Mahanine

Catalog Number	ACM28360498
CAS Number	28360-49-8
Synonyms	(3R)-3,11-Dihydro-3,5-dimethyl-3-(4-methyl-3-penten-1-yl)pyrano[3,2-a]carbazol-9-ol
Molecular Weight	347.4
InChI	InChI=1S/C23H25NO2/c1-14(2)6-5-10-23(4)11-9-18-21-19(12-15(3)22(18)26-23)17-8-7-16(25)13-20(17)24-21/h6-9,11-13,24-25H,5,10H2,1-4H3/t23-/m1/s1
InChI Key	DWMBXHWBPZZCTN-HSZRJFAPSA-N
Purity	95%+
Complexity	581
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	1
Exact Mass	347.18852904
Heavy Atom Count	26
Hydrogen Bond Acceptor Count	2
Hydrogen Bond Donor Count	2
Isomeric SMILES	CC1=CC2=C(C3=C1O[C@](C=C3)(C)CCC=C(C)C)NC4=C2C=CC(=C4)O
Monoisotopic Mass	347.18852904
PhysicalState	Powder
Rotatable Bond Count	3
Topological Polar Surface Area	45.2 Ų

Case Study

Action Mechanism of Mahanine as a Mitochondrial Complex III Inhibitor

Bhattacharya, Kaushik, et al. American journal of cancer research, 2014, 4(6), 629.

This work confirmed electron transport chain (ETC) complex III as one of the possible potential targets of mahanine, which has potent anti-GBM (glioblastoma multiforme) activity in both in vitro and in vivo models. Its mechanism of action includes the following aspects:
· Mahanine has the ability to cause G0/G1 arrest in GBM cells by increasing intracellular ROS through inhibition of mitochondrial ETC. This rise in ROS leads to activation of DNA damage response (DDR), resulting in upregulation of Chk1/Chk2 which are crucial for G0/G1 arrest. NAC-mediated scavenging of ROS generation decreased the likelihood of G0/G1 phase arrest in GBM cells induced by mahanine.
· Knockdown of Chk1/Chk2 also impacts the cell cycle inhibitory effects of mahanine. In addition to cyclin D1/cyclin D3, CDK4/CDK6 and CDC25A being downregulated during G0/G1 arrest, mahanine's ability to induce G0/G1 phase restriction has been confirmed in an in vivo mice model. Complex-III inhibition by mahanine leads to increased ROS production in hypoxia, resulting in higher G0/G1 arrest.
· Furthermore, GBM cells treated with mahanine show reduced tumor formation in vivo, decreased migration, formation of intracellular tube-like structures, and increased susceptibility to differentiation into astrocyte-like cells.

Mahanine Enhances Glucose Uptake in Skeletal Muscle and Adipocytes

Nooron, Nattakarn, et al. Biochemical and biophysical research communications, 2017, 494(1-2), 101-106.

Mahanine is a carbazole alkaloid with multiple biological activities, including anti-tumor, anti-inflammatory, antioxidant and anti-diabetic activities. This work investigated the effects of mahanine on glucose uptake and glucose transporter 4 (GLUT4) translocation in skeletal muscle and adipocytes. The results indicate that Mahanine has anti-diabetic potential to treat diabetes.
Glucose-lowering mechanism of mahanine
· Using a fluorescent glucose analogue (2-NBDG), the impact of mahanine on glucose uptake into the cell was investigated. Treatment with mahanine led to a dose-dependent increase in glucose uptake in L6 myotubes and adipocyte cells through activation of the Akt signaling pathway.
· The role of mahanine in insulin-signaling pathways was also analyzed. The study revealed that mahanine-induced Akt activation was reversed when co-treated with wortmannin, an Akt inhibitor.
· To assess the effect of mahanine on GLUT4 translocation to the cell membrane, western blot analysis was conducted. It was observed that mahanine significantly boosted the translocation of GLUT4 to the plasma membrane in L6 myotubes. Both insulin and mahanine were found to enhance GLUT4 translocation, with insulin leading to a 2.06±0.40 times increase and mahanine resulting in a 1.42±0.07 times increase compared to the control.

Custom Q&A

What is the chemical formula for Mahanine?

The chemical formula for Mahanine is C23H25NO2.

What is the molecular weight of Mahanine?

The molecular weight of Mahanine is 347.45.

What is the CAS number for Mahanine?

The CAS number for Mahanine is 28360-49-8.

What is the predicted boiling point of Mahanine?

The predicted boiling point of Mahanine is 548.0±50.0 °C.

What is the predicted density of Mahanine?

The predicted density of Mahanine is 1.168±0.06 g/cm3.

What is the pka value of Mahanine?

The pka value of Mahanine is 10.11±0.40.

What is the melting point of Mahanine?

The melting point of Mahanine is 100- loC.

What is the specific rotation of Mahanine?

Mahanine is laevorotatory, having [α]D - 24.4°.

What functional groups are present in Mahanine?

Mahanine contains two methyl groups, one phenolic hydroxyl, an imino group, and an unsaturated side chain.

Where else can Mahanine be found other than being synthesized?

Mahanine also naturally occurs in the leaves of Murraya koenigii Spreng.

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