phlegmarine, fawcettimine
Analytical method code:

Unspecified (F598A)
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

Lycopodium alkaloids derivative: phlegmarine, fawcettimine (unspecified)

Endpoint study #1: Ernst, E. Adverse effects of unconventional therapies in the elderly: A systematic review of the recent literature. journal of the american aging association, 2002, vol. 25, no. 1, p. 11–20. DOI: 10.1007/s11357-002-0002-3. [DOI link]

Study relevance:

Human health
Type of toxicological test:

case report (CHD060TT)
Tested organism:

Human (as organism) (A056J)
Sex:

Female
Route of exposure:

ORAL: UNSPECIFIED (OECD2234PL)
Control groups used:

no
Endpoint measured:

Dose not reported (CHD066EP)
Critical effect:

HEPATOTOXICITY (TOX02A)
Target tissue:

digestive: Liver (TT023A)
Effect description:

fever, nausea, fatigue and elevated liver enzymes
Effect or parameter linked to the endpoint:

no data (CHD002BE)
Internal remarks:

fever, nausea, fatigue and elevated liver enzymes

Endpoint study #2: Ying, You-Min., Liu, Xiao-Sa., Tong, Cui-Ping., Wang, Jian-Wei., Zhan, Zha-Jun., Shan, Wei-Guang. Lycopodium Alkaloids from Huperzia serrata. helvetica chimica acta, 2014, vol. 97, no. 10, p. 1433–1439. DOI: 10.1002/hlca.201400015. [DOI link]

Study relevance:

Human health
Substance:

huperzine A (RF-00003428-PAR)
Plant part:

Live plants (as part-nature) (A0BA0)
Preparation/Extraction method:

Solvent extraction (A0BZR)
Additional plant/substance description:

EtOH (95%)
Type of toxicological test:

in vitro (CHD061TT)
Tested organism:

Saccharomyces cerevisiae (as organism) (A0CPH)
Sex:

No data
Route of exposure:

OTHER (OECD0PL)
Control groups used:

yes
Endpoint measured:

Half maximal inhibitory concentration (CHD021EP)
Concentration unit:

Microgram/litre (G051A)
Effect concentration:

4846.4
Critical effect:

Digestive (TOX18A)
Target tissue:

Digestive (TT002A)
Effect description:

huperzine A displayed potent α-glucosidase inhibitory activity (IC50 20 μM) in S. cerevisiae
Effect or parameter linked to the endpoint:

enzyme inhibition (CHD032BE)
Internal remarks:

huperzine A displayed potent α-glucosidase inhibitory activity (IC50 20 μM) in S. cerevisiae

Endpoint study #3: Ying, You-Min., Liu, Xiao-Sa., Tong, Cui-Ping., Wang, Jian-Wei., Zhan, Zha-Jun., Shan, Wei-Guang. Lycopodium Alkaloids from Huperzia serrata. helvetica chimica acta, 2014, vol. 97, no. 10, p. 1433–1439. DOI: 10.1002/hlca.201400015. [DOI link]

Study relevance:

Human health
Substance:

huperzine B (RF-00003429-PAR)
Plant part:

Live plants (as part-nature) (A0BA0)
Preparation/Extraction method:

Solvent extraction (A0BZR)
Additional plant/substance description:

EtOH (95%)
Type of toxicological test:

in vitro (CHD061TT)
Tested organism:

Saccharomyces cerevisiae (as organism) (A0CPH)
Sex:

No data
Route of exposure:

OTHER (OECD0PL)
Control groups used:

yes
Endpoint measured:

Half maximal inhibitory concentration (CHD021EP)
Concentration unit:

Microgram/litre (G051A)
Effect concentration:

5126.8
Critical effect:

Digestive (TOX18A)
Target tissue:

Digestive (TT002A)
Effect description:

huperzine B displayed potent α-glucosidase inhibitory activity (IC50 20 μM) in S. cerevisiae
Effect or parameter linked to the endpoint:

enzyme inhibition (CHD032BE)
Internal remarks:

huperzine B displayed potent α-glucosidase inhibitory activity (IC50 20 μM) in S. cerevisiae

Endpoint study #4: Ying, You-Min., Liu, Xiao-Sa., Tong, Cui-Ping., Wang, Jian-Wei., Zhan, Zha-Jun., Shan, Wei-Guang. Lycopodium Alkaloids from Huperzia serrata. helvetica chimica acta, 2014, vol. 97, no. 10, p. 1433–1439. DOI: 10.1002/hlca.201400015. [DOI link]

Study relevance:

Human health
Substance:

lycopodine (RF-00003475-PAR)
Plant part:

Live plants (as part-nature) (A0BA0)
Preparation/Extraction method:

Solvent extraction (A0BZR)
Additional plant/substance description:

EtOH (95%)
Type of toxicological test:

in vitro (CHD061TT)
Tested organism:

Saccharomyces cerevisiae (as organism) (A0CPH)
Sex:

No data
Route of exposure:

OTHER (OECD0PL)
Control groups used:

yes
Endpoint measured:

Half maximal inhibitory concentration (CHD021EP)
Concentration unit:

Microgram/litre (G051A)
Effect concentration:

5126.8
Critical effect:

Digestive (TOX18A)
Target tissue:

Digestive (TT002A)
Effect description:

lycopodine-6a,11a-diol displayed potent α-glucosidase inhibitory activity (IC50 148.1 μM) in S. cerevisiae
Effect or parameter linked to the endpoint:

enzyme inhibition (CHD032BE)
Internal remarks:

lycopodine-6a,11a-diol displayed potent α-glucosidase inhibitory activity (IC50 148.1 μM) in S. cerevisiae