NCBI Taxonomy: 46447

Crotalaria incana (ncbi_taxid: 46447)

found 9 associated metabolites at species taxonomy rank level.

Ancestor: Crotalaria

Child Taxonomies: Crotalaria incana subsp. purpurascens

Senecionine

(1,6)Dioxacyclododecino(2,3,4-gh)pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-5,6-dimethyl-, (3Z,5R,6R,14aR,14bR)-

C18H25NO5 (335.1733)


Senecionine is a pyrrolizidine alkaloid isolated from the plant species of the genus Senecio. It has a role as a plant metabolite. It is a lactone, a pyrrolizidine alkaloid and a tertiary alcohol. It is functionally related to a senecionan. It is a conjugate base of a senecionine(1+). Senecionine is a natural product found in Dorobaea pimpinellifolia, Crotalaria micans, and other organisms with data available. Senecionine is an organic compound with the chemical formula C18H25NO5. It is classified as a pyrrolizidine alkaloid. See also: Petasites hybridus root (part of); Tussilago farfara flower (part of); Tussilago farfara leaf (part of). A pyrrolizidine alkaloid isolated from the plant species of the genus Senecio. D000970 - Antineoplastic Agents Annotation level-1 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2251 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 122 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 102 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 142 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 152 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 162 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 172 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 132 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 112 [Raw Data] CB082a_Senecionine_pos_40eV_CB000034.txt [Raw Data] CB082a_Senecionine_pos_10eV_CB000034.txt [Raw Data] CB082a_Senecionine_pos_30eV_CB000034.txt [Raw Data] CB082a_Senecionine_pos_20eV_CB000034.txt [Raw Data] CB082a_Senecionine_pos_50eV_CB000034.txt Senecionine (Senecionan-11,16-dione, 12-hydroxy-) is a pyrrolizidine alkaloid could be isolated from Senecio vulgaris. Senecionine decreases the activities of glutathione S-transferase, aminopyrine demethylase and arylhydrocarbon hydroxylase (AHH)[1][2][3]. Senecionine (Senecionan-11,16-dione, 12-hydroxy-) is a pyrrolizidine alkaloid could be isolated from Senecio vulgaris. Senecionine decreases the activities of glutathione S-transferase, aminopyrine demethylase and arylhydrocarbon hydroxylase (AHH)[1][2][3].

   

Retrorsine

(1R,4Z,6R,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione

C18H25NO6 (351.1682)


Retrorsine is a naturally occurring toxic pyrrolizidine alkaloid found in certain plants. Despite its toxicity, it may have several biological functions, both in the plants that produce it and in the organisms that ingest it. Here are some possible biological functions of Retrorsine: Defense Mechanism: In plants, Retrorsine likely serves as a chemical defense against herbivores and pathogens. Its toxicity can deter animals from feeding on the plant and can inhibit the growth of microbial pathogens. Allelopathy: Retrorsine may be involved in allelopathy, which is the process by which plants release chemicals into the environment to inhibit the growth of competing plants. This can help the producing plant secure resources such as light, water, and nutrients. Insecticidal Properties: The compound may have insecticidal properties, helping to protect the plant from insect pests. Medicinal Uses: In traditional medicine, plants containing Retrorsine have been used for their supposed medicinal properties, although the use is cautioned due to the compound's toxicity. Ecological Role: Retrorsine may play a role in the ecological interactions of the plant, affecting the behavior and population dynamics of herbivores and other organisms in the ecosystem. Cell Cycle Inhibition: In biological systems, Retrorsine has been shown to inhibit cell proliferation, particularly in liver cells. This property is of interest in medical research for understanding liver toxicity and cancer. Genotoxic Effects: Retrorsine can bind to DNA, causing genotoxic effects. This can lead to mutations and has implications for cancer research. Pharmacological Research: Due to its biological activity, Retrorsine is used in pharmacological research to study the mechanisms of toxicity, carcinogenesis, and potential therapeutic targets. It's important to note that while Retrorsine has these potential biological functions, its toxicity makes it hazardous to humans and animals, and it is not used in modern medicine due to the risks associated with its ingestion. Research on Retrorsine is typically focused on understanding its mechanisms of action and toxicity to inform safety guidelines and potential therapeutic applications. Origin: Plant; SubCategory_DNP: Alkaloids derived from ornithine, Pyrrolizidine alkaloids relative retention time with respect to 9-anthracene Carboxylic Acid is 0.363 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.358 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.361 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2325 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 177 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 117 INTERNAL_ID 147; CONFIDENCE Reference Standard (Level 1) CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 147 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 137 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 157 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 167 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 127 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 107 D000970 - Antineoplastic Agents Retrorsine is a naturally occurring toxic pyrrolizidine alkaloid. Retrorsine can bind with DNA and inhibits the proliferative capacity of hepatocytes. Retrorsine can be used for the research of hepatocellular injury[1][2]. Retrorsine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=480-54-6 (retrieved 2025-03-17) (CAS RN: 480-54-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

   

Anacrotine

MS000021518

C18H25NO6 (351.1682)


   

(1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione

4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione

C18H25NO6 (351.1682)


   

Integerrimine

4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione

C18H25NO5 (335.1733)


   

4-Ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione

4-Ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione

C18H25NO5 (335.1733)


   

4-ethylidene-7,16-dihydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione

4-ethylidene-7,16-dihydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione

C18H25NO6 (351.1682)


   

(1s,4z,7s,17s)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione

(1s,4z,7s,17s)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione

C18H25NO5 (335.1733)


   

(1r,4z,6r,7s,16s,17s)-4-ethylidene-7,16-dihydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione

(1r,4z,6r,7s,16s,17s)-4-ethylidene-7,16-dihydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione

C18H25NO6 (351.1682)