A New Pyrrole Alkaloid from Leccinum Extremiorientale

Abstract

Leccinum extremiorientale for the first time. Their structures were identified on the basis of 1D and 2D NMR spectroscopy as well as MS.Keywords: Leccinum extremiorientale, pyrrole alkaloids, 2-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl] acetic acid.Leccinum extremiorientale belongs to the higher fungus of the genus Leccinum in the family Boletaceae and grows worldwide, especially in the northern temperate zone. It is distributed mainly in Sichuan, Hubei, Yunnan, Guizhou, Guangxi, Tibet, and other places of China [1]. L. extremiorientale, commonly known as "Huanglaitou" in Chinese, is a very tasty mushroom. The exhaustive study on chemical constituents of some species in this family Boletaceae has been carried out [2][3][4][5]. Previous research on the chemical constituents of L. extremiorientale showed the presence of natural products including steroids, alkaloids, and monosaccharides [6,7]. In order to find new bioactive compounds from the genus Leccinum, a further chemical investigation of L. extremiorientale was carried out, which led to the first isolation of three pyrrole alkaloids, including a new one 2-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl] acetic acid (1) from the ethyl acetate extract of this fungus. This paper describes the isolation and structural elucidation of the new pyrrole alkaloid.Compound 1 was isolated as a white crystals and possessed the molecular formula C 9 H 11 NO 4 as established by HR-EI-MS (m/z 197.0690 [M] + ) and 13 C NMR spectra, indicating five unsaturation degrees. Its IR absorption bands at 1735 and 1683 cm -1 showed the presence of a carboxylic acid and an aldehyde group, respectively. The 1 H NMR spectrum of 1 (Table 1) showed one methoxyl singal [G 3.28 (3H, s)], two olefinic proton signals [G 7.01 (1H, d, J = 4.0 Hz), 6.31 (1H, d, J = 4.0 Hz)], and one aldehyde signal [9.45 (1H, s)]. The 13 C NMR and DEPT spectra (Table 1) of 1 displayed nine carbon resonances, including one methoxyl, two methylenes (one oxygenated), three methines (two olefinic), and three quaternary carbons.

Identification of a Novel Pyrrole Alkaloid from the Edible Mushroom Basidiomycetes-X (Echigoshirayukidake)

“…In contrast, compounds I and III were reported as active ingredients in the fruits of Lycium chinense [ 8 ] and Morus alba [ 11 ] that have hepatoprotective and macrophage activation functions, respectively. Compound I is also found in mushrooms such as Leccinum extremiorientale [ 12 ] and Inonotus obliquus [ 13 ]. Recently, the same types of pyrrole alkaloid derivatives have been isolated from the fruiting bodies of another edible mushroom Phlebopus portentosus [ 14 ], and it has been reported that they significantly attenuated H 2 O 2 -induced cell damage in human neuroblastoma SH-SY5Y cells [ 14 ].…”

2-Formylpyrrole natural products: origin, structural diversity, bioactivity and synthesis

“…4-(2-Formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl)butanoic acid (PBA) (65) was rst isolated from kako-bushi-matsu, a thermally processed Aconitum japonicum root product used in oriental medicine for its analgesic, diuretic and cardiac effects. 58 PBA (65) has been isolated no fewer than eleven times, [4][5][6][7]34,41,[58][59][60][61][62] and its methyl ether 66 no fewer than eight, [6][7][8]34,38,46,63,64 from both plant and fungal sources. The yield of PBA (65) from kako-bushi-matsu, which is prepared by autoclaving Aconitum roots at 110 C, was determined to be 10-fold greater than the yield of PBA (65) from Aconitum roots dried at 50-55 C. 58 This observation is consistent with the proposal that PBA is the product of Maillardtype reactions.…”

Determination of 8 Endogenous Alkaloid Components inBoletusUsing Ultrahigh-Performance Liquid Chromatography Combined with Quadrupole-Time of Flight Mass Spectrometry

“…Due to a wide variety of secondary metabolites from fungus and their biological activities, extensive attention has been paid to the researches of fungus both in China and abroad [2]. Boletus is popular because of its delicious taste, appreciated nutrition value [3], and a variety of medicinal effects [4]. e chemical composition of the Boletus was mainly terpenes, flavonoid [5], phenols [6], and alkaloids, which possessed comprehensive biological activities, such as antioxidant, antifatigue, antitumor, and anti-inflammatory [7,8].…”