Classification Term: 168391

Solanidines and alkaloid derivatives [ST0115] (ontology term: d5064fe18425fcf8a44e65ee0d7227a1)

Solanidines and alkaloid derivatives [ST0115]

found 19 associated metabolites at sub_class metabolite taxonomy ontology rank level.

Ancestor: Sterols [ST01]

Child Taxonomies: There is no child term of current ontology term.

Solanidine

(2S,4AR,4BS,6as,6BR,7S,7ar,10S,12as,13as,13BS)-4a,6a,7,10-tetramethyl-2,3,4,4a,4b,5,6,6a,6b,7,7a,8,9,10,11,12a,13,13a,13b,14-icosahydro-1H-naphtho[2,1:4,5]indeno[1,2-b]indolizin-2-ol

C27H43NO (397.3344468)


Solanidine is a steroid alkaloid fundamental parent, a 3beta-hydroxy-Delta(5)-steroid and a solanid-5-en-3-ol. It has a role as a plant metabolite and a toxin. It is a conjugate base of a solanidine(1+). Solanidine is a natural product found in Fritillaria delavayi, Fritillaria tortifolia, and other organisms with data available. Alkaloid from potato (Solanum tuberosum). Glycosides, (especies Solanines and chaconine) are trace toxic constits. of potato tubers (especies greened tubers), and interbreeding of potatoes with wild strains may increase their concn. or introduce other more toxic, solanidine glycosides Solanidine is a steroidal alkaloid, and its glycosides have been reported to have caused poisoning in man and animals. Solanidine is present in sera of healthy individuals and in amounts dependent on their dietary potato consumption. (PMID: 4007882). Solanidine is a cholestane alkaloid isolated from several potato species including Solanum demissum, Solanum acaule, and Solanum tuberosum. Solanidine can inhibit proliferation and exhibit obvious antitumor effect[1]. Solanidine is a cholestane alkaloid isolated from several potato species including Solanum demissum, Solanum acaule, and Solanum tuberosum. Solanidine can inhibit proliferation and exhibit obvious antitumor effect[1].

   

Tomatidine

5,7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2-piperidine]-16-ol

C27H45NO2 (415.345011)


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].

   

Solasodin

(3beta,22alpha,25R)-spirosol-5-en-3-ol

C27H43NO2 (413.3293618)


Acquisition and generation of the data is financially supported in part by CREST/JST. INTERNAL_ID 2286; CONFIDENCE Reference Standard (Level 1) CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2286 Solasodine (Purapuridine) is a steroidal alkaloid that occurs in plants of the Solanaceae family. Solasodine has neuroprotective, antifungal, hypotensive, anticancer, antiatherosclerotic, antiandrogenic and anti-inflammatory activities[1][2]. Solasodine (Purapuridine) is a steroidal alkaloid that occurs in plants of the Solanaceae family. Solasodine has neuroprotective, antifungal, hypotensive, anticancer, antiatherosclerotic, antiandrogenic and anti-inflammatory activities[1][2]. Solasodine (Purapuridine) is a steroidal alkaloid that occurs in plants of the Solanaceae family. Solasodine has neuroprotective, antifungal, hypotensive, anticancer, antiatherosclerotic, antiandrogenic and anti-inflammatory activities[1][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 (1033.5457308)


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].

   

Solasodine

5,7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2-piperidin]-18-en-16-ol

C27H43NO2 (413.3293618)


Solasodine is a poisonous glycoalkaloid chemical compound that occurs in plants of the Solanaceae family. Solasodine is found in many foods, some of which are peppermint, chinese cinnamon, alaska blueberry, and sweet rowanberry. Solasodine is found in eggplant. Solasodine is a poisonous glycoalkaloid chemical compound that occurs in plants of the Solanaceae family Solasodine (Purapuridine) is a steroidal alkaloid that occurs in plants of the Solanaceae family. Solasodine has neuroprotective, antifungal, hypotensive, anticancer, antiatherosclerotic, antiandrogenic and anti-inflammatory activities[1][2]. Solasodine (Purapuridine) is a steroidal alkaloid that occurs in plants of the Solanaceae family. Solasodine has neuroprotective, antifungal, hypotensive, anticancer, antiatherosclerotic, antiandrogenic and anti-inflammatory activities[1][2]. Solasodine (Purapuridine) is a steroidal alkaloid that occurs in plants of the Solanaceae family. Solasodine has neuroprotective, antifungal, hypotensive, anticancer, antiatherosclerotic, antiandrogenic and anti-inflammatory activities[1][2].

   

Solasodine

(4S,5R,6aR,6bS,8aS,8bR,9S,10R,11aS,12aS,12bS)-5,6a,8a,9-Tetramethyl-1,3,4,5,6,6a,6b,7,8,8a,8b,9,11a,12,12a,12b-hexadecahydrospiro[naphtho[2,1:4,5]indeno[2,1-b]furan-10,2-piperidin]-4-ol

C27H43NO2 (413.3293618)


Solasodine is an oxaspiro compound and steroid alkaloid sapogenin with formula C27H43NO2 found in the Solanum (nightshade) family. It is used as a precursor in the synthesis of complex steroidal compounds such as contraceptive pills. It has a role as a plant metabolite, a teratogenic agent, a diuretic, an antifungal agent, a cardiotonic drug, an immunomodulator, an antipyretic, an apoptosis inducer, an antioxidant, an antiinfective agent, an anticonvulsant, a central nervous system depressant and an antispermatogenic agent. It is an azaspiro compound, an oxaspiro compound, an alkaloid antibiotic, a hemiaminal ether, a sapogenin and a steroid alkaloid. It is a conjugate base of a solasodine(1+). Purapuridine is a natural product found in Solanum hazenii, Solanum americanum, and other organisms with data available. An oxaspiro compound and steroid alkaloid sapogenin with formula C27H43NO2 found in the Solanum (nightshade) family. It is used as a precursor in the synthesis of complex steroidal compounds such as contraceptive pills. Alkaloid from Solanum melanocerasum (garden huckleberry). alpha-Solanigrine is found in fruits. Origin: Plant; SubCategory_DNP: Steroidal alkaloids, Solanaceous alkaloids relative retention time with respect to 9-anthracene Carboxylic Acid is 1.206 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.202 Solasodine (Purapuridine) is a steroidal alkaloid that occurs in plants of the Solanaceae family. Solasodine has neuroprotective, antifungal, hypotensive, anticancer, antiatherosclerotic, antiandrogenic and anti-inflammatory activities[1][2]. Solasodine (Purapuridine) is a steroidal alkaloid that occurs in plants of the Solanaceae family. Solasodine has neuroprotective, antifungal, hypotensive, anticancer, antiatherosclerotic, antiandrogenic and anti-inflammatory activities[1][2]. Solasodine (Purapuridine) is a steroidal alkaloid that occurs in plants of the Solanaceae family. Solasodine has neuroprotective, antifungal, hypotensive, anticancer, antiatherosclerotic, antiandrogenic and anti-inflammatory activities[1][2].

   

Tomatidine

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

C27H45NO2 (415.345011)


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 (1033.5457308)


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].

   

Verazine

(20S,25S)-22,26-iminocholesta-5,22(N)-dien-3beta-ol

C27H43NO (397.3344468)


   

Etioline

(25S)-22,26-iminocholesta-5,22(N)-dien-3beta,16beta-diol

C27H43NO2 (413.3293618)


   

beta-Chaconine

solanid-5-en-3beta-yl 3-O-alpha-L-rhamnopyranosyl-(1-2)-beta-D-glucopyranoside

C39H63NO10 (705.4451738)


   

Demissidine

solanidan-3beta-ol

C27H45NO (399.350096)


[Raw Data] CB019_Demissidine_pos_50eV_rep000003.txt [Raw Data] CB019_Demissidine_pos_40eV_rep000003.txt [Raw Data] CB019_Demissidine_pos_30eV_rep000003.txt [Raw Data] CB019_Demissidine_pos_20eV_rep000003.txt [Raw Data] CB019_Demissidine_pos_10eV_rep000003.txt

   

Soladulcidine

(22R,25R)-spirosolan-3beta-ol

C27H45NO2 (415.345011)


   

Leptinidine

solanid-5-en-3beta,23S-diol

C27H43NO2 (413.3293618)


   

Teinemine

(22S,25S)-22,26-epiminocholest-5-ene-3beta,16alpha-diol

C27H45NO2 (415.345011)


   

25-iso-etioline

(25R)-22,26-iminocholesta-5,22(N)-dien-3beta,16beta-diol

C27H43NO2 (413.3293618)


   

22-iso-teinemine

(22R,25S)-22,26-epiminocholest-5-ene-3beta,16alpha-diol

C27H45NO2 (415.345011)


   

tomatidinol

(22S,25S)-spirosol-5-en-3beta-ol

C27H43NO2 (413.3293618)


   

20-epi-Verazine

(20R,25S)-22,26-iminocholesta-5,22(N)-dien-3beta-ol

C27H43NO (397.3344468)