Lupanine

Catalog Number	ACM550903
CAS Number	550-90-3
Structure
Synonyms	2-Oxosparteine
Molecular Weight	248.36
InChI	InChI=1S/C15H24N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h11-14H,1-10H2/t11-,12-,13-,14+/m0/s1
InChI Key	JYIJIIVLEOETIQ-XDQVBPFNSA-N
Melting Point	40-44 °C
Purity	95%+
Complexity	356
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	4
Exact Mass	248.188863393
Heavy Atom Count	18
Hydrogen Bond Acceptor Count	2
Hydrogen Bond Donor Count	0
Isomeric SMILES	C1CCN2C[C@@H]3C[C@H]([C@@H]2C1)CN4[C@@H]3CCCC4=O
Monoisotopic Mass	248.188863393
PhysicalState	Oil
Rotatable Bond Count	0
Topological Polar Surface Area	23.6 Ų

Case Study

Value-Added Biotransformation of Lupanine Through Degrading Strains

Parmaki, Stella, et al. Chemosphere, 2018, 193, 50-59.

Lupanine can act as a growth inhibitor for monocots and a promoter for dicots. The study explored the potential production capacity of lupanine by specific bacterial strains through biodegradation and biotransformation into a series of alkaloid-derived molecules (such as 17-oxolupanine).
Isolation of strains and microbial cultures with lupanine
· A basic growth medium (M9) was utilized for subcultures of microorganisms, with the following composition (g L-1): Na2HPO4·2H2O 8.5, KH2PO4 3.0, NaCl 0.5, NH4Cl 0.5, MgSO4 0.24, and lupanine 1.5. Microbial strains capable of utilizing lupanine as the primary carbon source were isolated from four different environmental samples.
· The inoculum was pregrown overnight at 31 °C in M9 supplemented with 1.5 g L-1 of lupanine. Aerobic strains were incubated in 100 mL flasks (with 25 mL working volume) while anaerobic strains were incubated in 35 mL serum bottles (with 25 mL working volume) in a shaking incubator at 100 rpm.
· Duplicate aerobic cultures were prepared by inoculating 3 mL of the pregrown cells into 500 mL flasks (with 150 mL working volume), while anaerobic cultures were prepared in a similar manner using 250 mL serum bottles (with 180 mL working volume). Anaerobic conditions were achieved by flushing the serum bottles with CO2.

Study on the Mechanism of Lupanine Improving Blood Glucose Homeostasis

Wiedemann, Mats, et al. Molecules, 2015, 20(10), 19085-19100.

The study investigated the effects of lupanine on pancreatic β-cell electrical activity, insulin secretion, and insulin gene expression. Additionally, the effects of lupanine on glucose tolerance and insulin sensitivity were tested in an in vivo model of type 2 diabetes. The effects of lupanine on pancreatic beta cells and animal models of type 2 diabetes include the following important aspects.
· To characterize the acute effects of lupanine, 20 mg/kg body weight (BW) of the alkaloid was administered orally to non-diabetic and diabetic rats. Results show that lupanine reduces plasma glucose concentrations and improves glycemic control in an in vivo diabetes model.
· Islets were stimulated with 8 and 15 mmol/L glucose in the presence or absence of lupanine. The results show that lupine increases glucose-induced insulin release.
· To examine whether the stimulatory effects of alkaloids are mediated through effects on the stimulation-secretion cascade, measurements of ion currents and plasma membrane potential (Vm) were performed. The results showed that lupanine reduced the current through KATP channels and altered the electrical activity of beta cells.
· In vivo studies have shown that lupanine improves glucose homeostasis in STZ diabetic animals but not in normoglycemic control animals.

Custom Q&A

How is lupanine used in biological studies?

Lupanine is used in biological studies with quinolizidine alkaloids in seeds of lupin genotypes of different origins.

What are some synonyms of lupanine?

Some synonyms of lupanine are 2-Oxosparteine, d-Lupanine, Lupanin, LUPANINE(SH), and 7,14-Methano-2H,11H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-11-one,dodecahydro-, (7S,7aR,14S,14aS)-.

What is the CAS number of lupanine?

The CAS number of lupanine is 550-90-3.

What is the molecular formula of lupanine?

The molecular formula of lupanine is C15H24N2O.

What is the molecular weight of lupanine?

The molecular weight of lupanine is 248.36.

What is the melting point of lupanine?

The melting point of lupanine is 40-44°.

What is the boiling point of lupanine?

The boiling point of lupanine is bp3 190-193°.

What is the density of lupanine?

The density of lupanine is 0.9789 (rough estimate).

What is the refractive index of lupanine?

The refractive index of lupanine is nD24 1.5444.

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