Amaryllidaceae alkaloids from Crinum latifolium with cytotoxic, antimicrobial, antioxidant, and anti-inflammatory activities

Biosynthesis and Biological Activities of Newly Discovered Amaryllidaceae Alkaloids

“…Gigancrinine (44) did not show any anti-AChE activity [63]. Molecular docking studies of zephycandidines (81), (83)(84)(85) and galantamine with AChE revealed that interactions with W286 and Y337 are necessary for inhibitory activity [30] [87]. Narcimatuline (88) was evaluated for its AChE, BChE, POP, and GSK-3β inhibitory activities and significant inhibited BChE, POP and GSK-3 activities, with IC 50 values of 5.9 ± 0.2, 29.2 ± 1.0 and 20.7 ± 2.4 µM, respectively, but only a weak activity against AChE with IC 50 value 489 ± 60 µM [89].…”

“…Several of these novel AAs belong to known structural types, while others harbor new structures. The 91 AAs were classified in this manuscript as I) norbelladine-type (1-6), II) cherylline-type (7, 8), III) galantamine-type (9-16), IV) lycorine-type (17-25), V) homolycorine-type (26)(27)(28)(29)(30), VI) crinine-type (31-50), VII) narciclasine-type (51), VIII) pretazettine-type (52-54), IX) montanine-type (55), and X) other types including AAs related to plicamine (56)(57)(58)(59)(60)(61)(62)(63)(64)(65)(66)(67), seco-plicamine (68-70), cripowellin (71)(72)(73)(74)(75)(76), mesembrine (77,78), and various others AAs (79)(80)(81)(82)(83)(84)(85)(86)(87)(88)(89)(90)(91). Structures of novel AAs belonging to the I to III scaffold types (norbelladine-, cherylline-, and galantamine-type) are depicted in Figure 3, whereas types IV and V (lycorine-and homolycorine-type) are represented in Figure 4.…”

“…From the whole dried plants of Zephyranthes candida, Zephycandidine A (81), a first naturally occurring imidazol[1,2-f] phenanthridine alkaloid was isolated and characterized by spectroscopic analyses and NMR calculations [87]. From the 95% EtOH extract of the whole dried plant of Z. candida, three new alkaloids, zephycandidines I-III (83)(84)(85) were isolated, and their structures were elucidated by spectroscopic methods (HR-ESIMS, 1 H NMR, 13 C NMR, DEPT, 1 H-1 H COSY, HSQC, HMBC, ROESY). The absolute configuration of zephycandidines II and III (84)(85) was estimated by ECD calculation, while the absolute configuration of zephycandidine I (83) was determined by single crystal X-ray diffraction using Cu Kα radiation [30].…”

“…From the 95% EtOH extract of the whole dried plant of Z. candida, three new alkaloids, zephycandidines I-III (83)(84)(85) were isolated, and their structures were elucidated by spectroscopic methods (HR-ESIMS, 1 H NMR, 13 C NMR, DEPT, 1 H-1 H COSY, HSQC, HMBC, ROESY). The absolute configuration of zephycandidines II and III (84)(85) was estimated by ECD calculation, while the absolute configuration of zephycandidine I (83) was determined by single crystal X-ray diffraction using Cu Kα radiation [30]. Sixteen new alkaloids belonging to the galantamine (11−16), plicamine (56−63), and seco-plicamine (68 and 69) types, together with eight known compounds, were isolated from the whole plant of Z. candida.…”

“…4,8-Dimethoxy-cripowellin C (71), 4,8-dimethoxy-cripowellin D (72), 9-methoxy-cripowellin B (73), and 4-methoxy-8-hydroxy-cripowellin B (74), together with one known alkaloid, cripowellin C were isolated from 95% EtOH extract of the bulbs of Crinum latifolium. Structural elucidation was performed by spectroscopic methods like NMR ( 1 H-1 H, COSY, HMQC, and HMBC) and mass spectrometry (HR-ESIMS) [84]. From the rhizome and fruits of Crinum asiaticum var.…”