Characterization of Limonoids Isolated from the Fruits of Melia toosendan and Their Antifeedant Activity against Pieris rapae

Abstract

We thank Prof. Dr. Jia-Mei Li in Henan Agricultural University for the identification of the plant material.The fruits of Melia toosendan SIEB. et ZUCC. (Meliaceae) are a source of bioactive limonoids that can be used as effective pesticides. In this study, two novel limonoids, 6-acetylsendanal and 6-ketocinamodiol, were isolated together with fourteen known compounds, namely four protolimonoids, six trichilin-class limonoids, and four Cseco limonoids. The structures of the new compounds were determined by extensive spectroscopic analyses (HR-ESI-MS, UV, IR, 1D and 2D NMR). The bioassay results revealed that eleven of the extracted limonoids exhibited interesting antifeedant activities against the larvae of Pieris rapae with AFC 50 values in the range of 0.11 -1.79 mM. Particularly, mesendanin H, with an AFC 50 value of 0.11 mM, exhibited a higher activity than the positive control toosendanin. Information on new bioactive limonoids may provide further insight into M. toosendan as a source of bioactive components.

Phytochemical Investigations and In Vitro Bioactivity Screening on Melia azedarach L. Leaves Extract from Nepal

“…Peak at 19.7 min with [M+H] + at m/z 613 was tentatively assigned to of salannal [17] . The main observed fragments were ions at m/z 553 (−60) corresponding to the loss of C 2 H 4 O 2 ascribable to neutral loss of acetic acid (substituent in C‐3) or methoxy formate moiety (chain in position C‐11); m/z 513 (−100) tiglic acid C 5 H 8 O 2 (C‐1), m/z 581 (−32) corresponding to the loss of formaldehyde (substituent at C‐4).…”

“…The chemical composition of M. azedarach is highly complex and have been subject to several investigations aimed to evaluate the presence of bioactive constituents [7,11–17] . Previous article revealed that leaves contains phenylpropanoids and flavonoids like myricetin, quercetin, kaempferol and isorhamnetin derivatives [13] .…”

“…Previous studies on the genus Melia have led to the isolation of a variety of structurally diverse compounds including triterpenoids, steroids, and limonoids. Limonoids have been mainly isolated from fruits and bark, showing the presence of highly diverse structures and broad range of bioactivities [17–21] . In this regard the information about the leaves composition of Nepalese M. azedarach are still scarce and the evaluation of the potential usefulness of such material as extraction source of bioactive constituents is still missing.…”

Antifeedant and Antifungal Activities of Metabolites Isolated from the Coculture of Endophytic Fungus Aspergillus tubingensis S1120 with Red Ginseng

“…The areas of the leaves consumed by the silkworm were measured by using piece together method, and the antifeedant activity (%) were calculated as the following [(CÀ T)/(C + T)] × 100, while C and T presented the consumed areas in the control and tested leaves, respectively. [16] Attraction rate ¼ ½ðTÀ CÞ=ðC þ TÞ� � 100…”

Limonoids From Choerospondias axillaris

“…Limonoids are widely found in leaves, bark, fruits, seeds, and kernels throughout the Meliaceae and Rutaceae. 1 This type of compound revealed various interesting biological effects such as antifeedant, 1,2 cytotoxic, 3,4 antibacterial, anti-human immunodeficiency virus, and human carboxylesterase 2 inhibitory 5 activities.…”