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Table 1 Recently isolated lycodine type Lycopodium alkaloids and theiracetylcholinesterase (AChE) inhibitory activity

From: Recently isolated lycodine-type Lycopodium alkaloids and their total synthesis: a review

Lycopodium alkaloid

Plant spp.

LC50

Reference

Complanadine A (2)

Lycopodium complanatum

[14]

Himeradine A (3)

Lycopodium chinense

[15]

Huperzinine N-oxide (4)

Lycopodium

casuarinoides

[16]

8,15-dihydrohuperzinine (5)

N-demethyl-obscurine (6)

Lycopodium serratum

[17]

Lycodine (1)

Casuarine A (7)

Lycopodium

casuarinoides

[18]

Casuarine B (8)

46.4 μM

N-demethyl-sauroxine (9)

Huperziasaururus

[19]

N-methylhydroxypropyllycodine (10)

Lycopodium japonicum

[20]

Huperserine E (11)

Huperzia serrata

6.71 μM

[21]

8,15-dihydrohuperzine A (12)

Huperziacarinata

2.6 μM

[22]

16-hydroxyhuperzine B (13)

Lycopodiastrumcasuarinoides

87.3 μM

[23]

N-methyl-11-acetoxyhuperzine B (14)

8,15-dihydrolycoparin A (15)

(7S,12S, 13R)-huperzine D-16-O-β-D-glucopyranoside (16)

N-demethylhuperzinine (17)

1.9 μM

Lycoparin C (18)

23.9 μM

N-methylhydroxypropyllycodine (10)

Lycopodium japonicum

[24]

Phlefargesiine A (19)

Phlegmariurusfargesii

[25]

16-hydroxylycodine (20)

Phlegmariurushenryi

[26]

Lycocasuarine A (21)

Lycopodiastrum

casuarinoides

> 100 μM

[27]

Lycocasuarine B (22)

> 100 μM

Lycocasuarine C (23)

7.4 μM

lycoannotine G (24)

Lycopodium annotinum

[28]

lycoannotine H (25)

Lycofargesiine A (26)

Huperziafargesii

[29]

Lycofargesiine B (27)

Lycofargesiine C (28)

8.63 μM

Lycofargesiine D (29)

12α-hydroxy-N-demethyl-sauroxine (30)

Phlegmariurussaururus

33.8 μM

[30]

N-methyllycodine (31)

547.5 μM

N-demethyl-sauroxine (9)

1.38 μM

Lycocasuarine I (32)

Lycopodiastrum

casuarinoides

> 200 μM

[31]

Lycocasuarine J (33)

> 200 μM

Lycocasuarine K (34)

171.9 μM

Lycocasuarine L (35)

> 200 μM

Lycocasuarine M (36)

97.2 μM

Lycocasuarine N (37)

112.1 μM

Lycocasuarine O (38)

137.8 μM

Lycocasuarine P (39)

127.8 μM

Lycocasuarine Q (40)

> 200 μM

Lycoplatyrine A (41)

Lycopodium

platyrhizoma

> 30 μM

[32]

Lycoplatyrine B (42)

> 30 μM

Lycoplanine D (43)