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Kostova, N.; Doncheva, T. Chemistry of Hypecoum Alkaloids. Encyclopedia. Available online: https://encyclopedia.pub/entry/49772 (accessed on 08 July 2024).
Kostova N, Doncheva T. Chemistry of Hypecoum Alkaloids. Encyclopedia. Available at: https://encyclopedia.pub/entry/49772. Accessed July 08, 2024.
Kostova, Nadezhda, Tsvetelina Doncheva. "Chemistry of Hypecoum Alkaloids" Encyclopedia, https://encyclopedia.pub/entry/49772 (accessed July 08, 2024).
Kostova, N., & Doncheva, T. (2023, September 28). Chemistry of Hypecoum Alkaloids. In Encyclopedia. https://encyclopedia.pub/entry/49772
Kostova, Nadezhda and Tsvetelina Doncheva. "Chemistry of Hypecoum Alkaloids." Encyclopedia. Web. 28 September, 2023.
Chemistry of Hypecoum Alkaloids
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This entry is adapted from the peer-reviewed paper 10.3390/d15091023

Genus Hypecoum Tourn. ex L. belongs to the poppy family Papaveraceae and comprises about 19 species occurring in Europe, Northern Africa and Asia. Hypecoum species have been widely used in traditional medicine as antipyretic, analgesic and anti-inflammatory remedies. The effects are associated with the biologically and pharmacologically active isoquinoline alkaloids in them such as protopines, protoberberines, benzophenanthridines, aporphines, simple isoquinolines, secoberbines, spirobenzylisoquinolines and others. 

isoquinoline alkaloids Hypecoum

1. Introduction

The flowering plants of the genus Hypecoum, belonging to the family Papaveraceae, subfamily Fumarioideae, are widely distributed in temperate areas from Europe to Africa to Southwestern Asia. It is represented by 19 species (23 synonyms), with 2 accepted subspecies and 1 ambiguous name [1]. These plants have recognized medicinal value and are used in different forms of traditional medicine in the treatment and prevention of many diseases—colds, pneumonia, pharyngitis, inflamed red eyes, hepatitis, cholecystitis and other [2][3][4][5][6]. Scientific investigations of the Hypecoum species show that many of the therapeutic effects of the plants are primarily related to the bioactive isoquinoline alkaloids found in them. The known alkaloids in the genus belong to the various classes of isoquinolines—protopines, protoberberines, benzophenanthridines, aporphines, simple isoquinolines, secoberbines, spirobenzylisoquinolines and others. Protopine is a predominant alkaloid isolated from all investigated plants of the genus [2][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24]. Besides being biologically active compounds, isoquinoline alkaloids are characteristic secondary metabolites in the family Papaveraceae and can be used for chemotaxonomic purposes [25].
In recent years, more than 40 alkaloids have been identified in Hypecoum species, and new alkaloid structures, along with their pharmacological activities, are reported every year, enriching the diversity of natural compounds. Some of them have promising properties for the treatment of important diseases such as inflammation, cancer and microbial infections [18][19][22][23][26][27][28][29].

2. Hypecoum alkaloids 

Alkaloids are a large group of N-containing natural compounds with diverse structures and a wide spectrum of pharmacological effects on human health. The Hypecoum species are recognized as important medicinal plants, biosynthesizing isoquinoline alkaloids as major active ingredients.
This section summarizes the alkaloid compounds that have been identified in the Hypecoum spp. since 1972 (Table 1) [2][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][27][30][31][32][33][34][35][36][37][38][39][40]. So far, a total of 86 naturally occurring alkaloids have been reported for ten plant species—H. procumbens, H. procumbens var. glaucescens, H. imberbe, H. lactiflorum, H. pendulum, H. trilobum, H. leptocarpum, H. erectum, H. ponticum and H. parviflorum. Based on their structures, the Hypecoum alkaloids can be divided into eight major groups: protopines (1–11), protoberberines (12–17), benzophenantridines (18–28), aporphines (29–33), simple isoquinolines (34–38), secoberbines (39–66), spirobenzilisoquinolines (67–73) and others (74–86). Two chemical structures have been detected in the literature with the name leptocarpine—protopine alkaloid 8 and alkaloid 82. Both compounds have been identified in H. leptocarpum [10][22][32]. On the other hand, the structure of alkaloid 41 has been published in the literature under two different names, dihydroleptopine and coryximine, isolated from H. leptocarpum [22][23][33]. Similarly, the newly found in H. erectum 2-(1,3-dioxolo [4,5-h]isoquinolin-7-yl)-4,5-dimethoxy-N-methyl-benzenethanamine has the same structure as the alkaloid leptocarmine (62), isolated from H. leptocarpum [19][23][24].
Table 1. Alkaloid structures reported for Hypecoum spp.
Alkaloids/Types Structure Species References
Protopines      
Protopine (1) Diversity 15 01023 i001 H. procumbens
H. procumbens var. glaucescens
H. imberbe
H. lactiflorum
H. pendulum
H. trilobum
H. leptocarpum
H. erectum
H. ponticum
H. parviflorum		 [2][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24]
Dihydroprotopine (2) Diversity 15 01023 i002 H. procumbens
H. imberbe
H. leptocarpum		 [17][24]
13-Oxoprotopine (3) Diversity 15 01023 i003 H. procumbens
H. erectum		 [15][19]
Cryptopine (4) Diversity 15 01023 i004 H. procumbens var. glaucescens
H. erectum
H. leptocarpum		 [2][11][13][19][20][21][22][23][30]
Allocryptopine (5) Diversity 15 01023 i005 H. lactiflorum
H. leptocarpum
H. procumbens
H. procumbens var. glaucescens
H. erectum		 [7][8][10][11][13][14][19][21][30][31]
13-Oxocryptopine (6) Diversity 15 01023 i006 H. erectum [19]
13-Oxoallocryptopine (7) Diversity 15 01023 i007 H. erectum [19]
Leptocarpine (8) * Diversity 15 01023 i008 H. leptocarpum [32]
Hunnemanine (9) Diversity 15 01023 i009 H. procumbens [15]
Bis[1,3]benzodioxolo[4,5-c:5′,6′-g]azecin-14(4H)-one, 5,6,7,13-tetrahydro-5-methyl-one (10) Diversity 15 01023 i010 H. erectum [19]
6,7,8,14-Tetrahydro-3,4-dimethoxy-6-methylbenzo
[c][1,3]benzodioxolo [5,6-g]azecin-15(5H)-one (11)		 Diversity 15 01023 i011 H. erectum [19]
Protoberberines      
(S)-Stylopine (12) Diversity 15 01023 i012 H. procumbens [17]
(S)-Scoulerine (13) Diversity 15 01023 i013 H. procumbens [8][15]
Coptisine (14) Diversity 15 01023 i014 H. procumbens
H. leptocarpum
H. erectum		 [8][14][20][23][30][31]
(S)-N-Methylstylopine (15) Diversity 15 01023 i015 H. lactiflorum
H. procumbens
H. ponticum		 [7][17][18]
(S)-N-Methylcanadine (16) Diversity 15 01023 i016 H. lactiflorum
H. erectum
H. procumbens
H. ponticum
H. leptocarpum		 [7][13][17][18][21]
Hydroprotopine (17) Diversity 15 01023 i017 H. leptocarpum [27]
Benzophenanthridines      
Chelerythrine (18) Diversity 15 01023 i018 H. procumbens
H. leptocarpum		 [8][14][30]
Chelirubine (19) Diversity 15 01023 i019 H. procumbens [8][14]
Dihydrochelirubine (20) Diversity 15 01023 i020 H. procumbens [17]
Sanguinarine (21) Diversity 15 01023 i021 H. procumbens
H. leptocarpum
H. trilobum
H. ponticum ,
H. imberbe		 [14][17][18][21][30]
Dihydrosanguinarine (22) Diversity 15 01023 i022 H. imberbe
H. leptocarpum
H. procumbens		 [9][10][15]
(R,S)-8-Methoxydihydrosanguinarine (23) Diversity 15 01023 i023 H. procumbens
H. leptocarpum
H. imberbe		 [8][9][10]
(S)-8-Hydroxymethyldihydrosanguinarine (24) Diversity 15 01023 i024 H. erectum [19]
8-Acetonyldihydrosanguinarine (25) Diversity 15 01023 i025 H. procumbens
H. leptocarpum		 [8][10]
(R,S)-Nitrotyrasanguinarine (26) Diversity 15 01023 i026 H. imberbe
H. pendulum
H. procumbens		 [9]
Oxysanguinarine (27) Diversity 15 01023 i027 H. procumbens [8][15]
Norsanguinarine (28) Diversity 15 01023 i028 H. procumbens
H. leptocarpum		 [8][15][23]
Aporphines      
(S)-Corydine (29) Diversity 15 01023 i029 H. procumbens
H. leptocarpum		 [30]
(S)-Isocorydine (30) Diversity 15 01023 i030 H. procumbens
H. procumbens var. glaucescens
H. leptocarpum		 [8][11][30]
(S)-Bulbocapnine (31) Diversity 15 01023 i031 H. imberbe [9]
(S)-Glaucine (32) Diversity 15 01023 i032 H. procumbens [8]
(S)-Magnoflorine (33) Diversity 15 01023 i033 H. procumbens
H. leptocarpum		 [30]
Simple isoquinolines      
Oxohydrastinine (34) Diversity 15 01023 i034 H. imberbe
H. leptocarpum
H. erectum		 [2][9][10][12][13][19][21][22][23][24][27]
Doryanine (35) Diversity 15 01023 i035 H. erectum [19]
N-Methylcorydaldine (36) Diversity 15 01023 i036 H. erectum
H. leptocarpum		 [13][19][23]
2-Methyl-1,2,3,4-tetrahydro
isoquinoline-7-carboxylic acid methyl ester (37)		 Diversity 15 01023 i037 H. erectum [19]
1,3,6,6-Tetramethyl-5,6,7,8-
tetrahydroisoquiolin-8-one (38)		 Diversity 15 01023 i038 H. erectum [19]
Secoberbines      
(S)-Corydalisol (39) Diversity 15 01023 i039 H. procumbens [8]
(S)-N-Methylcorydalisol (40) Diversity 15 01023 i040 H. lactiflorum [7]
(S)-Dihydroleptopine (41)
(Coryximine)		 Diversity 15 01023 i041 H. leptocarpum [22][23][33]
Hypecocarpinine (42) Diversity 15 01023 i042 H. leptocarpum [24]
Hypecocarpine (43) Diversity 15 01023 i043 H. leptocarpum [27]
Leptopinine (44) Diversity 15 01023 i044 H. leptocarpum [12]
Leptopine (45) Diversity 15 01023 i045 H. leptocarpum [12][21]
Leptopidine (46) Diversity 15 01023 i046 H. leptocarpum [12][21][22][23][24][27]
Hypepontine (47) Diversity 15 01023 i047 H. ponticum [17][18]
N-Methylcoryximine (48) Diversity 15 01023 i048 H. pendulum [34]
Hendersine B (49) Diversity 15 01023 i049 H. leptocarpum [23]
Procumbine (50) Diversity 15 01023 i050 H. procumbens
H. leptocarpum		 [30][35]
Leptopidinine (51) Diversity 15 01023 i051 H. leptocarpum [12][21][22]
Torulosine (52) Diversity 15 01023 i052 H. leptocarpum [23][33]
8-Oxohypecorinine N-oxide (53) Diversity 15 01023 i053 H. leptocarpum [33]
N-Methyldemethyltorulosine (54) Diversity 15 01023 i054 H. leptocarpum [23][33]
(R,S)-Hypecorinine (55) Diversity 15 01023 i055 H. procumbens
H. procumbens var. glaucescens
H. erectum		 [8][11][13][14][19][31][36]
(R,S)-8-Oxohypecorinine (56) Diversity 15 01023 i056 H. procumbens var. glaucescens [11]
Hypecorine (57) Diversity 15 01023 i057 H. erectum [14][31][36]
2,3-Dimethoxyhypecorinine (58) Diversity 15 01023 i058 H. erectum [19]
(S)-Peshawarine (59) Diversity 15 01023 i059 H. parviflorum [8][16]
Corydamine (60) Diversity 15 01023 i060 H. leptocarpum
H. erectum		 [10][19][22][23][24][31]
Corydamine acid (61) Diversity 15 01023 i061 H. leptocarpum [23]
Leptocaramine (62)
(2-(1,3-dioxolo [4,5-h]
isoquinolin-7-yl)-4,5-dimethoxy-N-methyl-benzeneethanamine)		 Diversity 15 01023 i062 H. leptocarpum
H. erectum		 [19][23][24]
N-Formylcorydamine (63) Diversity 15 01023 i063 H. erectum
H. procumbens		 [15][19]
2,3-Dimethoxy-N-formyl
corydamine (64)		 Diversity 15 01023 i064 H. erectum [19]
Hypecumine (65) Diversity 15 01023 i065 H. procumbens [15]
7-N-Methyl-7-N-oxide-2,3-di-
methoxycorydamine (66)		 Diversity 15 01023 i066 H. erectum [19]
Spirobenzylisoquinolines      
(S,S)-Hyperectumine B (67) Diversity 15 01023 i067 H. erectum [19]
(S,S)-2,3-Dimethoxyhyperectumine B (68) Diversity 15 01023 i068 H. erectum [19]
(R,S) and (S,R)-2,3-Dimethoxyhyperectine (69) Diversity 15 01023 i069 H. erectum [19]
(R,S) and (S,R)-Hyperectine (70) Diversity 15 01023 i070 H. leptocarpum
H. erectum		 [10][19][31][36][37]
(S,S) and (R,R)-Isohyperectine (71) Diversity 15 01023 i071 H. leptocarpum
H. erectum		 [10][12][37]
(R,R)-Sibiricine (72) Diversity 15 01023 i072 H. erectum [19]
(R,S)-Hypecoleptopine (73) Diversity 15 01023 i073 H. erectum
H. leptocarpum		 [21][33][38]
Other alkaloids      
(S)-N-Methylcoclaurine (74) Diversity 15 01023 i074 H. procumbens [17]
N-Methylsecoglaucine (75) Diversity 15 01023 i075 H. ponticum [17][18]
(R)-Turkiyenine (76) Diversity 15 01023 i076 H. procumbens
H. pendulum
H. imberbe		 [9][15][39][40]
(S)-Oxoturkiyenine (77) Diversity 15 01023 i077 H. pendulum [39]
Leptocarpinine (78) Diversity 15 01023 i078 H. leptocarpum [12]
Leptocarpinine B (79) Diversity 15 01023 i079 H. leptocarpum [23]
(S,S)-Trans-benzindenoazepines (80) Diversity 15 01023 i080 H. erectum [19]
(S,S)-O-Methylfumarostelline (81) Diversity 15 01023 i081 H. erectum [19]
Leptocarpine (82) * Diversity 15 01023 i082 H. leptocarpum [10][22]
Hypecoumine (83) Diversity 15 01023 i083 H. procumbens [2]
Hyperectumine (84)
(8S, 9R, 15R)
(8R, 9S, 15S)		 Diversity 15 01023 i084 H. erectum [25]
Dibenzooxazacycloundecine (85) Diversity 15 01023 i085 H. erectum [19]
Hypeisoxazole A (86)
(6S, 8R, 14R)
(6R, 8S, 14S)		 Diversity 15 01023 i086 H. erectum [38]
* Two chemical structures with the name leptocarpine (8, 82).

2.1. Protopine Alkaloids

The protopine alkaloids (1–11) represent the major class of alkaloids in the Hypecoum species (Table 1). Their structure includes a tricyclic frame with a carbonyl group at C-14 and methoxy- or methylendioxy- groups at C-2, C-3, C-9 and C-10. Alkaloids 3, 6 and 7 are further oxygenated at C-13. Although only eleven protopines have been identified in the genus, protopine (1) has been found in all studied Hypecoum species [2][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24]. Alkaloid 1 together with cryptopine (4) and allocryptopine (5) are the most pharmacologically studied and biologically active protopines in the genus. It has been established that these alkaloids possess potent anti-inflammatory, analgesic and antibacterial effect [13][19].

2.2. Protoberberine Alkaloids

The protoberberine alkaloids (12–17) are a small group of Hypecoum isoquinolines containing only six representatives (Table 1). Most of them are of the tetrahydroprotoberberine type (12, 13, 15–17), and only coptisine (14) is a typical protoberberine with a three aromatic ring system. Alkaloid 14 has shown significant cytotoxic activity against different cancer cell lines, which is probably related to the positive N-ion in its molecule [23].

2.3. Benzophenantridine Alkaloids

Eleven benzophenantridine alkaloids (18–28) have been identified in six Hypecoum species—H. procumbens, H. leptocarpum, H. trilobum, H. ponticum, H. imberbe and H. erectum (Table 1). Their structure includes a tetracyclic skeleton with an aromatic (18, 19, 21 and 28) or nonaromatic (20, 22–27) ring B. The alkaloids with three aromatic ring systems are usually in the form of quaternary ammonium salts (18, 19, 21) and those with non-aromatic ring B are usually C-8-substituted (23–27). Benzophenanthridine alkaloids are known to have diverse and significant biological properties, but so far, only 8-hydroxymethyldihydrosanguinarine (24), isolated from H. erectum, has been found to possess in vitro anti-inflammatory activity [19][41].

2.4. Aporphine Alkaloids

The alkaloids in this group (29–33) contain an aporphine skeleton with two aromatic rings and N-methyl function. Five aporphines have been isolated from four plant species—H. procumbens, H. procumbens var. glaucescens, H. leptocarpum and H. imberbe (Table 1). Alkaloids 29–32 are tertiary and only one—magnoflorine—(33) is a quaternary ammonium salt. Although alkaloids of this type are of great research interest due to their important biological properties such as cytotoxicity, antioxidation, immunoregulation, etc., the isolated Hypecoum aporphines have not been studied pharmacologically [42].

2.5. Simple Isoquinoline Alkaloids

The simple isoquinoline group includes five alkaloids (34–38) present in three Hypecoum species—H. imberbe, H. leptocarpum and H. erectum (Table 1). These alkaloids have the simplest structure, involving an isoquinoline nucleus which is C-6- and/or C-7-substituted. Compound 38 is, unusually, 1,3,6,6-tetramethylated and oxygenated at C-8. Several biological activities have been established for alkaloids 34, 36 and 38, including anti-inflammatory, antibacterial, anticancer and analgesic effects [13][19][27].

2.6. Secoberbine Alkaloids

The secoberbine alkaloids (39–66) are the largest group of isoquinoline alkaloids, consisting of 28 members, which have been identified in seven Hypecoum species—H. procumbens, H. procumbens var. glaucescens, H. leptocarpum, H. erectum, H. lactiflorum, H. erectum, H. ponticum and H. parviflorum (Table 1).
According to the chemical structure, the alkaloids are divided into three subgroups: 7,8-secoberbines—tricyclic (39–49) and tetracyclic (50–58); 7,8-14,7-bissecoberbine—peshawarine (59) and 6,7-secoberbines (60–66) [43]. All tricyclic 7,8-secoberbines in the Hypecoum species have substitutions at C-8 with -CH2OH or -COOH groups. Structure–activity relationship studies on these compounds have shown that the presence of the carboxyl group in coryximine (41), leptopidine (46) and hendersine B (49) is the probable reason for the low cytotoxicity against different tumor cell lines [23][27]. Furthermore, the quaternary alkaloid hypepontine 47, and -CH2OH substituted at C-8, has demonstrated good in vitro antibacterial and antifungal activity [18]. Among the tetracyclic 7,8-secoberbines, hypecorinine (55) and 2,3-dimethoxyhypecorinine (58) have been found to possess good antimicrobial and anti-inflammatory properties, respectively [13][19]. The alkaloids 60 and 62 of the 6,7-secoberbine subgroup have moderate cytotoxicity against different cancer cell lines, probably due to possessing the most electron-donating groups in their structures [23][24]. Moreover, 60 possesses potent anticancer activity, and its acidified form can be used as a potential regulator of diabetes mellitus [28][44].

2.7. Spirobenzylisoquinoline Alkaloids

Spirobenzylisoquinolines (67–73) are a small group isoquinolines with a “spiro” structure identified in two Hypecoum species—H. leptocarpum and H. erectum (Table 1). In these species, most of the spirobenzylisoquinoline alkaloids are C-8 linked via a C–C bond to an amide carbonyl group (67, 68) or 3-aminomaleimide group (69–71). Alkaloid 73 is spirobenzylisoquinoline with a unique 6/6/5/6/6 skeleton. Some of the isolated alkaloids, such as 68–70 and 72, have shown good anti-inflammatory activity via selective inhibition of inflammatory mediators [19].

2.8. Other Alkaloids

This group summarizes the Hypecoum alkaloids of various structural types (74–86) such as the benzylisoquinoline—N-methylcoclaurine (74), the phenantrene—N-methylsecoglaucine (75), the indenobenzazepines (80, 81), the phthalideisoquinoline—hypecoumine (83), the C19-benzylisoquinoline—hyperectumine (84) and alkaloids with unusual structures that cannot be assigned to any of the established groups (76–79, 82, 85, 86) (Table 1). The alkaloids 80, 81 and 84 have shown significant anti-inflammatory properties in different in vitro models [19].

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