Three new Lycopodium alkaloids from Huperzia carinata and Huperzia squarrosa

Phytochemicals from fern species: potential for medicine applications

“…Lycopodium alkaloids (Fig. 2) have been isolated and reported from 13 Huperziaceae species and varieties (Table 1) (Tong et al 2003b) 12-Epilycodoline N-oxide H. serrata ) 4,6-Dihydroxyserratidine H. serrata (Tan et al 2002d) 4-Hydroxyserratidine H. serrata (Tan et al 2002d) 4,6-Dihydroxylycopodine H. serrata 6-Hydroxylycopodine H. serrata (Yuan et al 1995) 6-Hydroxyserratidine H. serrata (Tan et al 2002d) 7-Hydroxylycopodine H. serrata Phytochem Rev (2017) 16:379-440 381 (Tong et al 2003b) Flabelliformine H. miyoshiana (Tong et al 2003b) Gnidioidine H. carinata (Thorroad et al 2014) Huperzine E H. serrata (Zhu et al 1996;Wang et al 2001) Huperzine F H. serrata (Zhu et al 1996;Wang et al 2001) Huperzine G H. serrata (Wang et al 1998(Wang et al , 2000 Huperzine O H. serrata (Wang et al 2000) Lucidioline H. serrata (Zhou et al 1993;Ma et al 1998) Lycocarinatine A H. carinata (Thorroad et al 2014) Lycodoline H. miyoshiana (Tong et al 2003b), H. serrata (Yuan et al 1995), H. carinata (Thorroad et al 2014) Lycopodine H. miyoshiana (Tong et al 2003b), H. serrata (Yuan et al 1995) Lycoposerramine K H. carinata (Thorroad et al 2014) Lycoposerramine U N-oxide H. squarrosa (Thorroad et al 2014) Miyoshianine A H. miyoshiana (Tong et al 2003b) Miyoshianine B…”

“…H. miyoshiana (Tong et al 2003b) Phlegmariurine B H. carinata (Thorroad et al 2014), H. squarrosa (Thorroad et al 2014) Sauroine H. saururus (Ortega et al 2004) Selagoline H. selago (Staerk et al 2004) Serratidine H. serrata (Tan et al 2002d), H. selago (Staerk et al 2004) II. Lycodine class 12-Epilycodine N-oxide H. squarrosa (Thorroad et al 2014) 6-Hydroxyhuperzine A H. serrata (Yuan and Zhao 2000) 8,15-Dihydrohuperzine A H. carinata (Thorroad et al 2014) Des-N-methyl-obscurine H. serrata (Yuan et al 1995) Huperserine E H. serrata Huperzine A H. serrata (Liu et al 1986a, b), H. selago (Staerk et al 2004), H. carinata (Thorroad et al 2014), Huperzia squarrosa (Thorroad et al 2014) Huperzine B…”

“…H. serrata (Liu et al 1986a, b) Huperzine C H. serrata (Liu and Huang 1994) Huperzine D H. serrata (Liu and Huang 1994) Huperzine U H. serrata (Tan et al 2003) Huperzinine H. serrata (Yuan and Wei 1988;Jiang et al 2014) Lycodine H. serrata (Yuan et al 1994) Lycoflexine N-oxide H. squarrosa (Thorroad et al 2014) N,N-Dimethylhuperzine A H. serrata (Hu et al 1992) N-Demethyl-sauroxine H. saururus (Vallejo et al 2013) N-Methyl-huperzine B H. serrata (Yuan and Wei 1988;Southon and Buckingham 1989) III. Fawcettimine class 11-Hydroperoxyphlegmariurine B H. serrata (Tan et al 2003) (Hirasawa et al 2012(Hirasawa et al , 2013.…”

New Lycopodine-Type Alkaloids from <i>Lycopodium carinatum</i>

“…Other isolated compounds from the crude alkaloidal fraction were lycopodine, 31) lycocarinatine A, 28) 12-epi-lycodoline N-oxide, 32) lycofoline, 30) anhydrolycodoline, 30) obscurumine C, 33) gnidioidine, 30) malycorin B, 29) fawcettimine, 34) lycoposerramine-C, 35) lycoposerramine-D, 35) lycoposerramine-P, 35) phlegmariurine A, 22) phlegmariurine B, 36) huperzine A, 5) huperzine C, 37) 13N-formyl huperzine A, 38) lycodoline, 32,39) and Chemical Conversion of Lycopocarinamine A (1) into Lycopocarinamine B (2) To a solution of lycopocarinamine A (1, 1.0 mg) in MeOH (0.5 mL) was added freshly prepared ether solution of CH 2 N 2 (excess). The mixture was stirred for 1 h at room temperature.…”

“…In this paper, we describe the structure elucidation of six new Lycopodium alkaloids having the lycopodine-type skeleton, which were isolated from L. carinatum, 27) and the structure revision of reported alkaloid lycocarinatine A. 28) …”