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Table 2 Various alkaloids from genus Fritillaria and their uses

From: Traditional uses, phytochemistry and pharmacology of genus Fritillaria—a review

S. No Species Chemical constituents Uses References
1 Fritillaria camtshatcensis Steroidal alkaloids: anrakorinine, veraalkamine, camtschatcanidine, hapepunine, solasodine, tomatidenol solanidine (1), kuroyurinidine (2) Kaneko et al. (1981a), Sashida et al. (1989), Mimaki and Sashida (1990a, b)
2 Fritillaria imperialis Ebeinone, dihydroimpranine (8), impranine (9) fetisinine (10), korsevine (11). Alkaloids: impericine (3) forticine (4), delavine (5), persicanidine A (6), imperialine (7) Cholinesterase inhibiting activity, asthma, sore throat, bronchitis, cough, scrofula, haemoptysis, dysuria and gland tumour Bailey (1966), Perry (1980), Sener (1994), (Farooq et al. 1994, Akhtar et al. 2002, 2003)
3 Fritillaria ebeiensis Alkaloids: hupehenidine, peimine (22) (verticine) (13) peiminine, verticinone (12), ebeiensine (38), ebeinone, ebeinine (48) steroidal alkaloid: ebeietinone. Ebeiedine (14), ebeiedinone (15), Isoverticine (23) Antitussive and expectorant effects, neuroprotective activity against 1-methyl-4-phenyl pyridinium (MPP+)-induced neuronal cell death in human dopaminergic neuroblastoma SH-SY5Y cells. Anti-AChE and Anti-BChE activity invitro. Strong antitumour activity in inhibiting the growth of the solid type of hepatoma and Ehrlich ascites carcinoma in mice Yu et al. (1985), Lee et al. (1988), Wu et al. (1989a), Ping et al. (1992), Li et al. (1995a, b), Lin et al. (2006a, b), Xu et al. (2011a, b)
4 F. cirrhosa Alkaloids: imperialine (7), verticinone (12), verticine (13), ebeiedine (14), ebeiedinone (15), chuanbeinone (16) imperialine-β-N-oxide, isoverticine (23), and isoverticine-β-N-oxide (45) Antitussive activity cough anti-inflammatory activity Chan et al. (1998), Li et al. (1999), Wang et al. (2011)
5 F. thunbergii Alkaloids: Solanidine (1), verticinone (12), verticine (13), ebeiedine (14), ebeiedinone (15), 1-Heptadecanol,Monoheptadecanoin( C 20H40O4) 5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-methoxy-4H-chromen-4-one( C17H14O7), Isorhamnetin(C16H12O7), Dihydroapigenin(Cl5Hl2O5), Kaempferol-3-O-α-L-rhamnoside(C21H20O10), Kaempferol-3-O-α-L-glucoside( C21H20O11), Kaempferitrin (C27H30O14), Peimisine (43), peimine (22), and peiminine, Steroidal alkaloids, dongbeinine (19) and dongbeirine (20), zhebeinine (21), zhebeinone (24), suchengbeisine, N-demethylpuqietinon, eduardinine (25), eduardine (26), zhebeirine (27), 3β-hydroxy-5α-jervanin-12-en-6-one (28), frithunbol A (29), frithunbol B (30) Antitussive and expectorant effects relieving cough, reducing sputum and also showing antioxidant power Kitajima et al. (1982a, b, c), Zhang et al. (1991, 1992, 1993b, c), Peng et al. (2012), Ruan et al. (2016), Kim et al. (2016), Zhou et al. (2017), Suh et al. (2018)
6 F. pallidiflora Imperialine (7); imperialine-3β-glucoside, Yibeinoside A, yibeinones A-D (39–42) -3β-D-glucoside, imperialine (7), imperialine βN-oxide, dongbeinine isosteroidal alkaloids: chuanbeinone (16), imperialine-β-N-oxide (44), isoverticine (23), and isoverticine-β-N-oxide (45). Steroidal alkaloids: Yibeinine (31), yubeinine (32), hupehenine (33), peimine (22), yibeinoside (34), (20R,22R,23R,25R)-3b,23-dihydroxy-N-methyl-veratram-13(17)-en-6-one (36) sipeimine (37); sinpeinine A (17), ebeiensine (38), yibeissine (46) [1 I-dehydro-60 × 0–5,6-dihydrojervine], yibeinoside B (47), yibeinoside C, yibeinine-3-O-β-D glucopyranoside, and (22 S, 23 R,25S)-22,26-epimino- 17,23—3β, 1 1 α-dihydroxy—5α-jerv- 12-ene-6-0ne Antitussive and expectorant effects relaxant effect against the KCl-induced and Ach-induced contraction of isolated tracheas. Cytotoxic activity against four tumour cell lines (LLC, A2780, HepG2, and A549) in a dose- and time-dependent manner. Chuanbeinone (16) was also reported to induce apoptosis, modify the balance of Bax/Bcl-2, arrest the cell cycle in the S phase, reduce the growth of transplantable LLC and S180 tumours in mice and activate caspase-3 protein cytotoxic activity against human C6 brain gliomas and Hela cervix cancer cell lines. Anti-AChE and Anti-BChE activity in vitro Liu et al. (1984), Li and Wu (1986), Xu et al. (1990a, b ), Mimaki and Sashida (1990a, b), Xu et al. (1992, 1993), Zhang et al. (b, d), Koketsu et al. (1996), Li et al. (1999), Dong et al. (2001), (Akhtar et al. 2002), Li et al. (2002), Chen et al. (2004), Lin et al. (2006a, b), Yokosuka and Mimaki (2008), Xiao et al. (2009), Zhang et al. (2011), Shen et al. (2012a, b), Xu et al. (2014), Wang et al. (2015), Li et al. (2016)
7 F. ussuriensis Isosteroidal alkaloids: imperialine (7), verticinone (12), isoverticine (23), verticine (13), ebeiedinone (15) and ebeiedine (14), pingbeimunone A (59), ussuriedine (60), benzofluoreno[2,1-b] quinolizine cevane-3,6,16,20-tetrol (61), ebeiedinone (15), pingbeimine C (62), verticine (13). steroidal alkaloids: pingbeinine (56) and pingbeininoside (57) Alkaloid: ussurienine (58), solanidine (1), imperialine (7) and peimisine (43) Potent antitussive alkaloid, verticinone has antitussive activity (and antitumour activity; inhibits the growth of human myelogenous leukaemia cell lines including HL-60 cells. Inhibition of angiotensin I-converting enzyme activity shown by verticinone, imperialine and peimisine alkaloids], low AChE inhibitory activities in vitro. Lowering arterial pressure, increasing cGMP and nitric oxide (NO)production in intact vascular tissues, decrease angiotensin-converting enzyme and angiotensin I-induced vasoconstriction. Inhibiting the production of MAPKs and inflammatory cytokine in mast cells. Cytotoxic effect against four tumour cell lines as human ovarian cancer cell line(A2780), Lewis lung carcinoma cell line (LLC), human lung carcinoma cell line (A549) and human hepatocellular carcinoma cell line (HepG2), inhibition of transplanted S180 and LLC tumours in a caspase-dependent apoptosis Ito et al. (1976), Kaneko et al. (1980, 1981a, b), Lee et al. (1988), Kitamura et al. (1988, 1989a, 1989b), Xu et al. (1990c, d), Pae et al. (2002), Kang et al. (2002), Oh et al. (2003), Yao et al. (2008), Yang and Duan (2011), Cho et al. (2011), Wang et al. (2015)
8 F. hupehensis Hupehenine (33), veratramine alkaloid, namely 22S,25S,5α-Vertramine-7(8),12(14)-diene-3β,13β,23β-triol-6-one. Alkaloids, (3β,5α,13α,23β)-7,8,12,14-tetradehydro-5,6,12,13-tetrahydro-3,13,23-trihydroxyveratraman-6-one (53), 3-O-acetoxy verticinone (54), 3-O-acetyl verticine (55), (3β,5α,6α)-6,20-dihydroxycevan-3-yl acetate. Ebeinine (48) and zhebeirine (26), 3β,23β-dihydroxy-7,12(14)-dien-5α- veratramin-6-one Cytotoxic activities against the human cervical squamous carcinoma (HeLa) and human hepatoma (HepG2) cell lines. Anti-AChE and Anti-BChE activity in vitro Li et al. (1990a, b), Zhang et al. (1991, 2007a, b, 2008b), Lin et al. (2006a, b)
9 F. persica Persica (3β,5α,13α,23β)-7,8,12,14-tetradehydro-5,6,12,13-tetrahydro-3,23-dihydroxyveratraman-6-one (52), nidine A, verticinone (12) and ebeiedin cerveratrum alkaloids: persicanidine A (6), (22S&25S)-5α,l7β -cevanine-3β,6β-diol, that is, delavine (5), delavine 3-O-β-D-glucopyranoside (67), persicanidine B (69) [(22S,25R)-5α,17β-cevanine-3β,6β-diol], and persicanidine B 3-O-β-D-glucopyranoside (68), five steroidal alkaloids, with structures reported as, (25R)-23,26-epimino-3β-hydroxy-5α-cholest-23(N)-ene-6,22-dione (70), (25R)-22,26-epimino-3β-hydroxy-5α-cholest-22(N)-ene-6,-one 3-O-β-D-glucopyranoside (71), (25R)-23,26-epimino-3β-hydroxy-5a-cholest-23(N)-ene-6,22-dione3-O-β-Dglucopyranoside (72), (20R,25R)-23,26-epimino-3β-hydroxy--cholest-23(N)-ene-6,22-dione3-O-β-D-glucopyranoside (73)and (20R,25R)-23,26-epimino-3β-hydroxy-5α-cholest-23(N)-ene-6,22-dione3-O-β-D-glucopyranoside (74) Inhibitory activity on cyclic AMP phosphodiesterase,  
10 F. puqiensis Steroidal alkaloids: puqiedinone and puqietinone (88), puqienine A (80), puqienine B (81), N-demethylpuqietinone (86), puqietinonoside (87), puqienines C-E (82–84), puqiedine 3α-puqiedin-7-ol (90), and puqienine F (85), a secosolanidine-type; puqietinedione (89), a jervines type; peimisine (43) Antitussive and antitumour activities activity against A549 human lung carcinoma cell line, BGC-823 human stomach adenocarcinoma cell line, SMMC-7721 human hepatocarcinoma cell line and against HL-60 human promyelocytic leukaemia cell line. Adenosine (143) is involved in decreasing the blood pressure, slowing the heart rate, relaxing the smooth muscle and sedative effects Wang et al. (1992), Lin et al. (1995), Jiang et al. (2005), Li et al. (2006a, b), Zhang et al. (2010)
11 Fritillaria roylei Alkaloids: peimine (22), peiminine, peimisine (43), peimiphine, peimidine, peimitidine, neutral principle: propeimin and sterol Antiasthmatic, antirheumatic, febrifuge, galactagogue, haemostatic, ophthalmic, oxytocic. Fever, burning sensation and phthisis Singh (2006)
12 F. walujewii Rgl Alkaloids: Peimissine, Imperialine (7)  
13 F. pontica Rutin and hyperoside Antioxidant activity, low antiradical activity Orhan et al. (2009)
14 F. delavayi Alkaloids: two cevanine-type delafrinone (64) and delafrine (65) and a natural solanidanine (22R,25S)-solanid-5α-enine-3β,5α,6β-triol (63) Chaunbeinone Delavidine Antimicrobial activity against Klebsiella pneumonia, antifungal activity against Fusarium moniliforme. Anti-AChE and anti-BChE activity in vitro Kaneko et al. (1988), Lin et al. (2006a, b), Cao et al. (2008)
15 Fritillaria wabuensis Alkaloid sinpeinine A (17), imperialine-3-β-glucoside (18), 3β-acetylimperialine verticinone (12), Imperialine (7), imperialine-β-N-oxide (44), isoverticine (23), isoverticine-β-N-oxide (45) Antiasthmatic activities antitussive, expectorant, and anti-inflammatory effects Zhang et al. (2003), Zhou et al. (2003), Lin et al. (2006a, b), Wang et al. (2012)
16 F. raddeana Raddeanine, Southon and Buckingham (1989)
17 Fritillaria unibracteata β-Sitosterol [,7-ketositosterol, 3-methoxy-4-(palmitoyloxy)benzaldehyde, and methyl octadecanoate peimisine-3-O-β-D-glucopyranoside (93), puqiedinone-3-O-β-D glucopyranoside (94), peimisine (43), puqiedinone and puqiedine (8) Show protective activity on injured hepatocytes and cytotoxic activity on human cancer cells in vitro protective effects of PC12 cells Wang et al. (1992), Lin et al. (1995), Zhang et al. (2005a, b), Jiang et al. (2006), Fiorentino et al. (2008), Zhang et al. (2011), Wei et al. (2013), Minakawa et al. (2013), Liu et al. (2014)
18 Fritillaria lichuanensis C-nor-D-homosteroidal alkaloids: lichuanine (91) and lichuanisinine (92) Pi et al. (2006a, b)
19 F. siechuanica Steroidal alkaloid, siechuansine (78), imperialine (7) and peimisine (43) Wang et al. (1992)
20 Fritillaria taipaiensis Steroidal alkaloid: taipaienine (79), chuanbeinone (16), imperialine (7), verticinone (12), perimissine and isovertisine Hu et al. (1993)
21 Fritillaria ningguoensis Alkaloids: ningpeisine (66), peimine (22), peiminine, isoverticine (23), and peimisine (43) Li et al. (1988)
22 F.maximowiczii Alkaloids: kuroyurinidine (2), 15,16-seco-22αH,25βH-solanida-5,14-dien-3β-ol O-β-D-glucopyranosyl-(1–4)-β-D-xylopyranoside (75),,23-isokuroyurinidine (76) and hapepunne 3-O-β-cellobioside (77) Qian and Nohara (1995)
23 F. monatha Pengbeimine B, Pengbeimine D Liu et al. (2007)
24 Fritillaria tortifolia Isosteroidal alkaloids, frititorines A–C (95–97), imperialinol (98), peimisine (43), peimisine-3-O-β-D-glucoside (99), ebeinine (48), imperialine (7), yubeinine (32), imperialine-3-O-β-D-glucoside (100), ebeiedinone (15), delavinone (101), and hupehenizioiside (102) Imperialine (7) has been reported to have significant potency in relaxing the isolated tracheas with imperialinol (98) Kaneko et al. (1985), Wu et al. (1989a, ), Huang et al. (1990), Wang et al. (1992), Zhang et al. (1993d), Lin et al. (1995), Zhang et al. (2011), Pi et al. (2006a, b), Hu et al. (2018)