NCBI Taxonomy: 462520

Senecio deferens (ncbi_taxid: 462520)

found 15 associated metabolites at species taxonomy rank level.

Ancestor: Senecio

Child Taxonomies: none taxonomy data.

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).

   

Senecionine N-oxide

(1R,4Z,6R,7R,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-14-oxido-2,9-dioxa-14-azoniatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione

C18H25NO6 (351.1682)


CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2301 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 146 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 176 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 116 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 136 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 166 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 156 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 106 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 126 Senecionine n-oxide is the primary product of pyrrolizidine alkaloid biosynthesis in root cultures of Senecio vulgaris. Senecionine N-oxide has anti-cancer activity

   

Senkirkin

Senkirkine

C19H27NO6 (365.1838)


CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 178 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 168 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 158 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 148 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 138 INTERNAL_ID 138; CONFIDENCE Reference Standard (Level 1) CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 128 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 118 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 108 INTERNAL_ID 2283; CONFIDENCE Reference Standard (Level 1) CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2283

   

Usaramine

(15E)-12,18-Dihydroxysenecionan-11,16-dione

C18H25NO6 (351.1682)


Usaramine is a pyrrolizidine alkaloid isolated from seeds of Crolatalaria pallida. Usaramine demonstrates a highlighted antibiofilm activity against Staphylococcus epidermidis by reducing more than 50\\% of biofilm formation without killing the bacteria[1]. Usaramine is a pyrrolizidine alkaloid isolated from seeds of Crolatalaria pallida. Usaramine demonstrates a highlighted antibiofilm activity against Staphylococcus epidermidis by reducing more than 50\% of biofilm formation without killing the bacteria[1].

   

Senecionine N-oxide

4-ethylidene-7-hydroxy-6,7-dimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium-14-olate

C18H25NO6 (351.1682)


   

12-Hydroxysenecionan-11,16-dione 4-oxide

(5R,6R,9a1R,14aR,Z)-3-ethylidene-6-hydroxy-5,6-dimethyl-2,7-dioxo-2,3,4,5,6,7,9,9a1,11,13,14,14a-dodecahydro-12H-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine 12-oxide

C18H25NO6 (351.1682)


Senecionine N-oxide is a tertiary amine oxide. It is functionally related to a senecionine. Senecionine N-oxide is a natural product found in Dorobaea pimpinellifolia, Senecio gallicus, and other organisms with data available. Senecionine n-oxide is the primary product of pyrrolizidine alkaloid biosynthesis in root cultures of Senecio vulgaris. Senecionine N-oxide has anti-cancer activity[1][2].

   
   

Senecionine N-oxide

Senecionine N-oxide

C18H26NO6+ (352.176)


   

Renardin

2,9-DIOXA-14-AZABICYCLO(9.5.1)HEPTADEC-11-ENE-3,8,17-TRIONE, 4-ETHYLIDENE-7-HYDROXY-6,7,14-TRIMETHYL-, (1R,4Z,6R,7R)-

C19H27NO6 (365.1838)


Senkirkine is a macrolide. Senkirkine is a natural product found in Tussilago farfara, Senecio gallicus, and other organisms with data available. See also: Petasites hybridus root (part of); Tussilago farfara flower (part of); Tussilago farfara leaf (part of).

   

1ST40320

(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-6-(hydroxymethyl)-5-methyl-, (3Z,5R,6S,14aR,14bR)-

C18H25NO6 (351.1682)


Retrorsine is a macrolide. Retrorsine is a natural product found in Crotalaria spartioides, Senecio malacitanus, and other organisms with data available. 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 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

retrorsine

C18H25NO6 (351.1682)


Annotation level-1

   

(1r,4z,6s,7r,11z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione

(1r,4z,6s,7r,11z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione

C19H27NO6 (365.1838)


   

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

(1s,4e,6s,7r,17s)-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)


   

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

(1r,6r,7s,17s)-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)