New Polyfunctional Phragmalin Limonoids from Neobeguea mahafalensis

Abstract

Neobeguea mahafalensis is used as a medicinal plant in Madagascar. A decoction of the stem bark of this species is reported to treat back pain. Recently, it was reported that a decoction of the root bark, containing two novel phragmalin limonoids as identified active constituents, exhibited an extraordinarily high potency and remarkably long duration in augmenting sexual activity in male rodents.From the dichloromethane extract of the root barks of N. mahafalensis, nine phragmalin limonoids were isolated, of which eight were novel compounds. The structures were established mainly by extensive use of 2D NMR spectroscopic techniques and high-resolution mass spectrometry. One of the new compounds named dodoguin displayed sleep-inducing activity in Swiss albino mice. The amount of 3-10 mg/kg of this compound induced sleep 18-22 min after its administration with a duration of 16-18 min.

Limonoids from Aphanamixis polystachya Leaves and Their Interaction with Hsp90

“…a Data measured in CDCl 3 ; b Overlapped signal; c Signal cannot be observed clearly from 1D and 2D NMR. Weak signals are due presumably to an instable hemiacetal function and tautomerism of the butenolide ring in solution tween H-2-C-8, H-9-C-8, H-11-C-14, H-17-C-14[17,18]. The HMBC correlations between δ 2.80/211.6 (H-2/C-30) and δ 3.85/ 211.6 (H-3/C-30) were in agreement with the presence of a keto group at C-30.…”

Research progress of meliaceous limonoids from 2011 to 2021

“…The rest, about a quarter of phragmalins, are isolated from 10 genera. 53,86,162,[183][184][185]191,199,206,213,[236][237][238]240,251,256,260,266,[303][304][305][306][307][308][309][310][311] The fragment of the ortho ester is one of the characteristics of phragmalin-class limonoids and only exists in phragmalins. Four classes of phragmalin orthoesters, 8,9,30-(C360-C399), 8,9,14-(C400, C445-C448), 8,9,11-(C401-C403, C420-C425), and 1,8,9-(C477-C599), have been summarized in previous reviews.…”

Chemistry and Biology of Novel Meliaceae Limonoids

“…Whereas in Toonacilianin H (396), the acetyl group from C6 to C12 are shuffled and C29 is acetylated. The acetyl group at C6 in Toonayunnanin J is deacetylated in Toonasinenine B (397). Ciliatasecone M (398) is a C12 hydroxy analog of compound (395).…”

“…At 1 µg/mL, compounds (1021, 1032, 1089, 1113, 1114, 1295, 1296, 1309) exhibited inhibitory activity against lipopolysaccharide induced NF-κB production in NF-κB luciferaseexpressing human embryonic kidney 293 (HEK293-NF-κB-luc) cells in vitro with relative inhibitory potency of 0.25, 0.18, 0.11, 0.23, 0.23, 0.10, 0.33, 0.69 respectively compared to positive control hydrocortisone with relative inhibitory value of 0.29 390 395,409,410,468,478 . In Swiss albino mice after 18-22 mins of administering 3-10 mg/kg of compound (1066) induced sleep with a duration of 16-18 min 397 . The in vivo pharmacological tests of compounds (1073, 1083), starting with a treatment from 0.004-0.4mg/kg/day for three consecutive days, over a three hour sampling period, induced a long-lasting augmentation of frequency and sustainment of mounting behavior in male rodents, with an effect lasting for up to 11 days post-treatment 400 .…”

“…. Compound (334, antiradical activities to the tested radical of 2,2-diphenyl-1picrylhydrazyl (DPPH) with IC 50 value of 73.1, 62.1, 59.2, 244.7, 51.3, 71.0, 104.0, 94.1, 99.7 μM respectively and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS .+ ) with IC 50 value of 167.3, 124.7, 119.8, 256.1, 109.7, 160.1, 52.2, 54.6 and 59.2 μM respectively while compounds(397,406,407) were inactive for antiradical activities to the tested radical of DPPH and ABTS .+214,62 . Compounds(382, …”