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CHAPTER 5 ALKALOIDS ISOLATED from SOUTH AFRICAN MENISPERMACEAE 5.1 Introduction

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242 CHAPTER 5 ALKALOIDS ISOLATED FROM SOUTH AFRICAN MENISPERMACEAE 5.1 Introduction The history of alkaloid chemistry, in structural terms, began in 1804, when Sertürner (the Paderborn apothecary) discovered the so-called principium somniferum in opium (Trommsdorf 1805*), which he reported the following year in the Journal der Pharmacie (Sertürner 1805*). The attention of scientists, however, was aroused only twelve years later by a publication appearing in the Annalen der Physik (Sertürner 1817*; Schmitz 1983*). There, Sertürner named his principium somniferum for the first time "morphium" (after Morpheus, the son or servant of sleep and creater of dream states in Ovid; altered to "morphinium" by the French physicist Gay- Lussac). Often, a very great deal of time would pass between the isolation of an alkaloid and the determination of both its structure and absolute configuration. In the case of strychnine 138, years passed by and for morphine 150 years (Hesse 2002). Today, it is usual to determine the structure of a substance in the year of its isolation, especially when it seems to possess pharmacological properties as promising as those of strychnine and morphine. There are three main types of alkaloids: i) True alkaloids have a heterocyclic ring with nitrogen and are derived from amino acids. ii) Proto alkaloids do not have a heterocyclic ring with nitrogen, but are also derived from amino acids. iii) Pseudo alkaloids have a heterocyclic ring with nitrogen, but are not derived from amino acids (they can be derived from terpenoids or purines). In true alkaloids the basic units of biogenesis are amino acids. The non-nitrogen containing rings or side chains are derived from terpene units and/or acetate, while methionine is responsible for the addition of methyl groups to nitrogen atoms. Alkaloids are basic and form water-soluble salts. Most alkaloids are well-defined crystalline substances that react with acids to form salts. In plants they may exist in the free state, as salts or as N-oxides. The criteria currently used for 243 alkaloid classification are biogenesis, structural relationship, biological origin and spectroscopic/spectrometric properties (chromophores in UV spectroscopy, ring systems in mass spectrometry) (Hesse 2002). Based on amino acid precursor, alkaloids can be further subdivided. The principal precursors are ornithine, lysine, nicotinic acid, tyrosine, tryptophan, anthranilic acid and histidine. Ornithine gives rise to pyrrolidine and trypane alkaloids, lysine to piperidine, quinolizidine and indolizidine alkaloids and nicotinic acid to pyridine alkaloids. Tyrosine produces phenylethylamines, tetrahydroisoquinoline, benzyltetrahydroisoquinoline, phenethylisoquinoline, terpenoid tetrahydroisoquinoline and Amaryllidaceae alkaloids. Tryptophan gives rise to β-carboline, terpenoid indole, quinoline, pyrroloindole and ergot alkaloids. Anthranilic acid acts as a precursor to quinazoline, quinoline and acridine alkaloids, while histidine gives imidazole derivates (Dewick 2002). 5.1.1 Known alkaloids of the Menispermaceae Up to the end of 1996, 1 858 alkaloids were described from 244 plants of the family Menispermaceae, with 813 citations (Barbosa-Filho et al. 2000). (S)-Norcoclaurine, a benzyltetrahydroisoquinoline, was identified as a very important intermediate in the formation of almost all the alkaloids present in plants of this family (Barbosa- Filho et al. 2000). The biosynthetic pathway for the formation of (S)-norcoclaurine is as follows: Phosphoenolpyruvic acid reacts with erythrose-4-phosphate to form shikimic acid, which reacts with phosphoenolpyruvic acid, followed by a series of steps to form phenylpyruvic acid which, after reductive amination, is transformed into phenylalanine. This amino acid may then undergo decarboxylation to form phenylethylamine or deamination to form phenylacetaldehyde. These two compounds may react to form (S)-norcoclaurine (Figure 5.1). 244 O O OH PO O OH PEP OH 1 H Phosphoenolpyruvic acid NH2 HO OH + OH OH Phenylalanine PO Shikimic acid O OH HO HO Erythrose-4-phosphate NH2 HO NH HO 2, 1 Dopamine 5 O H OH HO H NH2 , 3 4 HO HO S L-Tyrosine ( )-Norcoclaurine HO 4-Hydroxyphenylacetaldehyde Figure 5.1. Biosynthetic pathway for the formation of (S)-norcoclaurine. The enzymes involved in the process are: 1, Phenolase; 2, L-Tyrosine decarboxylase; 3, L-Tyrosine transaminase; 4, p- Hydroxyphenylpyruvate decarboxylase; 5, (S)-Norcoclaurine synthase. 245 Barbosa-Filho et al. (2000) created a biosynthetic map for the alkaloids identified in the Menispermaceae. The purpose was to show a probable biosynthetic relationship between the different classes of alkaloids isolated from this family (Figure 5.2) Bisbenzylisoquinoline (604) Phenanthrene (2) Proaporphine Aporphine (303) Stephaoxocane (5) (30) Aristolochic acid (4) Tropoloneisoquinoline (9) Azafluoranthene (11) Isooxoaporphine (9) Hirsutine (5) Cohirsine (4) BIQ Protoberberine (275) (59) Benzazepine (2) Morphinan (63) Hasubanane (78) Acutunine (9) Eribidine (7) Erythrina (28) Pavine (4) Isoquinoline alkaloids (5) Phenethylcinnamide alkaloids (5) Others (4) Figure 5.2. Probable biosynthetic relationships between the different classes of alkaloids isolated from plants of the family Menispermaceae. The numbers in brackets are the numbers of alkaloids isolated in each class. (BIQ = Benzylisoquinline alkaloids) 246 5.1.2 Classification of the alkaloids of the Menispermaceae The family Menispermaceae yielded 22 different types of alkaloids (Barbosa-Filho et al. 2000). To be considered as a separate type, there must be at least two different alkaloids with the same basic skeleton. In the case where only one alkaloid has been identified, these were classified as "Others" (Barbosa-Filho et al. 2000). I - Benzylisoquinoline alkaloids 6 N 7 2 8 1 N 12 11 1-Benzylisoquinoline alkaloids 1-Benzyltetrahyroisoquinoline alkaloids Abuta, Burasaia, Caryomene, Cissampelos, Stephania Cocculus, Cyclea, Pachygone, Parabaena, Sarcopetalum, Sciadotenia, Stephania, Tiliacora, Tinospora More than 100 alkaloids in the subtype 1-benzyltetrahydroisoquinoline are distributed throughout the families Annonaceae, Berberidaceae, Hernandiaceae, Lauraceae, Magnoliaceae, Menispermaceae, Papaveraceae, Ranunculaceae and Rhamnaceae. Alkaloids of this subtype represent 4% of the total number of alkaloids isolated from the family Menispermaceae. The genera in which they are most commonly found are Stephania (18) and Tiliacora (8). In the subtype 1-benzylisoquinoline only one alkaloid (papaverine) was identified in Stephania gracilenta (Khosa et al. 1987*). The most frequently cited alkaloid of this class (I) is coclaurine in the genera Abuta (1), Caryomene (1), Cocculus (4), Cyclea (2), Pachygone (1), Sarcopetalum (1), Sciadotenia (1) and Stephania (2). Other important alkaloids are reticuline (5 citations) and oblongine (4 citations). 247 II - Bisbenzylisoquinoline alkaloids This class of alkaloid is divided into several subtypes according to the number of bonds between the two monomers, the type of bond(s) and their relative position to each other. (a) One bond Diphenylether tail to tail Diphenyl ether head to tail NH NH O NH O NH Abuta, Albertisia, Caryomene, Menispermum, Cyclea Sciadotenia (b) Two bonds Diphenyl ether head to head Diphenyl ether head to head Diphenyl ether tail to tail Phenyl-Phenyl tail to tail O O HN NH HN NH O Abuta, Albertisia, Anisocycla, Arcangelisia, Caryomene, Cissampelos, Cocculus, Curarea, Tiliacora Cyclea, Limacia, Limaciopsis, Pycnarrhena, Sciadotenia, Sinomenium, Spirospermum, Stephania, Strychnopsis, Tiliacora 248 Diphenyl ether head to tail Phenylbenzyl ether head to tail Diphenyl ether tail to head Diphenyl ether tail to head H2C O NH O NH NH O NH Chondodendron, Cissampelos, Curarea, Cyclea, Epinetrum, Limaciopsis, Sciadotenia, Cissampelos, Cyclea Sinomenium, Stephania, Synclisia (c) Three Bonds Diphenyl ether head to head Diphenyl ether head to head Phenyl ether tail to tail Phenyl-phenyl tail to tail O O HN NH HN NH O O O Albertisia, Anisocycla, Cocculus, Pachygone, Pachygone, Tiliacora Stephania, Synclisia, Triclisia 249 Diphenyl ether head to tail Phenyl ether head to tail Phenyl ether tail to head Phenyl and benzylphenyl ether tail to head O O HN HN O O NH NH O OCH2 Cyclea Cissampelos, Cyclea This type of alkaloid, together with the aporphines and protoberberines are considered good chemical markers of the family Menispermaceae. These alkaloids are also present in the families of Annonaceae, Berberidaceae, Lauraceae and Ranunculaceae and represent 40% of the total number of alkaloids isolated from plants of the Menispermaceae family. It is frequently found in Stephania (171), Cyclea (87) and Cocculus (63). III - Proaporphine alkaloids NH Abuta, Anamirta, Caryomene, Cocculus, Diploclisia, Legnephora, Limacia, Menispermum, Pachygone, Sarcopetalum, O Sciadotenia, Stephania Proaporphines represent 2% of the total alkaloids isolated from Menispermaceae, predominantly in the genera Stephania (14), Caryomene (4), Cocculus (2) and Legnephora (2). 250 IV - Aporphine alkaloids Anamirta, Anisocycla, Chasmanthera, Cissampelos, Cocculus, Coscinium, Cyclea, Dioscoreophyllum, Diploclisia, Fibraurea, NH Heptacyclum, Kolobopetalum, Legnephora, Menispermum, Pachygone, Penianthus, Pycnarrhena, Rhigiocarya, Sinomenium, Stephania, Strychnopsis, Tiliacora, Tinomiscium, Tinospora, Triclisia More than 500 compounds are distributed between the families Annonaceae, Hernandiaceae, Lauraceae, Magnoliaceae, Menispermaceae, Monimiaceae, Ranunculaceae and
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  • Natural Heritage Resources of Virginia: Rare Vascular Plants

    Natural Heritage Resources of Virginia: Rare Vascular Plants

    NATURAL HERITAGE RESOURCES OF VIRGINIA: RARE PLANTS APRIL 2009 VIRGINIA DEPARTMENT OF CONSERVATION AND RECREATION DIVISION OF NATURAL HERITAGE 217 GOVERNOR STREET, THIRD FLOOR RICHMOND, VIRGINIA 23219 (804) 786-7951 List Compiled by: John F. Townsend Staff Botanist Cover illustrations (l. to r.) of Swamp Pink (Helonias bullata), dwarf burhead (Echinodorus tenellus), and small whorled pogonia (Isotria medeoloides) by Megan Rollins This report should be cited as: Townsend, John F. 2009. Natural Heritage Resources of Virginia: Rare Plants. Natural Heritage Technical Report 09-07. Virginia Department of Conservation and Recreation, Division of Natural Heritage, Richmond, Virginia. Unpublished report. April 2009. 62 pages plus appendices. INTRODUCTION The Virginia Department of Conservation and Recreation's Division of Natural Heritage (DCR-DNH) was established to protect Virginia's Natural Heritage Resources. These Resources are defined in the Virginia Natural Area Preserves Act of 1989 (Section 10.1-209 through 217, Code of Virginia), as the habitat of rare, threatened, and endangered plant and animal species; exemplary natural communities, habitats, and ecosystems; and other natural features of the Commonwealth. DCR-DNH is the state's only comprehensive program for conservation of our natural heritage and includes an intensive statewide biological inventory, field surveys, electronic and manual database management, environmental review capabilities, and natural area protection and stewardship. Through such a comprehensive operation, the Division identifies Natural Heritage Resources which are in need of conservation attention while creating an efficient means of evaluating the impacts of economic growth. To achieve this protection, DCR-DNH maintains lists of the most significant elements of our natural diversity.