Yuehchukene, a Novel Anti-implantation Indole Alkaloid fromMurraya paniculata

Abstract

Yuehchukene, 11beta-(3'-indolyl-7,9alpha,9beta-trimethyl-5beta,8,9,10beta-tetrahydroindano-[2,3- B]indole, a novel dimeric indole alkaloid from the roots of MURRAY A PANICULATA has potent anti-implantation activity in rats at 3 mg/kg P. O. dosing on pregnancy day 2.

Highly Diastereoselective [3+2] Cyclopenta[b]annulation of Indoles with2‐Arylcyclopropyl Ketones and Diesters

“…Cyclopentannulation of the indole 1a with phenyl 2-phenylcyclopropyl ketone (2c), with lesser cationic stabilization in comparison with 2a, was investigated next. Thus, the reaction of 1a with 2c in the presence of either BF 3 ·Et 2 O or TiCl 4 or other Lewis acids [Yb(OTf) 3 , SnCl 4 ] failed to yield the corresponding cyclopentannulated indole adduct and the only product isolated (with either BF 3 ·Et 2 O or TiCl 4 ) was found to be the 1,4-diaryl-3,4-dihydrocarbazole 4c (Scheme 3), whereas with Yb(OTf) 3 /CH 3 CN the indole 1a was recovered unchanged even after prolonged reaction time (48 h). On the other hand, the corresponding 3-methylindole 1e underwent smooth cyclopentaannulation with ketone 2c to give the cycloadduct 6e in 85 % overall yield as mixture of two diastereomers 6eЈ and 6eЈЈ (2:1) (entry 11, Table 2).…”

“…[4][5][6] Recently a cyclopenta [b]indole derivative has been identified as a promising prostaglandin D 2 (PGD 2 ) receptor antagonist in the alleviation of various allergic disorders. [7] Another class of naturally occurring cyclopenta [b]indole alkaloids are represented by kopsane, [8] possessing an architecturally beautiful tetracyclic propellane type annulated indole substructure exhibiting cholinergic activity.…”

Antinociceptive and bioactivity of leaves of Murraya paniculata (L.) Jack, Rutaceae

“…Structural features of a water soluble gum polysaccharide from Murraya paniculata in fruits was shown by Mondal et al (2001). Kong et al (1985) demonstrated the presence of a novel anti-implantation indole alkaloid.…”

Chemical composition and evaluation of acute toxicological, antimicrobial and modulatory resistance of the extract ofMurraya paniculata

“…Leaves of the genus Murraya have been commonly used as flavoring agents in Indian curry preparations since ancient times. On phytochemical investigation, researchers have reported that Murraya leaves contain flavonoids (Zhang et al, 2011(Zhang et al, , 2012, cinnamates, and coumarins (Aziz et al, 2010;Ito et al, 2005;Kinoshita & Shimada, 2002;Saied et al, 2008;Shabbir et al, 1997), alkaloids (Kong et al, 2007), and volatile oils (Chowdhury et al, 2008). These leaves have been found to be useful for hepatoprotective (Sathaye et al, 2011), antidiabetic (Arulselvan et al, 2006;Tembhurne & Sakarkar, 2009, 2010b, antimicrobial (Gautam et al, 2012b;Sundaram, 2011), anti-inflammatory (Gupta et al, 2010;Mathur et al, 2011), wound healing (Patidar et al, 2010), and antidiarrheal (Mandal et al, 2010) purposes.…”