Jacobine

Names

[ Name ]:
Jacobine

[Synonym ]:
(15R,20S)-15,20-Dihydro-15,20-epoxy-12-hydroxysenecionan-11,16-dione

Biological Activity

[Description]:

Jacobine is a pyrrolizidine alkaloid (PA) from Senecio jacobaea[1]. Jacobine is active against second instar larvae of thrips[2].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Others >> Others

[In Vitro]

Pyrrolizidine alkaloids (PAs) at plant concentration reduce thrips survival on average with 21%. Structurally related PAs affect survival of thrips differently. PA free bases reduce thrips survival more than the corresponding PA N-oxides[1][2].

[References]

[1]. Xiaojie Liu,et al.The effect of structurally related metabolites on insect herbivores: A case study on pyrrolizidine alkaloids and western flower thrips.Phytochemistry. 2017 Jun;138:93-103.

[2]. Mirka Macel,et al. Variation in pyrrolizidine alkaloid patterns of Senecio jacobaea. Phytochemistry. 2004 Apr;65(7):865-73.

Chemical & Physical Properties

[ Density]:
1.33g/cm3

[ Boiling Point ]:
574.1ºC at 760 mmHg

[ Melting Point ]:
228ºC

[ Molecular Formula ]:
C₁₈H₂₅NO₆

[ Molecular Weight ]:
351.39400

[ Flash Point ]:
301ºC

[ Exact Mass ]:
351.16800

[ PSA ]:
88.60000

[ LogP ]:
0.34190

[ Index of Refraction ]:
1.583

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NY5775000

CHEMICAL NAME :: Jacobine

CAS REGISTRY NUMBER :: 6870-67-3

BEILSTEIN REFERENCE NO. :: 0054580

LAST UPDATED :: 199612

DATA ITEMS CITED :: 10

MOLECULAR FORMULA :: C18-H25-N-O6

MOLECULAR WEIGHT :: 351.44

WISWESSER LINE NOTATION :: T55-12- 1A Q EN IOVX OVO BUTJ M1 NQ N1 K-& BT3OX CHJ C1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 77 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory stimulation

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 60 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: Sex chromosome loss and nondisjunction

TYPE OF TEST :: DNA damage

MUTATION DATA

TYPE OF TEST :: Unscheduled DNA synthesis

TEST SYSTEM :: Rodent - rat Liver

DOSE/DURATION :: 1 umol/L

REFERENCE :: CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 45,3125,1985 *** REVIEWS *** IARC Cancer Review:Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 10,275,1976 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 10,275,1976 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987 TOXICOLOGY REVIEW CTRRDO Cancer Treatment Reports. (Washington, DC) V.60-71, 1976-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 60,1171,1976

Safety Information

[ RIDADR ]:
UN 1544

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)