Classification Term: 1495

Spirosolanes and derivatives (ontology term: CHEMONTID:0001704)

found 8 associated metabolites at category metabolite taxonomy ontology rank level.

Ancestor: Steroidal alkaloids

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

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].

   

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].

   

N-Nitrosotomatidine

(1R,2S,4S,5S,6S,7S,8R,9S,12S,13S,16S,18S)-5,7,9,13-tetramethyl-1-nitroso-5-oxaspiro[pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2-piperidine]-16-ol

C27H44N2O3 (444.3351754)


N-Nitrosotomatidine belongs to the class of organic compounds known as spirosolanes and derivatives. These are steroidal alkaloids with a structure containing a spirosolane skeleton. Siporosolane is a polycyclic compound that is characterized by a 1-oxa-6-azaspiro[4.5]decane moiety where the oxolane ring is fused to a docosahydronaphth[2,1:4,5]indene ring system. Spirosolane arises from the conversion of a cholestane side-chain into a bicyclic system containing a piperidine and a tetrahydrofuran ring. N-Nitrosotomatidine is a moderately basic compound (based on its pKa). N-Nitrosotomatidine has been identified in tomatoes. Present in tomatoes. N-Nitrosotomatidine is found in garden tomato.

   

5alpha-Tomatidan-3-one

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

C27H43NO2 (413.3293618)


5alpha-Tomatidan-3-one is an alkaloid from roots of a Lycopersicon esculentum/Lycopersicon hirsutum hybri Alkaloid from roots of a Lycopersicon esculentum/Lycopersicon hirsutum hybrid.

   

23-Acetoxysoladulcidine

16-Hydroxy-5,7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2-piperidine]-3-yl acetic acid

C29H47NO4 (473.3504902)


(23R)-Acetoxytomatidine is an alkaloid from roots of a Lycopersicon esculentum/Lycopersicon hirsutum hybri

   

Ginsenoside I

2-{[2-(5-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-16-hydroxy-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl)-5-hydroperoxy-6-methylhept-6-en-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C48H82O20 (978.5399172)


Ginsenoside II is found in tea. Ginsenoside II is a constituent of Panax ginseng (ginseng).

   

Esculeogenin A

5-(hydroxymethyl)-7,9,13-trimethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2-piperidine]-3,16-diol

C27H45NO4 (447.33484100000004)


   

Solasodiene

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

C27H41NO (395.31879760000004)


Solasodiene belongs to spirosolanes and derivatives class of compounds. Those are steroidal alkaloids with a structure containing a spirosolane skeleton. Siporosolane is a polycyclic compound that is characterized by a 1-oxa-6-azaspiro[4.5]decane moiety where the oxolane ring is fused to a docosahydronaphth[2,1:4,5]indene ring system. Spirosolane arises from the conversion of a cholestane side-chain into a bicyclic system containing a piperidine and a tetrahydrofuran ring. Solasodiene is practically insoluble (in water) and a very strong basic compound (based on its pKa). Solasodiene can be found in potato, which makes solasodiene a potential biomarker for the consumption of this food product.