Progress on synthesis of benzylisoquinoline alkaloids in sacred lotus (<i>Nelumbo nucifera</i>)

Zhuyin Chen; Hedi Zhao; Sha Chen; Zhuyin Chen; Hedi Zhao; Sha Chen

doi:10.48130/MPB-2023-0020

Figures (1) Tables (1)

Figure 1.
Possible biosynthetic pathways of BIAs in sacred lotus.

No.	Alkaloid	Formula	Enantiomer	Organ	Reference
1-Benzylisoquinoline
1	Norcoclaurine	C₁₆H₁₇NO₃	(+)-R and (−)-S	L, E	[27−30]
2	Coclaurine	C₁₇H₁₉NO₃	(+)-R	L, E, F	[27,29,31]
3	Norjuziphine	C₁₇H₁₉NO₃	NS	F	[32]
4	Isococlaurine	C₁₇H₁₉NO₃	NS	F	[33]
5	N-Methylcoclaurine	C₁₈H₂₁NO₃	(−)-R	L, E, F	[27,29,31]
6	6-Demethyl-4'-O-methyl-N-methylcoclaurine	C₁₈H₂₁NO₃	NS	E	[29]
7	Norarmepavine	C₁₈H₂₁NO₃	(+)-R	F	[31]
8	N-Methylisococlaurine	C₁₈H₂₁NO₃	NS	L, E	[29,34]
9	Norroefractine	C₁₈H₂₁NO₃	NS	F	[33]
10	Juziphine	C₁₇H₁₉NO₃	NS	F	[33]
11	Armepavine	C₁₉H₂₃NO₃	(−)-R and (+)-S	L, E, S	[29,31,35,36]
12	4'-O-Methyl-N-methylcoclaurine	C₁₉H₂₃NO₃	NS	E	[29]
13	Lotusine	C₁₉H₂₄NO₃⁺	NS	E	[29]
14	Isolotusine	C₁₉H₂₄NO₃⁺	NS	E	[29]
15	4'-O-Methylarmepavine	C₂₀H₂₅NO₃	NS	L	[37]
Aporphine
16	Caaverine	C₁₇H₁₇NO₂	(−)-R	L	[35,38]
17	Asimilobine	C₁₇H₁₇NO₂	(−)-R	L, F	[31,38,39]
18	Glaziovine	C₁₈H₁₉NO₃	N/A	F	[33]
19	O-Nornuciferine	C₁₈H₁₉NO₂	(−)-R	L, F	[13,38,40]
20	N-Nornuciferine	C₁₈H₁₉NO₂	(−)-R	L, E, F	[13,29,38]
21	Lirinidine	C₁₈H₁₉NO₂	(−)-R	L, F	[13]
22	N-Methylasimilobine	C₁₈H₁₉NO₂	N/A	F	[32]
23	Roemerine	C₁₈H₁₇NO₂	(−)-R	L, F	[38,40−42]
24	Dehydronuciferine	C₁₉H₁₉NO₂	N/A	L, R	[13,34,41]
25	Dehydroanonaine	C₁₇H₁₃NO₂	N/A	L	[34]
26	Dehydroroemerine	C₁₈H₁₅NO₂	N/A	L	[34]
27	Pronuciferine	C₁₉H₂₁NO₃	(+)-R and (−)-S	L, E, F	[13,29,35,37]
28	Nuciferine	C₁₉H₂₁NO₂	(−)-R	L, E, F	[29,31,38,40]
29	7-Hydroxydehydronuciferine	C₁₉H₁₉NO₃	N/A	L	[38]
30	Lysicamine	C₁₈H₁₃NO₃	N/A	L, F	[13]
31	Cepharadione B	C₁₉H₁₅NO₄	N/A	L	[32]
32	Anonaine	C₁₇H₁₅NO₂	(−)-R	L, F	[38,41]
33	Liriodenine	C₁₇H₉NO₃	N/A	L	[38]
Bisbenzylisoquinoline
34	Nelumboferine	C₃₆H₄₀N₂O₆	NS	E, S	[41,43]
35	Liensinine	C₃₇H₄₂N₂O₆	1R,1'R	L, E, F, S	[39−41,44]
36	Isoliensinine	C₃₇H₄₂N₂O₆	1R,1'S	E	[40,44]
37	Dauriciline	C₃₆H₄₀N₂O₆	NS	S	[5]
38	6-Hydroxynorisoliensinine	C₃₆H₄₀N₂O₆	NS	E	[29]
39	N-Norisoliensinine	C₃₆H₄₀N₂O₆	NS	E	[29]
40	Nelumborine	C₃₆H₄₀N₂O₆	NS	E	[43]
41	Dauricinoline	C₃₇H₄₂N₂O₆	NS	S	[5]
42	Neferine	C₃₈H₄₄N₂O₆	1R,1'S	E, S	[40,41,44]
43	Dauricine	C₃₈H₄₄N₂O₆	NS	S, R	[45]
Tribenzylisoquinoline
1	Neoliensinine	C₆₃H₇₀N₃O₁₀	1R,1'S,1''R	E	[44]

Table 1.

Benzylisoquinoline alkaloids (BIAs) were identified in several organs of Nelumbo nucifera, together with their respective chemical formulas and stereochemical properties. L, lotus leaf; E, lotus embryo; F, lotus flower; S, lotus seed; R, lotus rhizome.