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]-alpha-L-arabinopyranoside, N(1), N(5), N(10)-tri-p-coumaroyl spermidine, N(1), N(5), N(10), N(14)-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. Among the isolated compounds, monocaffeoyl-tri-p-coumaroyl spermine showed the strongest free radical-scavenging activity, which was almost identical to that of alpha-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 alpha-tocopherol.
῍῍῍῍῍῍῍῍῍῍῍῍῍῍῍῍In order to develop a physiologically functional food material from Royal Jelly (RJ) proteins precipitated by ethanol, we tried to hydrolyze them using various proteases. As a result of *.. wtῌ-, h Orientase ONS hydrolysis treatment of ethanol-insoluble RJ proteins at /*, a newly obtained hydrolysate exhibited strong angiotensin I-converting enzyme (ACE) inhibitory activity (IC/* : *.*2, mg/ml). Singledose, oral administration of the hydrolysate (+ g/kg of rat weight) in +--week spontaneously hypertensive rats resulted in a significant reduction in the systolic blood pressure of ca. +, mmHg (P*.*/) at , and 0 h after administration. By performing gel permeation chromatography of the hydrolysate, followed by reversed phase HPLCs, eight ACE inhibitory peptides were isolated and identified. Trp-Val-Leu (IC/* : -,.. ῌM) and Tyr-Tyr-Ser-Pro (IC/* : +.-ῌM) were identified from natural resources for the first time. Some of the ACE inhibitory peptides were derived from the RJ-glycoprotein. Consequently, ethanol-insoluble RJ protein is thought to be a good resource as an antihypertensive food material. ̲῎Ώ̲ῳ´῎ ῐRJ, Apis mellifera Lῑ ῥQῙῖ̰̯Ὺ ̯ ῡQ̯̮̰ΊῠῗQ̰Ὺῌ ̯ῤῬ̱ῶ῎̲ ̯Q̳ ̮ῗ ῧ̰ QῢῡΰQῙΰῠῪ̯̮̰ +ῑ ῍ ῖῌ Ῐ Ῥ΅QQQΰQQ῞̰Ῥ̱ῶ῎̲̯Q̱̲ῷ`QQ̰ ῐ̲Qῌ Ῥ̱ῶ῎̲̯Q RJ ̳̮ῠῦQῑ ῥQ̮ΰΰῠ Ὺ̯̮ῢ̮ῤῗQQ̯̮̰῍ ̯Q RJ ῤ῟ῤQῠῠ῝̯ῥQQ̰Qῠ ,ῑ-ῑ ῌ Q̲Q Qῠ -ῑ.ῑ ῢῡῗ̮QῪ̯̮̰ῌ Q̯̰Q̲Q Qῠΰῥ +*ῌῸ̲΅ῌ,ῌ̱ῲ̲Q̰ῴῼ̲ῌ,ῌ῭`̱̲Qῗ῟ ῤQ̮ῠ῝̯Q̯῝̯̮̰ -ῑ.ῑ ῍ Ίῤ̰̮ΰῌ ̱ῲ̲QQῤ Ῥ̱ῶ῎̲ ̯QQ̮ῤQῤQῠΰ̯̮̯ῤQQῥQῩ̰ Ὺ̯̮̰̰ῤῤῌ RJ ῤQ῏QQῠ῝̯ῤQQQ̳ῥQ ΰ̯̮̯ῦῖ̰̯̮̰ῌ ῙΰῠQ̮̯̮̰Ῥ̱ῶ῎̲̯ Q RJ ̳̮ΰ̯̮̯̰QQῨῥ̳Ὶ̯̮̰῍ ΊῪῧ̯ῌ QQQQ̯ῥῙΰῠQQῤQQ῏ ΎQῠ ῝̯ῌ Q̮̳QQΰ̰̰̱̲ῷ`Qῖ̰ῤQ̮QῺΌ̱ ῤQQΎQῨ̯Ῐ̯ /ῑ῏1ῑ ῍ ̱̲ῷ`QῤQ̮QῺΌ̱ ῥQΰQ῞̰̯̳QΎQQ῟̰̯Ὶ̯ῢῙῌ ῍QῤῺ Ό̱ΰ̰̰QQ̲̳QQῠῗQQῪ̰ 1ῑ ῍ ῞̯ΰῸῴ QQ̯Q̮QῺΌ̱ΰ̰̰Q̲Q QῠΎQQ῝̯Ῐ ̯ 2ῑ ῗῌ RJ ̱̲ῷ`Qΰ̯̮̯̰Q QQΰ̰̰ Q̮ ̳̮ῗQQ̲QQΐQῼ̱ῴ ῐSHRῑ ῤQ̲Ύ̯̲ΰQ ῟̰ΊῠΎΊ̰ῖΰ῝̯̮̰ 3ῑ ῍ RJ ̱̲ῷ`QῤQ̲Q Qῠΰ̯̮̯ῥ Tokunaga ̰ +*ῑ ̰ῌ̯ῤ̮QΎ῝̯̮ ̰ῌ RJ ̱̲ῷ`QQΰῥQ̲Q QῠΎ̯῞̰ῺΌ̱ ῑῩῗQQ῞̰ΊῠῗΊ̰ῖῠῢ̰̯̯̮̰῍ ̯Ί̯ῌ Ῐ̮Q̯ῥ RJ ̱̲ῷ`Qῤ̯῞̰Q̲Q Q ῠΎΰῠQῥῤQ̮Ῥ̱ῶ῎̲̯Q RJ ̳̮ΰQῩῌ Q̮̳̮ῤQQῠQ̯ῺΌ̱ῤῌQΎQῨ̯῍ * ̮ ̮2+,ῌ2/2+ ̮ Q̮ QQQῒQ 0ῌ+*ῌ+
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