Table 4 Other chemical constituents found in genus Fritilalria and their uses

1

Fritillaria camtshatcensis

Two phenolic glycosides:(regaloside A) and 3,6-O-diferuloylsucrose

-

Shimomura et al. (1988)

2

Fritillaria imperialis

The volatile component: 3-methyl-2-butene-1- thiol, acetic acid, 2-nitroethanol, 3-hydroxy-2-butanone, 3-methylpentanol, 2,3-butanediol, n-hexanal, 3-methyl-2-butene-1-thiol, 3-pentene-2-ol, 1-hexanol, 1,2-dimethyl benzene, cyclohexanone, dihydro-3-methyl 2(3H)-furanone, benzaldehyde, 3-methyl-2(5H)-furanone, 3-hydroxy-4,4,dimethyl 2(3H)-furanone, acetophenone, 2-nonene-1-ol, octanoic acid, decanal, nonanoic acid,,4,6-trichlorophenol, tetradecane, pentadecane, 3,4-dimethyl-1,5-heptadiene,Cevarin, Cevacin

Prolyl endopeptidase inhibitory activity

Chopra et al. (1956), Atta-ur-Rahman et al. (2005), Helsper et al. (2006)

3

F. thunbergii

Volatile components: including the octadecatrienoic acid methyl esters and some aromatic aldehydes and ketones, such as benzene acetaldehyde and 1-(2-hydroxy-5- methylphenyl)-ethanone). twenty-one elements were identified,29 compounds from essential oils as, δ-selinene; δ-elemene;pentadecanoic acid (167); tetradecanoic acid; hexadecanoic acid, methyl ester; n-hexadecanoic acid; 9-hexadecenoic acid; kaur-15-ene; kaurene; heptadecanoic acid; 9,12-octadecadienoic acid (Z,Z)-, methyl ester; oleic acid (171); 9-tetradecenal, (Z)-; linoleic acid ethyl ester; 9,12-octadecadienoic acid, methyl ester, (E, E)-; L-( +)-Ascorbic acid 2,6-dihexadecanoate; butylated hydroxytoluene; ethyl 9-hexadecenoate; 1H-naphtho [2,1-B] pyran,3-ethenyldodecahydro-3,4a,7,7,10a-pentamethyl-; hexadecanoic acid ethyl ester; 9,11-octadecadienoic acid,methyl ester, (E, E)-; linoleic acid ethyl ester; 9,12-octadecadienoic acid; octadecanoic acid, ethyl ester; 2(1H)-phenanthrenone, 3,4,4a,4b,5,6,7, kaur-16-ene; rost-4-En-3-one, 17-hydroxy-, (17.β.); 8,10,10a-decahydro-1,1,4a,7,7-pentamethyl,[4aR-(4a.α., 4b.β.,10a.β.)]-; 3-methyleneandrostan-17-ol;and podocarp-7-en-3.β.-ol, 13.β.-methyl-13-vinyl- six nucleosides including guanosine, uridine (142), adenosine (143), cytidine, thymidine and inosine. Two sterols daucosterol and β-sitosterol, two carbohydrates sucroseand β-D-glucose4-1β-D-galactose. eighteen amino acids: leucine (153), glycine (152), methionine (160), histidine (150), tyrosine (149), threonine (158), isoleucine (151), alanine (156), tryptophan (148), lysine (147), cystine, aspartic acid, phenylalanine (164), valine (154), proline (159), glutamic acid, serine (161), and arginine (146), four nucleobases adenine, uracil (144), hypoxanthine and thymine, four fatty acids 2-monopalmitin, vernolic acid, 13(R)-hydroxy-octadeca-(9Z,11E,15Z)-trien-oic acid and picropodophyllotoxin, and three lignan zhebeiresinol, octahydrocurcumin and sauriol B

–

Jin et al. (1993), Zhang et al. (1993c, e), Wu and Zheng (1997), Wang et al. (2007), Yao et al. (2008), Liu et al. (2008), Zhang et al. (2008a), Liang et al. (2011), Zhang et al. (2011), Cao et al. (2012), Chen and Wang (2012), Cai et al. (2013, 2014), Lou et al. (2014), Zhou et al. (2014), Zhang et al. (2016), Zhou et al. (2017), Du et al. (2018)

4

F. pallidiflora

Steroidal saponins: pallidifloside D, allidifloside E, Pallidifloside G, Pallidifloside H and Pallidifloside,Yibeinoside A, imperialine-3β-D-glucoside, imperialine β-N-oxide,17 and one flavonoid: diosmetin (175) one coumarin: murrayone (176), one sphingolipid: 1-O-β-D-glucopyranosyl-(2S,3R,4E,8Z)-2-[(2-hydroxyoctadecanoyl) amido]-4,8-octadecadiene-1,3-diol (177) and nine fatty acids:Meristic acid C14:0 (166), Pentadecanoic acid C15:0(167), palmitic acid C 16:0(168), palmitoleic acid C16:1(169), stearin acid C18:0(170), oleic acid C18:1(171), linoleic acid C18:2 (172), linolenic acid C18:3(173), α-monopalmitin (174). steroidal saponins parispseudoside B (134) (1); (22S,25S)-26-O- β -D-glucopyranosyl-22,25-epoxyfurost-5-en-3 β,26-diol-3-O-[ α-L-rhamnopyranosyl (1 /2)]- β-D-glucopyranoside (2);(25R)-26-[β-D-glucopyranosyl]oxy]-3 β -[(O- α-L-rhamnopyranosyl-(1 / 2)-β-D-glucopyranosyl)oxy]-cholesta-5,17-diene-16,22-dione (3); 26-O- β-D-glucopyranosyl-3,26-dihydroxy-(25R)-5β -furost-12-on-20(22)-ene-3-O- α-L-rhamnopyranosyl-(1/2)- β -D-glucopyranoside, aspidistrin (138), gastrodin (139), phenolic glucosides 4-(β -D glucopyranosyloxy) benzoic acid (140), icariside D2(141), nucleoside compounds (uridine (142), uracil (144); adenosine (143); one amino acid (12), (S)-b-L-phenylalanine steroidal saponins, pallidiflosides D (122), E (123), G (124), H (125) and I (126) together with seven other steroidal saponins, namely spongipregnoloside A (127), smilaxchinoside C (128), timosaponin H1 (129), protobioside (130), polygonatoside B3 (131), polyphyllin V (132) and deltonin (133), steroidal saponins, pallidiflosides A (119), B (120) and C (121)

Antitussive activity, 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 induces apoptosis, modifies the balance of Bax/Bcl-2, arrests the cell cycle in the S phase, reduces the growth of transplantable LLC and S180 tumours in mice and activates caspase-3 protein. Cytotoxic activity against human C6 brain gliomas and Hela cervix cancer cell lines. Anti-AChE and Anti-BChE activity in vitro

Ellis et al. (1973), Miyase (1989), Xu et al. (1990a, b), Mimaki and Sashida (1990a, b), Zhang et al. (1993b, d), Jung et al. (1996), Koketsu et al. (1996), Meng et al. (1999), Dong et al. (2001), Stueber and Grant (2002), Tian et al. (2002), Yin et al. (2003), Chen et al. (2004), Geng et al. (2004), Lin et al. (2006a, b), Hou et al. (2006), Lin et al. (2006a, b), Yang et al. (2007), Shao et al. (2007), Ono et al. (2007), Hayes et al. (2007), Yokosuka and Mimaki (2008), Chen et al. (2008a, b), Zhou et al. (2008), Xiao et al. (2009), Shen et al. (2011, 2012a, b), Arya and Thakur (2013), Wang et al. (2015), Li et al. (2016), Utegenova et al. (2019)

5

F. hupehensis

Nonbasic constituents, such as fritillebin C, fritillebin D, cyclic peptide named cyclo(Leu-Val-Leu), 13_-hydroxy-7-oxoabiet-8(14)-en-19,6_-olide, thymidine, adenosine (143) and uridine (142), N-Demethylpuqietinone (126), hupeheninoside^. cycloartane-type triterpenoids; 25-hydroxyl-9,19-cycloart-22-ene-3-one, (23Z)-9,19-cycloart-23-ene-3a,25-diol, 9,19-cycloart-25-ene-3b,24j-diol

Cytotoxic activities against the human cervical squamous carcinoma (HeLa) and human hepatoma (HepG2) cell lines. Anti-AChE and Anti-BChE activity in vitro

Goebel and Schrempf (1972), Wu et al. (1999), Lin et al. (2006a, b), Pi et al. (2007, 2009), Zhang et al. (2008b), Tong (2016)

6

Fritillaria verticillata

Glucosylsterol: β-sitosterol-3-O-glucopyranoside

Antibacterial activity against Staphylococcus aureus, Bacillus subtillis and Micrococcus leuteus bacteria.i.e.; sortase inhibitory effect

Kim et al. (2003)

7

F. puqiensis

Three nucleosides and three bases: 2’-O-methyladenosine, uridine (142), adenosine (143), uracil (144), thymine and adenine

Antitussive and antitumour activities. Adenosine (143) is involved in decreasing the blood pressure, slowing the heart rate, relaxing the smooth muscle and sedative effects

Jiang et al. (2006), Zhou et al. (2008), Zhang et al. (2010)

8

F. delavayi

Volatile oil, sterol, glycosides, saponins, triterpenes, reducing compounds, polyoses, coumarins, quinones and flavonic glycosides. Uracil (144), cytidine, inosine, uridine (142), guanosine, thymidine, adenosine (143), hypoxanthine, adenine, and 2-deoxyadenosine

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), Duan et al. (2012), Maharjan et al. (2012)

9

Fritillaria unibracteata

Five amino γ-butenolides compounds, namely fritenolide A (178), B (179), C (180), D (181) and E (182), and β-sitosterol,7-ketositosterol 3-methoxy-4-(palmitoyloxy) benzaldehyde and met hyl octadecanoate

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)

10

Fritillaria taipaiensis

Seven nucleosides and nucleobases: uracil (144), cytidine, uridine (142), guanosine, thymidine, adenosine (143), and adenine

Huang et al. (2011)