Aphanamixins A–F, Acyclic Diterpenoids from the Stem Bark of <i>Aphanamixis polystachya</i>

Abstract

Six new acyclic diterpenoids named Aphanamixins A-F (1-6), together with two known compounds of nemoralisin and nemoralisin C, were isolated from the stem bark of Aphanamixis polystachya (WALL) J. N. BARKER. Their structures were established through a comprehensive analysis of NMR spectroscopic data and high resolution mass spectrometric data. The absolute configurations of carbon stereocenters were determined by means of auxiliary chiral α-methoxy-α-(trifluoromethyl)phenylacetic acid (MTPA) derivatives and circular dichroism (CD), respectively. All the new isolates were tested for their antiproliferative activity against HepG2, AGS, MCF-7, and A-549 cancer cell lines and they exhibited weak cytotoxicities (IC 50 >10 µM). Moreover, we highlighted that the six new diterpenoids characterized by acyclic skeleton was rarely seen in nature.

New 2-Benzoxazolinone Derivatives with Cytotoxic Activities from the Roots of <i>Acanthus ilicifolius</i>

“…Previously, the extract of A. ilicifolius and 2-benzoxazolinone derivatives have been proved to possess anti-tumor effects. 2,9) In present research, the new isolates showed better antiproliferative activities than the three known ones, which might be affected by the existence of substituted benzoyl moiety in their structures. Additionally, the four new compounds showed activities differing in degrees, in which they exhibited most potent activities against HepG2.…”

Phytochemistry and Pharmacology of <i>Munronia</i> Genus (Meliaceae)

“…The further chemical investigation on this species gave six new limonoid compounds, i.e. munronins A-F (21)(22)(23)(24)(25)(26). In compounds 23-26, the side chains were relatively rare in limonoid compounds, which is α,βunsaturated lactone, α,β-unsaturated lactam, and alkyne groups, respectively [57].…”

“…Meanwhile, ceramides 96 and 97 showed negative activity against Pieris brassicae L. For azadirachtin, munroniamide (2) showed only 10% mortality while 95 showed 50% mortality (azadirachtin was 100% mortality). Furthermore, Qi et al [51] also reported antifeedant activity of limonoids and munronins A-E (21)(22)(23)(24)(25) showed moderate activity with a mortality rate of about 10-20%, meanwhile munronin F (26) showed negative. Azadirachtin was used as a positive control in all the experiment.…”

“…Meliaceae is well known as a source of diverse natural compounds with interesting biological activity. Some compounds including sesquiterpenoids [2][3][4][5][6][7], triterpenoids [8][9][10][11][12][13][14][15][16][17][18], diterpenoids [19][20][21], steroids [22][23][24][25], limonoids [26][27], alkaloids [28][29], lignan [30][31][32], flavaglines [33][34][35], and flavonoids [36][37] have been successively extracted from this family. Those isolated compounds showed interesting biological activities including cytotoxic [38][39][40][41], insecticidal [42][43], antimycobacterial [6], antifungal [44][45], antiinflammatory [9,[46]…”

Untargeted Metabolomic Approach to Determine the Regulatory Pathways on Salicylic Acid-Mediated Stress Response in Aphanamixis polystachya Seedlings

“…Aphanamixis contains many secondary metabolites in which terpenoids are predominant, followed by flavonoids and alkaloids [21]. Many compounds like aphanamixin [22], aphapolin A and B [23], aphagranol [24], polystanin, aphanalide, nemordisin, meliasenin, and agladupols [25], aphanamene C [26], rohithukine [27], amooranin [28], and aphanin [29] were isolated and characterized from this tree. To determine the action of SA in stressed conditions, A. polystachya seedlings were grown in a controlled condition and induced with SA.…”