NCBI Taxonomy: 2589398

Solanum kieseritzkii (ncbi_taxid: 2589398)

found 12 associated metabolites at species taxonomy rank level.

Ancestor: Solanum

Child Taxonomies: none taxonomy data.

Tomatidine

(1R,2S,4S,5'S,6S,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-piperidine]-16-ol

C27H45NO2 (415.345)


Tomatidine is the aglycone derivative of tomatine. Tomatidine belongs to the chemical family known as Spirosolanes and Derivatives. These are steroidal alkaloids whose structure contains a spirosolane skeleton. Tomatine (the glycosylated form of tomatidine) is a mildly toxic glycoalkaloid or glycospirosolane found in the stems and leaves of tomato plants as well as in the fruit of unripened (green) tomatoes (up to 500 mg/kg). Red, ripe tomatoes have somewhat reduced amounts of tomatine and tomatidine. Both tomatine and tomatidine possess antimicrobial, antifungal and antiviral properties. Tomatidine has been shown to exhibit anti-virulence activity against normal strains of Staphylococcus aureus as well as the ability to potentiate the effect of aminoglycoside antibiotics (PMID: 24877760). Recent studies have shown that tomatidine stimulates mTORC1 signaling and anabolism, leading to accumulation of protein and mitochondria, and ultimately, cell growth. Furthermore, in mice, tomatidine has been shown to increase skeletal muscle mTORC1 signaling, reduce skeletal muscle atrophy, enhance recovery from skeletal muscle atrophy, stimulate skeletal muscle hypertrophy, and increase strength and exercise capacity (PMID: 24719321). Tomatidine has also been shown to significantly inhibit cholesterol ester accumulation induced by acetylated LDL in human monocyte-derived macrophages in a dose-dependent manner. Tomatidine also inhibits cholesterol ester formation in Chinese hamster ovary cells overexpressing acyl-CoA:cholesterol acyl-transferase (ACAT)-1 or ACAT-2, suggesting that tomatidine suppresses both ACAT-1 and ACAT-2 activities. The oral administration of tomatidine to apoE-deficient mice significantly reduces levels of serum cholesterol, LDL-cholesterol, and the size of atherosclerotic lesions (PMID: 22224814). Alkaloid from Lycopersicon esculentum (tomato). Tomatidine is found in garden tomato, garden tomato (variety), and potato. Tomatidine acts as an anti-inflammatory agent by blocking NF-κB and JNK signaling[1]. Tomatidine activates autophagy either in mammal cells or C elegans[2]. Tomatidine acts as an anti-inflammatory agent by blocking NF-κB and JNK signaling[1]. Tomatidine activates autophagy either in mammal cells or C elegans[2].

   

Tomatine

2-[(2-{[4,5-dihydroxy-2-(hydroxymethyl)-6-{5,7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2-piperidine]oxy}oxan-3-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

C50H83NO21 (1033.5457)


Tomatine is a mildly toxic glycoalkaloid or glycospirosolane (steroidal alkaloids whose structure contains a spirosolane skeleton) found in the stems and leaves of tomato plants as well as in the fruit of unripened (green) tomatoes (up to 500 mg/kg). Red, ripe tomatoes have somewhat reduced amounts of tomatine. A toxic dose of tomatine for an adult human would appear to require the consumption of at least 500 g of tomato leaves in one sitting (“Toxic Plants of North America” (Iowa State University Press, 2001)). Tomatine is known to have fungicidal and antimicrobial properties and is likely produced by tomato plants as a defense against bacteria, fungi, viruses, and insects (PMID: 19514731). Some microbes produce an enzyme called tomatinase which can degrade tomatine, rendering it ineffective as an antimicrobial (PMID: 18835993).Tomatine has historically been used as a reagent in analytical chemistry for precipitating cholesterol from solution (PMID: 4362143). When lab animals ingest tomatine, essentially all of it passes through the animal unabsorbed. Tomatine apparently binds to cholesterol in the digestive tract, and the largely insoluble combination is excreted — ridding the body of both the alkaloid and cholesterol. Experiments with hamsters have shown that both tomatine-rich green tomatoes and purified tomatine can substantially lower the levels of undesirable LDL cholesterol while maintaining normal levels of HDL (PMID: 10942315). Experiments with high-tomatine green tomato extracts were recently shown to strongly inhibit the growth of a number of human cancer cell lines including breast (MCF-7), colon (HT-29), gastric (AGS), and hepatoma (liver) (HepG2), as well as normal human liver cells (PMID: 19514731). Other studies have found that purified tomatine is an outstanding immunoadjuvant capable of stimulating potent antigen-specific humoral and cellular immune responses that contribute to protection against malaria, Francisella tularensis and regression of experimental tumors (PMID: 15193398). Tomatine is a mildly toxic glycoalkaloid or glycospirosolane (steroidal alkaloids whose structure contains a spirosolane skeleton) found in the stems and leaves of tomato plants as well as in the fruit of unripened (green) tomatoes (up to 500 mg/kg). Red, ripe tomatoes have somewhat reduced amounts of tomatine. A toxic dose of tomatine for an adult human would appear to require the consumption of at least 500 g of tomato leaves in one sitting (“Toxic Plants of North America” (Iowa State University Press, 2001)). Tomatine is known to have fungicidal and antimicrobial properties and is likely produced by tomato plants as a defense against bacteria, fungi, viruses, and insects (PMID: 19514731). Some microbes produce an enzyme called tomatinase which can degrade tomatine, rendering it ineffective as an antimicrobial (PMID: 18835993).Tomatine has historically been used as a reagent in analytical chemistry for precipitating cholesterol from solution (PMID: 4362143). When lab animals ingest tomatine, essentially all of it passes through the animal unabsorbed. Tomatine apparently binds to cholesterol in the digestive tract, and the largely insoluble combination is excreted — ridding the body of both the alkaloid and cholesterol. Experiments with hamsters have shown that both tomatine-rich green tomatoes and purified tomatine can substantially lower the levels of undesirable LDL cholesterol while maintaining norma D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents D000890 - Anti-Infective Agents > D000935 - Antifungal Agents Tomatine is a glycoalkaloid, found in the tomato plant (Lycopersicon esculentum Mill.). Tomatine elicits neurotoxicity in RIP1 kinase and caspase-independent manner. Tomatine promotes the upregulation of nuclear apoptosis inducing factor (AIF) in neuroblastoma cells. Tomatine also inhibits 20S proteasome activity[1]. Tomatine is a glycoalkaloid, found in the tomato plant (Lycopersicon esculentum Mill.). Tomatine elicits neurotoxicity in RIP1 kinase and caspase-independent manner. Tomatine promotes the upregulation of nuclear apoptosis inducing factor (AIF) in neuroblastoma cells. Tomatine also inhibits 20S proteasome activity[1].

   

Solasonine

(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2-[(1S,2S,4S,5R,6R,7S,8R,9S,12S,13R,16S)-5,7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2-piperidine]-16-yl]oxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol

C45H73NO16 (883.4929)


Solasonine is an azaspiro compound, an oxaspiro compound and a steroid. Solasonine is a natural product found in Solanum americanum, Solanum dimidiatum, and other organisms with data available. Solasonine is a steroidal glycoalkaloid isolated from Solanum nigrum L.. Solasonine has cytotoxicity to human gastric cancer cells[1]. Solasonine is a steroidal glycoalkaloid isolated from Solanum nigrum L.. Solasonine has cytotoxicity to human gastric cancer cells[1].

   

Solamargine

(2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[(1S,2S,4S,5R,6R,7S,8R,9S,12S,13R,16S)-5,7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2-piperidine]-16-yl]oxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol

C45H73NO15 (867.498)


Solamargine is an azaspiro compound, a steroid and an oxaspiro compound. Solamargine has been used in trials studying the treatment of Actinic Keratosis. Solamargine is a natural product found in Solanum pittosporifolium, Solanum americanum, and other organisms with data available. Solamargine, a derivative from the steroidal solasodine in Solanum species, exhibits anticancer activities in numerous types of cancer. Solamargine induces non-selective cytotoxicity and P-glycoprotein inhibition. Solamargine significantly inhibits migration and invasion of HepG2 cells by down-regulating MMP-2 and MMP-9 expression and activity[1][2]. Solamargine, a derivative from the steroidal solasodine in Solanum species, exhibits anticancer activities in numerous types of cancer. Solamargine induces non-selective cytotoxicity and P-glycoprotein inhibition. Solamargine significantly inhibits migration and invasion of HepG2 cells by down-regulating MMP-2 and MMP-9 expression and activity[1][2].

   

Solamargine

2-{[4-hydroxy-2-(hydroxymethyl)-6-{5,7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2-piperidin]-18-eneoxy}-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

C45H73NO15 (867.498)


Solamargine, also known as beta-solamarine, is a member of the class of compounds known as steroidal saponins. Steroidal saponins are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative. Solamargine is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Solamargine can be found in eggplant, which makes solamargine a potential biomarker for the consumption of this food product. Solamargine is a poisonous chemical compound that occurs in plants of the Solanaceae family, such as potatoes, tomatoes, and eggplants. It has been also isolated from Solanum nigrum fungal endophyte Aspergillus flavus. It is a glycoalkaloid derived from the steroidal alkaloid solasodine . Solamargine, a derivative from the steroidal solasodine in Solanum species, exhibits anticancer activities in numerous types of cancer. Solamargine induces non-selective cytotoxicity and P-glycoprotein inhibition. Solamargine significantly inhibits migration and invasion of HepG2 cells by down-regulating MMP-2 and MMP-9 expression and activity[1][2]. Solamargine, a derivative from the steroidal solasodine in Solanum species, exhibits anticancer activities in numerous types of cancer. Solamargine induces non-selective cytotoxicity and P-glycoprotein inhibition. Solamargine significantly inhibits migration and invasion of HepG2 cells by down-regulating MMP-2 and MMP-9 expression and activity[1][2].

   

Solasonine

2-{[3-hydroxy-2-(hydroxymethyl)-6-{5,7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2-piperidin]-18-eneoxy}-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C45H73NO16 (883.4929)


Solasonine, also known as alpha-solamargine or alpha-solamarine, (3beta,22alpha,25r)-isomer, is a member of the class of compounds known as steroidal saponins. Steroidal saponins are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative. Solasonine is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Solasonine can be found in eggplant, which makes solasonine a potential biomarker for the consumption of this food product. Solasonine is a poisonous chemical compound. It is a glycoside of solasodine. Solasonine occurs in plants of the Solanaceae family. Solasonine was one component of the unsuccessful experimental cancer drug candidate Coramsine . Solasonine is a steroidal glycoalkaloid isolated from Solanum nigrum L.. Solasonine has cytotoxicity to human gastric cancer cells[1]. Solasonine is a steroidal glycoalkaloid isolated from Solanum nigrum L.. Solasonine has cytotoxicity to human gastric cancer cells[1].

   

Tomatidine

5 alpha,20 beta(F),22 alpha(F),25 beta(F),27- azaspirostan-3 beta-ol

C27H45NO2 (415.345)


Tomatidine is a 3beta-hydroxy steroid resulting from the substitution of the 3beta-hydrogen of tomatidane by a hydroxy group. It is an azaspiro compound, an oxaspiro compound and a 3beta-hydroxy steroid. It is a conjugate base of a tomatidine(1+). It derives from a hydride of a tomatidane. Tomatidine is a natural product found in Solanum dunalianum, Solanum kieseritzkii, and other organisms with data available. CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 20 Tomatidine acts as an anti-inflammatory agent by blocking NF-κB and JNK signaling[1]. Tomatidine activates autophagy either in mammal cells or C elegans[2]. Tomatidine acts as an anti-inflammatory agent by blocking NF-κB and JNK signaling[1]. Tomatidine activates autophagy either in mammal cells or C elegans[2].

   

Tomatine

beta-D-Galactopyranoside, (3beta,5alpha,22beta,25S)-spirosolan-3-yl O-beta-D-glucopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-

C50H83NO21 (1033.5457)


Tomatine is a steroid alkaloid that is tomatidine in which the hydroxy group at position 3 is linked to lycotetraose, a tetrasaccharide composed of two units of D-glucose, one unit of D-xylose, and one unit of D-galactose. It has a role as an immunological adjuvant, a phytotoxin and an antifungal agent. It is a steroid alkaloid, a tetrasaccharide derivative, an alkaloid antibiotic, a glycoside and a glycoalkaloid. It is functionally related to a tomatidine. Lycopersicin is a natural product found in Solanum acaule, Solanum lycopersicoides, and other organisms with data available. An alkaloid that occurs in the extract of leaves of wild tomato plants. It has been found to inhibit the growth of various fungi and bacteria. It is used as a precipitating agent for steroids. (From The Merck Index, 11th ed) A steroid alkaloid that is tomatidine in which the hydroxy group at position 3 is linked to lycotetraose, a tetrasaccharide composed of two units of D-glucose, one unit of D-xylose, and one unit of D-galactose. D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents D000890 - Anti-Infective Agents > D000935 - Antifungal Agents Tomatine is a glycoalkaloid, found in the tomato plant (Lycopersicon esculentum Mill.). Tomatine elicits neurotoxicity in RIP1 kinase and caspase-independent manner. Tomatine promotes the upregulation of nuclear apoptosis inducing factor (AIF) in neuroblastoma cells. Tomatine also inhibits 20S proteasome activity[1]. Tomatine is a glycoalkaloid, found in the tomato plant (Lycopersicon esculentum Mill.). Tomatine elicits neurotoxicity in RIP1 kinase and caspase-independent manner. Tomatine promotes the upregulation of nuclear apoptosis inducing factor (AIF) in neuroblastoma cells. Tomatine also inhibits 20S proteasome activity[1].

   

(2s,3r,4r,5r,6s)-2-{[(2s,3r,4s,5r,6s)-4-hydroxy-2-(hydroxymethyl)-6-[(1s,2s,4s,5'r,6r,7s,8r,9s,12s,13r,16s)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-eneoxy]-5-{[(2s,3r,4r,5r,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

(2s,3r,4r,5r,6s)-2-{[(2s,3r,4s,5r,6s)-4-hydroxy-2-(hydroxymethyl)-6-[(1s,2s,4s,5'r,6r,7s,8r,9s,12s,13r,16s)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-eneoxy]-5-{[(2s,3r,4r,5r,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

C45H73NO15 (867.498)


   

(2r,3r,4r,5r,6s)-2-{[(2r,3r,4s,5s,6r)-5-hydroxy-6-(hydroxymethyl)-2-[(1s,2s,4s,5'r,6r,7s,8r,9s,12s,13r,16s)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-eneoxy]-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

(2r,3r,4r,5r,6s)-2-{[(2r,3r,4s,5s,6r)-5-hydroxy-6-(hydroxymethyl)-2-[(1s,2s,4s,5'r,6r,7s,8r,9s,12s,13r,16s)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-eneoxy]-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

C45H73NO16 (883.4929)


   

2-{[3-hydroxy-2-(hydroxymethyl)-6-{5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-eneoxy}-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

2-{[3-hydroxy-2-(hydroxymethyl)-6-{5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-eneoxy}-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C45H73NO16 (883.4929)


   

2-[(2-{[4,5-dihydroxy-2-(hydroxymethyl)-6-{5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidine]oxy}oxan-3-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

2-[(2-{[4,5-dihydroxy-2-(hydroxymethyl)-6-{5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidine]oxy}oxan-3-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

C50H83NO21 (1033.5457)