N1,N5,N10-(E)-tri-p-coumaroylspermidine

Natural Product Research, 2007, 21(8):726-732.

Antioxidant hydroxycinnamic acid derivatives isolated from Brazilian bee pollen.[Pubmed: 17616901]

One novel and three known hydroxycinnamic acid derivatives having antioxidant activities were isolated from a Brazilian bee pollen. They were identified as kaempferol 3-O-[2-O-p-coumaroyl]-α-L-arabinopyranoside, N1,N5,N10-tri-p-coumaroyl spermidine（N1,N5,N10-(E)-tri-p-coumaroylspermidine）, N1,N5,N10,N14-tetra-p-coumaroyl spermine, and monocaffeoyl-tri-p-coumaroyl spermine, respectively. The structure of the kaempferol glycoside was established on the basis of spectroscopic and chemical investigations.
CONCLUSIONS:
Among the isolated compounds, monocaffeoyl-tri-p-coumaroyl spermine showed the strongest free radical-scavenging activity, which was almost identical to that of α-tocopherol. On the other hand, the antioxidant effect of tri-p-coumaroyl spermidine on autooxidation of linoleic acid was strongest and nearly equal to that of α-tocopherol.

Journal of Agricultural & Food Chemistry, 1999, 47(3):1223.

Lipid, polyamide, and flavonol phagostimulants for adult western corn rootworm from sunflower (Helianthus annuus L.) pollen.[Pubmed: 10552441]

METHODS AND RESULTS:
Adult Diabroticites including western corn rootworm (WCR), Diabrotica virgifera virgifera LeConte, consume pollen of corn, squash, sunflower, and other species. Short-chain neutral amino acids in methanol-water extracts of pollen have been previously identified in our laboratory as strong phagostimulants for Diabrotica. Bioassay-driven fractionation was used to characterize the interacting lipid and midpolarity phagostimulants for adult WCR in Giant Gray Stripe sunflower, Helianthus annuus L., pollen. Lipids rich in omega3-linolenic acid including triglycerides, free fatty acids, phosphatidylethanolamines, phosphatidic acids, and phosphatidylcholines were highly phagostimulatory. Other important phagostimulatory components included a hydroxycinnamic acid-polyamine amide, N(1),N(5),N(10)-tri[(E)-p-coumaroyl]spermidine(N1,N5,N10-(E)-tri-p-coumaroylspermidine), and a flavonol, quercetin beta-3-O-glucoside.
CONCLUSIONS:
The structural characteristics of these phagoactive compounds and their role in the pollinivory specialization of rootworm beetles are discussed.