Solamargine

Last updated
Solamargine
Solamargine.svg
Names
IUPAC name
(22R,25R)-Spirosol-5-en-3β-yl α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranoside
Systematic IUPAC name
(2S,2′S,3R,3′R,4R,4′R,5R,5′R,6S,6′S)-2,2′-{[(2R,3S,4S,5R,6R)-4-Hydroxy-2-(hydroxymethyl)-6-{[(2S,2′R,4aR,4bS,5′R,6aS,6bR,7S,9aS,10aS,10bS)-4a,5′,6a,7-tetramethyl-1,2,3,4,4a,4b,5,6,6a,6b,7,9a,10,10a,10b,11-hexadecahydrospiro[naptho[2′,1′:4,5]indeno[2,1-b]furan-8,2′-piperidin]-2-yl]oxy}oxane-3,5-diyl]bis(oxy)}bis(6-methyloxane-3,4,5-triol)
Other names
Solamargin; δ-Solanigrine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C45H73NO15/c1-19-9-14-45(46-17-19)20(2)30-28(61-45)16-27-25-8-7-23-15-24(10-12-43(23,5)26(25)11-13-44(27,30)6)57-42-39(60-41-36(53)34(51)32(49)22(4)56-41)37(54)38(29(18-47)58-42)59-40-35(52)33(50)31(48)21(3)55-40/h7,19-22,24-42,46-54H,8-18H2,1-6H3/t19-,20+,21+,22+,24+,25-,26+,27+,28+,29-,30+,31+,32+,33-,34-,35-,36-,37+,38-,39-,40+,41+,42-,43+,44+,45-/m1/s1 Yes check.svgY
    Key: MBWUSSKCCUMJHO-ZGXDEBHDSA-N Yes check.svgY
  • InChI=1/C45H73NO15/c1-19-9-14-45(46-17-19)20(2)30-28(61-45)16-27-25-8-7-23-15-24(10-12-43(23,5)26(25)11-13-44(27,30)6)57-42-39(60-41-36(53)34(51)32(49)22(4)56-41)37(54)38(29(18-47)58-42)59-40-35(52)33(50)31(48)21(3)55-40/h7,19-22,24-42,46-54H,8-18H2,1-6H3/t19-,20+,21+,22+,24+,25-,26+,27+,28+,29-,30+,31+,32+,33-,34-,35-,36-,37+,38-,39-,40+,41+,42-,43+,44+,45-/m1/s1
    Key: MBWUSSKCCUMJHO-ZGXDEBHDBL
  • O([C@H]8[C@H](O[C@@H]5C/C4=C/C[C@H]3[C@@H]6C[C@@H]2O[C@@]1(NC[C@H](C)CC1)[C@@H](C)[C@@H]2[C@@]6(C)CC[C@@H]3[C@@]4(C)CC5)O[C@H](CO)[C@@H](O[C@@H]7O[C@@H](C)[C@H](O)[C@@H](O)[C@H]7O)[C@@H]8O)[C@@H]9O[C@H]([C@H](O)[C@@H](O)[C@H]9O)C
Properties
C45H73NO15
Molar mass 868.071 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Solamargine is a cytotoxic chemical compound that occurs in plants of the family Solanaceae, such as potatoes, tomatoes, and eggplants. [1] [2] It has been also isolated from Solanum nigrum fungal endophyte Aspergillus flavus . [3] It is a glycoalkaloid derived from the steroidal alkaloid solasodine.

Contents

Solamargine was one component of the unsuccessful experimental cancer drug candidate Coramsine.

See also

Related Research Articles

<span class="mw-page-title-main">Endophyte</span>

An endophyte is an endosymbiont, often a bacterium or fungus, that lives within a plant for at least part of its life cycle without causing apparent disease. Endophytes are ubiquitous and have been found in all species of plants studied to date; however, most of the endophyte/plant relationships are not well understood. Some endophytes may enhance host growth and nutrient acquisition and improve the plant's ability to tolerate abiotic stresses, such as drought, and decrease biotic stresses by enhancing plant resistance to insects, pathogens and herbivores. Although endophytic bacteria and fungi are frequently studied, endophytic archaea are increasingly being considered for their role in plant growth promotion as part of the core microbiome of a plant.

<span class="mw-page-title-main">Solanine</span> Glycoalkaloid poison found in the nightshade family of plants

Solanine is a glycoalkaloid poison found in species of the nightshade family within the genus Solanum, such as the potato, the tomato, and the eggplant. It can occur naturally in any part of the plant, including the leaves, fruit, and tubers. Solanine has pesticidal properties, and it is one of the plant's natural defenses. Solanine was first isolated in 1820 from the berries of the European black nightshade, after which it was named. It belongs to the chemical family of saponins.

<i>Solanum lycocarpum</i> Species of flowering plant

Solanum lycocarpum, or wolf apple, is common in the Brazilian savanna, the Cerrado ecoregion. The plant is called lobeira or fruta-do-lobo in Portuguese.

<i>Solanum americanum</i> Species of flowering plant in the nightshade family Solanaceae

Solanum americanum, commonly known as American black nightshade, small-flowered nightshade or glossy nightshade, is a herbaceous flowering plant of wide though uncertain native range. The certain native range encompasses the tropics and subtropics of the Americas, Melanesia, New Guinea, and Australia.

<i>Solanum nigrum</i> Species of flowering plant in the nightshade family Solanaceae

Solanum nigrum, the European black nightshade or simply black nightshade or blackberry nightshade, is a species of flowering plant in the family Solanaceae, native to Eurasia and introduced in the Americas, Australasia, and South Africa. Ripe berries and cooked leaves of edible strains are used as food in some locales, and plant parts are used as a traditional medicine. Some other species may also be referred to as "black nightshade".

Coramsine (SBP002) was an experimental cancer drug that was evaluated in preliminary clinical trials, but was abandoned by Solbec Pharmaceuticals Ltd after the results were insufficient for them to raise investment capital to continue its development.

<i>Epichloë</i> Genus of fungi

Epichloë is a genus of ascomycete fungi forming an endophytic symbiosis with grasses. Grass choke disease is a symptom in grasses induced by some Epichloë species, which form spore-bearing mats (stromata) on tillers and suppress the development of their host plant's inflorescence. For most of their life cycle however, Epichloë grow in the intercellular space of stems, leaves, inflorescences, and seeds of the grass plant without incurring symptoms of disease. In fact, they provide several benefits to their host, including the production of different herbivore-deterring alkaloids, increased stress resistance, and growth promotion.

<span class="mw-page-title-main">Fungus</span> Biological kingdom, separate from plants and animals

A fungus is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and molds, as well as the more familiar mushrooms. These organisms are classified as one of the traditional eukaryotic kingdoms, along with Animalia, Plantae and either Protista or Protozoa and Chromista.

<span class="mw-page-title-main">Tomatine</span> Chemical compound

Tomatine is a glycoalkaloid, found in the stems and leaves of tomato plants, and in the fruits at much lower concentrations. Chemically pure tomatine is a white crystalline solid at standard temperature and pressure.

<span class="mw-page-title-main">Loline alkaloid</span> Class of chemical compounds

A loline alkaloid is a member of the 1-aminopyrrolizidines, which are bioactive natural products with several distinct biological and chemical features. The lolines are insecticidal and insect-deterrent compounds that are produced in grasses infected by endophytic fungal symbionts of the genus Epichloë. Lolines increase resistance of endophyte-infected grasses to insect herbivores, and may also protect the infected plants from environmental stresses such as drought and spatial competition. They are alkaloids, organic compounds containing basic nitrogen atoms. The basic chemical structure of the lolines comprises a saturated pyrrolizidine ring, a primary amine at the C-1 carbon, and an internal ether bridge—a hallmark feature of the lolines, which is uncommon in organic compounds—joining two distant ring carbons. Different substituents at the C-1 amine, such as methyl, formyl, and acetyl groups, yield loline species that have variable bioactivity against insects. Besides endophyte–grass symbionts, loline alkaloids have also been identified in some other plant species; namely, Adenocarpus species and Argyreia mollis.

<span class="mw-page-title-main">Solasodine</span> Chemical compound

Solasodine is a poisonous alkaloid chemical compound that occurs in plants of the family Solanaceae such as potatoes and tomatoes. Solasonine and solamargine are glycoalkaloid derivatives of solasodine. Solasodine is teratogenic to hamster fetuses in a dose of 1200 to 1600 mg/kg. Literature survey reveals that solasodine has diuretic, anticancer, antifungal, cardiotonic, antispermatogenetic, antiandrogenic, immunomodulatory, antipyretic and various effects on central nervous system.

<span class="mw-page-title-main">Solasonine</span> Chemical compound

Solasonine is a glycoalkaloid that is found in Solanum plants of the family Solanaceae. Solasonine is a poisonous chemical compound when used at high levels. It is a glycoside of solasodine. Glycoalkaloids such as Solasonine have various applications including pharmacology, cancer treatments and even a role as a pesticide.

<span class="mw-page-title-main">Chaconine</span> Chemical compound

α-Chaconine is a steroidal glycoalkaloid that occurs in plants of the family Solanaceae. It is a natural toxicant produced in green potatoes and gives the potato a bitter taste. Tubers produce this glycoalkaloid in response to stress, providing the plant with insecticidal and fungicidal properties. It belongs to the chemical family of saponins. Since it causes physiological effects on individual organism, chaconine is considered to be defensive allelochemical. Solanine is a related substance that has similar properties.

<span class="mw-page-title-main">Scopoletin</span> Chemical compound

Scopoletin is a coumarin found in the root of plants in the genus Scopolia such as Scopolia carniolica and Scopolia japonica, in chicory, in Artemisia scoparia, in the roots and leaves of stinging nettle, in the passion flower, in Brunfelsia, in Viburnum prunifolium, in Solanum nigrum, in Datura metel, in Mallotus resinosus, or and in Kleinhovia hospita. It can also be found in fenugreek, vinegar, some whiskies or in dandelion coffee. A similar coumarin is scoparone. Scopoletin is highly fluorescent when dissolved in DMSO or water and is regularly used as a fluorimetric assay for the detection of hydrogen peroxide in conjunction with horseradish peroxidase. When oxidized, its fluorescence is strongly suppressed.

<span class="mw-page-title-main">Plant use of endophytic fungi in defense</span>

Plant use of endophytic fungi in defense occurs when endophytic fungi, which live symbiotically with the majority of plants by entering their cells, are utilized as an indirect defense against herbivores. In exchange for carbohydrate energy resources, the fungus provides benefits to the plant which can include increased water or nutrient uptake and protection from phytophagous insects, birds or mammals. Once associated, the fungi alter nutrient content of the plant and enhance or begin production of secondary metabolites. The change in chemical composition acts to deter herbivory by insects, grazing by ungulates and/or oviposition by adult insects. Endophyte-mediated defense can also be effective against pathogens and non-herbivory damage.

<i>Solanum macrocarpon</i> Species of fruit and plant

Solanum macrocarpon otherwise known as the African eggplant : añara), Surinamese eggplant or Vietnamese eggplant is a plant of the family Solanaceae. S. macrocarpon is a tropical perennial plant that is closely related to the eggplant. S. macrocarpon originated from West Africa, but is now widely distributed in Central and East Africa. The plant also grows in the Caribbean, South America, and some parts of Southeast Asia. S. macrocarpon is widely cultivated for its use as a food, its medicinal purposes, and as an ornamental plant.

<span class="mw-page-title-main">Solanidine</span> Chemical compound

Solanidine is a poisonous steroidal alkaloid chemical compound that occurs in plants of the family Solanaceae, such as potato and Solanum americanum. Human ingestion of solanidine also occurs via the consumption of the glycoalkaloids, α-solanine and α-chaconine, present in potatoes. The sugar portion of these glycoalkaloids hydrolyses in the body, leaving the solanidine portion. Solanidine occurs in the blood serum of normal healthy people who eat potato, and serum solanidine levels fall markedly once potato consumption ceases. Solanidine from food is also stored in the human body for prolonged periods of time, and it has been suggested that it could be released during times of metabolic stress with the potential for deleterious consequences. Solanidine is responsible for neuromuscular syndromes via cholinesterase inhibition.

<i>Epicoccum nigrum</i> Species of fungus

Epicoccum nigrum is a species of fungus in the phylum Ascomycota. A plant pathogen and endophyte, it is a widespread fungus which produces coloured pigments that can be used as antifungal agents against other pathogenic fungi. The fluorescent stain epicocconone is extracted from it.

<span class="mw-page-title-main">Lolitrem B</span> Chemical compound

Lolitrem B is one of many toxins produced by a fungus called Epichloë festucae var. lolii), which grows in Lolium perenne. The fungus is symbiotic with the ryegrass; it doesn't harm the plant, and the toxins it produces kill insects that feed on ryegrass. Lolitrem B is one of these toxins, but it is also harmful to mammals. The shoots and flowers of infected ryegrass have especially high concentrations of lolitrem B, and when livestock eat too much of them, they get perennial ryegrass staggers. At low doses the animals have tremors, and at higher doses they stagger, and at higher yet doses the animals become paralyzed and die. The blood pressure of the animals also goes up. The effect of the lolitrem B comes on slowly and fades out slowly, as it is stored in fat after the ryegrass is eaten. The condition is especially common in New Zealand and Australia, and plant breeders there have been trying to develop strains of fungus that produce toxins only harmful to pests, and not to mammals.

<span class="mw-page-title-main">Mucoromycota</span> Diverse group of molds

Mucoromycota is a division within the kingdom fungi. It includes a diverse group of various molds, including the common bread molds Mucor and Rhizopus. It is a sister phylum to Dikarya.

References

  1. Al Chami, L.; Mendez, R.; Chataing, B.; et al. (2003). "Toxicological effects of α-solamargine in experimental animals". Phytotherapy Research. 17 (3): 254–8. doi:10.1002/ptr.1122. PMID   12672156. S2CID   86042610. Archived from the original on 2012-06-16. Retrieved 2009-09-01.
  2. Blankemeyer, J. T.; McWilliams, M. L.; Rayburn, J. R.; et al. (1998). "Developmental toxicology of solamargine and solasonine glycoalkaloids in frog embryos". Food and Chemical Toxicology. 36 (5): 383–9. doi:10.1016/s0278-6915(97)00164-6. PMID   9662413.
  3. El-Hawary, S.s.; Mohammed, R.; AbouZid, S.f.; et al. (2016-04-01). "Solamargine production by a fungal endophyte of Solanum nigrum". Journal of Applied Microbiology. 120 (4): 900–911. doi: 10.1111/jam.13077 . ISSN   1365-2672. PMID   26811095.