The Phytochemistry and Pharmacology of Tulbaghia, Allium, Crinum and Cyrtanthus: ‘Talented’ Taxa from the Amaryllidaceae
Abstract
:1. Introduction
2. The Genus Tulbaghia
2.1. Botanical Description
2.2. Geographical Distribution and Traditional Uses of Tulbaghia Species
2.3. Phytochemistry of Tulbaghia
2.4. Pharmacological Studies of Tulbaghia Species
2.4.1. Antimicrobial and Antiparasitic Activity
2.4.2. Anticancer Activity
2.4.3. Antioxidant Activity
2.4.4. Antidiabetic, Anticardiovascular and Antithrombogenic Activity
2.4.5. Miscellaneous Pharmacological Activity
3. The Genus Allium
3.1. Botanical Description
3.2. Traditional Uses of Genus Allium
3.3. Phytochemistry of Allium
3.4. Pharmacological Effects of Allium
3.4.1. Antimicrobial Activities
3.4.2. Antioxidant Properties
3.4.3. Anti-Inflammatory Properties
3.4.4. Anticancer Activity
3.4.5. Other Pharmacological Effects of Allium Species
4. The Genus Crinum
4.1. Geographical Distribution of Crinum
4.2. Traditional Uses of Crinum
4.3. Phytochemistry of Crinum
4.4. Pharmacological Activities of Crinum
4.4.1. Anti-Inflammatory and Analgesic Effects
4.4.2. Anticancer and Cytotoxicity Effects
4.4.3. Antimicrobial Properties
4.4.4. Antioxidant Properties
4.4.5. Other Pharmacological Properties
5. The Genus Cyrtanthus
5.1. Botanical Description
5.2. Geographical Distribution
5.3. Traditional Uses
5.4. Phytochemistry of Cyrtanthus
5.5. Pharmacological Activities
5.5.1. Antioxidant Activity
5.5.2. Anti-Inflammatory Activity
5.5.3. Inhibition of Acetylcholinesterase
5.5.4. Antimicrobial Activity
5.5.5. Cytotoxic Activity
5.5.6. Miscellaneous Pharmacological Activities
6. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Abbreviations
References
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Plant Species | Geographical Distribution | Traditional Uses | References |
---|---|---|---|
T. violacea | Indigenous to the Eastern Cape, KwaZulu-Natal, Gauteng, Free State and Mpumalanga Provinces of South Africa. | The leaves and bulbs are used in the management of fever and colds, tuberculosis, asthma, and stomach problems. The leaves are eaten as vegetables and for the management of oesophageal cancer. It is also used as a snake repellent. | [8,50] |
T. alliacea | Native to South Africa and grows mostly in the Eastern Cape and southern KwaZulu-Natal Provinces of South Africa. | Its bruised rhizome is used locally in bathwater to relieve fever, rheumatism, and paralysis, and in small doses as a laxative. T. alliacea is used for the management of stomach problems, asthma, and pulmonary tuberculosis. Its rhizome infusion is administered as an enema. | [8,51] |
T. simmleri | Native to the South African Drakensberg mountains growing as isolated plants on rocky ledges. | Bulbs and leaves are used as a remedy for gastrointestinal ailments, enemas, high blood pressure, heart problems, chest complaints, high cholesterol, constipation, rheumatism, asthma, fever, pulmonary tuberculosis, earache, human immunodeficiency virus (HIV), paralysis, and cardiovascular diseases. | [50,52] |
T. acutiloba | Found in the rainfall regions of southern Africa, occurring in the Eastern Cape, KwaZulu-Natal, Limpopo, Free State, Gauteng, North West, and Mpumalanga Provinces of South Africa, as well as in Lesotho, Swaziland and Botswana. | T. acutiloba leaves are used as a culinary herb and snake repellent. It is used to treat barrenness, flu, bad breath, and as an aphrodisiac. It is also cultivated to keep snakes away from the homestead. | [8] |
T. natalensis | Although native to South Africa, but is now grown worldwide. | It is used as a culinary herb and snake repellent. | [53] |
T. cernua | Commonly found in the Eastern Cape, Free State, Gauteng, KwaZulu-Natal, Limpopo, Mpumalanga, North West and Western Cape Provinces of South Africa. | It is used for ornamental purposes. | [8] |
T. leucantha | Widely distributed in southern Africa including Botswana, Lesotho, South Africa, Swaziland, Zambia, and Zimbabwe. | Its rhizome is scraped clean and boiled in stews or roasted as a vegetable. Its leaves and stems are used as a culinary herb and protective charm. | [53] |
T. ludwigiana | Commonly found in the Eastern Cape, KwaZulu-Natal, Northern Provinces of South Africa and in Swaziland. | It is traditionally used as a love charm. | [53] |
Country | No. of Documents * |
---|---|
South Africa | 99 |
United Kingdom | 15 |
United States | 12 |
Czech Republic | 8 |
Italy | 7 |
India | 6 |
Germany | 5 |
Australia | 3 |
China | 3 |
Belgium | 2 |
Disease | No. of Published Studies # |
---|---|
Antimicrobial | 26 |
Cancer | 11 |
Antioxidant | 13 |
Diabetes | 2 |
Cardiovascular | 12 |
Antithrombogenic | 2 |
Miscellaneous | 17 |
Plant Species | Extraction Solvent | Plant Part Used | Biological Activity | References |
---|---|---|---|---|
T. violacea | Dichloromethane | Bulbs | MIC ranging from 20 to 300 µg/mL against Bacillus subtilis, methicillin-resistant S. aureus, S. epidermidis, E. coli, K. pneumoniae, P. aeruginosa, C. albicans and C. parapsilosis. | [67] |
T. violacea | Hexane and ethanol | Flowers and callus cultures | Moderate to strong broad-antimicrobial (E. coli, P. aeruginosa, S. aureus, Aspergillus niger and C. albicans) activity observed by zone of inhibition in the agar well disc diffusion method. | [68] |
T. violacea | Water | Bulbs | Significant reduction in A. flavus β-glucan and chitin synthesis corresponding to a dose-dependent inhibition of the enzymes β-glucan and chitin synthase, respectively.This results in inhibition of ergosterol production in the fungus. | [70,71] |
T. violacea | Acetone | Bulbs | Varied light intensities, pH and watering frequencies substantially impacted both growth and potency of plant extracts against the fungi F. oxysporum. | [73,74] |
T. violacea | Water | Roots, bulbs, leaves and flowers | Significantly compromised population densities of the nematode M. incognita race 2 on tomato roots and in the soil. | [75] |
T. violacea | Dichloromethane | Bulbs | Antiparasitic activity against T. brucei (IC50 = 2.83 µg/mL) and L. tarentolae (IC50 = 6.29 µg/mL). | [67] |
Plant Species | Extraction Solvent | Plant Part Used | Biological Activity | References |
---|---|---|---|---|
T. violacea | Methanol | Leaves and roots | Marked time- and dose-dependent cytotoxic effect on cancer cell lines. Induced apoptosis using p53-independent pathway. | [78] |
T. violacea | Methanol, butanol, and hexane | Leaves | Methanol extract was prolific against multiple cell lines. Hela and ME-180 cell lines treated with methanol and hexane extracts showed an increase in caspase 3/7 activity. Both methanol and hexane extracts induced a 10-fold increase in expression of p53 gene in Hela cells. | [79] |
T. violacea | Methanol:water:formic acid (80:20:0.1, v/v/v) | Flowers | Demonstrated activity against ovarian tumor cells. | [80] |
T. violacea | Water and methanol | Leaves | Water-soluble extract emerged as the most cytotoxic (IC50 = 314 µg/mL), compared to the methanol extract (IC50 = 780 µg/mL), against the MDA-MB-231 triple-negative breast cancer cell line. Water-soluble extract prevented cell migration completely for 13 h at 300 µg/mL. | [82] |
T. violacea | Hexane and ethanol | Flowers and callus cultures | Extracts showed marked cytotoxicity (60–74% growth inhibition at 250 µg/mL) against three different cell lines (Hep G2, PC-3 and MCF-7). | [68] |
T. violacea | Acetone and water | Leaves | Anticancer activity against oral cancer with an IC50 (acetone extract) of 0.2 mg/mL; IC50 (water extract) of 1 mg/mL. | [84] |
T. violacea | Methanol:water (1:1) | Whole plants | Two pro-apoptotic glucopyranosides d-fructofuranosyl-β (2→6)-methyl-α-d-glucopyranoside and β-d-fructofuranosyl-(2→6)-α-d-glucopyranoside isolated and identified as active anticancer agents in the plant. | [85] |
T. violacea | Water | Whole plants | MoA of the three compounds, namely methyl-α-d-glucopyranoside, d-fructofuranosyl-β (2→6)-methyl-α-d-glucopyranoside and β-d-fructofuranosyl-(2→6)-α-d-glucopyranoside isolated from the water extract, deciphered to be through induction of apoptosis by targeting the mitochondrial (intrinsic) pathway | [86] |
Plant Species | Extraction Solvent | Plant Part Used | Biological Activity | References |
---|---|---|---|---|
T. violacea | Water | Leaves | Dose-dependent antioxidant activity measured using the DPPH (Log IC50 = 0.49 mg/mL) and ABTS (Log IC50 = 0.24 mg/mL) assays | [92] |
T. violacea | Methanol/water/formic acid (80:20:0.1, v/v/v) | Flowers | Marked antioxidant activity was observed using 3 different types of assays, namely DPPH, FRAP and TREC | [80] |
T. acutiloba | Hydro-methanolic extracts | Roots, rhizomes, leaves and flowers | Dose-dependent antioxidant activity observed with the rhizome extract emerging as the most active plant part (IC50 DPPH = 0.202 mg/mL and peak scavenging activity of 95) | [91] |
T. violacea | Hexane and ethanol | Flowers and callus cultures | Dose-dependent antioxidant activity with IC50 ranging from 1.933 to 7.350 mg/mL in the DPPH assay | [68] |
T. violacea | Acetone | Leaves | IC50 DPPH = 0.08 mg/mL; IC50 ABTS = 0.03 mg/mL | [84] |
T. acutiloba | Acetone | Leaves | IC50 DPPH = 0.16 mg/mL; IC50 ABTS = 0.07 mg/mL | [84] |
T. alliacea | Acetone | Leaves | IC50 DPPH = 0.06 mg/mL; IC50 ABTS = 0.06 mg/mL | [84] |
T. cernua | Acetone | Leaves | IC50 DPPH = 0.21 mg/mL; IC50 ABTS = 2.34 mg/mL | [84] |
T. leucantha | Acetone | Leaves | IC50 DPPH = 0.39 mg/mL; IC50 ABTS = 0.03 mg/mL | [84] |
T. ludwigiana | Acetone | Leaves | IC50 DPPH = 0.26 mg/mL; IC50 ABTS = 0.09 mg/mL | [84] |
T. natalensis | Acetone | Leaves | IC50 DPPH = 2.70 mg/mL; IC50 ABTS = 0.04 mg/mL | [84] |
Plant Species | Extraction Solvent | Plant Part Used | Biological Activity | References |
---|---|---|---|---|
Diabetes | ||||
T. violacea | Methanol | Rhizome | Attenuated diabetes associated physiological complications in streptozotocin-induced diabetic rats. | [96] |
T. violacea | Methanol | Rhizome | Noticeably reduced blood glucose and serum lipid (TG, TC, and VLDL) levels while raising plasma insulin in a streptozotocin-induced diabetic rat model. | [97] |
Cardiovascular | ||||
T. violacea | Methanol | Leaves | Markedly reduced systolic BP, diastolic BP, mean arterial pressure and the heart rate in both age-induced and spontaneous hypertensive rats. | [98] |
T. violacea | Methanol | Rhizome | 50 mg/kg significantly improved kidney function in vivo. | [99] |
T. acutiloba | Hydro-methanolic extracts | Roots, rhizomes, leaves and flowers | All extracts inhibited the Angiotensin-1-Converting Enzyme in vitro (> 50 % inhibition at a concentration range of 125–1000 μg/mL). Extracts of leaves demonstrated activity comparable to that of the control drug ramipril. | [91] |
Antithrombogenic | ||||
T. violacea | Water | Leaves | Noticeable inhibition of platelet adhesion by a novel scaffold consisting of polycaprolactone incorporated with 10 % (w/w) plant extracts. | [90] |
T. violacea | Water | Leaves | Marked inhibition of platelet adhesion (70% inhibition at 0.1 mg/mL within 15 min post-exposure). | [92] |
Plant Species | Extraction Solvent | Plant Part Used | Biological Activity | References |
---|---|---|---|---|
T. violacea | Methanol/water/formic acid (80:20:0.1, v/v/v) | Flowers | Reduced 1-42 β-amyloid peptide formation and arrested oxidative stress in vivo. | [80] |
T. violacea | Methanol | Leaves | Demonstrated in vivo anticonvulsant activity by attenuating tonic convulsions induced by either pentylenetetrazole, bicuculline, picrotoxin, strychnine or NMDLA. | [102] |
T. violacea | Acetone | Mixture of leaves and bulbs | Marked tick repellence properties of fungus-exposed plants at low treatment concentrations (5 % w/v and 10 % w/v). | [59] |
T. violacea | Water | Leaves, stems, and roots | Induced conspicuous genotoxicity effects at high test concentrations (250, 500 and 1000 µg/mL) in the A. cepa assay. | [103] |
T. violacea | Water and ethanol | Leaves, stems, and roots | Broad murine macrophage antiproliferative and cytotoxicity activity influenced by both extract test concentrations, type of solvent and plant part used. | [104] |
Plant Species | Mode of Preparation | Traditional Medicinal Uses | Reference |
---|---|---|---|
A. cepa | Raw, juice of bulb or rhizome, paste, decoctions, cataplasm, maceration, infusion | Alopecia, antilithic (stone disease), anti-obesity, blood purifying, bronchitis, constipation, cardiovascular disease, cough, diabetes, eye diseases, erectile dysfunction, fever, hearing loss, headaches, hemorrhoids, epilepsy, oligomenorrhea, jaundice, lower gastrointestinal bleeding, prostate cancer, rheumatism, rubefacient, sinusitis, stomach pains, snake bites, skin diseases, teeth disorders, reduce flatulence, wound healing | [133,134,135] |
A. sativum | Extracts of leaves or bulb | Antiseptic, anthelmintic, antithrombotic, antilipidemic, aphrodisiac, anti-greying of hair, bronchitis, carminative, cough, colic, cancers (gastric, prostate, colorectal adenomatous polyps, squamous cell carcinoma), diabetes, diaphoretic, dysentery, eczema, facial paralysis, fever, flatulence, galactagogue, high blood pressure, intestinal worms, liver disorders, rheumatism, scabies, tetanus, stomach pains, tuberculosis | [135,136,137,138,139] |
A. umbilicatum | Raw or cooked bulb, leaves, flowers | Non-specific reduction in blood cholesterol levels, tonify digestive and circulatory systems | [116] |
A. victoralis | Fresh, pickled, boiled and salted flowers, leaves and roots | Appetizer, amenorrhea, pediatric otitis, bronchitis, diarrhea, dropsy, expectorant, hypofunction of stomach, inflammatory eye diseases, meteorism, gastroenteritis, heart diseases (atherosclerosis), rheumatism | [140] |
A. ascalonicum/A. cepa var aggregatum | Bulb and leaves | Allergies, appetizer, cold, cancers, fever, obesity, rheumatoid arthritis, soothes nerves, diabetes, post-menopausal syndrome | [141,142,143,144,145] |
A. chinense | Flower, leaves, roots, seedpods | Angina pectoris, astringent, bronchitis, carminative, chest pains, diarrhea, expectorant, pleurisy, tenesmus in cases of dysentery, reducing cholesterol, tonic to the digestive and circulatory systems | [146] |
A. tuberosum | Raw or cooked leaves, roots, oils from seed | Asthma, abdominal pain, carminative, cuts and wounds, diabetes, diarrhea, kidney and bladder weakness, nocturnal emission, urinary incontinence, spermatorrhea, stomachic | [147] |
A. griffithianum | Leaves and bulb | Carminative, colic indigestion, dyspepsia, diabetes control | |
A. oreoprasum | Leaves and bulb | Cough and cold, diabetes control, diarrhea, dysentery, fever, gastritis, oedema, headache, jaundice, stomachache, rheumatism, numbness of limbs | [124] |
Plant Species | Plant Part | Country | Isolated Compounds | Bioactivity | References |
---|---|---|---|---|---|
A. ursinum L. | Leaves, underground parts, fresh flowers | Poland Bulgaria | 1,2-di-O-α-linolenoyl-3-O-β-d-galactopyranosyl-sn-glycerol; β-sitosterol3-O-β-d-glucopyranoside; kaempferol 3-O-β-glucopyranoside and kaempferol 3-O-β-neohesperidoside. (-S-)-spirost-5-en-3β-ol tetrasaccharide, (25R)-spirost-5,25(27)-dien-3 β-ol tetrasaccharide, 3-hydroxypregna-5,16-dien-20-one glycoside. Thymidine, adenosine, astragalin (kaempferol-3-O-β-d-glucopyranoside, kaempferol-3-O-β-d-glucopyranosyl-7-O-β-d-glucopyranoside, kaempferol-3-O-β-d-neohesperoside, and kaempferol-3-O-β-d-neohesperoside-7-O-β-d glucopyranoside. | Anti-ADP-aggregation activity in human blood platelets. Inhibition of human platelet aggregation. Cytotoxic activity against murine melanoma B16 and sarcoma XC. | [148,149,150,151] |
A. mongolicum | Aerial parts | China | Mongoflavonoids A1, A2, A3, A4, B1, B2 and monogophenosides A1, A2, A3, B. | Increase in the height of mouse small intestine. | [152] |
A. cepa. A. cepa L. | Pigmented scales of red onion, bulbs, red onion skin waste | Naples | Quercetin. 3-O-(3″-O-β-glucopyranosyl-6″-O-malonyl-β-glucopyranoside)-4-O-β-glucopyranoside, cyanidin 3,4′-di-O-β-glucopyranoside, cyanidin-4′-O-β-glucoside, peonidin 3-O-(6 ″-O-malonyl-β-glucopyranoside). 5-hydroxy-3-methyl-4-propylsulfanyl-5H-furan-2-one, (hydroxymethyl) furfural, acetovanillone, methyl 4-hydroxyl cinnamate and ferulic acid methyl ester. 3-O-β-glucopyranoside and 3-O-(6″-O-malonyl-β-glucopyranoside) of 5-carboxypyranocyanidin. Ceposide A, ceposide B and ceposide C. Spiraeoside (4′-O-glucoside of quercetin). Onionin A1, onionin A2, onionin A3, onionin B1 and B2. Onionin A1 (3,4-dimethyl-5-(1E-propenyl)-tetrahydrothiophen-2-sulfoxide-S-oxide). Cyanidin 3-glucoside (Cy 3-Glc), 3-malonylglucoside (Cy3-MaGlc), cyanidin 3-laminaribioside (Cy 3-Lam) and 3-malonyllaminaribioside (Cy 3-MaLam). | Anti-inflammatory and immunomodulatory effect. Induction of quinone reductase. Antifungal activity. Radical scavenging, anti-inflammatory, inhibition of the expression of B-cell lymphoma 2. Suppression of tumor progression in mouse ovarian cancer (Onionin A1). Suppression of tumor-cell proliferation through the inhibition of polarization of M2 activated macrophages. | [153,154,155,156,157,158,159,160,161] |
A. sativum. A. sativum L. var. voghiera. A. sativum L. | Root, protobulb, leaf sheath and blade, bulbs, tuber | Italy | Nerolidol, α-pinene, terpinolene. Voghieroside A1/A2, voghieroside B1/B2, voghieroside C1/C2, voghieroside D1/D2 and voghieroside E1/E2. Adenosine and guanosine. | Antifungal activity against Sclerotium cepivorum. Antimicrobial activity. Strong inhibitory effect on human platelet aggregation generated by 2 μM ADP in both primary and secondary waves (adenosine). | [162,163,164] |
A. schoenoprasum | Whole plant, pale-purple flowers | (20S, 25S)-spirost-5-en-3β, 12β,21-triol 3-O-α-L-rhamnopyranosyl-(1→2)-β-d-glucopyranoside, (20S, 25S)-spirost-5-en-3β, 11α,21-triol 3-O-α-L-rhamnopyranosyl-(1→2)-β-d-glucopyranoside, laxogenin 3-O-α-L-rhamnopyranosyl--(1→2)-[β-d-glucopyranosyl-(1→4)]-[β-d-glucopyranoside, (25R)-5α-spirostan-3β, 11α-diol 3-O-β-d-glucopyranosyl-(1→4)]-β-d-galactopyranoside. (cyanidin 3-O-β-glucosideAII) (kaempferol 3-O-(2-O-β-glucosylFIII-β-glucosideFII)-7-O-β-glucosiduronic acid FIV) malonate AIII (AII-6→AIII-1, FIV-2→AIII-3), 1, (cyanidin 3-O-(3-O-acetyl-β-glucosideAII) (kaempferol 3-O-(2-O-β-glucosylFIII-β-glucosideFII)-7-O-β-glucosiduronic acid FIV) malonate AIII (AII-6→AIII-1, FIV-2→AIII-3), 2, and 7-O-(methyl-O-β-glucosiduronateFIV). | Cytotoxicity against HCT 116 and HT-29 human colon cancer lines. | [165,166] | |
A. minutiflorum Regel | Bulbs | Minutoside A, minutoside B, Minutoside C, alliogenin, neoagigenin | Antifungal activity. | [167] | |
A. neapolitanum | Extracts | 3-O-{[2-O-α-1-rhamnopyrnosyl-4-O-β-d-glucopyranosyl]-β-d-glucopyranoside}, isorhamnetin; 3-O-{[2-O-α-1-rhamnopyrnosyl-6-O-β-d-glucopyranosyl]-β-d-glucopyranoside}, isorhamnetin; 3-O-{[2-O-α-1-rhamnopyranosyl-4-O-β-d-glucopyranosyl]-β-d-glucopyranoside}-7-O-β-d-glucopyranoside and isorhamnetin; 3-O-{[2-O-α-1-rhamnopyranosyl-6-O-β-d-gentiobiosyl]-β-d-glucopyranoside}. | Antiplatelet aggregation activity. | [168] | |
A. tripedale | Bulbs, leaves | Iran | 6,7-dimethoxy-N-trans-caffeoyltyramine; N-trans-feruloyltyramine. (+)-S-(1-butenyl)-L-cysteine sulfoxide (homoisoalliin), S-(1-butenyl)-L-cysteine (desoxyhomoisoalliin). | NR. | [167,168] |
A. porrum L. | Bulbs | Kaempferol 3-O-[2-O-(trans-3-methoxy-4-hydroxycinnamoyl)-β-d-galactopyranosyl]-(1→4)-O-β-d-glucopyranoside; Kaempferol 3-O-[2-O-(trans-3-methoxy-4-hydroxycinnamoyl)-β-d-glucopyranosyl]-(1→6)-O-β-d-glucopyranoside. (25R)-5 α-spirostan-3 β, 6 β-diol 3-O-[O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside}; (25R)-5 α-spirostan-3 β, 6 β-diol 3-O-{O-β-d-glucopyranosyl-(1→3)-O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-galactopyranosyl-(1→4)-β-d-galactopyranoside} | Antiplatelet aggregation activity. Antifungal activity. | [169,170,171] | |
A. chinense. A. chinense G. Don | Bulbs | Chinenoside II and chinenoside III. (25 R,S)-5 α-Spirostan-3β-ol tetrasaccharide, (25R)-3 β-hydroxy-5 α-spirostan-6-one di- and tri-saccharides. Xiebai-saponin I (laxogenin 3-O-β-xylopyranosyl (1→4)-[α-arabinopyranosyl (1→6)-β-glucopyranoside), laxogenin 3-O-α-arabinopyranosyl (1→6)-β-glucopyranoside, laxogenin, isoliquiritigenin, isoliquiritigenin-4-O-glucoside, and β-sitosterol glucoside. | Inhibition of cAMP phosphodiesterase. Antitumor-promoting activity (laxogenin). | [172,173,174,175] | |
A. macrostemon. A. macrostemon Bunge | Bulbs, leaves | Japan | Macrostemonoside G (26-O-β-d-glucopyranosyl-22-hydroxy-5-β-furost-25(27)-ene-3 β,12 β,26 triol 3-O-β-d-glucopyranosyl(1-->2)-β-d-galactopyranoside) and I (26-O-β-d-glucopyranosyl-22-hydroxy-5 β-furost-25(27)-ene-12-one-3 β,26-diol 3-O-β-d-glucopyranosyl(1→2)-β-d-galactopyranoside). tigogenin-3-O-β-d-glucopyranosyl(1-->2) [β-d-glucopyranosyl(1→3)1]-β-d-glucopyranosyl(1→4)-β-d-galactopyranoside (1) and tigogenin-3-O-β-d-glucopyranosyl(1→2)[β-d-glucopyranosyl (1→3)(6-O-acetyl-β-d-glucopyranosyl)] (1→4)-β-d-galactopyranoside (2). Macrostemonoside E-(25R)-26-O-β-d-glucopyranosyl-5 α-furost-20(22)-ene-3 β,26-diol-3-O-β-d-glucopyranosyl (1→2) [β-d-glucopyranosyl (1→3)]-β-d-glucopyranosyl (1→4)-β-d-galactopyranoside; Macrostemonoside F(II)-(25R)-26-O-β-d-glucopyranosyl-5 β-furost-20(22)-ene-3 β,26-diol-3-O-β-d-glucopyranosyl (1→2)-β-d-galactoside. Allimacronoid A (1-O-(E)-feruloyl-β-d-glucopyranosyl (1-2)-[β-d-glucopyranosyl (1-6)]-β-d-glucopyranose), Allimacronoid B (1-O-(E)-feruloyl-{β-d-glucopyranosyl (1-4)-[β-d-glucopyranosyl (1-2)]}-[β-d-glucopyranosyl (1-6)]-β-d-glucopyranose) and Allimacronoid Cn1-O-(E)-feruloyl-{β-d-glucopyranosyl (1-6)-[β-d-glucopyranosyl (1-2)]}-[β-d-glucopyranosyl (1-6)]-β-d-glucopyranose. | In vitro inhibition of ADP-induced human platelet aggregation (macrostemonoside G). Inhibitory activity against rabbit platelet aggregation induced by ADP (1). | [176,177,178,179] |
A. schubertii | Bulbs | (25R and S)-5 α-spirostan-2 α,3 β,6 β-triol 3-O-β-d-glucopyranosyl-(1→2)-O-[4-O-benzoyl-β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside, (25R and S)-5 α-spirostan-2α,3β,6 β-triol 3-O-β-d-glucopyranosyl-(1→2)-O-[3-O-benzoyl-β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside, (25R and S)-5 α-spirostan-2α,3β,6 β-triol 3-O-β-d-glucopyranosyl-(1→2)-O-[4-O-(3S)-3-hydroxy-3-methylglutaroyl-β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside and 26-O-β-d-glucopyranosyl-(25R and S)-5 α-furostan-2α,3β,6β,22 zeta,26-pentol 3-O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside. | NR. | [180] | |
A. tuberosum | Seeds | Shanghai | (2α, 3β, 5α, 25S)-2,3,27-trihydroxyspirostane 3-O-α-L-rhamnopyranoyl-(1→2)-O-[α-L-rhamnopyranosyl-(1→4)]-β-d-glucopyranoside. Tuberoside J-(25R)-5 α-spirostan-2α,3 β,27-triol 3-O-α-L-rhamnopyranosyl-(1-->2)-β-d-glucopyranoside; Tuberoside K-(25R)-5α-spirostan-2α,3β 27-triol 3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-d-glucopyranoside; and Tuberoside L-27-O-β-d-glucopyranosyl-(25R)-5α-spirostan-2α,3 β,27-triol 3-O-α-d-rhamnopyranosyl-(1-->2)-[α-L-rhamnopyranosyl-(1→4)]-β-d-glucopyranoside. Tuberoside M-(25S)-5β-spirostane-β,3 β-diol 3-O-α-L-rhamnopyranosyl-(1→4)-β-d-glucopyranoside. Tuber-ceramide (N-(2′,3′-dihydroxy-tetracosenoyl)-2-amino-1,3,4-trihydroxy octadecane), and Cerebroside (N-(2′,3′-dihydrox-tetra-cosenoyl)-2-amino-1,3,4-trihydroxy octadecane). | Tuberoside M inhibits the proliferation of the human promyelocytic leukemia cell line (HL-60) | [181,182,183] |
A.albopilosum and A. ostrowskianum | Bulbs | (25 R and S)-5 α-spirostane-2α, 3 β,6 β-triol 3-O-(O-β-d-glucopyranosyl-(1→2)-O-[3-O-acetyl-β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside), (25R)-2-O-[(S)-3-hydroxy-3-methylglutaroyl]-5 α-spirostane-2α, 3β, 6β-triol 3-O-(O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1— >3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside), (22S)-cholest-5-ene-1β, β,16 β,22-tetraol 1-O-α-L-rhamnopyranoside 16-O-(O-α-L-rhamnopyranosyl-(1→3)-β-d-glucopyranoside), 1β, 3β, 16β-trihydroxycholest-5-en-22-one 1-O-aα-L-rhamnopyranoside 16-O-(O-α-L-rhamnopyranosyl-(1→3)-β-d-glucopyranoside), 1β,3β,16 bβ-trihydroxy-5 α-cholestan-22-one 1-O-α-L-rhamnopyranoside 16-O-(O-α-L-rhamnopyranosyl-(1→3)-β-d-glucopyranoside) and (22S)-cholest-5-ene-1β,3β, 16β,22-tetraol 16-O-(O-β-d-glucopyranosyl-(1→3)-β-d-glucopyranoside). | NR. | [184] | |
A.fistulosum. A.fistulosum L. | Whole plant, leaves, seeds | Iran | Fistulomidate A ((1Z,2E)-Methyl3-(3,4-dimethoxyphenyl)-N-(4-hydroxyphenethyl) acrilimidate) and Fistulomidate B ((1Z,2E)-Methyl3-(3,4-dihydroxyphenyl)-N-(4-hydroxyphenethyl)acrilimidat). Onionin A1, onionin A2, and onionin A3. Glycerol mono-(E)-8,11,12-trihydroxy-9-octadecenoate, tianshic acid, 4-(2-formyl-5-hydroxymethylpyrrol-1-yl) butyric acid, p-hydroxybenzoic acid, vanillic acid, and daucosterol. | Antibacterial and cytotoxic activity. Suppression of tumor progression in mouse ovarian cancer (onionin A1). Inhibition of the growth of Phytophtohora capsici on V8 media (glycerol mono-(E)-8,11,12-trihydroxy-9-octadecenoate and V). | [159,185,186] |
A.carolinianum DC | Bulb | Mongolia | Cinnamoylphenethylamine derivative | Weak cytotoxic activity | [187] |
A.ampeloprasum var. porrum (Leek) | Plant parts | A-β- d -glucopyranoside | Anticancer activity against MCF-7 human breast cancer cell. | [187] | |
A.ascalonicum L. | China | Ascalonicoside C-(25R)-26-O-β-d-glucopyranosyl-22-hydroxy-5α-furost-2-one-3β,5,6β, 26-tetraol-3-O-α-L-rhamnopyranosyl-(1→2)-β-d-glucopyranoside. Ascalonicoside d-(25R)-26-O-β-d-glucopyranosyl-22-methoxy-5α-furost-2-one-3β,5,6β, 26-tetraol-3-O-α-L-rhamnopyranosyl-(1→2)-β-d-glucopyranoside. (25R)-26-O-β-d-glucopyranosyl-22-hydroxy-5-ene-furostan-3β,26-diol-3-O-α-L-rhamnopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→4)-[ α-L-rhamnopyranosyl-(1→2)]-β-d-glucopyranoside. 25R)-26-O-β-d-glucopyranosyl-22-hydroxy-5-ene-furostan-3β, 26-diol-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-arabinofuranosyl-(1→4)]-β-d-glucopyranoside. | NR. | [188,189] | |
A.siculum | Bulbs | Zwanenburg, The Netherlands | (Z)-Butanethial S-oxide, (R(S),R(C),E)-S-(1-butenyl)cysteine S-oxide (homoisoalliin). | NR. | [190] |
A.chrysanthum | Barks | Guangzhou, China | Chrysanthumones A (6″,6″-dimethyl-4″,5″-dihydropyrano [2″,3″: 8,7]-6″′,6″′-dimethyl-prenyl-4″′,5″′-dihydropyrano [2″′,3″′:2′,3′]apigenin) and B ((E)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-1-enyl)-4H-chromen-4-one). | NR. | [191] |
A. L. melanocrommyum section Megaloprason. | Bulbs | Central Asia | L-(+)-S-(2-pyridyl)-cysteine sulfoxide. | NR. | [192] |
A.ampeloprasum L. | Bulbs | United States of America | Ampeloside Bs1 (apigenin 3-O-β-glucopyranosyl (1 → 3)-β-glucopyranosyl (1 → 4)-β-galactopyranoside), ampelosides Bf1 ((25R)-26-O-β-glucopyranosyl-22-hydroxy-5α-furostane-2α,3β,6β,26-tetraol-3-O-β-glucopyranosyl(1 → 3)-β-glucopyranosyl-(1 → 4)-β-galactopyranoside) and Bf2 ((25R)-26-O-β-glucopyranosyl-22-hydroxy-5α-furostane-2α,3β,6β,26-tetraol-3-O-β-glucopyranosyl(1 → 4)-β-galactopyranoside). | Weak antifungal activity by ampeloside Bs1. | [193] |
A.bakeri Reg. | Tuber | Adenosine, guanosine, and tryptophan, β-sitosterol β-d-glucoside. | Strong inhibitory effect on human platelet aggregation generated by 2 μM ADP in both primary and secondary waves (adenosine). | [162] | |
A.victorialis var. platyphyllum | Aerial parts, bulbs | Korea | Gitogenin 3-O-lycotetroside, astragalin and kaempferol 3, 4′-di-O-β-d-glucoside. | Cytotoxic activity. | [194] |
A.nutans L. | Underground plant parts | Deltoside, nolinofuroside D, 25R Δ(5)-spirostan 3β-ol-3-O-α-L-rhamnopyranosyl(1-->2)-[β-d-glucopyranosyl(1→4)]-O-β-d-galactopyranoside and 25R Δ(5)-spirostan 1 β, 3β-diol 1-O-β-d-galactopyranoside. | NR. | [195] | |
A.giganteum | Bulbs | Japan | 3-O-acetyl-(24S,25S)-5α-spirostane-2α,3β,5α,6β,24-pentol 2-O-β-d-glucopyranoside. | Inhibition of cAMP phosphodiesterase activity. | [196] |
A.hookeri Thwaites | Rhizomes | China | Di-2-propenyl trisulfide, diallyl disulfide, and dipropyl trisulfide. | Antimicrobial activity against Aspergillus fumigatus and C. albicans. | [197] |
Plant Species | Plant Part | Country | Isolated Compounds | Bioactivity | References |
---|---|---|---|---|---|
C. x amabile C. x amabile Donn ex Ker Gawl | Bulbs Stems, roots | Ecuador Brazil Thailand | Haemanthamine/crimine-type alkaloid. Lycorine-type alkaloid Galanthamine-type alkaloid. Augustine N-oxide, buphanisine N-oxide. Amabiloid A. | Anticholinesterase (anti-AChE) and antibutyrylcholinesterase (anti-BuChE) activity. | [249,250,251] |
C. defixum Ker-Gawl | Bulbs | India | Hydrazide derivative. (E)-N-[(E)-2-butenoyl]-2-butenoylhydrazide. | Anti-genotoxic activity. | [252] |
C. moorei | Bulblets | Cherylline, crinamidine, crinine, epibuphanisine, lycorine, powelline, undulatine, 1-epideacetylbowdensine, 3-O-acetylhamayne. 3-[4′-(8′-aminoethyl) phenoxy] bulbispermine, mooreine. | NR. | [253] | |
C. biflorum | Bulbs | Senegal | 5,6,7-trimethoxy-3-(4 hydroxybenzyl) chroman-4-one, 3-hydroxy-5,6,7-trimethoxy-3-(4-hydroxybenzyl) chroman-4-one, 3-hydroxy-5,6,7-trimethoxy-3-(4-methoxybenzyl) chroman-4-one, 5,6,7-trimethoxy-3-(4-methoxybenzyl) chroman-4-one, (E)-N-(4-hydroxyphenethyl)-3-(4-hydroxyphenyl) acrylamide. | Anticancer, anti-AChE, anti-glucosidase activity. | [254,255] |
C. asiaticum C. asiaticum var. sinicum C. asiaticum L. C. asiaticum var. japonicum. C. asiaticum L. var. sinicum. | Seeds, rhizome, fruits Bulbs, stems, leaves | Beijing, China, Hainan Province, Japan, Island of Jeju in Korea | Flavonoids Isopowellaminone. (2R,3S)-7-methoxyflavan-3-ol (1:), (2R,3S)-7-hydroxy-flavan-3-ol (2:), (2R,3S)-2 ′-hydroxy-7-methoxy-flavan-3-ol (3:). Norgalanthamine. Crinamine CAL-n. Crijaponine A, crijaponine B, ungeremine, lycorine, 2-O-acetyllycorine, 1,2-O-diacetyllycorine, (-)-crinine, 11-hydroxyvittatine, hamayne,(+)-epibuphanisine, crinamine, yemenine A, epinorgalanthamine. Criasiaticidine A, pratorimine, Lycorine, 4′-hyd’oxy-7-methoxyflavan. Crinamine, lycorine, norgalanthamine, epinorgalanthamine. Asiaticumines A, asiaticumines B. | Inhibitory activity against LPS-induced nitric oxide production. Anticancer activity (against cervical cancer SiHa cells). Inhibition of platelet aggregation. Promotion of hair growth through dermal papilla proliferation. Inhibition of the growth of HepG2 tumor cells. Anti-AChE activity, cytotoxic activity. Cytotoxic against Meth-A (mouse sarcoma) and Lewis lung carcinoma (mouse lung carcinoma). Inhibition of the activity of hypoxia inducible factor-1 (crinamine). Cytotoxicity. | [256,257,258,259,260,261,262,263,264,265,266] |
C. kirkii Baker | Bulbs | Noraugustamine, 4aN-dedihydronoraugustamine, 3-O-acetylsanguinine, 1,2-diacetyllycorine. | Antiparasitic activity against Trypanosoma brucei (T. brucei) rhodesiense, Trypanosoma cruzi (T. cruzi). | [267,268] | |
C. macowanii | Bulbs | Macowine, lycorine, cherylline, crinine, krepowine, powelline, buphanidrine, crinamidine, undulatine, 1-epideacetylbowdensine, 4a-dehydroxycrinamabine. | NR. | [249] | |
C. firmifolium | Leaves | Madagascar | 2-alkylquinolin-4(1H), 2-alkylquinolin-4(1H). | Antiplasmodial activity. | [269] |
C. latifolium | Bulbs Leaves | China. Hanoi, Vietnam | 4,8-dimethoxy-cripowellin C. 4,8-dimethoxy-cripowellin D, 9-methoxy-cripowellin B, 4-methoxy-8-hydroxy-cripowellin B, cripowellin C. C. latines A, C. latines B and C. latines C. 4-senecioyloxymethyl-3,4-dimethoxycoumarin, 5,6,3 ′-trihydroxy-7,8,4 ′-trimethoxyflavone. 4-methyloxysenecioyl-6,7-dimethoxycoumarin, 5,6,3′-trihydroxy-7,8,4′trimethoxyflavone. | Cytotoxic against tumor cell lines, antimicrobial activity, antioxidant activity. Inhibitory activity against human umbilical venous endothelial cells. | [270,271,272] |
C. scillifolium | Bulbs | Scillitazettine, scilli-N-desmethylpretazettine. | Mild antiplasmodial activity | [273] | |
C. zeylanicum (L) | Bulbs, leaves, flowers, fruits | Cuba Sri Lanka | Crinine, Lycorine, 11-O-acetoxyambelline, ambelline, 6-hydroxybuphanidrine, 6-ethoxybuphanidrine, 3-acetylhamayne, 6-hydroxycrinamine, hamayne, 6-methoxycrinamine. | Antiproliferative effect. | [246,274] |
C. jagus (J. Thomps) Dandy | Bulbs, leaves | Senegal Ghana | Gigantelline, gigantellinine, gigancrinine, sanguinine, cherylline, lycorine, crinine, flexinine, hippadine. Galanthamine, galanthamine N-oxide, powelline. | Anti-AChE activity, inhibitors of TcAchE, hAChE and hBChE | [275,276] |
C. abyscinicum Hochst. ExA. Rich | Bulbs | Ethiopia | 6-hydroxycrinamine, lycorine. | Antiproliferative activity against A2780 epithelial ovarian cancer and MV4-11 acute myeloid leukemia cell lines. | [277] |
C. erubescens | Above ground plant parts | Puntarenas, Costa Rica | Cripowellin A, cripowellin B, cripowellin C, cripowellin D, hippadine. | Antiplasmodial activity. | [278] |
C. yemense | Bulbs | Yemen | 6-hydroxy-2H-pyran-3-carbaldehyde. Yemenines A, B and C, 1, (+)-bulbispermine, (+)-crinamine, (+)-6-hydroxycrinamine, (-)-lycorine. | Tyrosinase inhibitor. Inhibit nitric oxide production, induce nitric oxide synthase. | [277,278,279,280] |
C. bulbispermum C. bulbispermum III | Bulbs | Egypt | 8-hydroxylycorin-7-one, 2-deoxylycorine, vittatine, 11-hydroxyvittatine, hippamine. 4-hydroxy-2′,4′-dimethoxydihydrochalcone, 4,5-methylenedioxy-4′-hydroxy-2-aldehyde [1,1′-biphenyl], hippacine, 4′-hydroxy-7-methoxyflavan-3-ol, 2(S),3′,4′-dihydroxy-7-methoxy flavan, isolarrien, isoliquiritigenin, liquiritigenin. Bulbispermine. | NR. | [281,282,283] |
C. powellii | Bulbs | Switzerland Colombia | Linoleic acid ethyl ester, alkaloid hippadine, calleryanin, 4′-hydroxy-7-methoxyflavan. Lycorine, 1-O-acetyllycorine, ismine. | AChE inhibitor (linoleic acid ethyl ester). Inhibition of topoisomerase 1 activity. | [284,285] |
C. glaucum | Bulbs | Nigeria | Hamayne, lycorine, haemanthamane, crinamine. | Choline esterase inhibitory activity. | [286] |
C. purpurascens | Leaves | Cameroon | 4,5-ethano-9,10-methlenedioxy-7-phenanthridone, 4,5-ethano-9-hydroxy-10-methoxy-7-phenanthridone, α-d-glucopyranoside. | Antibacterial activity | [287] |
Lineage | Location | Species | References |
---|---|---|---|
Clade A | Southern Africa Grassland Southeastern African temperate grasslands Grassland of the Highveld in the northern parts Subtropical Indian Ocean Coastal Belt East Africa and Angola | C. attenuatus, C. macowanii, C. epiphyticus, C. mackenii subsp. cooperi, C. huttonii, C. macmasteri, C. suaveolens, C. stenanthus var. stenanthus, C. flanaganii C. tuckii var. transvaalensis C. angustifolius, C. fergusoniae C. aureolinus, C. mackenii subsp. Mackenii, C. brachyscyphus C. breviflorus | [328] |
Clade B | Baviaanskloof Mountains and Eastern Cape (Fynbos and Albany Thicket Biomes) Semi-arid Succulent Karoo Greater Cape Region (“the Cape”) Coastal and inland mountains of the southern Cape Cape Peninsula into the Eastern Cape | C. labiatus, C. montanus C. herrei C. carneus, C. elatus, C. guthrieae, C. labiatus, C. leptosiphon, C. leucanthus, C. montanus, C. odorus C. collinus C. ventricosus | [328] |
Clade C | Albany Thicket Biome Savanna Biome Northwards from the Albany region through South Africa, Zimbabwe, Western Mozambique and East Africa into Sudan Albany Thicket and Savanna Biomes Extends beyond the Savanna Biome into the Sub-Escarpment and Highveld grasslands Fynbos Biome Southern parts of the Nama Karoo | C. flammosus, C. spiralis C. eucallus, C. galpinii C. sanguineus C. helictus C. contractus C. wellandii C. smithiae | [328] |
Plant Species | Traditional Uses | Compounds | Pharmacological Activities | References |
---|---|---|---|---|
C. obliquus | Chronic cough, headache and scrofula | 5,7-dihydroxy-6-methoxy-3-(4′-methoxybenzyl)chroman-4-one, 5,7-dihydroxy-6-methoxy-3-(4′-hydroxybenzyl)chroman-4-one | Antioxidant activity | [338] |
C. contractus | Mental illness, protective charm against evil spirits | NarciclasineNarciprimine | Anti-inflammatory activity (via inhibition of E-selectin, blockade of the expression of endothelial adhesion molecule ICAM-1)Acetylcholinesterase inhibitor | [337] |
C. breviflorus | Emesis, worm infestations, protective charm against evil spirits | haemanthamine, lycorine, crinamine hydrochloride and tazettine | Antihelminthic | [337,342] |
C. elatus | Cough, headache, labor induction | Haemanthamine, zephyranthine, galanthamine and 1,2-O-diacetylzephyranthine | Antiprotozoan activity, selective cytotoxic activity | [43,44,337] |
C. falcatus | Not known to be used by the traditional South African people | Papyramine, epipapyramine, maritidine, O-methylmaritidine and tazettine | Antibacterial activity against B. subtilis S. aureus and E. coli, mutagenicity, cytotoxic activity | [342,343,344] |
C. suaveolens | No traditional use has been reported | Captan | Mutagenicity, anti-inflammatory activity via inhibition of COX-2, fungicide | [342,344] |
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Danquah, C.A.; Minkah, P.A.B.; Agana, T.A.; Moyo, P.; Ofori, M.; Doe, P.; Rali, S.; Osei Duah Junior, I.; Amankwah, K.B.; Somuah, S.O.; et al. The Phytochemistry and Pharmacology of Tulbaghia, Allium, Crinum and Cyrtanthus: ‘Talented’ Taxa from the Amaryllidaceae. Molecules 2022, 27, 4475. https://doi.org/10.3390/molecules27144475
Danquah CA, Minkah PAB, Agana TA, Moyo P, Ofori M, Doe P, Rali S, Osei Duah Junior I, Amankwah KB, Somuah SO, et al. The Phytochemistry and Pharmacology of Tulbaghia, Allium, Crinum and Cyrtanthus: ‘Talented’ Taxa from the Amaryllidaceae. Molecules. 2022; 27(14):4475. https://doi.org/10.3390/molecules27144475
Chicago/Turabian StyleDanquah, Cynthia Amaning, Prince Amankwah Baffour Minkah, Theresa A. Agana, Phanankosi Moyo, Michael Ofori, Peace Doe, Sibusiso Rali, Isaiah Osei Duah Junior, Kofi Bonsu Amankwah, Samuel Owusu Somuah, and et al. 2022. "The Phytochemistry and Pharmacology of Tulbaghia, Allium, Crinum and Cyrtanthus: ‘Talented’ Taxa from the Amaryllidaceae" Molecules 27, no. 14: 4475. https://doi.org/10.3390/molecules27144475