NCBI Taxonomy: 308559

Lobelia inflata (ncbi_taxid: 308559)

found 35 associated metabolites at species taxonomy rank level.

Ancestor: Lobelia

Child Taxonomies: none taxonomy data.

Lobeline

Ethanone, 2-(6-(2-hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenyl-, (2R-(2alpha,6alpha(S*)))-

C22H27NO2 (337.2042)


(-)-lobeline is an optically active piperidine alkaloid having a 2-oxo-2-phenylethyl substituent at the 2-position and a 2-hydroxy-2-phenylethyl group at the 6-position. It has a role as a nicotinic acetylcholine receptor agonist. It is a piperidine alkaloid, a tertiary amine and an aromatic ketone. Lobeline is a natural product found in Lobelia sessilifolia, Lobelia inflata, and other organisms with data available. An alkaloid that has actions similar to NICOTINE on nicotinic cholinergic receptors but is less potent. It has been proposed for a variety of therapeutic uses including in respiratory disorders, peripheral vascular disorders, insomnia, and smoking cessation. D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D005731 - Ganglionic Stimulants C78272 - Agent Affecting Nervous System > C47796 - Cholinergic Agonist > C73579 - Nicotinic Agonist D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018679 - Cholinergic Agonists D019141 - Respiratory System Agents relative retention time with respect to 9-anthracene Carboxylic Acid is 0.733 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.728

   

Amyrin

(3S,4aR,5R,6aR,6bR,8S,8aR,12aR,14aR,14bR)-4,4,6a,6b,8a,11,11,14b-Octamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-eicosahydro-picen-3-ol

C30H50O (426.3861)


Beta-amyrin is a pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants. It has a role as a plant metabolite and an Aspergillus metabolite. It is a pentacyclic triterpenoid and a secondary alcohol. It derives from a hydride of an oleanane. beta-Amyrin is a natural product found in Ficus pertusa, Ficus septica, and other organisms with data available. See also: Calendula Officinalis Flower (part of); Viburnum opulus bark (part of); Centaurium erythraea whole (part of). A pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants. β-Amyrin, an ingredient of Celastrus hindsii, blocks amyloid β (Aβ)-induced long-term potentiation (LTP) impairment. β-amyrin is a promising candidate of treatment for AD[1]. β-Amyrin, an ingredient of Celastrus hindsii, blocks amyloid β (Aβ)-induced long-term potentiation (LTP) impairment. β-amyrin is a promising candidate of treatment for AD[1].

   

Cadaverine

Pentamethylenediamine dihydrochloride

C5H14N2 (102.1157)


Cadaverine is a foul-smelling diamine formed by bacterial decarboxylation of lysine that occurs during protein hydrolysis during putrefaction of animal tissue. However, this diamine is not purely associated with putrefaction. It is also produced in small quantities by mammals. In particular, it is partially responsible for the distinctive smell of urine and semen. Elevated levels of cadaverine have been found in the urine of some patients with defects in lysine metabolism. Cadaverine is toxic in large doses. In rats it had a low acute oral toxicity of more than 2000 mg/kg body weight .; Cadaverine is a foul-smelling molecule produced by protein hydrolysis during putrefaction of animal tissue. Cadaverine is a toxic diamine with the formula NH2(CH2)5NH2, which is similar to putrescine. Cadaverine is also known by the names 1,5-pentanediamine and pentamethylenediamine. Cadaverine is a foul-smelling diamine formed by bacterial decarboxylation of lysine that occurs during protein hydrolysis during putrefaction of animal tissue. However, this diamine is not purely associated with putrefaction. Cadaverine is a toxic diamine with the formula NH2(CH2)5NH2, which is similar to putrescines NH2(CH2)4NH2. Cadaverine is also known by the names 1,5-pentanediamine and pentamethylenediamine. It is also produced in small quantities by mammals. In particular, it is partially responsible for the distinctive smell of urine and semen. Elevated levels of cadaverine have been found in the urine of some patients with defects in lysine metabolism. Cadaverine is toxic in large doses. In rats it had a low acute oral toxicity of more than 2000 mg/kg body weight. Cadaverine can be found in Corynebacterium (PMID:27872963). Acquisition and generation of the data is financially supported in part by CREST/JST. C78272 - Agent Affecting Nervous System > C66880 - Anticholinergic Agent KEIO_ID C032

   

Piperideine

1-Piperideine

C5H9N (83.0735)


   

5-Aminopentanal

5-Amino-pentanal

C5H11NO (101.0841)


The aminoaldehydes 5-aminopentanal, derived from the oxidation of the diamines putrescine and cadaverine,is produced utilizing a copper amine oxidase (CAO) from Euphorbia characias latex and tested with in vitro cultivation of Leishmania infantum promastigotes.Whereas the aminoaldehydes derived from the oxidation of the diamines were stimulating factors for growth of Leishmania infantum promastigotes, the aldehydes derived from polyamines oxidation had a drastic inhibitory effect on the vitality and growth of these parasites. Thus, a double scenario arises, showing the use of aldehydes from diamines to obtain a large number of organisms of Leishmania infantum promastigotes to use in serological studies, whereas the aldehydes derived from polyamines could be used as a new strategy for therapeutic treatment against these parasites. [HMDB]. 5-Aminopentanal is found in many foods, some of which are watermelon, sorrel, medlar, and cornmint. The aminoaldehydes 5-aminopentanal, derived from the oxidation of the diamines putrescine and cadaverine,is produced utilizing a copper amine oxidase (CAO) from Euphorbia characias latex and tested with in vitro cultivation of Leishmania infantum promastigotes.Whereas the aminoaldehydes derived from the oxidation of the diamines were stimulating factors for growth of Leishmania infantum promastigotes, the aldehydes derived from polyamines oxidation had a drastic inhibitory effect on the vitality and growth of these parasites. Thus, a double scenario arises, showing the use of aldehydes from diamines to obtain a large number of organisms of Leishmania infantum promastigotes to use in serological studies, whereas the aldehydes derived from polyamines could be used as a new strategy for therapeutic treatment against these parasites.

   
   

Lobelanine

2-[(2S,6R)-1-methyl-6-(2-oxo-2-phenyl-ethyl)piperidin-2-yl]-1-phenyl-ethanone

C22H25NO2 (335.1885)


Lobelanine is a member of acetophenones. Lobelanine is a natural product found in Lobelia sessilifolia, Lobelia inflata, and other organisms with data available. Lobelanine (8,10-Diphenyllobelidione) is a chemical precursor for the biosynthesis of Lobeline. Lobeline is a partial nicotinic agonist and is used as a smoking cessation agent[1][2]. Lobelanine (8,10-Diphenyllobelidione) is a chemical precursor for the biosynthesis of Lobeline. Lobeline is a partial nicotinic agonist and is used as a smoking cessation agent[1][2].

   

beta-Amyrin palmitate

4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl hexadecanoate

C46H80O2 (664.6158)


Beta-amyrin palmitate, also known as B-amyrin palmitic acid, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Beta-amyrin palmitate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Beta-amyrin palmitate can be found in black elderberry, which makes beta-amyrin palmitate a potential biomarker for the consumption of this food product.

   

Inflatine

2-[6-(2-hydroxy-2-phenylethyl)-1-methylpiperidin-2-yl]-1-phenylethan-1-one

C22H27NO2 (337.2042)


D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D005731 - Ganglionic Stimulants D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018679 - Cholinergic Agonists D019141 - Respiratory System Agents

   

Lobetyolin

2-[(1,7-dihydroxytetradeca-4,12-dien-8,10-diyn-6-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

C20H28O8 (396.1784)


   

β-Amyrin

beta-amyrin-H2O

C30H50O (426.3861)


Beta-amyrin, also known as amyrin or (3beta)-olean-12-en-3-ol, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Thus, beta-amyrin is considered to be an isoprenoid lipid molecule. Beta-amyrin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Beta-amyrin can be synthesized from oleanane. Beta-amyrin is also a parent compound for other transformation products, including but not limited to, erythrodiol, glycyrrhetaldehyde, and 24-hydroxy-beta-amyrin. Beta-amyrin can be found in a number of food items such as thistle, pepper (c. baccatum), wakame, and endive, which makes beta-amyrin a potential biomarker for the consumption of these food products. The amyrins are three closely related natural chemical compounds of the triterpene class. They are designated α-amyrin (ursane skeleton), β-amyrin (oleanane skeleton) and δ-amyrin. Each is a pentacyclic triterpenol with the chemical formula C30H50O. They are widely distributed in nature and have been isolated from a variety of plant sources such as epicuticular wax. In plant biosynthesis, α-amyrin is the precursor of ursolic acid and β-amyrin is the precursor of oleanolic acid. All three amyrins occur in the surface wax of tomato fruit. α-Amyrin is found in dandelion coffee . β-Amyrin, an ingredient of Celastrus hindsii, blocks amyloid β (Aβ)-induced long-term potentiation (LTP) impairment. β-amyrin is a promising candidate of treatment for AD[1]. β-Amyrin, an ingredient of Celastrus hindsii, blocks amyloid β (Aβ)-induced long-term potentiation (LTP) impairment. β-amyrin is a promising candidate of treatment for AD[1].

   

Cadaverine

pentane-1,5-diamine

C5H14N2 (102.1157)


An alkane-alpha,omega-diamine comprising a straight-chain pentane core with amino substitutents at positions 1 and 5. A colourless syrupy liquid diamine with a distinctive unpleasant odour, it is a homologue of putresceine and is formed by the bacterial decarboxylation of lysine that occurs during protein hydrolysis during putrefaction of animal tissue. It is also found in plants such as soyabean. C78272 - Agent Affecting Nervous System > C66880 - Anticholinergic Agent

   

1-Piperideine

1-Piperideine

C5H9N (83.0735)


   

5-Aminopentanal

5-aminopentanal

C5H11NO (101.0841)


An omega-aminoaldehyde that is pentanal which is substituted at position 5 by an amino group. It is an intermediate in the biosynthesis of L-lysine derived alkaloids.

   

(-)-Lobeline

(-)-Lobeline

C22H27NO2 (337.2042)


An optically active piperidine alkaloid having a 2-oxo-2-phenylethyl substituent at the 2-position and a 2-hydroxy-2-phenylethyl group at the 6-position.

   

2-[(2r,6s)-6-[(2s)-2-hydroxybutyl]-1-methyl-3,6-dihydro-2h-pyridin-2-yl]-1-phenylethanone

2-[(2r,6s)-6-[(2s)-2-hydroxybutyl]-1-methyl-3,6-dihydro-2h-pyridin-2-yl]-1-phenylethanone

C18H25NO2 (287.1885)


   

(3s,4as,6ar,6bs,8ar,12ar,14as,14br)-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl hexadecanoate

(3s,4as,6ar,6bs,8ar,12ar,14as,14br)-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl hexadecanoate

C46H80O2 (664.6158)


   

2-[(2r,6s)-6-(2-oxo-2-phenylethyl)piperidin-2-yl]-1-phenylethanone

2-[(2r,6s)-6-(2-oxo-2-phenylethyl)piperidin-2-yl]-1-phenylethanone

C21H23NO2 (321.1729)


   

2-[6-(2-hydroxybutyl)-1-methyl-3,6-dihydro-2h-pyridin-2-yl]-1-phenylethanone

2-[6-(2-hydroxybutyl)-1-methyl-3,6-dihydro-2h-pyridin-2-yl]-1-phenylethanone

C18H25NO2 (287.1885)


   

2-{[(4e,12e)-1,7-dihydroxytetradeca-4,12-dien-8,10-diyn-6-yl]oxy}-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol

2-{[(4e,12e)-1,7-dihydroxytetradeca-4,12-dien-8,10-diyn-6-yl]oxy}-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol

C26H38O13 (558.2312)


   

(1r)-2-[(2s,6r)-6-[(2s)-2-hydroxy-2-phenylethyl]piperidin-2-yl]-1-phenylethanol

(1r)-2-[(2s,6r)-6-[(2s)-2-hydroxy-2-phenylethyl]piperidin-2-yl]-1-phenylethanol

C21H27NO2 (325.2042)


   

(2r,3r,4s,5s,6r)-2-{[(4e,6s,7r,12e)-1,7-dihydroxytetradeca-4,12-dien-8,10-diyn-6-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2r,3r,4s,5s,6r)-2-{[(4e,6s,7r,12e)-1,7-dihydroxytetradeca-4,12-dien-8,10-diyn-6-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C20H28O8 (396.1784)


   

(2r,3r,4s,5s,6r)-2-{[(4e,6s,7r,12e)-1,7-dihydroxytetradeca-4,12-dien-8,10-diyn-6-yl]oxy}-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol

(2r,3r,4s,5s,6r)-2-{[(4e,6s,7r,12e)-1,7-dihydroxytetradeca-4,12-dien-8,10-diyn-6-yl]oxy}-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol

C26H38O13 (558.2312)


   

2-[6-(2-oxo-2-phenylethyl)piperidin-2-yl]-1-phenylethanone

2-[6-(2-oxo-2-phenylethyl)piperidin-2-yl]-1-phenylethanone

C21H23NO2 (321.1729)


   

(1s)-2-[(2s,6s)-6-[(2s)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanol

(1s)-2-[(2s,6s)-6-[(2s)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanol

C22H29NO2 (339.2198)


   

1-phenyl-2-[(2s)-piperidin-2-yl]ethanone

1-phenyl-2-[(2s)-piperidin-2-yl]ethanone

C13H17NO (203.131)


   

(2r,3r,4r,5s,6r)-2-[(1,7-dihydroxytetradeca-4,12-dien-8,10-diyn-6-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

(2r,3r,4r,5s,6r)-2-[(1,7-dihydroxytetradeca-4,12-dien-8,10-diyn-6-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

C20H28O8 (396.1784)


   

2-[1-methyl-6-(2-oxo-2-phenylethyl)piperidin-2-yl]-1-phenylethanone

2-[1-methyl-6-(2-oxo-2-phenylethyl)piperidin-2-yl]-1-phenylethanone

C22H25NO2 (335.1885)


   

2-[(1,7-dihydroxytetradeca-4,12-dien-8,10-diyn-6-yl)oxy]-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol

2-[(1,7-dihydroxytetradeca-4,12-dien-8,10-diyn-6-yl)oxy]-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol

C26H38O13 (558.2312)


   

2-[(2s,6r)-6-[(2r)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone

2-[(2s,6r)-6-[(2r)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone

C22H27NO2 (337.2042)


   

2-[6-(2-hydroxy-2-phenylethyl)piperidin-2-yl]-1-phenylethanol

2-[6-(2-hydroxy-2-phenylethyl)piperidin-2-yl]-1-phenylethanol

C21H27NO2 (325.2042)


   

1-phenyl-2-(piperidin-2-yl)ethanone

1-phenyl-2-(piperidin-2-yl)ethanone

C13H17NO (203.131)


   

(4e,12e)-tetradeca-4,12-dien-8,10-diyne-1,6,7-triol

(4e,12e)-tetradeca-4,12-dien-8,10-diyne-1,6,7-triol

C14H18O3 (234.1256)


   

(2r,3r,4s,5s,6r)-2-{[(4e,6r,7r,12e)-1,7-dihydroxytetradeca-4,12-dien-8,10-diyn-6-yl]oxy}-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol

(2r,3r,4s,5s,6r)-2-{[(4e,6r,7r,12e)-1,7-dihydroxytetradeca-4,12-dien-8,10-diyn-6-yl]oxy}-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol

C26H38O13 (558.2312)


   

2-{[(4e,12e)-1,7-dihydroxytetradeca-4,12-dien-8,10-diyn-6-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

2-{[(4e,12e)-1,7-dihydroxytetradeca-4,12-dien-8,10-diyn-6-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C20H28O8 (396.1784)