Solanaceae family

Enantioselective syntheses of (+)- and (—[-calystegines By have determined that (+)-calystegine, (lR,2S,3R,4S,5R)-l,2,3,4-tetrahydroxynortropane, is the natural molecule [89,90], while the absolute configuration of natural (—[-calystegine A3 has been established as (lR,2S,3R,5R)-l,2,3-trihydroxynortropane by the syntheses 

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Obtained as a syrup from plants of the Solanaceae family. Intensely poisonous, its action resembles that of atropine. Sedative in small doses. 

Potato type II (Potll) inhibitors are disulfide-rich peptides of approximately 50 amino acids in size. They were first discovered in leaves, seeds, and other organs of Solanaceae and are a source of much interest as plant defense proteins. Recently, Barta et analyzed expressed sequence tag (EST) and genomic data and discovered 11 genes that code for Potll inhibitors in various monocotyledonous and dicotyledonous plants. Potll inhibitors are expressed as large precursor proteins that contain up to eight sequence repeats of the inhibitor precursor. In one particularly fascinating case from the ornamental tobacco (N. data), the precursor adopts a circular permuted structure.Barta et al. observed that genes outside the Solanaceae family seem... 

Atropine-like effects - dry mouth, dilated pupils, confusion, hallucinations, memory lose Solanaceae family -jimsonweed, henbane, deadly nightshade (Atropa belladonna), angles trumpet (atropine and scopolamine) Clinical effects of many of the plants recognized since ancient times. Deaths are rare but children vulnerable. Hallucinations from muscarine and psilocybin... 

Altogether 50 different anthocyanins (Figure 10.15) have been reported to occur in the Solanaceae family, Reports on anthocyanins from the genus Solanum, including potatoes... 

Tobacco is a member of the nightshade (Solanaceae) family and its scientific name is Nicotiana tabacum. The name nicotine comes from Nicotiana after the French ambassador Jean Nicot (1530—1600). Nicot became familiar with tobacco when he was serving as ambassador to Portugal. Impressed with its use as a medicinal herb, Nicot sent seeds and cuttings back to the French Queen Catherine de Medici (1519—1589) in 1560, noting its therapeutic properties. Tobacco was called nicotiana and this was used for the scientific name. 

In contrast to TA of the Solanaceae family cocaine from Erythroxylaceae coca contains a substituted 3(1 -hydroxytropanc (3(i-tropinc, pseudotropine) skeleton (ecgonine methyl ester) (Fig. 1). 

Another fruitful means of identifying pharmacologically active natural products has been that of folk law remedies, many of which are plant products. Typical examples include alkaloids, such as atropine (from plants of the Solanaceae family, known to the ancient Greeks) and reserpine (from Rauwolfia serpentina, the snakeroot), which is popular in India as a herbal remedy for use as a tranquilizer or antihypertensive. Other chapters in the book relate to stigmines (based on phy-sostigmine, an anticholinesterase alkaloid from the Calabar bean in West Africa) that are used to treat Alzheimer s disease (Chapter 11-12), and opioid receptor ligands (based on morphine, the most important alkaloid of the opium poppy) for pain relief and as antitussives (Chapter 11-11). 

The Solanaceae family includes not only deadly nightshade (Atropa belladonna—hence atropine) plants but also potatoes and tomatoes. Parts of these plants also contain toxic alkaloids for example, you should not eat green potatoes because they contain the toxic alkaloid solanine. 

The acid fragmentation of suitably substituted bicyclo[2.2.2]octanes to cyclohexenones and subsequent ring closure to spirovetivanes via ir-cation cyclization has been used by Murai for a highly stereoselective isolubimin (56) synthesis. (56) has been considered to play an important role in the bio-genetic pathway of various spirovetivane phytoalexins in the Solanaceae family. Treatment of methyl... 

Pepper plants have been used for years as herbal remedies for pain. The therapeutically useful pepper plants are members of the Solanaceae family. There are two primary species whose dried fruit is commonly used Capsicum fmtescens and C. annum. The actual active ingredient, capsaicin, is extracted from an oleoresin that represents up to 1.5% of the plant. Two major components in the oleoresin (among several) are capsaicin and 6.7-dihydrocapsaicin. Volatile oils and vitamins A and C occur in large quantities. The amount of ascorbic acid in the capsaicin oleoresin is reportedly 4 to 6 times that in an orange. ... 

Atropine is the racemic mixture of l- and o-hyoscya-mine and possesses 50% of the antimuscarinic potency of L-hyoscyamine. Atropine is derived from components of the Belladonna plant and is also present in other plants from the Solanaceae family. Women in ancient times often dripped the plant s juices into their eyes, causing mydriasis and thereby enhancing their beauty. In Italian, Belladonna translates to beautiful lady . In the United States, the atropine autoinjector has been in use since 1973 for the treatment of exposures to chemical warfare nerve agents and insecticides. 

The cDNA from N. plumbaginifolia was used to isolate cDNAs encoding ZE from pepper (Capsicum annuum L. cv. Yolo Wonder) and from a wilt-related tomato (Lycopersicon esculentum Mill.) (Bouvieret al., 1996, Burbidge et al., 1997). All three are members of the Solanaceae family. The N. plumbaginifolia ZE encodes a polypeptide of 663 amino acids with a mature protein estimated at 613 amino acids. As already noted, unlike the de-epoxidase, the native epoxidase has not been purified and therefore, the N-terminal amino acid has not been identified directly. The proposed N-terminal amino acid is based on a... 

Plants in the Solanaceae family produce a variety of alkaloids, some of them having a considerable therapeutic importance. One such group of alkaloids possesses a tropane nucleus. Tropane alkaloids are structurally related natural products having in common the azabicyclo[3.2.1]octane structure and therefore the systematic name for tropane is 8-methyl-8 azabicyclo[3.2.1]octane (Fig. 1). The majority of these alkaloids are esters between organic acids and hydroxytropanes. 3a-Hydroxytropane, called tropine, is the amino alcohol most frequently encountered. In addition, its 3 (3-isomer (pseudotropine), the di- (3,6- 3,7- or 6,7-) and trihydroxylated... 

Despite the fact that a large number of tropanes is known, pharmacologically important alkaloids in which the nitrogenous base is esterified with tropic acid (or a derivative), are apparently unique in the Solanaceae family [4]. 

Hygrine-type alkaloids are very often detected in members of the Solanaceae family which contain tropane alkaloids. In particular, cuscohygrine is present in nearly all cases. In a similar way but in a smaller number of genera, hygrine is distributed in plants which contain tropane alkaloids, as for example in the Erythroxylum species (Erythroxylaceae). 

Tropane alkaloids mainly occur in the Solanaceae family but are also found in other families such as Convolvulaceae, Erythroxylaceae, Proteaceae and Rhizophoraceae. Less frequently, tropane alkaloids have been mentioned in the Euphorbiaceae, Brassicaceae and Olacaceae families which show no taxonomic relationships with Solanaceae. In several species of Erythroxylum, the tropane alkaloids are characterized by a 3 3-hydroxy function and a carboxyl group at C-2 of the tropane nucleus. The most famous representant of this group is cocaine (Fig. 2). In Table 1 the distribution of tropane alkaloids in the plant kingdom is indicated. 

Solanaceae comprises 2666 species in some 96 genera of herbs, shrubs and a few trees [6]. These plants can be found around the world except in the arctic regions. However, the largest areas of distribution are in South and Central America along the Pacific Coast, where 60 genera have been identified. The Solanaceae family is of great economical importance for its... 

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