The Legume botanical family Fabaceae

Alkaloids derived from L-ornithine, L-lysine, and L-trypthophan occur in the Legume plant family (Fabaceae Juss.) (Table 9). This plant family is the third largest botanical family, with 650 genera and 18000 species in the humid tropics, sub-tropics, temperate and sub-arctic zones around the Globe118. L-ornithine-derived alkaloids such as senecionine are present in the genus Crota (Crotalaria L.).

The most typical alkaloids for this botanical family are L-lysine (Figure 16) derived alkaloids, such as lupinine, sparteine, lupanine, angustifoline, epilupinine, anagyrine and so on. Lysine alkaloids occur in many species belonging to the legume family. They are quinolizdine alkaloids occurring in the large and very diverse genus Lupine (Lupinus L.) (Figure 17), and in the genus of Broom plants (Cytisus L.). Both the genus Swainsona (Swain-sona L.) and the genus of Blackbean plants (Castanospermum L.) contain swainsonine and castanospermine. Przybylak et al.119 have detected 46 compounds from 6 Mexican lupin species (Lupinus rotundiflorus, Lupinus montanus, Lupinus mexicanus, Lupinus elegans, Lupinus madrensis, Lupinus exaltatus). From among 46 detected compounds it was possible to identify unambiguously 24 of them. Most of the identified alkaloids are from lupanine group:

Botanical Forms and Parts

Characteristics

Botanical forms

Some typical genera

Herbs

Shrubs

Lianes

Vines

Trees

Acacia

Adesmia

Aeschynomene

Albizia

Arachis

Astragalus

Baptisia

Bauhinia

Caesalpinia

Calliandra

Cassia

Cercis

Chamaecrista

Crotalaria

Dalbergia

Dalea

Delonix

Desmodium

Erythrina

Gleditsia

Glycine

Indigofera

Inga

Lathyrus

Leucaena

Lonchocarpus

Lotus

Lupinus

Meliotus

Milletia

Mimosa

Parkia

Parkinsonia

Phaseolus

Pisum

Pithecellobium

Robinia

Rhynchosia

Senna

Swartzia

Botanical Forms and Parts Characteristics

Tamarindus

Tephrosia

Trifolium

Vicia

Wisteria

Special characteristic Often twining or climbing

Hairs

Leaves Alternate

Stipulate

Flowers Regular or irregular

Usually bisexual Fruits A legume

Seeds Big or small seed coo"

ch2 ch,

nh2 ^nh

L-lysine

Figure 16. L-lysine is a precursor of piperidine, quinolizidine and indolizidine alkaloids.

sparteine, ammodendrine, epiaphyllidine, epiaphylline, tetrahydrorhombifo-line, 17-oxosperteine, 5,6-dehydro-a-isolupanine, angustifoline, a-isolupanine, aphyllidine, 5,6-dehydrolupanine, lupanine, aphylline, 11,12-dehydrolupanine, dehydrooxosparteine, 3^-hydroxylupanine, multiflorine, 17-oxolupanine, 13a-hydroxylupanine, 3^, 13a-dihydroxylupanine, 13a-angeloylolupanine, 13 a-tigloyloxylupanine and 4^-tigloyloxylupanine. Matrine has been isolated from Sophora subprostata Chun et T. Chen149. Moreover, in plants belonging to the Legume family (Fabaceae L.) alkaloids derived from L-tryptophan also occur. Eserine, eseramine, physovenine and geneserine are all examples of these kind of alkaloids, which occur, for example, in the Calabar bean (Physostigma venenosum L.). Erysovine and wrythraline are high toxic alkaloids in Erythrina lysistemon. Lou et al.130 have isolated two alkaloids, 2-methoxyl-3-(3-indolyl)-propionic acid and 2-hydroxyl-3-[3-(1-N-methyl)-indolyl] propionic acid, in

Calabar Bean

Figure 17. (a) Structure of the seed testa of the Washington lupine (Lupinus polyphyllus Lindl.). Transmission electron microscope (TEM) research proved large structural diversity inside both the genus Lupinus L. and the species. The picture shows exotesta (exo), mesotesta (meso) and endotesta (endo), cotyledon (C), the parts which differ in the species and varieties Lupinus spp. In the testa and part of the storage cells, alkaloids are present; (b) Alkaloidal Lupinus polyphyllus Lindl. in flowering stage.

Figure 17. (a) Structure of the seed testa of the Washington lupine (Lupinus polyphyllus Lindl.). Transmission electron microscope (TEM) research proved large structural diversity inside both the genus Lupinus L. and the species. The picture shows exotesta (exo), mesotesta (meso) and endotesta (endo), cotyledon (C), the parts which differ in the species and varieties Lupinus spp. In the testa and part of the storage cells, alkaloids are present; (b) Alkaloidal Lupinus polyphyllus Lindl. in flowering stage.

peanut skins (Arachis hypogaea L.). These alkaloids had not previously been found in natural sources130. Moreover, Wanjala et al.138 have isolated and identified several new alkaloids in Erythrina latissim, widespread in Botswana, Zimbabwe and South Africa. One alkaloid named (+)-erysotrine shows bioimpact as an antimicrobial agent. Moreover, Tanaka et al.150 have reported on a new alkaloid in Erythrina poeppigiana, a plant found in central and South America. This alkaloid, 8-oxo-a-erythroidine epoxine, is similar to other alkaloids previously found in this species, such as erysodine, erysovine, a-erythroidine, ^-erythroidine and dihydro-^-erythroidine151152. Recently, from the flowers of broad beans (Vicia faba L.) N-[(3R, 7R)-(-)-jasmonoyl]-(S)-dopa and N-[(3R,7R)-(-)-jasmonoyl]-dopamine were isolated by Kramell et al.153. These alkaloids are tyrosine-derived compounds. All alkaloids occurring in Fabaceae have both biological and ecological significance.

The occurrence of some important alkaloids in nature is shown in Table 10.

Table 10 Occurrence of some important alkaloids in the nature

Precursor Compound of Alkaloid Derivation

Occurrence in Nature

Family

Species

Alkaloids

L-ornithine-derived alkaloids

Solanaceae

Atropa belladonna

Datura innoxia Datura stramonium Datura metel Datura sanguine Duboisia

As Atropa As Atropa As Atropa As Atropa As Atropa myoporoides Hyoscyamus niger Hyoscyamus muticus Mandragora

As Atropa As Atropa As Atropa officinarum Scopolia carniolica Withana somnifera

As Atropa

Withasomnine

Cinnamylcocaine a-truxilline

Truxilline

Methylecgonine

Tropine

Hygrine

Hygroline

Cuscohygrine

Erythroxylaceae Erythroxylum coca

Erythroxylum truxilense

34

Alkaloids

- Secrets of Life

Table 10

(Continued)

Precursor Compound of

Occurrence in Nature

Alkaloid Derivation

Family

Species

Alkaloids

Boraginaceae

Heliotropium indicum

Indicine-N-oxide

Cynoglossum spp.

Indicine-N-oxide

Symphytum officinale

Acetyl-intermedine

Acetyl-lycopsamine

Asteraceae

Senecio vulgaris

Senecionine

Senecio jacobaea

Senecionine

Fabaceae

Crotalaria spp.

Senecionine

Capparidaceae

Boscia angustifolia

Stachydrine

4 -hydroxystachydrine

L-lysine derived

Punicaceae

Punica granatum

Pelletierine

alkaloids

Pseudopelletierine

Methylpelletierine

Anaferine

Crassulaceae

Lobelia inflata

Obeline

Lobelanine

Sedum acre

Sedamine

Piperaceae

Piper nigrum

Piperine

Piperidine

Fabaceae

Baptisia alba

Anagyrine

Cytisine

Sparteine

Thermopsine

Lupinus albus

Albine

Angustifoline

Lupanine

Sparteine

Lupinus luteus

Lupinine

Sparteine

Lupinus polyphyllus

Lupanine

Lupinus angustifolius

Angustifoline

Lupinus hispanicus

Lupinine

Epilupinine

Lupinus latifolius

Anagiryne

Cytisus scoparius

Sparteine

Swainsona canescens

Swainsonine

Castanospermum

Castanospermine

australe

Definition, Typology and Occurrence of Alkaloids

35

Table 10

(Continued)

Precursor Compound

Occurrence in Nature

of Alkaloid Derivation

Family

Species

Alkaloids

L-tyrosine derived Graminae

Hordeum vulgare

Hordenine

alkaloids

Tyramine

Cactaceae

Lophophora williamsii

Mescaline

Anhalamine

Anhalonine

Anhalonidine

Papaveraceae

Corydalis spp.

Salsolinol

Menispermaceae

Chondrodendron

Curare

tomentosum

Tubocurarine

Cissampelos pereira

Fangchinoline

Cyclea barbata

Fangchinoline

Cyclea peltata

Fangchinoline

Stephania dinklagei

N -methyllirio

dendronine

2-O-N-dimethyl

liriodendronine

Dicentrinone

Corydine

Aloe-emodin

Stephania tetrandra

Tetrandrine

Stephanine

Fangchinoline

Stephania

Fangchinoline

harnandifolica

Triclisia subcordata

Fangchinoline

Loganiaceae

Strychnos toxifera

Tubocurarine

Papaveraceae

Papaver somniferum

Morphine

Codeine

Thebaine

Papaverine

Narcotine

Narceine

Isoboldine

Berberidaceae

Berberis spp.

Berberine

Berbamine

Hydroxyacanthin

Glaucine

Mahonia spp.

Berberine

Nandina domestica

(+)-nantenine

Precursor Compound of Alkaloid Derivation

Occurrence in Nature

Family

Species

Alkaloids

Ranunculaceae

Fumariaceae

Liliaceae

Rubiaceae

Amaryllidaceae

Hydrastis canadiensis Thalictrum orientale Corydalis spp.

Corydalis flabellate

Dicentra spp.

Kreysigia multiflora

Colchicum autumnale

Cephaelis ipecacuanha

Mitragyna speciosa Leucojum vernum

Lycorus radiata

Galanthus spp.

Galanthus plicatus ssp.

Pancratium sickenbergeri

Berberine

Hydrastine

Fangchinoline

Fuzitine

Bicuculline

Metiodine

Spallidamine

Sanguidimerine

Oxosanguinarine

Bicuculline

Metiodine

Autumnaline

Floramultine

Kreysigine

Colchicine

Emetine Cephaeline Secologanin Ipecoside

Mitragynine

Lycorine

Homolycorine

2-O-acetyllycorine

Leucovernine

Acetylleucoverine

N-demethylgalanthamine

Hippeasterine

9-O-demethylhomolycorine 5 a-hydroxyhomolycorine 11-hydroxyvittatine

Lycorine

Galanthamine

Galanthindole

Hippadine

Trispheridine

Pseudolycorine

Haemanthidine

Norgalanthamine

Haemanthamine

Table 10 (Continued)

Precursor Compound

Occurrence in Nature

of Alkaloid Derivation

Family

Species

Alkaloids

Vittatine

Pancracine

Lycorine

Zephyranthes citrina

Galanthine

Haemanthamine

Lycorine

Lycorenine

Oxomaritidine

Martidine

Vittatine

L-tryptophan-derived Agaricacea

Psilocybe semilanceata

Psilocin

alkaloids

Psylocybin

Cynocybe spp.

Psilocin

Psilocybin

Panaeolus spp.

Psilocin

Psylocybin

Stropharia spp.

Psilocin

Psilocybin

Graminae

Hordeum vulgare

Gramine

Secale cereale (with

Ergotamine

C. purpurea)

Triticum aestivum (with

Ergotamine

C. purpurea)

Triticale (with

Ergotamine

C. purpurea)

Elaeagnaceae

Elaeagnus angustifolia

Elaeagnine

Zygophyllaceae

Peganum harmala

Harman, harmine

Rubiaceae

Pausinystalia yohimbe

Yohimbine

Ophiorrhiza mungos

Camptothecin

Apocynaceae

Alstonia macrophylla

Talcarpine

Pleiocarpamine

Alstoumerine

2-O-epiantirhine

Alstonerine

Alstophyline

Macralstonine

Alstomacrophyline

Villalstonine

Alstomacroline

Macrocarpamine

Precursor Compound Occurrence in Nature of Alkaloid Derivation

Family Species Alkaloids

Alstonia scholaris

Menilamine

Aspidosperma

Fendlerine

megalocarpon

Aspidoalbine

Aspidolimidin

Rauvolia capra

Quinine

Rauvolfia serpentina

Reserpine

Rescinnamine

Ajmalicine

Rauvolfia canescens

Reserpine

Rescinnamine

Deserpine

Rauvolfia vormitoria

Reserpine

Rescinnamine

Catharanthus roseus

Ajmalicine

Catharanthine

Vindoline

Vinblastine

Vincristine

Vindesine

Alioline

Ochrosia elliptica

Ellipticine

Ervatmia heyneana

Camptothecin

Loganiaceae

Strychnos icaja

Sungucine

Isosungucine

Strychnos nux-vomica

Strychnine

Brucine

Strychnos toxifera

Curare

C-toxiferine

Alcuronium

Strychnos

Isostrychnopentamine

usambarensis

Poaceae

Arundo donax

Arundamine

Arundacine

Rubiaceae

Cinchona officinalis

Quinine

Quininidine

Cinchonine

Cinchonidine

Cinchona succirubra

Quinine

Cinchonidine

Quinidine

Cinchona calisaya

Quinine

Cinchonidine

Quinidine

Precursor Compound of Alkaloid Derivation

Occurrence in Nature

Family

Species

Alkaloids

Corynanthe pachyceras

Ophiorrhiza mungos Sterculiaceae Waltheria douradinha Nyssaceae Camptotheca acuminata Icacinaceae Nothapodytes foetida

Merilliodendron megacarpum Pyrrenacantha klaineana Fabaceae Arachis hypogaea

Physostigma venenosum

Erythrina lysistemon

Erythrina latissima Erythrina poeppigiana

Convolvulaceae Ipomea violacea

Rivea corymbosa

Asteraceae

Centaurea schischkinii

Corynanthine a-yohimbine

Dihydrocorynantheine

Corynantheine

Corynantheidin

Camptothecin

Waltherione-A

Camptothecin

Camptothecin Camptothecin

Camptothecin

indolyl)-propionic acid

methyl)-indolyl]propionic acid

Eserine

Eseramine

Physovenine

Geneserine

Erysovi ne

Erythraline

(+)-erysotrine

8-oxo-a-erythroidine-

epoxine

Erysovine a-erythroidine

ß-erythroidine

Dihydro-ß-erythroidine

Ergoline

Ergotamine

Ergine

Ergoline

Ergotamine

Ergine

Afzelin

Apigenin

Arctigenin

Astragalin

Schischkinin

Precursor Compound of Alkaloid Derivation

Occurrence in Nature

Family

Species

Alkaloids

L-histidine-derived alkaloids

Anthranilic acid-derived alkaloids

Nicotinic acid-derived alkaloids

Acetate-derived alkaloids

Phenylalanine-derived alkaloids

Cactaceae Dolichothele sphaerica

Rutaceae Pilocarpus microphyllus

Pilocarpus jaborandi

Zygophyllaceae Peganum harmala Acanthaceae Justicia adhatoda

Rutaceae

Solanaceae

Discoreaceae

Euphorbiaceae

Palmae

Umbelliferae Pinaceae

Dictamus albus

Helietta longifoliata

Skimmia japónica

Acronychia baueri Melicope fareana Melicope semecarpifolia Ruta graveolens

Nicotiana tabacum

Discorea dregeana Ricinus communis Areca catechu

Conium maculatum Pinus spp.

Zygophyllaceae Nitraria komarovii

Ephedraceae

Nitraria sibirica

Ephedra intermedia

Ephedra geriardiana

Dolichotheline

Pilocarpine Pilosine Pilocarpine Pilosine

Harmin Vaccine Dictamnine Skimmianine

Maculosine

Helietidine

Flindersine

Kokusaginine

Dictamnine Skimmianine

Acronycine

Melicopicine

Melicarpine

Semecarpine Rutacridone

Anabasine

Discorine

Ricinine

Arecoline

Pyridine

Coniine Pinidine Komavine Acetylkomavine

Dihydroschoberine Nitrabirine N-oxide

Ephedrine

Cathinone

Cathine

Ephedrine

Cathinone

Cathine

Precursor Compound

Occurrence in Nature

of Alkaloid Derivation

Family

Species

Alkaloids

Ephedra major

Ephedrine

Cathinone

Cathine

Celastraceae

Catha edulis

Norpseudoephedrine

Solanaceae

Capsicum annuum

Capsaicin

Terpenoid alkaloids

Apocynaceae

Skytanthus acutus

ß-skytanthin

Actinidiaceae

Actinida polygama

Actinidine

Celastraceae

Tripterygium wilfordii

Dihydroagarofuran

Gentianaceae

Gentiana lutea

Gentiopicroside

Ranunculaceae

Aconitum arcuatum

Arcutin

Aconitum coreanum

Acorone

Accoridine

Corypidine

Coryphine

Tangutisine

Aconitum karacolicum

12-acetylnepelline

Cammaconine

Karacoline

Karakanine

Nepelline

Songorine

Aconitum napellus

Aconitine

Aconitum sinomontanum

Sinomontanine

Aconitum vulparia

Aconitine

Delphinium berbeyi

Methyllycaconitine

Barbine

Delphinium corymbosum

Delcorine

Delsonine

Delphinium occidentale

Methyllycaconitine

Barbine

Delphinium glaucescens

Methyllycaconitine

Barbine

Delphinium poltoratskii

Ajacine

Anthranoyllycoctonine

Candelphine

Delphyrine

Delpoline

Delsonine

Karacoline

Lycococtine

Precursor Compound

Occurrence in Nature

of Alkaloid Derivation

Family

Species

Alkaloids

Steroid alkaloids Solanaceae Liliaceae

Solanum tuberosum Lycopersicon esculentum Veratrum album

Solanidine

Tomatine

Jervine

Cyclopamine

Cycloposine

Protoveratrine A

Protoveratrine B

Veratrum lobelianum Veratrum californicum

O-acetylfervine

Jervine Cyclopamin Cycloposine Protoveratrine A Protoveratrine B

Veratrum viride

Jervine Cyclopamin Cycloposine Protoveratrine A Protoveratrine B

Apocynaceae

Holarrhena floribunda Holarrhena antidysenterica

Holaphyllamin Conessine

Purine alkaloids Rubiaceae

Theophylline

Theobromine

Theophylline

Theobromine

Theophylline

Theobromine

Theaceae

Theophylline

Theobromine

Aquifoliaceae

Ilex paraguensis

Caffeine Theobromine

Ilex cassine Ilex vormitoria

Caffeine

Theobromine

Theophylline

Caffeine

Theobromine

Theophylline

Precursor Compound of Alkaloid Derivation

Occurrence in Nature

Family

Species

Alkaloids

Moss alkaloids

Sapinidaceae Paullinia cupana

Sterculiaceae Cola nitida

Cola acuminata Theobroma cacao

Lycopodiaceae Lycopodium annotinum

Lycopodium complanatum Lycopodium cernuum Huperzia serrata

Fungus alkaloids

Bacter alkaloids

Animal alkaloids

Bryozoa

Saxidomus Salamandra

Aspergillus terreus

Rhizopus, Penicillium, Claviceps purpurea (with Secale cereale)

Pseudomonas tabaci Pseudomonas aeruginosa

Flustra foliacea

Saxidomus giganteus Salamandra maculosa

Salamandra samandarine

Guaranine

Theophylline

Theobromine

Caffeine

Theobromine

Caffeine

Theobromine

Theobromine

Caffeine

Annotinine

Lycodine

Lycopodine

Cernuine Huperzine A Huperzine J Huperzine K Huperzine L Phlegmariurine

Asterrelenin

Terretonin

Territrem A

Territrem B

Chanoclavine

Ergoline

Ergotamine

Tabtoxin Pyocyanine

Deformylflustrabromin

Lustrabromine

Flustramine

Saxitoxin

Tetrodotoxin

Samandarine

Samandarone

Samandaridine

Cycloneosamandaridine

Cycloneosamandione

Samandenone

Table 10 (Continued)

Precursor Compound of Alkaloid Derivation

Occurrence in Nature

Family

Occurrence in Nature

Dendrobatidae

Rhinotermitidae

Coccinellidae

Staphylinidae

Species

Alkaloids

Phyllobates aurotaenia

Cardiotoxin

Neurotoxin

Batrachotoxin

Homobatrachotoxin

Dendrobates

Histrionicotoxin

histrionicum

Dihydroisohistrionico

toxin

Gephyrotoxin

Dendrobates pumilio

Pumiliotoxin

Pumiolotoxin A

Pumiliotoxin B

Pseudophryne coriacea

Pseudophrynaminol

Castor fiberei

Castoramine

Moschus moschiferus

Muscopyridine

Solenopsis invicta

Cassine

Dontomachus hastatus

Dialkylpyrazine

Ontomachus brunneus

Trialkylpyrazine

Reticuliterms flavipes

Norharman

Ticulitermes virginica

Norharmane

Glomeris marginata

Glomerin

Homoglomerin

Polyzonium rosalbum

Polyzonimine

Adalia bipunctata

Adaline

Coccinella

Coccinelline

septempunctata

Podamine

Pilachna varivestis

Epilachnene

Podamia convergens

Convergine

Podamine

Myrrha octodecimguttata

Myrrhine

Propeleine

Propylea

Propyleine

quatuordecimpunctata

Chilocorus cacti

Stenusine

Paederus fuscipes

(+)-pederin

Mammals

Mymonoptera

Formicidae

Rhinotermitidae

Diploda

Coleoptera

Coccinellidae

Staphylinidae

Sources: Refs [7, 23, 2B, 31, 32, 33, 3S, 36, 37, 3B, 39, 41, 42, 43, 44, 4S, 47, 4B, 49, SC, S1, S2, S3, SS, S6, 62, 64, 7S, BS, 12C, 121, 122, 123, 124, 12S, 126, 127, 12B, 129, 13C, 131, 132, 133, 134, 13S, 136, 137, 13B,

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  • LAURA BRUCE
    Why is alkaloid present in family fabacea?
    2 years ago

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