Spermidine and Flavonoid Conjugates from Peanut (Arachis hypogaea) Flowers

Abstract

A new spermidine triamide derivative has been isolated from peanut flowers and identified as N (1)-acetyl- N (5), N (10)-di- p-( EE)-coumaroylspermidine on the basis of detailed analysis of NMR, MS, and UV data. Two other spermidine conjugates, N (1), N (5), N (10)-tri- p-( EEE)-coumaroylspermidine and di- p-( EE)-coumaroylspermidine, as well as four flavonoid conjugates (quercetin-3-glucoside, quercetin-3-glucuronide, isorhamnetin-3-glucoside, and isorhamnetin-3-glucuronide) that have been previously reported in organs of other plants, have been found in this study in peanut ( Arachis hypogaea L.), a representative of the Leguminosae family, for the first time. The dynamics of photoisomerization in the spermidine conjugates have been investigated.

Studies into the phenolic patterns of different tissues of pineapple (Ananas comosus [L.] Merr.) infructescence by HPLC-DAD-ESI-MS n and GC-MS analysis

“…The fragment ion at m/z 346 may result from the loss of 2-methoxy-4-vinylphenol (150 amu). A similar mass fragmentation has been previously proposed for N,N′-di-pcoumaroylspermidine isomers [39]. (c) assigned to S-p-coumaryl, S-coniferyl and Ssinapylglutathione, respectively.…”

“…Only the latter two compounds were reported previously as pineapple constituents [7,10] (39). Whilst the latter compound was previously reported to be a characteristic constituent of pineapple juice and the fruit, the structurally related S-coniferyl-L-cysteine is reported for the first time [7,9,10].…”

Isolation and identification of spermidine derivatives in tea (Camellia sinensis) flowers and their distribution in floral organs

“…13 C NMR (125 MHz, dissolved in CD 3 OD): p ‐coumaroyl systems: δ 169.2–169.4 (C‐9′, 9″, 9″′), 160.5–160.7 (C‐4′, 4″, 4″′), 144.4 (C‐7″), 141.8–142.2 (C‐7′, 7″′), 130.9 (C‐2″, 6″), 130.6 (C‐2′, 6′, 2″′, 6″′), 127.9 (C‐1″), 127.6–127.7 (C‐1′, 1″′), 118.5 (C‐8″′), 118.2/118.4 (C‐8′), 116.7/116.8 (C‐3′, 3″, 3″′, 5′, 5″, 5″′), 114.9 (C‐8″); spermidine system: δ 47.6/49.0 (C‐6), 45.7/47.0 (C‐4), 39.9/40.1 (C‐9), 37.9/38.2 (C‐2), 28.9/30.6 (C‐3), 27.9/28.0 (C‐8), 26.3/27.8 (C‐7). The NMR data agree with those published in the literature 11, 20…”

“…Moreover, several characteristic metabolites such as spermidine–phenolic acid conjugates present in tea flowers were identified and their distribution in floral organs was investigated. Spermidine–phenolic acid conjugates are a widely distributed group of plant secondary metabolites concentrated in the floral parts of plants 11–18. In the past few years, enormous strides have been made in understanding the diverse roles played by spermidine–phenolic acid conjugates in plants, including defence against wounding, pathogens and insects, floral induction, flower formation, sexual differentiation, tuberisation, cell division and cytomorphogenesis (reviewed by Facchini et al 19).…”

Composition of polyphenol and polyamide compounds in common ragweed (Ambrosia artemisiifolia L.) pollen and sub-pollen particles

“…6. Peak at retention time 2.93, with m/z of the [MÀH] À ion of 598.2573 showed characteristic fragmentation pattern (Sobolev et al, 2008) with fragments at m/z 478, attributed to the loss of 120 Da fragment from p-coumaric residue ([MÀH] À AHOAC6A H4ACH@CH), m/z 436 (loss of coumaroyl residue) and m/z 358 (loss of 120 Da fragment at N 5 and breakage of CAC bond of the caffeoyl residue linked at N 10 ). The compound was identified as di-coumaroyl caffeoyl spermidine.…”