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Review

The Occurrence and Bioactivities of Amaryllidaceae Alkaloids from Plants: A Taxonomy-Guided Genera-Wide Review

1
Research School of Chemistry, The Australian National University, Acton 2601, Australia
2
School of Medicine and Psychology, The Australian National University, Acton 2601, Australia
3
John Curtin School of Medical Research, The Australian National University, Acton 2601, Australia
*
Author to whom correspondence should be addressed.
Plants 2025, 14(13), 1935; https://doi.org/10.3390/plants14131935
Submission received: 30 April 2025 / Revised: 9 June 2025 / Accepted: 16 June 2025 / Published: 24 June 2025

Abstract

The distribution of Amaryllidaceae alkaloids, with a focus on their chemodiversity, has been reported previously, but not at a genera-wide diversity level. This review provides a comprehensive survey of the occurrence of Amaryllidaceae alkaloids across the genera of the Amaryllidaceae family. This survey is taxonomically guided by the National Center for Biotechnology Information (NCBI) Taxonomy Browser, with targeted keyword searches conducted in the Chemical Abstracts Service (CAS) SciFinder-n and PubMed. The family Amaryllidaceae comprises over 1214 species across three subfamilies: Agapanthoideae (1 genus, 5 species), Allioideae (3 genera plus 11 subgenera, 617 species), and Amaryllidoideae (58 genera plus 13 subgenera, 592 species). Amaryllidaceae alkaloids have been identified exclusively in 36 of the 58 genera and 6 of the 13 subgenera within the Amaryllidoideae subfamily. To date, more than 600 Amaryllidaceae alkaloids have been isolated, predominantly from this subfamily—hence the designation “Amaryllidaceae alkaloids”. These alkaloids display a wide spectrum of biological activities, including acetylcholinesterase inhibition, anti-inflammatory, antioxidant, antimicrobial, antidiabetic, and anticancer effects. A notable example is galanthamine (also known as galantamine), an FDA-approved drug marketed under the brand names Reminyl™ (Janssen Research Foundation, Beerse, Belgium, 2001) and Razadyne™ (Johnson & Johnson Pharmaceutical Research, New Brunswick, NJ, USA, 2004) for the treatment of mild to moderate Alzheimer’s disease, due to its potent acetylcholinesterase-inhibitory activity. Galanthamine has been isolated from species belonging to the genera Cyrtanthus, Galanthus, Leucojum, Lycoris, Narcissus, Ungernia, Chlidanthus, Crinum, Eucharis, Eustephia, Pancratium, and Phaedranassa. Lycorine is another widely distributed alkaloid found across multiple genera, and it has been extensively studied for its diverse bioactivities. Given the remarkable chemical diversity and bioactivity of Amaryllidaceae alkaloids, along with the many underexplored genera and species, further research into Amaryllidaceae species and their alkaloids is strongly warranted to support the discovery and development of novel therapeutic agents.

1. Introduction

Alkaloids can be classified into several categories, including heterocyclic alkaloids; alkaloids with exocyclic nitrogen atoms; aliphatic amines; putrescine-, spermidine-, and spermine-derived alkaloids; peptide alkaloids; terpene and steroid alkaloids; and dimeric (bis-)alkaloids [1]. Among these, Amaryllidaceae alkaloids represent one of the most common and pharmacologically significant classes of heterocyclic alkaloids found in the plant kingdom, often regarded as nature’s gift to humanity. To date, over 636 Amaryllidaceae alkaloids have been isolated and identified from the Amaryllidaceae family [2], hence the name. Notably, galanthamine (or galantamine) is a well-known example that was among the earliest drugs used clinically to treat mild to moderate Alzheimer’s disease, following its FDA approval under the brand names Reminyl™ (Janssen Research Foundation, Beerse, Belgium, 2001) and Razadyne™ (Johnson & Johnson Pharmaceutical Research, New Brunswick, NJ, USA, 2004). A recent systemic review confirms that galantamine (at recommended doses of 16 mg to 24 mg daily) slows a decline in memory and the ability to perform self-care activities at 6 months and 2 years after treatment for people with dementia due to Alzheimer’s disease [3].
Although the distribution of the Amaryllidaceae has been reported in an excellent review of chemodiversity, chemotaxonomy, and chemoecology [2], it was focused on the chemodiversity of 17 types of Amaryllidaceae alkaloids. This review aims to conduct a genera-wide survey on the occurrence of Amaryllidaceae alkaloids in the Amaryllidaceae family—covering its genera and species—as listed in the Taxonomy Browser of the National Center for Biotechnology Information (NCBI) (accessed on 31 January 2025). The presence of Amaryllidaceae alkaloids was investigated using a combination of keywords, Amaryllidaceae, alkaloids, occurrence, isolation, and detection, alongside the names of the family, genera, subgenera, and species. Searches were conducted using the Chemical Abstracts Service (CAS) SciFinder-n database, up to 31 January 2025. In addition, this review discusses reported biological and pharmacological activities based on literature searches performed via PubMed (also up to 31 January 2025) using a combination of Amaryllidaceae and/or alkaloid keywords with bioactivity-related keywords including anti-acetylcholinesterase, anti-inflammatory, antioxidant, antimicrobial, antidiabetic, and anticancer.

2. Genera and Species from the Family Amaryllidaceae

The Amaryllidaceae family, which belongs to the Asparagales order, comprises more than 100 genera and approximately 1200 species [4]. These species are widely distributed across tropical and subtropical regions of the world, including Africa, Australia, Eurasia, and the Americas.
The family Amaryllidaceae are monocotyledons, perennial herbs with bulbs. Occasionally, in genera Clivia and Cryptostephanus and some Scadoxus species, rhizomes instead of bulbs are observed [5]. According to the NCBI Taxonomy ID 4668 for Amaryllidaceae [6], the Amaryllidaceae family comprises 1214 species distributed across 62 genera plus 24 subgenera, classified within three subfamilies: Agapanthoideae, Allioideae, and Amaryllidoideae (Table 1).
The 62 genera plus 24 subgenera identified in this review are fewer than the approximately 100 genera estimated by Ji and Meerow [4]. According to the Angiosperm Phylogeny Website, the Amaryllidaceae family under the order Asparagales comprises 73 genera and 1605 species [7]. It is important to note that the 1214 species listed in Table 1 do not include many unclassified species, which may explain why this number is lower than the 1605 species reported by the Angiosperm Phylogeny Website, but is close to—or slightly higher than—the 1200 species documented by Ji and Meerow. Such discrepancies among different taxonomic classification systems are common and expected.
The NCBI Taxonomy Database includes a disclaimer stating that it is not an authoritative source for nomenclature or classification and advises consulting the relevant scientific literature for the most reliable information. Nevertheless, the database serves as a valuable resource for researchers beyond the field of taxonomy. Accordingly, its classification system for the Amaryllidaceae family is utilized in this review as a framework to survey the occurrence of Amaryllidaceae alkaloids.
The family Amaryllidaceae is divided into three subfamilies: Agapanthoideae, Allioideae, and Amaryllidoideae. The occurrence of alkaloids across these subfamilies and under their genera is the focus of this taxonomic-guided genera-wide review.
Plants in the family Amaryllidaceae have yielded more than 636 reported alkaloids, including both structurally characterized and tentatively identified compounds [2,8]. Several attempts have been made to classify the massive number of Amaryllidaceae alkaloids. Norbelladine, lycorine, homolycorine, crinine, haemanthamine, narciclasine, tazettine, montanine, and galanthamine form nine major types with a unifying numbering system of the different skeletons [9]. Fifteen types of structures [10] and eighteen types [11] were also grouped. Twenty Amaryllidaceae alkaloid types were proposed [12], and they represent the diversity of alkaloid structures, as depicted in Figure 1.

3. Alkaloids from Subfamily Agapanthoideae

The subfamily Agapanthoideae is the first of the three subfamilies within the Amaryllidaceae family and includes a single genus, Agapanthus, comprising five species, A. africanus, A. campanulatus, A. caulescens, A. coddii, and A. praecox, as summarized in Table 2.
To date, no specific Amaryllidaceae alkaloids have been reported in these five Agapanthus species (Table 2). However, one study examining the dichloromethane extract of Agapanthus campanulatus roots detected the presence of alkaloids using TLC separation and the Dragondorff reagent [13].

4. Alkaloids from Subfamily Allioideae

The subfamily Allioideae is the second of the three subfamilies within the Amaryllidaceae family and includes three genera, Allieae, Gilliesieae, and Tulbaghieae, comprising 617 species (Table 3).
The genus Allieae comprises 524 species, none of which have been found to contain Amaryllidaceae alkaloids, based on the SciFinder search described above. However, three studies have reported the presence of other types of alkaloids, including alline [16], 1,2,3,4-tetrahydro-4-hydroxy-4-quinolin carboxylic acid [15], and two indole-type alkaloids—canthin-6-one and 8-hydroxy-canthin-6-one [14].
The genus Gilliesieae includes nine subgenera—Beauverdia, Gilliesia, Latace, Leucocoryne, Miersia, Nothoscordum, Speea, Tristagma, and Zoellnerallium—with a total of 75 species. To date, no Amaryllidaceae alkaloids have been reported in any of these species.
The genus Tulbaghieae consists of two subgenera: Prototulbaghia and Tulbaghia (Table 2). The subgenus Prototulbaghia includes a single species, P. siebertii, with no reports of Amaryllidaceae alkaloids. The subgenus Tulbaghia comprises 17 species, among which two species, T. cernua and T. ludwigiana, were reported to exhibit acetylcholinesterase (AChE) inhibitory activity at a concentration of 1 mg/mL of ethanol extract [17]. However, the active constituents were not identified or isolated.

5. Alkaloids from Subfamily Amaryllidoideae

The subfamily Amaryllidoideae is the third of the three subfamilies within the Amaryllidaceae family and includes 58 genera plus 13 subgenera with a total of 592 species (Table 4). The thirteen subgenera include three—Clinanthus, Pamianthe, and Paramongaia—which belong to the genus Clinantheae and ten—Famatina, Hippeastrum, Paposoa, Phycella, Placea, Rhodolirium, Rhodophiala, Sprekelia, Traubia, and Zephyranthes—which fall under the genus Hippeastreae.
The subfamily Amaryllidoideae is the primary source of Amaryllidaceae alkaloids. Due to the widespread occurrence of these alkaloids within this subfamily, each genus and subgenus has been surveyed for the presence of Amaryllidaceae alkaloids as reported in the scientific literature (Table 4). The alkaloids from each genus or subgenus within the subfamily Amaryllidoideae are surveyed and categorized into three groups:
  • Isolated Amaryllidaceae alkaloids;
  • Detected and identified (but not isolated) Amaryllidaceae alkaloids;
  • No reported Amaryllidaceae alkaloids from the subfamily Amaryllidoideae.

5.1. Isolated Amaryllidaceae Alkaloids from the Subfamily Amaryllidoideae

5.1.1. Genus Amaryllis

The genus Amaryllis has three species (Table 4), including A. munita, A. paradisicola, and A. belladonna. Amaryllis belladonna has been extensively studied for the Amaryllidaceae alkaloids. In 1984, a new alkaloid, anhydrolycorinium chloride, was isolated together with the known acetylcaranine, ambelline, and undulatine from A. bellodonna. The identification of these new and known alkaloids was characterised using UV-VIS, FT-IR, MS, and proton and carbon NMR. The ED50 value against the murine P-388 lymphocytic leukemia was also studied and found to be 1.4, 0.23, and 1.6 µg/mL for anhydrolycorinium chloride, acetylcaranine, and ambelline, respectively [18]. Using HPLC-UV-MS, in 1996, Queckenberg et al. identified nine additional alkaloids which were not reported in A. belladonna before, including anhydrolycorin-7-one, 6-OH-buphanisine, 6-OH-crinine, crinine, galanthine, hippadine, ismine, pratorimine, and pratosine [19].
The new alkaloid (−)-amarbellisine was isolated together with five known alkaloids, (−)-lycorine, (−)-pancracine, (+)-vittatine, (+)-11-hydroxyvittatine, and (+)-hippeastrine, from A. belladonna L. [20]. Cho and coworkers isolated 1,4-dihydroxy-3-methoxypowellan, distichamine, 11-O-acetylambelline, ambelline, acetylcaranine, and hippadine from Amaryllis belladonna Steud. bulbs [21]. In one study, four alkaloids, belladine, undulatine, buphanidrine, and acetylcaranine, were isolated from A. belladonna [17] and studied for their inhibition of acetylcholine esterase in a search to find a better inhibitor than galanthamine, a clinically useful drug for Alzheimer’s disease. Acetylcaranine was found to be the most active towards acetylcholine esterase (AChE), with an IC50 of 11.7 ± 0.7 μM, which is comparable to that of galanthamine (IC50 = 6.19 ± 2.60 μM).

5.1.2. Genus Ammocharis

The genus Ammocharis has six species (Table 4), including A. angolensis, A. baumii, A. coranica, A. longifolia, A. nerinoides, and A. tinneana. From fresh bulbs of A. tinneana, sixteen alkaloids were isolated, and 2D NMR techniques were used for the structural elucidation [22]. 6α-Hydroxycrinamidine and 6α-hydroxyundulatine were reported for the first time together with known alkaloids: seven alkaloids have a 1,2-β-epoxide group and are 1,2-β-epoxyambelline, 11-O-acetyl-1,2β-epoxyambelline, 6α-hydroxycrinamidine, 6α-hydroxyundulatine, flexinine, 1,2-β-epoxyambelline, and 11-O-acetyl-1,2-β-epoxyambelline; six alkaloids are crinine-type, including ambelline, 11-O-accetylambelline, xrinine, powelline, buphanidine, and buphanisine, and three lycorine-type alkaloids including lycorine, sternbergine, and 9-O-demethylpluviine.
From the bulbs of A. coranica, eight alkaloids were isolated: lycorine, acetylcaranine, and crinamine have been reported previously, but 1-O-acetyllycorine, hippadine, 6a-hydroxypowelline, and hamayne were reported from other members of the Amaryllidaceae only, and 1-O-acetyl-9-O-demethylpluviine has not been reported previously [23]. In a recent study of A. coranica, three new alkaloids, golceptine (lycorine type), 6α-hydroxybuphanidrine, and charisine (crinine-type), were isolated, together with the known hippadine, lycorine, caranine, acetylcaranine, and 1-O-acetyl-9-O-demethylpluviine [24].

5.1.3. Genus Boophone

The genus Boophone has three species, including B. disticha, B. haemanthoides, and B. haemanthoides. From B. disticha crinine, buphanamine, buphanidrine, distichamine, and buphanisine were isolated and characterized [25]. Distichamine, lycorine, undulatine, buphanidrine, ambelline, buphanisine, crinine, and distichaminol were isolated from B. haemanthoides [26]. The ethanolic extract of the bulbs of B. disticha contains buphanidrine and distichamine, having an antibacterial activity against both Gram-positive and Gram-negative bacteria, with the best MIC of 0.063 mg/mL [27].
Boophone haemanthoides was shown to be a novel source of the known β-crinane alkaloids, distichamine, buphanidrine, buphanisine, and crinine. Of note is the presence of distichamine in B. haemanthoides, previously identified only in B. disticha, and its significance as a distinctive chemotaxonomic marker for the genus Boophone [28].
One new compound, 1-O-acetylbuphanamine, and four known crinane alkaloids were isolated chromatographically from the ethanol extract of the bulbs of B. disticha [29]. From a B. haemanthoides extract, three Amaryllidaceae alkaloids, distichamine, 1α,3α-diacetylnerbowdine, and hippadine, were isolated [30].

5.1.4. Genus Brunsvigia

The genus Brunsvigia has eight species, including B. bosmaniae, B. comptonii, B. gregaria, B. orientalis, B. radula, B. radulosa, B. cf. radulosa Spies 7629, and B. striata. From B. josephin crinine, buphanisine, buphanidrine, undulatine, 3-O-acetylhamayne, hamayne, crinamine, ambelline, and sternbergine were isolated together with a new josephinine [31]. Four known alkaloids, lycorine, 1,2-di-O-acetyllycorine, ambelline, and crinine, were isolated from the bulbs of B. littoralis [32].
The bulbs of B. radulosa yielded a new alkaloid, 1-O-acetylnorpluviine, together with the known alkaloids 1-epideacetylbowdensine, crinamine, crinine, hamayne, lycorine, anhydrolycorin-7-one, and sternbergine [33].

5.1.5. Genus Calostemma

The genus Calostemma has two species (Table 4), including C. luteum and C. Purpureum. The bulbs of C. purpureum yield a major component of lycorine and three minor components of haemanthamine, crimidine, and powelline [34].
From the C. purpureum extract, incartine, lycorine, and galanthine were identified as well as trace amounts of other alkaloids of the lycorine, homolycorine, and tazettine types [35].

5.1.6. Genus Chlidanthus

The genus Chlidanthus has two species (Table 4), including C. boliviensis and C. fragrans. In 1956, from 2 kg of C. fragrans bulbs, Biot obtained 0.45 g of lycorine, 0.31 g of chlidanthine, and 0.98 g of tazettine [36].
Fifteen known Amaryllidaceae alkaloids of five structure types were from the bulbs of C. fragrans, using capillary GC-MS. The fifteen alkaloids were identified as galanthamine, chlidanthine, buphanisine, narwedine, belladine, 6-deoxytazettine, N-demethylbelladine, 6-O-methylpretazzetine, tazzetine, undulatine, lycorine, ambelline, 3-epimacronine, acetylnerbowdine, and bowdesine. The main alkaloids were tazzetine (tazettine-type), chlidanthine (galanthamine-type), belladine (belladine-type), and lycorine (lycorine-type) [37]
Eleven Amaryllidaceae alkaloids were isolated from fresh bulbs of C. fragrans, and the crinine-type Amaryllidaceae alkaloid undulatine showed a promising acetylcholinesterase and prolyl oligopeptidase inhibition activity with IC50 values of 23.0 μM and 1.96 mM, respectively [38].

5.1.7. Genus Clinantheae (With Three Subgenera)

The genus Clinantheae has three subgenera, Clinathus, Pamianthe, and Paramongaia (Table 4). The subgenus Clinathus has six species, including C. coccineus, C. humilis, C. imasumacc, C. incarnatus, C. mirabilis, and C. ruber.
The fresh bulb of Clinanthus microstephium is extracted with methanol and fractionated using chromatographic techniques. The analysis of the fractions using GC/MS and NMR resulted in the identification of seven known compounds, such as anhydrolycorine, 11,12-dehydroanhydrolycorine, hippeastrine, 1-O-butenoyllycorine, 1-O-(3-hydroxybutanoyl)lycorine, lycorine, and 6-hydroxymaritidine [39].
The subgenus Pamianthe has two species (Table 4), including P. ecollis and P. peruviana. The subgenus Paramongaia has four species (Table 4), including P. milagroantha, P. multiflora, P. viridiflora, and P. weberbaueri. No report of Amaryllidaceae alkaloids was found from the SciFinder search for both subgenera.

5.1.8. Genus Clivia

The genus Cliva has nine species (Table 4), including C. caulescens, C. gardenia, Clivia cf. gardenii ‘robust’, C. miniate, C. mirabilis, C. nobilis, C. robusta, Clivia × cyrtanthiflora, and Clivia × nimbicola. Interestingly, C. caulescens has rhizomes, instead of bulbs [5].
From C. caulescens alkaloids hippeastrine, haemanthamine, (11S)-11-hydroxyvittatine, lycorine, and sterbergine were isolated, whereas haemanthamine, haemanthidine in its free base and quaternary salt form, and tazettine in the quaternary salt were isolated from C. gardenii [40].
Kornienko and Evidente reported the isolation of clivonine, clivatine, nobilisitine A, and nobilisitine B from C. miniata and rystilline, clivimine, nobilisine, and hyamine from C. nobilis [41]. Nobilisitine A, nobilisitine B, and 5-O-acetylnobilisitine A were also isolated from C. nobilis [42].
Lycorine was isolated as the active component responsible for the pronounced antiviral activity of crude extracts from the roots and leaves of C. miniata Regel. In addition, clivimine, clivonine, and cliviamartine were also isolated and characterized; however, these alkaloids did not exhibit antiviral properties [43].

5.1.9. Genus Crinum

The genus Crinum has 68 species (Table 4), and some important species are highlighted here. The genus has been studied extensively and attracted several comprehensive reviews on the Crinum alkaloids, as in Phytochemistry [44], the review covering the period from 1985 to 2000 [45] and the review focusing on C. latifolium [46].
The Ghosal review presented 46 Amaryllidaceae alkaloids isolated from various Crinum species [44], whereas the Tram review presented 68 Amaryllidaceae alkaloids [45], including ambelline, augustamine, augustine, (−)buphanisine, (−)crinamidine, (+)crinamine, (−)crinine, (−)1,2-di-O-acetyllycorine, (−)galanthamine, (+)haemanthamine, hamayne, hippadine, hipeastrine, (−)6-α-hydroxybuphanisine, (+)6-hydroxycrinamine, ismine, (−)lycorine, powelline, pratorimine, pratorinine, pratosine, O-methylpratorimine, O-methyl-pratorinine, and the 3-epimer of criwelline.
Hippadine, lycorine, hippeastrine, masonine, and crinine have been isolated from C. firmifolium; lycorine, crinine, and 6-hydroxycrinamine have been isolated from C. hardyi; lycorine, 6-hydroxycrinamine, and pseudolycorine have been isolated from C. pronkii; and a novel lycorine-related iminium salt, the 6,7,11b,11c-didehydrolycorinium salt, was isolated from bulbs of both C. firmifolium and C. hardyi [47].
Novel 4,8-dimethoxy-cripowellin, 4,8-dimethoxy-cripowellin, 9-methoxy-cripowellin, and 4-methoxy-8-hydroxy-cripowellin, along with one known alkaloid, cripowellin, were isolated from the 95% ethanol extract of the bulbs of C. latifolium. These compounds exhibited cytotoxic, antimicrobial, antioxidant, and anti-inflammatory activities [48].
Fifteen alkaloids—8α-ethoxyprecriwelline, N-desmethyl-8α-ethoxypretazettine, N-desmethyl-8β-ethoxypretazettine, bulbispermine, 1-O-acetyllycorine, epivittatine, crinamine, 3-O-acetylhamayne, 6-hydroxycrinamine, epibuphanisine, powelline, crinine, cherylline, crinamidine, and 1-epideacetylbowdensine—were isolated from C. bulbispermum and C. moorei [49].
From the bulbs of C. pratense, lycorine, 1,2-diacetyllycorine, ambelline, narcissidine, and three phenanthridone alkaloids, viz. hippadine, pratorinine, and anhydrolycorin-7-one, were isolated and characterized [50]. Sixteen additional Amaryllidaceae alkaloids were isolated from the bulbs of C. kirkii Baker, including two previously unknown compounds, noraugustamine and 4a,N-dedihydronoraugustamine [51].

5.1.10. Genus Crossyne

The genus Crossyne has two species (Table 4), including C. flava and C. guttata. Crossyne guttata yielded the alkaloids crinamine and epibuphanisine [52]. The four compounds isolated from C. flava are pancratinine B, bufanidrine, buphanisine, and epibuphanisine [53]
Distichamine was isolated from an ethanolic fraction of C. guttata along with two known alkaloids, crinamine and epibuphanisine. Distichamine, a rare β-crinane alkaloid previously reported only from the genus Boophone, is now found in the genus Crossyne, suggesting that it may be more widespread within the subfamily Amaryllidaceae [54].

5.1.11. Genus Cybistetes

The genus Cybistetes has one species (Table 4), C. longifolia, in which three alkaloids, 6-hydroxycrinamine, lycorine, and pseudolycorin were isolated and identified [55].

5.1.12. Genus Cyrtanthus

The genus Crytanthus has 44 species (Table 4). Two species, C. elatus and C. obliquus, are showcased with isolated alkaloids here. Zephyranthine and 1,2-O-diacetylzephyranthine were isolated from C. elatus [56]. The ethanolic extract of C. obliquus (L.f.) Ait yielded a new dinitrogenous alkaloid obliquine, 3S,4αS,11S,10βS-3,4,4α,13,11,5,6-heptahydro-5[2-(4-hydroxyphenyl)ethyl]-3-methoxy-13-methyl-[1,3]dioxolo[4,5-g]indolo[3,3α-c]-isoquinolin-12-one, along with five known alkaloids: 11α-hydroxygalanthamine, 3-epimacronine, narcissidine, tazettine, and trisphaeridine [57].

5.1.13. Genus Eucharis

The genus Eucharis has nine species (Table 4), and E. amazonica is showcased with isolated alkaloids here. From 1.2 kg of the dried bulbs and leaves of flowering E. amazonica, thirteen alkaloids have been isolated, including 7-methoxyoxoassoanine (12 mg), 6-O-methylpretazettine (6 mg), and apohaemanthamine (49 mg), as newly reported from this species, together with lycorine (64 mg), ismine (26 mg), trisphaeridine (21 mg), tazettine (156 mg), 3-epimacronine (24 mg), haemanthamine (16 mg), galanthamine (81 mg), 3-O-methylgalanthamine (41 mg), vittatine (42 mg), and 8-O-demethylmaritidine (47 mg) [58].

5.1.14. Genus Eustephia

The genus Eustephia has one species (Table 4), E. yuyuensis. Three alkaloids were isolated from bulb, with the major alkaloid being lycorine and the minor being galanthamine and galanthine [59].

5.1.15. Genus Galanthus

The genus Galanthus has 25 species (Table 4). The isolation of galanthamine from various species in the genus Galanthus has been reviewed [60]. The phytochemistry of Amaryllidaceae alkaloids in Galanthus species has been recently reviewed [61].
From G. nivalis, Berkov and coworkers isolated and identified two new alkaloids, 3,3′-O-(3′,3″-dihydroxybutanoyl)hamayne and 11,3′-O-(3′,3″-dihydroxybutanoyl)hamayne, together with six known alkaloids, 3,11-O-(3′,3″-dihydroxybutanoyl)hamayne, 3,11,3′-O-(3′,3″,3‴-trihydroxybutanoyl)hamayne, 8-O-demethylvasconine, tazettine, epimacronine, and ismine. From G. elwesii, the group also isolated and identified one new alkaloid, 2-O-(3′-hydroxybutanoyl)lycorine, together with two known alkaloids, 2-O-(3′-acetoxybutanoyl)lycorine and incartine. In addition, from both species, the known alkaloids hamayne, 11-O-(3′-hydroxybutanoyl)hamayne, and lycorine were isolated and identified. All structures were determined using EI-MS, HR-MS, CD, and 1D and 2D NMR, including COSY, NOESY, HMQC, and HMBC [62].
(+)-5-methoxy-9-O-demethylhomolycorine, (+)-galwesine, (+)-9-O-demethylgalwesine, (+)-16-hydroxygalwesine, (+)-16-hydroxy-9-O-demethylgalwesine, and galasine, were isolated from whole plants of Galanthus elwesii. Additionally, 12 known alkaloids, (−)-galanthamine, (−)-sanguinine, (−)-leucotamine, (−)-O-methylleucotamine, (+)-narwedine, (−)-N-demethylgalanthamine, (+)-11-hydroxyvittatine, (+)-9-O-demethylhomolycorine, (−)-lycorine, (−)-galanthine, hordenine, and (E)-N-feruloyltyramine, were also obtained [63].
Tazettine, galanthamine, sanguinine, and haemanthamine were isolated from G. cilicicus [64]. Three new alkaloids, oxoincartine, 3,11-O-diacetyl-9-O-demethylmaritidine, and 11-O-acetyl-9-O-demethylmaritidine, together with seven known compounds, namely incartine, galanthamine, galanthine, 9-O-methylpseudolycorine, N,O-dimethylnorbelladine, hordenine, and vittatine, were isolated from G. fosteri Baker [65].
Two new Amaryllidaceae alkaloid N-oxides, incartine N-oxide and lycorine N-oxide, along with one β-carboline alkaloid, 1-acetyl-β-carboline, and six known alkaloids—incartine, N-trans-feruloyltyramine, lycorine, O-methylnorbelladine, vittatine, and 11-hydroxyvittatine—were isolated from G. rizehensis Stern [66]. Also, two new alkaloid N-oxides—1-O-acetyldihydromethylpseudolycorine N-oxide and 11-hydroxyvittatine N-oxide—plus ten known alkaloids—arolycoricidine, haemanthamine, O-methylnorbelladine, narcidine, dihydrolycorine, 8-O-demethylmaritidine, stylopine and protopine, nicotinic acid, and tyramine—were isolated from G. trojanus A.P. Davis & N. Ozhatay [67].

5.1.16. Genus Haemanthus

The genus Haemanthus has 12 species (Table 4) from which Amaryllidaceae alkaloids have been isolated. The roots of H. kalbreyeri contain a new phenanthridone alkaloid, kalbretorine, and a new glucosyloxy alkaloid, kalbreclasine. Additionally, six known alkaloids, viz. haemanthamine, haemanthidine, hippadine, lycorme, narciclasine, and pratorimine, previously reported from other Amaryllidaceous plants, have now also been isolated from this species [68]. On the other hand, the bulbs of H. kalbreyeri contain two new alkaloids, 7-deoxypancratistatine and pancratiside (i.e., pancratistatine-2-O-β-D-glucoside), together with known alkaloids, narciclasine, 7-deoxynarciclasine, and pancratistatine [69].

5.1.17. Genus Hieronymiella

The genus Hieronymiella has two species (Table 4), including H. argentina and H. peruviana. Nine alkaloids, including galanthamine, sanguinine, and chlidanthine, were isolated from the extract of H. argentina [70], and twenty-two alkaloids, most of them of the homolycorine-type and galanthamine-type, were identified in the extracts of H. peruviana by means of GC-MS and UPLC-MS/MS [71].

5.1.18. Genus Hippeastreae (With 10 Subgenera)

The genus Hippeastreae has ten subgenera (Table 4): Famatina, Hippeastrum, Paposoa, Phycella, Placea, Rhodolirium, Rhodophiala, Sprekelia, Traubia, and Zephyranthes. Alkaloids have been isolated from four subgenera of Hippeastrum, Rhodolirium, Rhodophiala, and Zephyranthes. They are presented below.

5.1.19. Hippeastrum Species

From 12 kg of H. vittatum, 0.79 g of lycorine, 0.05 g of homolycorine, 0.15 g of chlidathine, 0.95 g of hemanthamine, 0.15 g of hippeastrine, and 0.3 g of vittatine were isolated and identified [36]. Tazettine and haemanthamine were identified from the 0.02% total alkaloids obtained from the bulbs of H. bifidum [34].
The application of GC–MS resulted in the identification of two crinine-type alkaloids, aulicine and 3-O-methyl-epimacowine, from the indigenous Brazilian species H. aulicum and H. calyptratum, respectively. In addition, two alkaloids, 11-oxohaemanthamine and 7-methoxy-O-methyllycorenine, were isolated from H. aulicum [72].
A new lycosinine derivative, 9-O-demethyllycosinine, was isolated from the endemic Brazilian Hippeastrum breviflorum Herb., Amaryllidaceae, along with the well-known alkaloids lycosinine and lycorine [73]. Hippeastrum albiflos yielded homolycorine, albomaculine, and the O-methyl-lycorenium salt. From H. pauculifolius, homolycorine, a novel paucamine isolated as a salt, together with the quaternary salts of homolycorine, montanine, and manthidine were obtained. Form H. deformis, coccinine, montanine, and the quaternary salt of manthidine were isolated [74].
From the bulbs of the Vietnamese H. equestre Herb, two new alkaloids, 3-O-emethyltazettine and egonine, have been isolated [75]. Their structures were established by UV, MS, NMR, and CD. It is interesting to note that the identified alkaloid egonine was the alkaloid of the mesembrine-type or mesembrinone-type, usually isolated from Sceletium species, not belonging to the family Amaryllidaceae. This is why Sceletium alkaloids are sometimes discussed together with Amaryllidaceae alkaloids [76].

5.1.20. Rhodolirium speciosum

From R. speciosum, 1-O-acetyl-5,6-dehydrolycorine, 1-O-acetyl-lycorine, and 1,2-O-diacetyl-5,6-dehydrolycorine were separated using pH-zone-refinement centrifugal partition chromatography and identified using NMR and GC-MS [77].

5.1.21. Rhodophiala bifida

The bulbs of R. bifida consisted of montanine, vitattine, hemanth amine, hemanthidine, tazettine, corianicine, and traces of lycorine and O-acetylmontanine [78].

5.1.22. Zephyranthes species

Alkloids in Zephyranthes species have been reviewed [79]. Alkaloids have been found in Z. andersoniana, Z. candida, Z. carinata, Z. citrina, Z. concolor, Z. flava, Z. grandiflora, Z. lancasteri, Z. robusta, Z. rosea, Z. sulphurea, Z. tubispatha, and Z. texana
Eleven new alkaloids identified as six types of 12-acetylplicamine, N-deformyl-seco-plicamine, plicamine, 4α-epi-plicamine, seco-plicamine, and lycorine, along with fifteen known alkaloids, were isolated from the whole plants of Z. carinata [80]. Also, three new Amaryllidaceae alkaloids, named zephycandidines I-III, were isolated from Z. candida. Zephycandidines I and III with new framework types represent the first example of 7-phenyl-hexahydroindole and 5,2′-dimethyl-biphenyl-2-ylamine alkaloids, respectively [81].
Alkaloids in seeds [82] and flowers [83] of Z. flava were studied. The flowers contain four new alkaloidal phospholipids, 2-O-glyarophosphoryllycorine, phosphatidyllycorines, phosphatidylpscudolycorines, and phosphatidyllycorinium methocation, whereas the seeds contain two new alkaloids, zefbetaine and zeflabetaine, together with known alkaloids of crinamine, haemanthamine, lycorine, maritidine, methylpseudolycorine, pretaxettine Haemanthidine, pseudolycorine, narciclassine, pratorimine, kalbreclassine, lycorine-1-O-β-D-glucoside, pseudolycorine-1-O-β-D-glucoside, betaines, criasbetaine, and ungeremine.
Twenty-six structurally diverse Amaryllidaceae alkaloids were isolated from whole plants of Z. candida. These include ten novel compounds—zephyranines A to I and 6-O-ethylnerinine—as well as two previously undescribed natural products, zephyranthine-6-one and 3-O-deacetyl-sternbergine. The study evaluated nine distinct alkaloid frameworks for their acetylcholinesterase inhibitory and anti-inflammatory activities [84].
(+)-Epimaritidine, a new alkaloid from Z. rosea, together with known alkaloids crinamine and haemanthamine are reported [85]. Phytochemical investigation of the 95% ethanol extract of the whole plants of Z. grandiflora led to the isolation of six new 4α-epi-plicamine-type alkaloids, named zephygranditines A-F, along with three novel 11,12-seco-plicamine-type alkaloids [86].
The bulbs and aerial parts of Z. concolor (Lindl.) Benth. & Hook. f., an endemic Mexican species, contain the alkaloids chlidanthine, galanthamine, galanthamine N-oxide, lycorine, galwesine, and epinorgalanthamine [87]. Eight alkaloids have been isolated from Z. citrina (Amaryllidaceae), including oxomaritidine, which is reported for the first time from a natural source [88].

5.1.23. Genus Hymenocallis

The genus Hymenocallis has 40 species (Table 4), and some species are showcased here. The bulbs of H. littoralis, H. crassifolia, and H. caymanensis contain isolated tazettine and lycorine, whereas H. occidentalis contains tazettine, lycorine, and nivaline; and H. speciosa has a major component of lycorine with minor components of tazettine, urceoline, hippeastrine, and haemanthamine [34].
In searching the sources of pancratistatin, a promising anticancer agent, Hymenocallis species representing a broad geographical selection were investigated. Pancratistatin was isolated from H. speciosa (Singapore), H. variegata (Singapore), H. pedalis (Seychelles), H. expansa (Bermuda), and H. sonoranensis (Mexico) [89].
From Hymenocallis x festalis Hort. Ex Schmarse, a hybrid of H. longipetala and H. narcissiflora, a new phenanthridine-type alkaloid 3-methoxy-8,9-methylenedioxy-3,4-dihydrophenanthridine (2 mg, from 8 kg of fresh bulbs) and 3-Methoxy-3,4-dihydrotrisphaeridine were isolated [90].

5.1.24. Genus Ismene

The genus Ismene has six species (Table 4), including I. amancaes, I. hawkesii, I. longipetala, I. narcissiflora, I. vargasii, and Ismene x deflexa. The plant extract of I. amancaes contains lycoramine, a galanthamine-type alkaloid, identified by GC-MS [91].

5.1.25. Genus Lapiedra

The genus Lapiedra has one species (Table 4), L. martinezii. From this species, homolycorine N-oxide and O-methyllycorenine N-oxide were isolated, and the authors claimed that they represented the first examples of naturally occurring N-oxides from the Amaryllidaceae [92]. From the methanolic extract of L. martinezii, a new alkaloid, N-methyl-assoaninium chloride, has been isolated together with hippadine, narcissidine, and ungiminorine [93]. N-Chloromethyl-narcisidinium chloride was also isolated but is probably an artifact formed during the isolation process. In another study on L. martinezii by the same group, the known alkaloid ismine, was isolated together with three phenatridine alkaloids, 8,9-methylenedioxophenantridine, N-methyl-8,9-methylenedioxy-6-phenantridone, and N-methyl-8,9-methylenedioxy-phenantridinium chloride [94].

5.1.26. Genus Leucojum

The genus Lapiedra has two species (Table 4), including L. aestivum and L. vernum, from which alkaloids have been isolated.
Leucojun vernum contains leucovernine, acetylleucovernine, and 9-O-demethylhomolycorine [95].
A new alkaloid, N-(14-methylallyl)norgalanthamine, together with five known alkaloids, N-allylnorgalanthamine, galanthamine, epinorgalanthamine, narwedine, and lycorine, were isolated from mother liquors (waste material) obtained after the industrial production of galanthamine hydrobromide from Leucojum aestivum leaves [96]. The production of galanthamine from the tissue culture of Leucojum leaves was studied [97].

5.1.27. Genus Lycoris

The genus Lycoris has 25 species (Table 4), and alkaloids were extensively isolated as highlighted below.
The investigation of the 80% EtOH extract of the bulbs of L. aurea led to the isolation of six new alkaloids, 2-demethyl-isocorydione, 8-demethyl-dehydrocrebanine, 1-hydroxy-anhydrolycorin-7-one, (+)-1,2-dihydroxy-anhydrolycorine N-oxide, 5,6-dihydro-5-methyl-2-hydroxyphenanthridine, and (+)-8-hydroxy-homolycorine-α-N-oxide, in addition to two known compounds, isocorydione and anhydrolycorin-7-one [98].
Dihydrocaranine, dihydrolycorine, 7-oxodihydrolycorine, 3,4-dihydroanhydrolycorine, norbelladine, 2α-hydroxy-O-methyloduline, 3β-methoxy-6,11-dihydroxycrinane, 3β,11-dihydroxycrinane, 6β-acetoxycrinamine, 3α,6β-diacetyl-bulbispermine, 3α-hydroxy-6β-acetylbulbispermine, 3α-methoxy-6β-acetylbulbispermine, N-demethyl-8α-ethoxypretazettine, and N-demethyl-8β-ethoxypretazettine were also found in L. radiata [99].
From the bulbs of L. radiata, 2α-methoxy-6-O-ethyloduline, O-demethyllycoramine, and N-chloromethyl ungiminorine were isolated as new alkaloids together with the known compounds of radiatine, 2α-hydroxy-6-O-methyloduline, O-ethyllycorenine, O-methyllycorenine, 9-O-demethylhomolycorine, 9-O-demethyl-2α-hydroxyhomolycorine, hippeastrine, lycoramine N-oxide, O-demethyllycoramine, lycoramine, galanthamine N-oxide, sanguine, galanthamine, (−)-epi-zephyranthine, dihydrolycorine, lycorine, hippamine, 4-O-methyllycorine, pseudolycorine, pluviine, pancratinine, (−)-3-O-methylpancracine, pancracine, narciclasine, and 2′-deoxythymidine [100].
Four new Amaryllidaceae alkaloids—(+)-1-hydroxy-ungeremine, (+)-6β-acetyl-8-hydroxy-9-methoxy-crinamine, (+)-2-hydroxy-8-demethyl-homolycorine-α-N-oxide, and (+)-N-methoxycarbonyl-2-demethyl-isocorydione—along with two known compounds, (+)-6β-acetyl-crinamine and 8-demethyl-homolycorine-α-N-oxide, were isolated from the ethanol extract of the bulbs of L. radiata [101]. Also, a new lycorine-type alkaloid, 1-O-(3’S)-hydroxybutanoyllycorine, together with four known alkaloids of galanthamine, lycoramine, sternbergine, and ungiminorine were isolated from L. traubii [102].
The bulbs of L. caldwellii afforded four new alkaloids, (+)-N-methoxylcarbonyl-nandigerine, (+)-N-methoxycarbonyl-lindcarpine, (+)-10-O-methylhernovine N-oxide, and (+)-3-hydroxy-anhydrolycorine N-oxide [103]. Lycoris sprengeri contains lycosprenine, narcissidine, tortuosine, 2α-methoxy-6-O-methyllycorenine, lycoramine, montabuphine, and crinasiadine [104].

5.1.28. Genus Narcissus

The genus Narcissus (commonly known as daffodils) has 97 species (Table 4), and alkaloids have been reported extensively. A total of 92 Amaryllidaceae alkaloids were reported up to July 2005 from about 40 wild species, and 100 cultivars of the genus Narcissus were isolated and reviewed [105].
The bulbs of N. bicolor growing in Spain afforded three new alkaloids, bicolorine, 5,6-dihydrobicolorine, and oxoassoanine-N-oxide, whose structures were determined by mass and spectral analyses. Three known alkaloids, pretazettine, 9-O-demethylhomolycorine, and 3-epimacronine, were also isolated [106].
The aerial parts of N. papyraceus contain three new alkaloids, O-methylpapyramine, O-methylmaritidine, and 9-O-demthylhomolycorine N-oxide, together with lycorine, papyramine, pseudolycorine, homolycorine, and 9-O-demethylhomolycorine [107].
The whole plant of N. radinganorum contains three Amaryllidaceae alkaloids—homolycorine, 8-O-demethylhomolycorine, and 9-O-demethylmaritidine—with the third compound being reported for the first time [108]. From N. pallidullus, mesembrenone and roseine were isolated [109].
Seven alkaloids were isolated from fresh bulbs of N. angustifolius subsp. transcarpathicus, with nangustine being the 5,11-methanomorphanthridine alkaloid with a C-3/C-4 substitution, and reported for the first time [110]. In another study, eleven alkaloids were isolated from the whole plants of N. bujei, with 11-O-acetylhaemanthamine and bujeine being reported for the first time [111].
Homolycorine was isolated from N. confusus Pugsley, and its chirality was determined by an X-ray crystallographic analysis of the hydrochloride dihydrate [112]. Ismine was isolated from several Narcissus species [113]. A study on the isolation and acetylcholinesterase inhibition found four alkaloids—(−)-9-O-methylpseudolycorine, (−)-narcissidine, (−)-pancratinine-C, and (+)-9-O-demethyl-2-α-hydroxyhomolycorine—isolated from N. tazetta subsp. tazetta L. [114].
From the fresh bulbs of Narcissus cv. Professor Einstein, a new lycorine-type alkaloid, 7-oxonorpluviine, was isolated together with 23 known alkaloids of masonine, homolycorine, ismine, caranine, galanthamine, narwedine, lycoraminone, pluviine, incartine, galanthine, lycoramine, epinorgalanthamine, norlycoramine, haemanthamine, hippeastrine, epimaritidine, lycorine, tazettine, eugenine, norpluviine, 9-O-demethylmaritidine, pancracine, and 9-O-demethylhomolycorine [115].

5.1.29. Genus Nerine

The genus Nerine has nine species (Table 4), including N. alta, N. bowdenii, N. humilis, N. huttoniae, N. laticoma, N. masonorum, N. platypetala, N. sarniensis, and N. undulata.
From 1 kg of N. undulata, 0.51 g of lycorine, 0.03 g of ambelline, 0.05 g of undulatine, 0.04 g of base N, 0.07 g of nerispine, and 0.7 g of crispine were obtained [36]. Nerine bowdenii Watson contains filifoline, buphanisine, 11-O-acetylambelline, ambelline, and undulatine [116].
N-Demethylbelladine, 6a-methoxybuphanidrine, and filifoline were isolated and identified as new alkaloids in addition to the known alkaloids of belladine and 6a-methoxybuphanidrine from N. filifolia [117]. A new mesembrine-type alkaloid, named sarniensine, was isolated together with tazettine, lycorine, and 3-epimacronine from N. sarniensis. Lycorine and 3-epimacronine are reported from this species for the first time [118].

5.1.30. Genus Pancratium

The genus Pancratium has 14 species (Table 4). This genus has been reviewed in Volume 68 (2010) of The Alkaloids [119].
The isolated alkaloids from the genus (the most studied species is P. mancratium) were grouped under eight types [119]:
(1)
Lycorenine type, which includes hippeastrine, (+)-9-O-demethylhomolycorine, 10-norneronine, and pancratinine A;
(2)
Lycorine type, which includes pancrassidine, galanthane, hippadine, 3,4-dihydroanhydrolycorine, hihydrocaranine, dihydrolycorine, ungeremine, zefbetaine, ungiminorine N-oxide, and pancratinine D;
(3)
Montanine type, which includes pancracine from P. maritimum and P. sickenbergeri; pancratinine B, and pancratinine C from P. canariense;
(4)
Narciclasine type, which includes pancratistatin, narciclasine, and its glycosidic derivative;
(5)
Tazettine type, which includes tazettine and deoxytazettine from P. maritimum and pretazettine from Pancratium biflorum;
(6)
Galanthamine type, which includes galanthamine, N-norgalanthamine, N-formylgalanthamine, habranthine, lycoramine, N-norlycoramine, and 3-O-acetyllycoramine;
(7)
Cranine type, which includes crinine, crinan-3-one, buphanisine, macowine, (−)-3β-methoxy-6,11-dihydroxycrinane, and (−)-3β-11-dihydroxycrinane; and
(8)
Haemanthamine, which includes haemanthamine, vittatine, 11-hydroxyvittatine, maritidine, haemanthidine, ent-6-hydroxybufanisine, 8-demethylmaritidine, 9-demethylmaritidine, crinamine, and 6-O-methylhaemanthidine.
Pancratium canariense possessed 12 alkaloids, including 1-O-acetyl-8-norpluviine, ungiminorine, pancratinine, 10-norneronine, littatine, 11-hydroxyvitattine, 6-O-methylhaemanthidine, 6-O-methylhaemanthidine, and pancracine [109].
Ungeremine and zefbetaine were isolated from Egyptian P. maritimum [120]. 11α-hydroxy-O-methylleucotamine was isolated for the first time from P. illyricum L., which contains eight known alkaloids: lycorine, 2-hydroxyhomolycorine, vittatine, galanthamine, sanguinine, habranthine, leucotamine, and O-methylleucotamine [121].
Ungiminorine N-oxide was isolated from P. maritimum, and the authors claimed that they represented the first examples of naturally occurring N-oxides from the Amaryllidaceae [92].

5.1.31. Genus Phaedranassa

The genus Phaedranassa has eight species (Table 4), including P. carmiolii, P. cinerea, P. dubia, P. lehmannii, P. schizantha, P. tunguraguae, P. ventricose, and P. viridiflora.
Bulbs (771 g) of P. dubia were found to contain a new phaedranamine (12 mg) together with seven known alkaloids: pseudolycorine (28 mg), haemanthamine (15 mg), sanginine (5 mg), epinorgalanthamine (4 mg), galanthamine (5 mg), zefbetaine (8 mg), and ungeremine (6 mg) [122].

5.1.32. Genus Scadoxus

The genus Scadoxus has four species (Table 4), including S. puniceus, S. cinnabarinus, S. membranaceus, and S. multiflorus. Haemanthamine and haemanthidine were isolated from S. puniceus [123].

5.1.33. Genus Sternbergia

The genus Sternbergia has eight species (Table 4), including S. candida, S. clusiana, S. colchiciflora, S. greuteriana, S. lutea, S. pulchella, S. sicula, and S. vernalis.
Bulbs of S. clusiani were found to contain the following seven known alkaloids: lycorine, galanthamine, haemanthamine, haemanthidine, 11-hydroxyvittatine, crinine, and isotazettine [124]. From the bulbs of S. lutea a new compound was isolated and named sternbergine, which was elucidated as 1-O-acetylisopseudolycorine. Previously isolated alkaloids lycorine, tazettine, hippeastrine, galanthine, galantham lycorine, galanthamine, hippeastrine, and tazzetine were also found [125].
The crinine-type alkaloids (+)-buphanisine and (−)-siculine were isolated from S. sicula, while (−)-epimaritinamine and (−)-mariti namine were found in S. lutea [126]. Aerial parts of S. lutea isolated 1% lycorine and 0.18% pancratine, as compared to the bulbs of this plant, which has 0.21% lycorine, 0.052% tazettine, and 0.028% pancratine [127]. Twenty-one alkaloids and related compounds were found in S. colchiciflora. Ten alkaloids were isolated, and their structures confirmed by NMR, MS, and CD measurements [128]. The Sternbergia clusiana of Turkish origin yielded four alkaloids, lycorine, haemant hamine, haemanthidine, and tazettine [129].

5.1.34. Genus Ungernia

The genus Ungernia has two species (Table 4), including U. flava and U. tadschicorum.
Ungernia alkaloids have been reviewed up to 1980 [130]. About 20 alkaloids representing structural types of lycorine, crinine, lycorenine, galanthamine, and tazettine were isolated from the genus, including U. tadshicorum, U. severzovii, U. victoris, U. vvedenskyi, U. trisphaera, and U. ferganica.
Most of the isolation work was reported by Russian scientists on the Ungernia species grown in Russia; for example, ungvedine was isolated from U. vvedenskyi [131]. The extracting of 11 kg of powdered dry leaves of U. spiralis (moistened with 8% ammonia) with chloroform, treating the extract with 10% sulfuric acid, and alkalizing it with an ammonia solution produced 0.11% lycorine, 0.75 g of galanthamine, 0.3 g of ungeremine, 0.2 g of hippeastrine, and 0.15 g of tazettine [127].

5.1.35. Genus Urceolina

The genus Urceolina has two species (Table 4), U. microcrater and U. peruviana. The bulbs of U. miniata contain 0.13% alkaloids consisting of 52% tazettine, 31% haemanthamine, 4% lycorine, and two new alkaloids in the 4% yield, namely urceoline and urminine [34].

5.1.36. Genus Worsleya

The genus Worsleya has two species (Table 4), W. procera and W. rayneri. Fifteen alkaloids from W. procera roots were identified by GC-MS, and seven of them were isolated [132]. The seven isolated alkaloids are ismine, trisphaeridine, tazettine, galanthine, lycorine, homolycorine, and albomaculine.

5.2. Detected and Identified Amaryllidaceae Alkaloids from the Subfamily Amaryllidoideae

The genera in the subfamily Amaryllidoideae, where Amaryllidaceae alkaloids are detected or tentatively identified (but not isolated) as summarized in Table 4, are detailed in Table 5 below.

5.3. The Genera from the Subfamily Amaryllidoideae with No Amaryllidaceae Alkaloids Reported

Genera in subfamily Amaryllidoideae, where Amaryllidaceae alkaloids have not been reported (undetected, unidentified, or un-isolated) as summarised in Table 4, are detailed here.
No Amaryllidacea alkaloids were found in the Amaryllidaceae alkaloid profiling using GC-MS for the two species A. cedarbergense and A. lanceolatum in the genus Apodolirion (Table 4) and for seven species, G. afra, G. britteniana, G. ciliaris, G. grandiflora, G. lanuginose, G. namaquensis, and G. verticillate, in the genus Gethyllis (Table 4) [137].
The following genera and species were only found in phylogenetic studies [133]:
(1)
Genus Caliphruria (Table 4), three species C. korsakoffi, C. subedentata, and C. teneraz;
(2)
Genus Cryptostephanus (Table 4), two species C. haemanthoides and C. vansonii;
(3)
Genus Eremocrinum (Table 4), one species E. albomarginatum;
(4)
Genus Eucrosia (Table 4), six species E. aurantiaca, E. bicolor, E. dodsonii, E. eucrosioides, E. mirabilis, and E. stricklandii;
(5)
Genus Hannonia (Table 4), one species H. hesperidum;
(6)
Genus Haylockia (Table 4), one species H. Herb., 1830;
(7)
Genus Hessea (Table 4), seven species H. breviflora, H. pilosula, H. pulcherrima, H. speciosa, H. stellaris, H. stenosiphon, and H. zeyheri;
(8)
Genus Namaquanula (Table 4), one species N. bruce-bayeri;
(9)
Genus Pabellonia (Table 4), one species P. Quezada & Martic;
(10)
Genus Plagiolirion (Table 4), one species P. horsmannii;
(11)
Genus Rauhia (Table 4), three species R. decora, R. multiflora, and R. staminosa;
(12)
Genus Stemmatium (Table 4), one species S. Phil., 1873;
(13)
Genus Stenomesson (Table 4), eight species S. aurantiacum, S. chloranthum, S. ecuadorense, S. flavum, S. leucanthum, S. miniatum, S. pearcei, and S. variegatum;
(14)
Genus Strumaria (Table 4), ten species S. aestivalis, S. bidentata, S. chaplinii, S. discifera, S. picta, S. salteri, S. spiralis, S. tenella, S. truncate, and S. watermeyeri;
(15)
Genus Vagaria (Table 4), two species V. ollivieri and V. parviflora.

6. Bioactivities of Amaryllidaceae Alkaloids for Drug Discovery

Amaryllidaceae alkaloids occur mainly in the subfamily Amaryllidoideae and have only recently been reported in another family, Asparagaceae, but under the same order of Asparagales as the family Amaryllidaceae. From Hosta plantaginea of the genus Hosta in the family Asparagaceae, five new benzylphenethylamine alkaloids, hostasine, 8-demethoxyhostasine, 8-demethoxy-10-O-methylhostasine, 10-O-methylhostasine, and 9-O-demethyl-7-O-methyllycorenine along with twelve known compounds were isolated [138]. The reason why plants produce alkaloids almost exclusively from the subfamily Amaryllidoideae but not Agapathiodeae and Alliodeae remains unclear, although general evolutionary mechanisms underlying the secondary metabolite diversity are likely at play [139]. It is possible that these alkaloids play a critical role in the plants’ survival, serving ecological or defensive functions. One might even say that nature has generously bestowed these compounds for the benefit of humanity.
The isolation of the alkaloids has been extensively conducted in the genera Crinum, Galanthus, Hippeastrum, Lycoris, Narcissus, Pancratium, and Zephyranthes. Lycorine is a very common Amaryllidaceae alkaloid, and its effects include the regulation of autophagy; the induction of cancer cell apoptosis; and anti-inflammatory, antifungal, antiviral, antimalarial, and antitumor effects [140]. The clinically used galanthamine has been isolated from the genera Cyrtanthus, Galanthus, Leucojum, Lycoris, Narcissus, Ungernia, Chlidanthus, Crinum, Eucharis, Eustephia, Pancratium, and Phaedranassa. Chromatographic techniques for separation and isolation as well as spectroscopic methods and single-crystal X-ray diffraction techniques for the characterisation of herbal biomolecules [141] are extensively used in the isolation and identification of Amaryllidaceae alkaloids. Drug discovery from the Amaryllidaceae alkaloids and the family Amaryllidaceae plant resources is ongoing and warranted.
The chemistry and bioactivities of Amaryllidaceae alkaloids, remarkable natural products gifted by Mother Nature, have garnered significant attention for their potential in drug discovery and therapeutic innovation. These alkaloids, characterized by their structural diversity and complex biosynthesis, are extensively reviewed in the literature for their broad pharmacological relevance [8,142,143]. The discussion that follows is intended as a focused appreciation of their bioactivity, with a particular emphasis on acetylcholinesterase inhibition—a key target in Alzheimer’s disease—as well as their anti-inflammatory, antioxidant, antimicrobial, antidiabetic, and anticancer properties. These multifaceted activities underscore the continued importance of Amaryllidaceae alkaloids as promising leads in the search for novel, plant-derived medicinal compounds.

6.1. Inhibiting Acetylcholinesterase (Anti-Alzheimer’s)

Acetylcholinesterase (AChE) is an enzyme found in the synaptic cleft (the gap between nerve cells) and neuromuscular junctions. Its main function is to break down the neurotransmitter acetylcholine (ACh) into acetate and choline, terminating the nerve signal. When AChE is inhibited, acetylcholine levels remain elevated, leading to a prolonged stimulation of cholinergic receptors. In the case of Alzheimer’s disease, drugs like galathamine inhibit acetylcholinesterase and boost cholinergic transmission in the brain, improving memory and cognition. Galantamine can stimulate presynaptic and postsynaptic nicotinic receptors, which can then increase the release of neurotransmitters such as ACh and glutamate, directly stimulating the neuronal function [144].
A comprehensive study on Narcissus tazetta subsp. tazetta L. reported that 11-hydroxygalanthine and narcissidine inhibit acetylcholinesterase significantly [114]. In a related study, 100 micrograms of extracts from Crinum jagus (Thomps.), Crinum × amabile Donn, Crinum zeylanicum (L.) L. (all Amaryllidaceae), and Agapanthus praecox subsp. orientalis (F.M. Leight.) F.M. Leight. (Liliaceae) inhibited the acetylcholinesterase (AChE) activity, as detected using a TLC bioautographic method [145]
Earlier investigations showed that chlidanthine at 2.4 × 10−5 M and galanthamine N-oxide at 2.6 × 10−5 M inhibited electric eel AChE, although both were approximately five times less potent than galanthamine, while galwesine at 10−3 M was inactive [87]. Additionally, in testing 23 pure Amaryllidaceae alkaloids and 26 extracts from different Narcissus species, 7 alkaloids—belonging to the galanthamine and lycorine skeleton types—exhibited AChE inhibitory effects, with sanguinine proving to be the most active and even surpassing galanthamine [146].
In a recent review, the IC50 values of alkaloids in major Amaryllidaceae alkaloid types inhibiting AChE have been summarized [142]. Anti-Alzheimer’s effects of the alkaloids from Galanthus spp. are also reviewed [147]. The AChE inhibitory activity of extracts and compounds from the plants of the Amaryllidoideae subfamily has been explored in the literature over the last two decades [148]. The anti-cholinesterase potential of 26 alkaloids from Urceolina Rchb., Clinanthus Herb., and Stenomesson Herb. was also reviewed [149]

6.2. Anti-Inflammatory

Lycorine and narciclasine displayed potent effects against pain, swelling, asthma, and arthritis in a recent review summarizing 140 anti-inflammatory principles from Amaryllidaceae plants [150]. In a separate study, 51 species from the Amaryllidaceae family were identified for their traditional use in treating inflammation across 32 countries [151].
Zephyranine B, haemanthamine, haemanthidine, 11-hydroxyvittatine, and 8-demethoxy-10-O-methylhostasine demonstrated a potent anti-inflammatory activity by inhibiting the LPS-induced nitric oxide (NO) production in RAW264.7 mouse macrophages, with IC50 values of 21.3, 4.6, 12.2, 5.6, and 17.4 μM, respectively; a structure–activity relationship (SAR) analysis and molecular docking studies indicated that an effective acetylcholinesterase (AChE) inhibition requires interactions with key active site residues, Trp286 and Tyr337 [84].
Galanthamine, lycorine, narciclasine (lycoricidinol), and crinamine have been shown to act as anti-inflammatory agents, targeting the cholinergic anti-inflammatory pathway [12]. Narciclasine inhibits leukocyte–endothelial interactions by blocking endothelial activation processes through the loss of TNF receptor 1 [152].
Additionally, five Amaryllidaceae alkaloids—4,8-dimethoxy-cripowellin, 9-methoxy-cripowellin, 4-methoxy-8-hydroxy-cripowellin, and cripowellin—exhibited a significant inhibition of COX-1 (>64%) and COX-2 (>90%), which was comparable to positive controls [48]. Narciclasine has also been demonstrated to exert profound anti-inflammatory effects in vivo [153]. Norbelladine at 0.25 μM inhibited the COX-1 and COX-2 activity by 51% and 25%, respectively, and at 10 μM inhibited the NF-κB activation by 23% [154].

6.3. Antioxidant

9-methoxy-cripowellin and 4-methoxy-8-hydroxy-cripowellin exhibited a notable antioxidant activity in the ABTS.+ and DPPH tests [48]. Norbelladine, at a concentration of 10 μM, was able to quench the DPPH-radical by 31% and reduce superoxide radicals generated from xanthine oxidase by 33% [154]. Additionally, lycorine administered intraperitoneally at doses of 1.0 mg/kg and 1.5 mg/kg significantly reduced rat paw oedema induced by carrageenan, achieving a 53.45% and 36.42% inhibition, respectively, compared to the 95.70% inhibition observed with indomethacin (3 mg/kg, i.p.) [155]. Antioxidant activities of montanine [156], five alkaloids from Crinum latifolium [48], and the methanolic extracts of Hieronymiella peruviana bulbs [71] were reported.

6.4. Antimicrobial

The methanol extract of Crinum jagus demonstrated a broad-spectrum antimicrobial activity, with minimum inhibitory concentration (MIC) values ranging from 1 to 500 mg/L against a panel of microorganisms. Notably, the extract showed a strong activity against Mycobacterium smegmatis, Salmonella typhi, and Pseudomonas aeruginosa, which are typically difficult to eradicate. The extracts were administered orally to rats at doses of 30, 150, and 300 mg/kg [157]. Similarly, 9-methoxy-cripowellin and 4-methoxy-8-hydroxy-cripowellin exhibited a significant antimicrobial activity, displaying IC50 values below 0.50 mM against eight tested bacterial strains [48]. Antimicrobial activities of montanine were reported [156].

6.5. Antidiabetic

Galantamine exhibits antidiabetic effects by stimulating the cholinergic pathway through acetylcholinesterase (AChE) inhibition and activating the efferent vagus nerve via its action as α7 nAChR agonist. Acting as a neural bridge between the liver, pancreatic cells, and adipose tissue, galantamine influences the insulin secretion, pancreatic cell mass, energy expenditure, glucose metabolism, hepatic glucose and glycogen synthesis, systemic insulin sensitivity, and fat distribution between the liver and peripheral tissues [158].

6.6. Anticancer

Five Amaryllidaceae alkaloids:4,8-dimethoxy-cripowellin, 9-methoxy-cripowellin, 4-methoxy-8-hydroxy-cripowellin, and cripowellin—demonstrated a potent cytotoxicity against seven lung cancer cell lines with IC50 values below 30 nM [48]. Similarly, four alkaloids—(+)-1-hydroxy-ungeremine, (+)-6β-acetyl-8-hydroxy-9-methoxy-crinamine, (+)-2-hydroxy-8-demethyl-homolycorine-α-N-oxide, and (+)-N-methoxylcarbonyl-2-demethyl-isocorydione—exhibited significant cytotoxic activities against eight tumour cell lines, including CCF-STTG1, CHG-5, SHG-44, U251, BGC-823, HepG2, and SK-OV-3 [101].
In another study, crinine, 6-hydroxybuphanidrine, and 6-ethoxybuphanidrine showed antiproliferative effects against human tumour cell lines, with crinine being the most potent (IC50 = 14.04 μM against HL-60/Dox). Crinine also induced apoptosis in a dose-dependent manner in HL-60 and MDA-MB-231 cell lines [159]. Using the noncancerous cell line MRC-5 human fibroblasts as a control and the WST-1 metabolic activity assay, the growth of nine cancer cell lines was inhibited by pancracine (a montanine-type alkaloid), with IC50 values ranging from 2.20 to 5.15 µM [115].
In a recent review, the IC50 values of major Amaryllidaceae alkaloid types inhibiting the growth of various cancer cell lines have been summarized [142]. Cytotoxic aspects of Amaryllidaceae alkaloids in Galanthus species have been recently reviewed, including the structural types of galanthamine, homolycorine, haemanthamine, galanthindole, graciline, and other types [61].

6.7. Other Bioactivities

Amaryllidaceae alkaloids have demonstrated a wide range of bioactivities. Several studies have reported antiviral, antiparasitic, and DNA-binding activities. Lycorine inhibited the Poliomyelitis virus at concentrations as low as 1 mg/mL, although higher concentrations (>25 mg/mL) were cytotoxic [43]. A broader review of the antiviral effects of Amaryllidaceae plants [160] and Amaryllidaceae alkaloids [161] was also conducted recently.
The alkaloids ungeremine, pseudolycorine, and haemanthamine exhibited a good antiparasitic activity against Trypanosoma brucei rhodesiense, T. cruzi, and Plasmodium falciparum, with IC50 values below 3.66 μM [122]. Additionally, lycorine and 1,2-di-O-acetyllycorine, isolated from Brunsvigia littoralis, showed a significant antimalarial activity against Plasmodium falciparum, while crinamine, with an α-configuration ethano bridge, exhibited potent antimalarial properties in QSAR studies [162]. Furthermore, the DNA binding activity of twenty Amaryllidaceae alkaloids across various skeletal types revealed that nine alkaloids showed >90% binding, comparable to vinblastine, and three additional compounds demonstrated moderate activity [163].
Meanwhile, other pharmacological activities have been identified for Amaryllidaceae alkaloids. Lycorine caused a significant increase in the contractility and heart rate in isolated perfused guinea pig hearts, an effect abolished by propranolol, suggesting the β-adrenergic receptor stimulation [124]. Lycorine also exhibited hepatoprotective effects at a dose of 2.0 mg/kg i.p. against carbon tetrachloride-induced acute liver toxicity in rats [155].

7. Conclusions

This review has surveyed the occurrence and bioactivities of Amaryllidaceae alkaloids across 62 genera plus 24 subgenera from the three subfamilies—Agapanthoideae, Allioideae, and Amaryllidoideae—within the family Amaryllidaceae. Species were identified based on listings from the National Center for Biotechnology Information (NCBI) Taxonomy Browser, with the literature of the occurrence and bioactivities sourced through PubMed and the Chemical Abstracts Service (CAS) SciFinder-n platform. More than 600 Amaryllidaceae alkaloids have been isolated, predominantly from 36 of the 58 genera in the Amaryllidoideae subfamily. These alkaloids exhibit a wide range of biological activities, including acetylcholinesterase inhibition and anti-inflammatory, antioxidant, antimicrobial, antidiabetic, and anticancer effects. Given the rich chemical diversity and bioactivity of Amaryllidaceae alkaloids and many unexplored genera and species, the further study of Amaryllidaceae species and alkaloids is warranted to support the discovery and development of novel therapeutic agents.

Author Contributions

Conceptualization, G.D.L., R.W.L. and P.N.S.; methodology, G.D.L. and R.W.L.; formal analysis, G.D.L. and P.V.; writing—original draft preparation, G.D.L. and R.W.L.; writing—review and editing, G.D.L., P.V. and R.W.L. All authors have read and agreed to the published version of the manuscript.

Funding

P.V. acknowledges the scholarship supported by the Australian Research Council Industrial Transformation Training Centre for Facilitated Advancement of Australia’s Bioactives (Grant IC210100040).

Acknowledgments

G.D.L. thanks the support of the past and current Directors of the Research School of Chemistry, the Australian National University. The authors gratefully acknowledge Henry M. Fales of the NHLBI Laboratory of Applied Mass Spectrometry, NIH, Bethesda, who provided a collection of over 700 Amaryllidaceae alkaloid samples to Martin G. Banwell at the Research School of Chemistry, Australian National University, Canberra. The original work on the Family Amaryllidaceae Plants for the Source of Amaryllidaceae Alkaloids (T-171) was presented to the RACI National Congress: “Chemistry: Catalysing solutions to global challenges”, 3–8 July 2022, Brisbane Exhibition and Convention Centre, Queensland, Australia.

Conflicts of Interest

The authors declare no conflicts of interest.

References

  1. Hesse, M. Alkaloids: Nature’s Curse or Blessing? Wiley-VCH: New York, NY, USA, 2002; p. 413. [Google Scholar]
  2. Berkov, S.; Osorio, E.; Viladomat, F.; Bastida, J. Chemodiversity, chemotaxonomy and chemoecology of Amaryllidaceae alkaloids. Alkaloids Chem. Biol. 2020, 83, 113–185. [Google Scholar] [CrossRef]
  3. Lim, A.W.Y.; Schneider, L.; Loy, C. Galantamine for dementia due to Alzheimer’s disease and mild cognitive impairment. Cochrane Database Syst. Rev. 2024, 11, CD001747. [Google Scholar] [CrossRef] [PubMed]
  4. Ji, Z.; Meerow, A. Amaryllidaceae. In Flora of China; Wu, Z., Raven, P., Hong, D.Y., Eds.; Science Press: Beijing, China; Missouri Botanical Garden Press: St. Louis, MO, USA, 2000; Volume 24, pp. 264–273. [Google Scholar]
  5. Spies, P.; Groble, J.; Spices, J. A review of phylogenetic relationships in the genus Clivia. Philos. Trans. Genet. 2011, 1, 168–207. [Google Scholar]
  6. National Center for Biotechnology Informaton. Taxonomy Browser, Amaryllidaceae. Available online: https://www.ncbi.nlm.nih.gov/Taxonomy/Browser/wwwtax.cgi?mode=Tree&id=4668&lvl=3&keep=1&srchmode=1&unlock (accessed on 31 January 2025).
  7. Stevens, P. Angiosperm Phylogeny Website. Available online: https://www.mobot.org/mobot/research/APweb/ (accessed on 4 January 2022).
  8. Ding, Y.; Qu, D.; Zhang, K.M.; Cang, X.X.; Kou, Z.N.; Xiao, W.; Zhu, J.B. Phytochemical and biological investigations of Amaryllidaceae alkaloids: A review. J. Asian Nat. Prod. Res. 2017, 19, 53–100. [Google Scholar] [CrossRef]
  9. Bastida, J.; Lavilla, R.; Viladomat, F. Chapter 3 Chemical and Biological Aspects of Narcissus Alkaloids. In THE ALKALOIDS: Chemistry and Biology; Cordell, G., Ed.; Elsevier: Amsterdam, The Netherlands, 2006; Volume 63, pp. 87–179. [Google Scholar]
  10. Jin, Z. Amaryllidaceae and Sceletium alkaloids. Nat. Prod. Rep. 2007, 24, 886–905. [Google Scholar] [CrossRef] [PubMed]
  11. Jin, Z. Amaryllidaceae and Sceletium alkaloids. Nat. Prod. Rep. 2013, 30, 849–868. [Google Scholar] [CrossRef]
  12. Li, R.; Palit, P.; Lin, G.; Li, R. Amaryllidaceae Alkaloids as Anti-inflammatory Agents Targeting Cholinergic Anti-inflammatory Pathway: Mechanisms and Prospects. In Evidence-Based Validation of Traditional Medicines; Mandal, S., Chakraborty, R., Ses, S., Eds.; Springer Nature: Singapore, 2021; pp. 97–116. [Google Scholar]
  13. Fawole, O.A.; Ndhlala, A.R.; Amoo, S.O.; Finnie, J.F.; Van Staden, J. Anti-inflammatory and phytochemical properties of twelve medicinal plants used for treating gastro-intestinal ailments in South Africa. J. Ethnopharmacol. 2009, 123, 237–243. [Google Scholar] [CrossRef]
  14. O’Donnell, G.; Gibbons, S. Antibacterial activity of two canthin-6-one alkaloids from Allium neapolitanum. Phytother. Res. 2007, 21, 653–657. [Google Scholar] [CrossRef]
  15. Sang, S.; Mao, S.; Lao, A.; Chen, Z. A new alkaloid from the seeds of Allium tuberosum. Tianran Chanwu Yanjiu Yu Kaifa 2000, 12, 1–3. [Google Scholar]
  16. Tashkhodzhaev, B.; Samikov, K.; Yagudaev, M.R.; Antsupova, T.P.; Shakirov, R.; Yunusov, S.Y. Structure of alline. Chem. Nat. Compd. 1985, 21, 645–649. [Google Scholar] [CrossRef]
  17. Sibanyoni, M.N.; Chaudhary, S.K.; Chen, W.; Adhami, H.R.; Combrinck, S.; Maharaj, V.; Schuster, D.; Viljoen, A. Isolation, in vitro evaluation and molecular docking of acetylcholinesterase inhibitors from South African Amaryllidaceae. Fitoterapia 2020, 146, 104650. [Google Scholar] [CrossRef] [PubMed]
  18. Pettit, G.; Gaddamidi, V.; Goswami, A.; Cragg, G. Antineoplastic Agents, 99. Amaryllis belladonna. J. Nat. Prod. 1984, 47, 796–801. [Google Scholar] [CrossRef]
  19. Queckenberg, O.R.; Frahm, A.W.; Müller-Doblies, D.; Müller-Doblies, U. Reinvestigation of Amaryllis belladonna. Phytochem. Anal. 1996, 7, 156–160. [Google Scholar] [CrossRef]
  20. Evidente, A.; Andolfi, A.; Abou-Donia, A.H.; Touema, S.M.; Hammoda, H.M.; Shawky, E.; Motta, A. (-)-Amarbellisine, a lycorine-type alkaloid from Amaryllis belladonna L. growing in Egypt. Phytochemistry 2004, 65, 2113–2118. [Google Scholar] [CrossRef] [PubMed]
  21. Cho, N.; Du, Y.; Valenciano, A.L.; Fernandez-Murga, M.L.; Goetz, M.; Clement, J.; Cassera, M.B.; Kingston, D.G.I. Antiplasmodial alkaloids from bulbs of Amaryllis belladonna Steud. Bioorg Med. Chem. Lett. 2018, 28, 40–42. [Google Scholar] [CrossRef]
  22. Machocho, A.; Chhabra, S.C.; Viladomat, F.; Codina, C.; Bastida, J. Alkaloids from Ammocharis tinneana. Phytochemistry 1999, 51, 1185–1191. [Google Scholar] [CrossRef]
  23. Koorbanally, N.; Mulholland, D.A.; Crouch, N. Alkaloids and triterpenoids from Ammocharis coranica (Amaryllidaceae). Phytochemistry 2000, 54, 93–97. [Google Scholar] [CrossRef]
  24. Raghoo, M.; Crouch, N.R.; Koorbanally, N.A. A novel and unusual tetramethoxylated crinine alkaloid from Ammocharis coranica (Amaryllidaceae). S. Afr. J. Bot. 2021, 137, 451–454. [Google Scholar] [CrossRef]
  25. Neergaard, J.S.; Andersen, J.; Pedersen, M.E.; Stafford, G.I.; Staden, J.V.; Jäger, A.K. Alkaloids from Boophone disticha with affinity to the serotonin transporter. S. Afr. J. Bot. 2009, 75, 371–374. [Google Scholar] [CrossRef]
  26. Nair, J.J.; Rárová, L.; Strnad, M.; Bastida, J.; Van Staden, J. Alkaloids from Boophone haemanthoides (Amaryllidaceae). Nat. Prod. Commun. 2013, 8, 1705–1710. [Google Scholar] [CrossRef]
  27. Cheesman, L.; Nair, J.J.; van Staden, J. Antibacterial activity of crinane alkaloids from Boophone disticha (Amaryllidaceae). J. Ethnopharmacol. 2012, 140, 405–408. [Google Scholar] [CrossRef]
  28. Nair, J.J.; Manning, J.C.; Van Staden, J. Distichamine, a chemotaxonomic marker for the genus Boophone Herb. (Amaryllidaceae). S. Afr. J. Bot. 2012, 83, 89–91. [Google Scholar] [CrossRef]
  29. van Rensburg, E.; Zietsman, P.C.; Bonnet, S.L.; Wilhelm, A. Alkaloids from the Bulbs of Boophone disticha. Nat. Prod. Commun. 2017, 12, 1934578X1701200911. [Google Scholar] [CrossRef]
  30. Ibrakaw, A.S.; Omoruyi, S.I.; Ekpo, O.E.; Hussein, A.A. Neuroprotective Activities of Boophone haemanthoides (Amaryllidaceae) Extract and Its Chemical Constituents. Molecules 2020, 25, 5376. [Google Scholar] [CrossRef]
  31. Viladomat, F.; Bastida, J.; Codina, C.; Campbell, W.E.; Mathee, S. Alkaloids from Brunsvigia josephinæ. Phytochemistry 1994, 35, 809–812. [Google Scholar] [CrossRef]
  32. Campbell, W.E.; Nair, J.J.; Gammon, D.W.; Bastida, J.; Codina, C.; Viladomat, F.; Smith, P.J.; Albrecht, C.F. Cytotoxic and antimalarial alkaloids from Brunsvigia littoralis. Planta Medica 1998, 64, 91–93. [Google Scholar] [CrossRef]
  33. Campbell, W.E.; Nair, J.J.; Gammon, D.W.; Codina, C.; Bastida, J.; Viladomat, F.; Smith, P.J.; Albrecht, C.F. Alkaloids from South African amaryllidaceae: Bioactive alkaloids from Brunsvigia radulosa. Phytochemistry 2000, 53, 587–591. [Google Scholar] [CrossRef] [PubMed]
  34. Boit, H.G.; Dopke, W. Amaryllidaceous alkaloids. XVIII. Alkaloids from Urceolina, Hymenocallis, Elisena, Calostemma, Eustephia, and Hippeastrum. Chem. Ber. 1957, 90, 1827–1830. [Google Scholar] [CrossRef]
  35. Jensen, B.S.; Christensen, S.B.; Jäger, A.K.; Rønsted, N. Amaryllidaceae alkaloids from the Australasian tribe Calostemmateae with acetylcholinesterase inhibitory activity. Biochem. Syst. Ecol. 2011, 39, 153–155. [Google Scholar] [CrossRef]
  36. Boit, H. Amaryllidaceous alkaloids. XI. Alkaloids of Chlidanthus fragrans, Valotta purpurea, Nerine undulata, and Hippeastrum vittatum. Chem. Berichte 1956, 89, 1129–1134. [Google Scholar] [CrossRef]
  37. Cahlikova, L.; Macakova, K.; Zavadil, S.; Jiros, P.; Opletal, L.; Urbanova, K.; Jahodar, L. Analysis of Amaryllidaceae alkaloids from Chlidanthus fragrans by GC-MS and their cholinesterase activity. Nat. Prod. Commun. 2011, 6, 603–606. [Google Scholar] [CrossRef] [PubMed]
  38. Cahlíková, L.; Hrabinová, M.; Kulhánková, A.; Benesová, N.; Chlebek, J.; Jun, D.; Novák, Z.; Macáková, K.; Kunes, J.; Kuca, K.; et al. Alkaloids from Chlidanthus fragrans and their acetylcholinesterase, butyrylcholinesterase and prolyl oligopeptidase activities. Nat. Prod. Commun. 2013, 8, 1541–1544. [Google Scholar] [CrossRef]
  39. Adessi, T.G.; Borioni, J.L.; Pigni, N.B.; Bastida, J.; Cavallaro, V.; Murray, A.P.; Puiatti, M.; Oberti, J.C.; Leiva, S.; Nicotra, V.E.; et al. Clinanthus microstephium, an Amaryllidaceae Species with Cholinesterase Inhibitor Alkaloids: Structure−Activity Analysis of Haemanthamine Skeleton Derivatives. Chem. Biodivers. 2019, 16, e1800662. [Google Scholar] [CrossRef] [PubMed]
  40. Crouch, N.R.; Mulholland, D.A.; Pohl, T.L.; Ndlovu, E.; van Wyk, B.E. The ethnobotany and chemistry of the genus Clivia (Amaryllidaceae). S. Afr. J. Bot. 2003, 69, 144–147. [Google Scholar] [CrossRef]
  41. Kornienko, A.; Evidente, A. Chemistry, Biology, and Medicinal Potential of Narciclasine and its Congeners. Chem. Rev. 2008, 108, 1982–2014. [Google Scholar] [CrossRef]
  42. Evidente, A.; Abou-Donia, A.H.; Darwish, F.A.; AMer, M.; Kassem, F.; Hammoda, H.M.; Motta, A. Nobilisitine A and B, two masanane!type alkaloids from Clivia nobilis. Phytochemistry 1999, 65, 1151–1155. [Google Scholar] [CrossRef]
  43. Ieven, M.; Vlietinck, A.J.; Vanden Berghe, D.A.; Totte, J.; Dommisse, R.; Esmans, E.; Alderweireldt, F. Plant antiviral agents. III. Isolation of alkaloids from Clivia miniata Regel (Amaryllidaceae). J. Nat. Prod. 1982, 45, 564–573. [Google Scholar] [CrossRef]
  44. Ghosal, S.; Saini, K.; Razdan, S. Crinum alkaloids: Their chemistry and biology. Phytochemistry 1985, 24, 2141–2156. [Google Scholar] [CrossRef]
  45. Tram, N.T.N.T.; Titorenkova, T.V.; St. Bankova, V.; Handjieva, N.V.; Popov, S.S. Crinum L. (Amaryllidaceae); Elsevier B.V: Amsterdam, The Netherlands, 2002; Volume 73, pp. 183–208. [Google Scholar]
  46. Yadav, S.K.; Sharma, Y.K. A review: Plant profile, phytochemistry and pharmacology of Crinum latifolium. World J. Pharm. Res. 2020, 9, 2493–2501. [Google Scholar] [CrossRef]
  47. Aldhaher, A.H.S.; Langat, M.K.; Knirsch, W.; Andriantiana, J.L.; Mulholland, D.A. Isoquinoline alkaloids from three Madagascan Crinum (Amaryllidaceae) species. Biochem. Syst. Ecol. 2018, 77, 7–9. [Google Scholar] [CrossRef]
  48. Chen, M.X.; Huo, J.M.; Hu, J.; Xu, Z.P.; Zhang, X. Amaryllidaceae alkaloids from Crinum latifolium with cytotoxic, antimicrobial, antioxidant, and anti-inflammatory activities. Fitoterapia 2018, 130, 48–53. [Google Scholar] [CrossRef]
  49. Elgorashi, E.E.; Zschocke, S.; Van Staden, J. The anti-inflammatory and antibacterial activities of Amaryllidaceae alkaloids. S. Afr. J. Bot. 2003, 69, 448–449. [Google Scholar] [CrossRef]
  50. Ghosal, S.; Rao, P.; Jaiswal, D.; Kumar, V.; Frahm, A. Alkaloids of crinum pratense. Phytochemistry 1981, 20, 2003–2007. [Google Scholar] [CrossRef]
  51. Machocho, A.K.; Bastida, J.; Codina, C.; Viladomat, F.; Brun, R.; Chhabra, S.C. Augustamine type alkaloids from Crinum kirkii. Phytochemistry 2004, 65, 3143–3149. [Google Scholar] [CrossRef]
  52. Naidoo, D.; Roy, A.; Slavětínská, L.P.; Chukwujekwu, J.C.; Gupta, S.; Van Staden, J. New role for crinamine as a potent, safe and selective inhibitor of human monoamine oxidase B: In vitro and in silico pharmacology and modeling. J. Ethnopharmacol. 2020, 248, 112305. [Google Scholar] [CrossRef] [PubMed]
  53. Omoruyi, S.I.; Ibrakaw, A.S.; Ekpo, O.E.; Boatwright, J.S.; Cupido, C.N.; Hussein, A.A. Neuroprotective Activities of Crossyne flava Bulbs and Amaryllidaceae Alkaloids: Implications for Parkinson′s Disease. Molecules 2021, 26, 3990. [Google Scholar] [CrossRef]
  54. Naidoo, D.; Manning, J.C.; Slavětínská, L.P.; Van Staden, J. Isolation of the antibacterial alkaloid distichamine from Crossyne Salisb. (Amaryllidaceae: Amaryllideae: Strumariinae). S. Afr. J. Bot. 2021, 137, 331–334. [Google Scholar] [CrossRef]
  55. Campbell, W.E.; Dlova, M.C.; Makhesha, P.A.; Paterson, F.W. Alkaloids from Cybistetes longifolia. Planta Medica 1992, 58, 299. [Google Scholar] [CrossRef]
  56. Herrera, M.; Machocho, A.; Nair, J.; Campbell, W.; Brun, R.; Viladomat, F.; Codina, C.; Bastida, J. Alkaloids from Cyrtanthus elatus. Fitoterapia 2001, 72, 444–448. [Google Scholar] [CrossRef]
  57. Brine, N.D.; Campbell, W.E.; Bastida, J.; Herrera, M.R.; Viladomat, F.; Codina, C.; Smith, P.J. A dinitrogenous alkaloid from Cyrtanthus obliquus. Phytochemistry 2002, 61, 443–447. [Google Scholar] [CrossRef]
  58. Cabezas, F.; Ramirez, A.; Viladomat, F.; Codina, C.; Bastida, J. Alkaloids from Eucharis amazonica (Amaryllidaceae). Chem. Pharm. Bull. 2003, 51, 315–317. [Google Scholar] [CrossRef] [PubMed]
  59. Boit, H.G.; Dopke, W. Alkaloids of the Amaryllidaceae. XVIII. Alkaloids from Urceolina, Hymenocallis, Elisena, Calostemma, Eustephia, and Hippeastrum. Chem. Ber. 1957, 90, 1827. [Google Scholar] [CrossRef]
  60. Henrich, M. Chapter 4—Galanthamine from Galanthus and Other Amaryllidaceae—Chemistry and Biology Based on Traditional Use. In THE ALKALOIDS: Chemistry and Biology; Cordell, G., Ed.; Academic Press: London, UK, 2010; Volume 68, pp. 156–165. [Google Scholar]
  61. Georgiev, B.; Sidjimova, B.; Berkov, S. Phytochemical and Cytotoxic Aspects of Amaryllidaceae Alkaloids in Galanthus Species: A Review. Plants 2024, 13, 3577. [Google Scholar] [CrossRef] [PubMed]
  62. Berkov, S.; Cuadrado, M.; Osorio, E.; Viladomat, F.; Codina, C.; Bastida, J. Three new alkaloids from Galanthus nivalis and Galanthus elwesii. Planta Medica 2009, 75, 1351–1355. [Google Scholar] [CrossRef]
  63. Latvala, A.; Onur, M.; Gozler, T.; Linden, A.; Kivcak, B.; Hesse, M. Alkaloids of galanthus elwesii. Phytochemistry 1995, 39, 1229–1240. [Google Scholar] [CrossRef]
  64. Kaya, G.I.; Uzun, K.; Bozkurt, B.; Onur, M.A.; Somer, N.U.; Glatzel, D.K.; Fürst, R. Chemical characterization and biological activity of an endemic Amaryllidaceae species: Galanthus cilicicus. S. Afr. J. Bot. 2017, 108, 256–260. [Google Scholar] [CrossRef]
  65. Emir, A.; Emir, C.; Bozkurt, B.; Ali Onur, M.; Bastida, J.; Unver Somer, N. Alkaloids from Galanthus fosteri. Phytochem. Lett. 2016, 17, 167–172. [Google Scholar] [CrossRef]
  66. Sarikaya, B.B.; Kaya, G.I.; Onur, M.A.; Viladomat, F.; Codina, C.; Bastida, J.; Somer, N.U. Alkaloids from Galanthus rizehensis. Phytochem. Lett. 2012, 5, 367–370. [Google Scholar] [CrossRef]
  67. Kaya, G.I.; Sarıkaya, B.; Onur, M.A.; Somer, N.U.; Viladomat, F.; Codina, C.; Bastida, J.; Lauinger, I.L.; Kaiser, M.; Tasdemir, D. Antiprotozoal alkaloids from Galanthus trojanus. Phytochem. Lett. 2011, 4, 301–305. [Google Scholar] [CrossRef]
  68. Ghosal, S.; Lochen, R.; Kumar, Y.; Srivastava, R. Alkaloids of Haemanthus kalbrryeri. Phytochemistry 1985, 24, 1825–1828. [Google Scholar] [CrossRef]
  69. Ghosal, S.; Singh, S.; KUMAR, V.; Srivastava, R. Isocarbostyril alkaloids from haemanthus kalbreyeri. Phytochemistry 1989, 28, 611–613. [Google Scholar] [CrossRef]
  70. Ortiz, J.E.; Garro, A.; Pigni, N.B.; Aguero, M.B.; Roitman, G.; Slanis, A.; Enriz, R.D.; Feresin, G.E.; Bastida, J.; Tapia, A. Cholinesterase-inhibitory effect and in silico analysis of alkaloids from bulbs of Hieronymiella species. Phytomedicine 2018, 39, 66–74. [Google Scholar] [CrossRef]
  71. Llalla-Cordova, O.; Ortiz, J.E.; Tallini, L.R.; Torras-Claveria, L.; Bastida, J.; Luna, L.C.; Feresin, G.E. Alkaloid Profile, Anticholinesterase and Antioxidant Activities, and Sexual Propagation in Hieronymiella peruviana (Amaryllidaceae). Plants 2025, 14, 281. [Google Scholar] [CrossRef] [PubMed]
  72. de Andrade, J.P.; Guo, Y.; Font-Bardia, M.; Calvet, T.; Dutilh, J.; Viladomat, F.; Codina, C.; Nair, J.J.; Zuanazzi, J.A.S.; Bastida, J. Crinine-type alkaloids from Hippeastrum aulicum and H. calyptratum. Phytochemistry 2014, 103, 188–195. [Google Scholar] [CrossRef]
  73. Sebben, C.; Giordani, R.B.; de Andrade, J.P.; Berkov, S.; Osorio, E.J.; Sobral, M.; de Almeida, M.V.; Henriques, A.T.; Bastida, J.; Zuanazzi, J.Â.S. New lycosinine derivative from Hippeastrum breviflorum. Rev. Bras. De Farmacogn. 2015, 25, 353–355. [Google Scholar] [CrossRef]
  74. Crouch, N.R.; Pohl, T.L.; Mulholland, D.A.; Ndlovu, E.; van Staden, J. Alkaloids from three ethnomedicinal Haemanthus species: H. albiflos, H. deformis and H. pauculifolius (Amaryllidaceae). S. Afr. J. Bot. 2005, 71, 49–52. [Google Scholar] [CrossRef]
  75. Pham, L.H.; Gründemann, E.; Wagner, J.; Bartoszek, M.; Döpke, W. Two novel Amaryllidaceae alkaloids from Hippeastrum equestre Herb.: 3- O-demethyltazettine and egonine. Phytochemistry 1999, 51, 327–332. [Google Scholar] [CrossRef]
  76. Jin, Z.; Yao, G. Amaryllidaceae and Sceletium alkaloids. Nat. Prod. Rep. 2019, 36, 1462–1488. [Google Scholar] [CrossRef]
  77. Correa, D.I.; Pastene-Navarrete, E.; Bustamante, L.; Baeza, M.; Alarcon-Enos, J. Isolation of three lycorine type alkaloids from Rhodolirium speciosum (Herb.) ravenna using pH-zone- refinement centrifugal partition chromatography and their acetylcholinesterase inhibitory activities. Metabolites 2020, 10, 309. [Google Scholar] [CrossRef]
  78. Wildman, W.C.; Brown, C.L.; Michel, K.H.; Bailey, D.T.; Heimer, N.E.; Shaffer, R.; Murphy, C.F. Alkaloids from Rhodophiala bifida, Crinum erubescens, and Sprekelia formosissima. Pharmazie 1967, 22, 725. [Google Scholar]
  79. Katoch, D.; Singh, B. Phytochemistry and pharmacology of genus Zephyranthes. Med. Aromat. Plants 2015, 4, 212/211–212/218. [Google Scholar] [CrossRef]
  80. Zhan, G.; Zhou, J.; Liu, J.; Huang, J.; Zhang, H.; Liu, R.; Yao, G. Acetylcholinesterase Inhibitory Alkaloids from the Whole Plants of Zephyranthes carinata. J. Nat. Prod. 2017, 80, 2462–2471. [Google Scholar] [CrossRef]
  81. Zhan, G.; Liu, J.; Zhou, J.; Sun, B.; Aisa, H.A.; Yao, G. Amaryllidaceae alkaloids with new framework types from Zephyranthes candida as potent acetylcholinesterase inhibitors. Eur. J. Med. Chem. 2017, 127, 771–780. [Google Scholar] [CrossRef]
  82. Ghosal, S.; Sushil, K.; Singh, S.; Srivasta, R. Alkaloids of Zephxuanthes flava. Phytochemistry 1986, 25, 1975–1978. [Google Scholar] [CrossRef]
  83. Ghosal, S.; Singh, S.; Unnikrishnan, G. Phosphatldylpyrrolophenanthridine alkaloids from Zephyranthes flava. Phytochemistry 1987, 26, 823–828. [Google Scholar] [CrossRef]
  84. Zhan, G.; Gao, B.; Zhou, J.; Liu, T.; Zheng, G.; Jin, Z.; Yao, G. Structurally diverse alkaloids with nine frameworks from Zephyranthes candida and their acetylcholinesterase inhibitory and anti-inflammatory activities. Phytochemistry 2023, 207, 113564. [Google Scholar] [CrossRef] [PubMed]
  85. Ghosal, S.; Razdan, S. (+)-Epimaritidine, an alkaloid from Zephyranthes rosea. Phytochemistry 1985, 24, 635–637. [Google Scholar] [CrossRef]
  86. Wang, H.-Y.; Qu, S.-M.; Wang, Y.; Wang, H.-T. Cytotoxic and anti-inflammatory active plicamine alkaloids from Zephyranthes grandiflora. Fitoterapia 2018, 130, 163–168. [Google Scholar] [CrossRef]
  87. Reyes-Chilpa, R.; Berkov, S.; Hernandez-Ortega, S.; Jankowski, C.K.; Arseneau, S.; Clotet-Codina, I.; Este, J.A.; Codina, C.; Viladomat, F.; Jaume, B. Acetylcholinesterase-inhibiting alkaloids from Zephyranthes concolor. Molecules 2011, 16, 9520–9533. [Google Scholar] [CrossRef]
  88. Herrera, M.R.; Machocho, A.K.; Brun, R.; Viladomat, F.; Codina, C.; Bastida, J. Crinane and lycorane type alkaloids from Zephyranthes citrina. Planta Med. 2001, 67, 191–193. [Google Scholar] [CrossRef]
  89. Pettit, G.R.; Pettit, G.R., 3rd; Groszek, G.; Backhaus, R.A.; Doubek, D.L.; Barr, R.J.; Meerow, A.W. Antineoplastic agents, 301. An investigation of the Amaryllidaceae genus Hymenocallis. J. Nat. Prod. 1995, 58, 756–759. [Google Scholar] [CrossRef] [PubMed]
  90. Hohmann, J.; Forgo, P.; Szabó, P. A new phenanthridine alkaloid from Hymenocallis X festalis. Fitoterapia 2002, 73, 749–751. [Google Scholar] [CrossRef] [PubMed]
  91. Soto-Vasquez, M.R.; Rodriguez-Munoz, C.A.; Tallini, L.R.; Bastida, J. Alkaloid Composition and Biological Activities of the Amaryllidaceae Species Ismene amancaes (Ker Gawl.) Herb. Plants 2022, 11, 1906. [Google Scholar] [CrossRef]
  92. Suau, R.; Gómez, A.I.; Rico, R.; Tato, M.P.V.; Castedo, L.; Riguera, R. Alkaloid N-oxides of amaryllidaceae. Phytochemistry 1988, 27, 3285–3287. [Google Scholar] [CrossRef]
  93. Suau, R.; Gomez, A.I.; Rico, R. Alkaloids of Lapiedra martinezii. An. De. Quim. 1990, 86, 672–674. [Google Scholar]
  94. Suau, R.; Gómez, A.I.; Rico, R. Ismine and related alkaloids from Lapiedra martinezii. Phytochemistry 1990, 29, 1710–1712. [Google Scholar] [CrossRef]
  95. Forgo, P.; Hohmann, J. Leucovernine and Acetylleucovernine, Alkaloids from Leucojum v ernum. J. Nat. Prod. 2005, 68, 1588–1591. [Google Scholar] [CrossRef]
  96. Berkov, S.; Codina, C.; Viladomat, F.; Bastida, J. N-Alkylated galanthamine derivatives: Potent acetylcholinesterase inhibitors from Leucojum aestivum. Bioorganic Med. Chem. Lett. 2008, 18, 2263–2266. [Google Scholar] [CrossRef]
  97. Stanilova, M.; Molle, E.; Yanev, S. Chapter 5—Galanthamine Production by Leucojum aestivum Cultures In Vitro. In THE ALKALOIDS: Chemistry and Biology; Cordell, G., Ed.; Academic Press: London, UK, 2010; Volume 68, pp. 167–210. [Google Scholar]
  98. Song, J.H.; Zhang, L.; Song, Y. Alkaloids from Lycoris aurea and their cytotoxicities against the head and neck squamous cell carcinoma. Fitoterapia 2014, 95, 121–126. [Google Scholar] [CrossRef]
  99. Feng, T.; Wang, Y.-Y.; Su, J.; Li, Y.; Cai, X.-H.; Luo, X.-D. Amaryllidaceae Alkaloids from Lycoris radiata. Helv. Chim. Acta 2011, 94, 178–183. [Google Scholar] [CrossRef]
  100. Li, X.; Yu, H.Y.; Wang, Z.Y.; Pi, H.F.; Zhang, P.; Ruan, H.L. Neuroprotective compounds from the bulbs of Lycoris radiata. Fitoterapia 2013, 88, 82–90. [Google Scholar] [CrossRef]
  101. Liu, Z.M.; Huang, X.Y.; Cui, M.R.; Zhang, X.D.; Chen, Z.; Yang, B.S.; Zhao, X.K. Amaryllidaceae alkaloids from the bulbs of Lycoris radiata with cytotoxic and anti-inflammatory activities. Fitoterapia 2015, 101, 188–193. [Google Scholar] [CrossRef] [PubMed]
  102. Toriizuka, Y.; Kinoshita, E.; Kogure, N.; Kitajima, M.; Ishiyama, A.; Otoguro, K.; Yamada, H.; Omura, S.; Takayama, H. New lycorine-type alkaloid from Lycoris traubii and evaluation of antitrypanosomal and antimalarial activities of lycorine derivatives. Bioorg Med. Chem. 2008, 16, 10182–10189. [Google Scholar] [CrossRef] [PubMed]
  103. Cao, P.; Pan, D.-S.; Han, S.; Yu, C.-Y.; Zhao, Q.-J.; Song, Y.; Liang, Y. Alkaloids from Lycoris caldwellii and their particular cytotoxicities against the astrocytoma and glioma cell lines. Arch. Pharmacal Res. 2013, 36, 927–932. [Google Scholar] [CrossRef] [PubMed]
  104. Van Goietsenoven, G.; Andolfi, A.; Lallemand, B.; Cimmino, A.; Lamoral-Theys, D.; Gras, T.; Abou-Donia, A.; Dubois, J.; Lefranc, F.; Mathieu, V.R.; et al. Amaryllidaceae Alkaloids Belonging to Different Structural Subgroups Display Activity against Apoptosis-Resistant Cancer Cells. J. Nat. Prod. 2010, 73, 1223–1227. [Google Scholar] [CrossRef]
  105. Bastida, J.; Lavilla, R.; Viladomat, F. Chapter 3 Chemical and Biological Aspects of Narcissus Alkaloids. Alkaloids Chem. Biol. 2006, 63, 87–179. [Google Scholar]
  106. Viladomat, F.; Bastida, J.; Tribo, G.; Codina, C.; Rubiralta, M. Alkaloids from Narcissus bicolor. Phytochemistry 1990, 29, 1307–1310. [Google Scholar] [CrossRef]
  107. Suau, R.; Rico, R.; Garcia, A.I.; Gomez, A.I. New Amaryllidaceae alkaloids from Narcissus papyraceus Ker-Gawler. Heterocycles 1990, 31, 517. [Google Scholar] [CrossRef]
  108. Bastida, J.; Llabres, J.M.; Viladomat, F.; Codina, C.; Rubiralta, M.; Feliz, M. 9-O-Demethylmaritidine: A new alkaloid from Narcissus radinganorum. Planta Med. 1988, 54, 524. [Google Scholar] [CrossRef]
  109. Bastida, J.; Codina, C.; Viladomat, F.; Rubiralta, M.; Quirion, J.-C.; Weniger, B. Narcissus Alkaloids, XV. Roserine from Narcissus pallidulus. J. Nat. Prod. 1992, 55, 134–136. [Google Scholar] [CrossRef]
  110. Labrana, J.; Machocho, A.K.o.; Kricsfalusy, V.; Brun, R.; Codina, C.; Viladomat, F.; Bastida, J. Alkaloids from Narcissus angustifolius subsp. transcarpathicus (Amaryllidaceae). Phytochemistry 2002, 60, 847–852. [Google Scholar] [CrossRef]
  111. Labrana, J.; Choy, G.; Solans, X.; Font-Bardia, M.; De La Fuente, G.; Viladomat, F.; Codina, C.; Bastida, J. Narcissus alkaloids. Part 25. Alkaloids from Narcissus bujei (Amaryllidaceae). Phytochemistry 1998, 50, 183–188. [Google Scholar] [CrossRef]
  112. Viladomat, F.; Bastida, J.; Codina, C.; Solans, X.; Font-Bardia, M. Homolycorine hydrochloride dihydrate. Acta Crystallogr. Sect. C Cryst. Struct. Commun. 1999, C55, 385–387. [Google Scholar] [CrossRef]
  113. Viladomat, F.; Codina, C.; Bastida, J.; Solans, X.; Font-Bardia, M. Ismine. Acta Crystallogr. 1998, 54, 81–82. [Google Scholar] [CrossRef]
  114. Karakoyun, C.; Bozkurt, B.; Coban, G.; Masi, M.; Cimmino, A.; Evidente, A.; Unver Somer, N. A comprehensive study on narcissus tazetta subsp. tazetta L.: Chemo-profiling, isolation, anticholinesterase activity and molecular docking of amaryllidaceae alkaloids. S. Afr. J. Bot. 2020, 130, 148–154. [Google Scholar] [CrossRef]
  115. Breiterova, K.; Koutova, D.; Marikova, J.; Havelek, R.; Kunes, J.; Majorosova, M.; Opletal, L.I.; Host’Alkova, A.; Jenco, J.; Rezacova, M.; et al. Amaryllidaceae alkaloids of different structural types from Narcissus L. cv. Professor einstein and their cytotoxic activity. Plants 2020, 9, 137. [Google Scholar] [CrossRef]
  116. van Rijn, R.M.; Rhee, I.K.; Verpoorte, R. Isolation of acetylcholinesterase inhibitory alkaloids from Nerine bowdenii. Nat. Prod. Res. 2010, 24, 222–225. [Google Scholar] [CrossRef]
  117. Nair, J.J.; Campbell, W.E.; Brun, R.; Viladomat, F.; Codina, C.; Bastida, J. Alkaloids from Nerine filifolia. Phytochemistry 2005, 66, 373–382. [Google Scholar] [CrossRef]
  118. Masi, M.; van der Westhuyzen, A.E.; Tabanca, N.; Evidente, M.; Cimmino, A.; Green, I.R.; Bernier, U.R.; Becnel, J.J.; Bloomquist, J.R.; van Otterlo, W.A.; et al. Sarniensine, a mesembrine-type alkaloid isolated from Nerine sarniensis, an indigenous South African Amaryllidaceae, with larvicidal and adulticidal activities against Aedes aegypti. Fitoterapia 2017, 116, 34–38. [Google Scholar] [CrossRef]
  119. Cedrón, J.C.; Del Arco-Aguilar, M.; Estévez-Braun, A.; Ravelo, Á.G. Chemistry and Biology of Pancratium Alkaloids. Alkaloids Chem. Biol. 2010, 68, 1–37. [Google Scholar] [CrossRef]
  120. Abou-Donia, A.; Abib, A.; El Din, A.; Evidente, A.; Gaber, M.; Scopa, A. Two betaine-type alkaloids from Egyptian Pancratium marztimum. Phytochemistry 1992, 31, 2139–2141. [Google Scholar] [CrossRef]
  121. Iannello, C.; Pigni, N.B.; Antognoni, F.; Poli, F.; Maxia, A.; de Andrade, J.P.; Bastida, J. A potent acetylcholinesterase inhibitor from Pancratium illyricum L. Fitoterapia 2014, 92, 163–167. Fitoterapia 2014, 92, 163–167. [Google Scholar] [CrossRef]
  122. Osorio, E.J.; Berkov, S.; Brun, R.; Codina, C.; Viladomat, F.; Cabezas, F.; Bastida, J. In vitro antiprotozoal activity of alkaloids from Phaedranassa dubia (Amaryllidaceae). Phytochem. Lett. 2010, 3, 161–163. [Google Scholar] [CrossRef]
  123. Naidoo, D.; Slavětínská, L.P.; Aremu, A.O.; Gruz, J.; Biba, O.; Doležal, K.; Van Staden, J.; Finnie, J.F. Metabolite profiling and isolation of biologically active compounds from Scadoxus puniceus, a highly traded South African medicinal plant. Phytother. Res. 2018, 32, 625–630. [Google Scholar] [CrossRef] [PubMed]
  124. Abdalla, S.; Zarga, M.A.; Sabri, S. Alkaloids of Sternbergia clusiani and effects of lycorine on guinea-pig isolated pulmonary artery and heart. Fitoterapia 1993, 64, 518–523. [Google Scholar]
  125. Evidente, A.; Iasiello, I.; Randazzo, G. Isolation of Sternbergine, a New Alkaloid From Bulbs of Sternbergia lutea. J. Nat. Prod. 1984, 47, 1003–1008. [Google Scholar] [CrossRef]
  126. Pabuççuoglu, V.; Richomme, P.; Gözler, T.; Kivçak, B.; Freyer, A.J.; Shamma, M. Four New Crinine-Type Alkaloids from Sternbergia Species. J. Nat. Prod. 1989, 52, 785–791. [Google Scholar] [CrossRef]
  127. Allayarov, K.B.; Abdusamatov, A.; Yunusov, S.Y. Alkaloids of Ungernia spiralis and Sternbergia lutea. Chem. Nat. Compd. 1970, 6, 143. [Google Scholar] [CrossRef]
  128. Berkov, S.; Bastida, J.; Tsvetkova, R.; Viladomat, F.; Codina, C. Alkaloids from Sternbergia colchiciflora. Z. Für Naturforschung C. A J. Biosci. 2009, 64, 311–316. [Google Scholar] [CrossRef]
  129. Tanker, M.; Çitoglu, G.; Gümühel, B.; Hener, B. Alkaloids of Sternbergia clusiana and their analgesic effects. Pharm. Biol. 1996, 34, 194–197. [Google Scholar] [CrossRef]
  130. Kadyrov, K.A.; Abdusamatov, A.; Yunusov, S.Y. Ungernia alkaloids. Chem. Nat. Compd. 1980, 16, 525–540. [Google Scholar] [CrossRef]
  131. Kadyrov, K.A.; Abdusamatov, A.; Yunusov, S.Y. Ungvedine—A new alkaloid from Ungernia vvedenskyi. Chem. Nat. Compd. 1979, 15, 513–514. [Google Scholar] [CrossRef]
  132. Gonring-Salarini, K.L.; Conti, R.; de Andrade, J.P.; Borges, B.J.P.; Aguiar, A.C.C.; de Souza, J.O.; Zanini, C.L.; Oliva, G.; Tenorio, J.C.; Ellena, J.; et al. In vitro Antiplasmodial Activities of Alkaloids Isolated from Roots of Worsleya procera (Lem.) Traub (Amaryllidaceae). J. Braz. Chem. Soc. 2019, 30, 1624–1633. [Google Scholar] [CrossRef]
  133. Larsen, M.M.; Adsersen, A.; Davis, A.P.; Lledó, M.D.; Jäger, A.K.; Rønsted, N. Using a phylogenetic approach to selection of target plants in drug discovery of acetylcholinesterase inhibiting alkaloids in Amaryllidaceae tribe Galantheae. Biochem. Syst. Ecol. 2010, 38, 1026–1034. [Google Scholar] [CrossRef]
  134. de Paiva, J.R.; Souza, A.S.Q.; Pereira, R.C.A.; Ribeiro, P.R.; Zocolo, G.J.; de Brito, E.S.; Pessoa, O.D.L.; Canuto, K.M. Development and Validation of a UPLC-ESI-MS Method for Quantitation of the Anti-Alzheimer Drug Galantamine and other Amaryllidaceae Alkaloids in Plants. J. Braz. Chem. Soc. 2020, 31, 265–272. [Google Scholar] [CrossRef]
  135. Ortiz, J.E.; Berkov, S.; Pigni, N.B.; Theoduloz, C.; Roitman, G.; Tapia, A.; Bastida, J.; Feresin, G.E. Wild Argentinian Amaryllidaceae, a new renewable source of the acetylcholinesterase inhibitor galanthamine and other alkaloids. Molecules 2012, 17, 13473–13482. [Google Scholar] [CrossRef]
  136. Huaylla, H.; Llalla, O.; Torras-Claveria, L.; Bastida, J. Alkaloid profile in Pyrolirion albicans Herb. (Amaryllidaceae), a Peruvian endemic species. S. Afr. J. Bot. 2020, 136, 76. [Google Scholar] [CrossRef]
  137. Bay-Smidt, M.G.K.; Jäger, A.K.; Krydsfeldt, K.; Meerow, A.W.; Stafford, G.I.; Van Staden, J.; Rønsted, N. Phylogenetic selection of target species in Amaryllidaceae tribe Haemantheae for acetylcholinesterase inhibition and affinity to the serotonin reuptake transport protein. S. Afr. J. Bot. 2011, 77, 175–183. [Google Scholar] [CrossRef]
  138. Wang, Y.-H.; Zhang, Z.-K.; Yang, F.-M.; Sun, Q.-Y.; He, H.-P.; Di, Y.-T.; Mu, S.-Z.; Lu, Y.; Chang, Y.; Zheng, Q.-T.; et al. Benzylphenethylamine Alkaloids from Hosta plantaginea with Inhibitory Activity against Tobacco Mosaic Virus and Acetylcholinesterase. J. Nat. Prod. 2007, 70, 1458–1461. [Google Scholar] [CrossRef]
  139. Jeneke-Kodama, H.; Müller, R.; Dittmann, E. Evolutionary mechanisms underlying secondary metabolite diversity. In Natural Compounds as Drugs Volume I (Progress in Drug Research Volume 65); Petersen, F., Amstutz, R., Eds.; Birkhäuser Basel: Basel, Switzerland, 2008; pp. 120–140. [Google Scholar] [CrossRef]
  140. Xiao, H.; Xu, X.; Du, L.; Li, X.; Zhao, H.; Wang, Z.; Zhao, L.; Yang, Z.; Zhang, S.; Yang, Y.; et al. Lycorine and organ protection: Review of its potential effects and molecular mechanisms. Phytomedicine 2022, 104, 154266. [Google Scholar] [CrossRef]
  141. Lin, G.; Li, R. Analytical characterisation of herbal biomolecules. In Herbal Biomolecules in Healthcare Applications; Mandal, S., Nayak, A., Dhara, A., Eds.; Acadmic Press: Oxford, UK, 2022; pp. 121–144. [Google Scholar]
  142. He, M.; Qu, C.; Gao, O.; Hu, X.; Hong, X. Biological and pharmacological activities of amaryllidaceae alkaloids. RSC Adv. 2015, 5, 16562–16574. [Google Scholar] [CrossRef]
  143. Cahlikova, L.; Breiterova, K.; Opletal, L. Chemistry and Biological Activity of Alkaloids from the Genus Lycoris (Amaryllidaceae). Molecules 2020, 25, 4797. [Google Scholar] [CrossRef]
  144. Fennell, C.; van Staden, J. Crinum species in traditional and modern medicine. J. Ethnopharmacol. 2001, 78, 15–26. [Google Scholar] [CrossRef]
  145. Calderon, A.I.; Cubilla, M.; Espinosa, A.; Gupta, M.P. Screening of plants of Amaryllidaceae and related families from Panama as sources of acetylcholinesterase inhibitors. Pharm. Biol. 2010, 48, 988–993. [Google Scholar] [CrossRef] [PubMed]
  146. Lo’pez, S.; Bastida, J.; Viladomat, F.; Codina, C. Acetylcholinesterase inhibitory activity of some Amaryllidaceae alkaloids and Narcissus extracts. Life Sci. 2002, 71, 2521–2529. [Google Scholar] [CrossRef]
  147. Babashpour-Asl, M.; Kaboudi, P.S.; Barez, S.R. Therapeutic and medicinal effects of snowdrop (Galanthus spp.) in Alzheimer’s disease: A review. J. Educ. Health Promot. 2023, 12, 128. [Google Scholar] [CrossRef] [PubMed]
  148. Berkov, S.; Atanasova, M.; Georgiev, B.; Bastida, J.; Doytchinova, I. The Amaryllidaceae alkaloids: An untapped source of acetylcholinesterase inhibitors. Phytochem. Rev. 2022, 21, 1415–1443. [Google Scholar] [CrossRef]
  149. Tallini, L.R.; Acosta Leon, K.; Chamorro, R.; Osorio, E.H.; Bastida, J.; Jost, L.; Oleas, N.H. Alkaloid Profiling and Anti-Cholinesterase Potential of Three Different Genera of Amaryllidaceae Collected in Ecuador: Urceolina Rchb., Clinanthus Herb. and Stenomesson Herb. Life 2024, 14, 924. [Google Scholar] [CrossRef]
  150. Nair, J.J.; van Staden, J. Anti-inflammatory Principles of the Plant Family Amaryllidaceae. Planta Med. 2024, 90, 900–937. [Google Scholar] [CrossRef]
  151. Nair, J.J.; van Staden, J. Anti-inflammatory effects of the plant family Amaryllidaceae. J. Ethnopharmacol. 2024, 327, 117943. [Google Scholar] [CrossRef]
  152. Stark, A.; Schwenk, R.; Wack, G.; Zuchtriegel, G.; Hatemler, M.G.; Braeutigam, J.; Schmidtko, A.; Reichel, C.A.; Bischoff, I.; Fuerst, R. Narciclasine exerts anti-inflammatory actions by blocking leukocyte-endothelial cell interactions and down-regulation of the endothelial TNF receptor 1. FASEB J. 2019, 33, 8771–8781. [Google Scholar] [CrossRef] [PubMed]
  153. Furst, R. Narciclasine—An Amaryllidaceae Alkaloid with Potent Antitumor and Anti-Inflammatory Properties. Planta Med. 2016, 82, 1389–1394. [Google Scholar] [CrossRef] [PubMed]
  154. Park, J.B. Synthesis and characterization of norbelladine, a precursor of Amaryllidaceae alkaloid, as an anti-inflammatory/anti-COX compound. Bioorg Med. Chem. Lett. 2014, 24, 5381–5384. [Google Scholar] [CrossRef]
  155. Citoglu, G.S.; Acikara, O.B.; Yilmaz, B.S.; Ozbek, H. Evaluation of analgesic, anti-inflammatory and hepatoprotective effects of lycorine from Sternbergia fisheriana (Herbert) Rupr. Fitoterapia 2012, 83, 81–87. [Google Scholar] [CrossRef] [PubMed]
  156. Castilhos, T.S.; Giordani, R.B.; Henriques, A.T.; Menezes, F.S.; Zuanazzi, J.A.S. In vitro evaluation of the antiinflammatory, antioxidant and antimicrobial activities of the montanine alkaloid. Rev. Bras. Farmacogn. 2007, 17, 209–214. [Google Scholar] [CrossRef]
  157. Minkah, P.A.B.; Danquah, C.A. Anti-infective, anti-inflammatory and antipyretic activities of the bulb extracts of Crinum jagus (J. Thomps.) Dandy (Amaryllidaceae). Sci. Afr. 2021, 12, e00723. [Google Scholar] [CrossRef]
  158. Kaur, J.; Melkani, I.; Singh, A.P.; Singh, A.P.; Bala, K. Galantamine: A review update. J. Drug Deliv. Ther. 2022, 12, 167–173. [Google Scholar] [CrossRef]
  159. Berkov, S.; Romani, S.; Herrera, M.; Viladomat, F.; Codina, C.; Momekov, G.; Ionkova, I.; Bastida, J. Antiproliferative Alkaloids from Crinum zeylanicum. Phytother. Res. 2011, 25, 1686–1692. [Google Scholar] [CrossRef]
  160. Nair, J.J.; van Staden, J. Antiviral Effects of the Plant Family Amaryllidaceae. Nat. Prod. Commun. 2023, 18, 1934578X231162781. [Google Scholar] [CrossRef]
  161. Nair, J.J.; van Staden, J. Antiviral alkaloid principles of the plant family Amaryllidaceae. Phytomedicine 2023, 108, 154480. [Google Scholar] [CrossRef]
  162. Campbell, W.E.; Gammon, D.W.; Nair, J.J.; Codina, C.; Bastida, J.; Viladomat, F.; Smith, P.J.; Albrecht, C.F. Structure Activity Studies on Alkaloids from Indigenous Amaryllidaceous Species; Vieweg: Ridgecrest, CA, USA, 1998; p. 327. [Google Scholar]
  163. Schmeda-Hirschmann, G.; Astudillo, L.; Bastida, J.; Viladomat, F.; Codina, C. DNA binding activity of amaryllidaceae alkaloids. Bol. Soc. Chil. Quim. 2000, 45, 515–518. [Google Scholar]
Figure 1. Structures of 20 Amaryllidaceae alkaloids representing the diversity of alkaloid types.
Figure 1. Structures of 20 Amaryllidaceae alkaloids representing the diversity of alkaloid types.
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Table 1. The family Amaryllidaceae with three subfamilies and over one thousand species.
Table 1. The family Amaryllidaceae with three subfamilies and over one thousand species.
SubfamilyGenusSpecies a
AgapanthoideaeAgapanthus5 + unclassified
AllioideaeAllieae524 + unclassified
Gilliesieae (+9 subgenera b)75 + unclassified
Tulbaghieae (+2 subgenera c)18 + unclassified
Amaryllidoideae58 genera (+13 subgenera d)592 + unclassified
Total62 genera (+24 subgenera)1214 + unclassified
a Based on “Taxonomy ID 4668, Amaryllidaceae” by the National Center for Biotechnology Information (website accessed to 31 January 2025). The variation in the species is not counted. b See Table 3 for the names of 9 subgenera. c See Table 3 for the names of 2 subgenera. d See Table 4 for the names of 13 subgenera.
Table 2. The subfamily Agapanthoideae and Amaryllidaceae alkaloids.
Table 2. The subfamily Agapanthoideae and Amaryllidaceae alkaloids.
GeneraSpecies aAmaryllidaceae Alkaloids b
AgapanthusA. africanus
A. campanulatus
A. caulescens
A. coddii
A. praecox
In all five species, no Amaryllidaceae alkaloids were reported. A. campanulatus (root extract) showed positive alkaloid tests [13].
a Based on “Taxonomy ID 4668, Amaryllidaceae” by the National Center for Biotechnology Information (website accessed to 31 January 2025). b Based on the key word search in SciFindern using species names + Amaryllidaceae and/or alkaloids.
Table 3. The subfamily Allioideae and Amaryllidacea alkaloids.
Table 3. The subfamily Allioideae and Amaryllidacea alkaloids.
GeneraSpecies (Numbers) aAmaryllidaceae Alkaloids b
AllieaeAllium spp. (524)No Amaryllidaceae alkaloids were found. Other alkaloids were reported [14,15,16].
GilliesieaeUnder 9 subgenera:
Beauverdia spp. (4)
Gilliesia spp. (7)
Latace spp. (1)
Leucocoryne spp. (19)
Miersia spp. (5)
Nothoscordum spp. (20)
Speea spp. (2)
Tristagma spp. (15)
Zoellnerallium spp. (2)
No Amaryllidaceae alkaloids were reported among a total of 75 species.
TulbaghieaeUnder 2 subgenera:
Prototulbaghia spp. (1)
Tulbaghia spp. (17)
Among a total of 18 species T. cernua and T. ludwigiana extracts (1 mg/mL ethanol) inhibited AChE [17].
a Based on “Taxonomy ID 4668, Amaryllidaceae” by the National Center for Biotechnology Information (website accessed 31 January 2025). b Based on the key word search in SciFindern using species names + alkaloids or Amaryllidaceae alkaloids.
Table 4. Subfamily Amaryllidoideae: genera and species with isolated, detected, or no reported Amaryllidaceae alkaloids.
Table 4. Subfamily Amaryllidoideae: genera and species with isolated, detected, or no reported Amaryllidaceae alkaloids.
GenusSpp. aAA bGenusSpp. aAA b
Acis8D cHymenocallis40Iso
Amaryllis3Iso dIsmene6Iso
Ammocharis6IsoLapiedra1Iso
Apodolirion2- eLeptochiton1-
Boophone3IsoLeucojum2Iso
Brunsvigia8IsoLycoris25Iso
Caliphruria3-Namaquanula1-
Calostemma3IsoNarcissus97Iso
Carpolyza0-Nerine9Iso
Cearanthes0-Pabellonia0-
Chlidanthus2DPancratium14Iso
Clinantheae: f Phaedranassa8Iso
Clinanthus6IsoPlagiolirion1-
Pamianthe2-Proiphys2D
Paramongaia4-Pyrolirion3D
Clivia9IsoRauhia3-
Crinum68IsoScadoxus4Iso
Crossyne2IsoShoubiaonia1-
Cryptostephanus2-Stemmatiumu-
Cybistetes0-Stenomesson8-
Cyrtanthus44IsoSternbergia8Iso
Eremocrinum1-Strumaria10-
Eucharis9IsoUngernia2Iso
Eucrosia6-Urceolina2Iso
Eurycles1IsoVagaria2-
Eustephia1IsoWorsleya2Iso
Galanthus25Iso
Gethyllis7-
Griffinia7D
Haemanthus12Iso
Hannonia1-
Haylockia1-
Hessea7-
Hieronymiella2Iso
Hippeastreae: g
Famatina0-
Hippeastrum29Iso
Paposoa1-
Phycella16D
Placea0-
Rhodolirium3Iso
Rhodophiala1Iso
Sprekelia1Iso
Traubia10
Zephyranthes36Iso
Notes: a Spp., means species numbers in the corresponding genera or subgenera based on “Taxonomy ID 4668, Amaryllidaceae” by the National Center for Biotechnology Information (website accessed to 31 January 2025). b AA, means Amaryllidaceae alkaloids surveyed using a combination of key words searched in SciFindern using species names + alkaloids or “Amaryllidaceae alkaloids” in the CAS SciFindern. c D, means AA detected or identified but not isolated. d Iso, means AA was isolated. e -, means AA not reported (not detected, not identified, and not isolated). f Genus Clinanthea contains three subgenera: Clinanthus, Pamianthe, and Paramongaia. g Genus Hippeastreae contains 10 subgenera: Famatina, Hippeastrum, Paposoa, Phycella, Placea, Rhodolirium, Rhodophiala, Sprekelia, Traubia, and Zephyranthes.
Table 5. Subfamily Amaryllidoideae: genera and species with detected or tentatively identified (but not isolated) Amaryllidaceae alkaloids.
Table 5. Subfamily Amaryllidoideae: genera and species with detected or tentatively identified (but not isolated) Amaryllidaceae alkaloids.
Genus Species Detection or Identification Reference
Acis A. autumnalis; A. fabrei; A. longifolia; A. nicaeensis; A. rosea; A. tingitana; A. trichophylla; A. valentine Acis valentina NR349 contained glanathamine-type alkaloids, and A. autumnalis NR346 contained lycorine-type and other Amaryllidaceae alkaloids. [133]
Griffinia G. alba; G. espiritensis; G. gardneriana; G. hyacinthine; G. nocturna; G. parviflora; G. rochae Griffinia nocturna was studied by UPLC-ESI-MS) for simultaneous analysis of galantamine, pseudolycorine, sanguinine, and narciclasine. [134]
Phycella (subgenerus of Hippeastreae) P. angustifolia: P. arzae; P. australis; P. chilensis; P. cyrtanthoides; P. aff. cyrtanthoides Garcia 4163; P. davidii; P. germainii; P. herbertiana; P. ignea; P. lutea; P. maulensis; P. ornate; P. aff. ornata Garcia 726; P. scarlatina Chloroform basic extracts from P. herbertiana contained galanthamine detected by GC-MS. [135]
Proiphys P. amboinensis; P. cunninghamii In P. amboinensis ext., haemanthamine and lycorine were identified and trace amounts of alkaloids of the lycorine and homolycorine types were found. [35]
Pyrolirion P. albicans; P. cutleri; P. tubiflorum Leaves of P. albicans analysed by GC-MS were found to contain galanthamine, chlidanthine, tazettine, and lycorine, and those in the bulbs were galanthamine, N-demethylgalanthamine, vittatine/crinine, montanine, pancracine, sternbergine, lycorine, and hippeastrine. [136]
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Lin, G.D.; Vishwakarma, P.; Smith, P.N.; Li, R.W. The Occurrence and Bioactivities of Amaryllidaceae Alkaloids from Plants: A Taxonomy-Guided Genera-Wide Review. Plants 2025, 14, 1935. https://doi.org/10.3390/plants14131935

AMA Style

Lin GD, Vishwakarma P, Smith PN, Li RW. The Occurrence and Bioactivities of Amaryllidaceae Alkaloids from Plants: A Taxonomy-Guided Genera-Wide Review. Plants. 2025; 14(13):1935. https://doi.org/10.3390/plants14131935

Chicago/Turabian Style

Lin, G. David, Pinky Vishwakarma, Paul N. Smith, and Rachel W. Li. 2025. "The Occurrence and Bioactivities of Amaryllidaceae Alkaloids from Plants: A Taxonomy-Guided Genera-Wide Review" Plants 14, no. 13: 1935. https://doi.org/10.3390/plants14131935

APA Style

Lin, G. D., Vishwakarma, P., Smith, P. N., & Li, R. W. (2025). The Occurrence and Bioactivities of Amaryllidaceae Alkaloids from Plants: A Taxonomy-Guided Genera-Wide Review. Plants, 14(13), 1935. https://doi.org/10.3390/plants14131935

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