Leccinine A, an endoplasmic reticulum stress-suppressive compound from the edible mushroom Leccinum extremiorientale

Choi, Jae-Hoon; Ozawa, Nobuhiko; Yamakawa, Yasuhiro; Nagai, Kazuo; Hirai, Hirofumi; Kawagishi, Hirokazu

doi:10.1016/j.tet.2011.05.052

Cited by 19 publications

(12 citation statements)

References 22 publications

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“…Fresh fruiting bodies of the mushroom collected in Japan have been reported to contain (2S,2 R,3R,4E,8E)-N-2 -hydroxyoctadecanoyl-2-amino-9-methyl-4,8-heptadecadiene-1,3-diol, 5α,6α-epoxy-3β-hydroxy-(22E)-ergosta-8(14),22-dien-7-one, ergosterol peroxide, cerevisterol and 9α-hydroxycerevisterol [200]. The in vitro antioxidant and antimicrobial potentials of extracts of R. botrytis were investigated by several research groups [26,[201][202][203][204] [4,58,205]. Leccinine A (84) and pyrrolezanthine (85) (see structures in Figure 16), were initially isolated from the mature fruiting bodies collected in Japan and showed protective activity against endoplasmic reticulum stress-dependent cell death [205].…”

Section: Ramaria Botrytis (Pers) Bourdotmentioning

confidence: 99%

“…The in vitro antioxidant and antimicrobial potentials of extracts of R. botrytis were investigated by several research groups [26,[201][202][203][204] [4,58,205]. Leccinine A (84) and pyrrolezanthine (85) (see structures in Figure 16), were initially isolated from the mature fruiting bodies collected in Japan and showed protective activity against endoplasmic reticulum stress-dependent cell death [205]. Ito et al isolated (8E,12Z)-10,11-dihydroxyoctadeca-8,12-dienoic acid and leccinine A, reporting their growth regulatory activity against lettuce [206].…”

Section: Ramaria Botrytis (Pers) Bourdotmentioning

confidence: 99%

“…Polysaccharide [199], Extract [202][203][204] -A novel ubiquitin-like protein [196] Glucan (immunostimulating activity) [198] Rugiboletus extremiorientalis (Lj.N. Vassiljeva) G. Wu & Zhu L. Yang ---Leccinine A (84) (protective activity against endoplasmic reticulum stress-dependent cell death [205] and plant growth regulatory activity [206]). (8E,12Z)-10,11-dihydroxyoctadeca-8,12-dienoic acid (plant growth regulatory activity [206]).…”

Section: Thelephora Ganbajun M Zangmentioning

confidence: 99%

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Bioactive Phytochemical Constituents of Wild Edible Mushrooms from Southeast Asia

et al. 2020

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Mushrooms have a long history of uses for their medicinal and nutritional properties. They have been consumed by people for thousands of years. Edible mushrooms are collected in the wild or cultivated worldwide. Recently, mushroom extracts and their secondary metabolites have acquired considerable attention due to their biological effects, which include antioxidant, antimicrobial, anti-cancer, anti-inflammatory, anti-obesity, and immunomodulatory activities. Thus, in addition to phytochemists, nutritionists and consumers are now deeply interested in the phytochemical constituents of mushrooms, which provide beneficial effects to humans in terms of health promotion and reduction of disease-related risks. In recent years, scientific reports on the nutritional, phytochemical and pharmacological properties of mushroom have been overwhelming. However, the bioactive compounds and biological properties of wild edible mushrooms growing in Southeast Asian countries have been rarely described. In this review, the bioactive compounds isolated from 25 selected wild edible mushrooms growing in Southeast Asia have been reviewed, together with their biological activities. Phytoconstituents with antioxidant and antimicrobial activities have been highlighted. Several evidences indicate that mushrooms are good sources for natural antioxidants and antimicrobial agents

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Section: Ramaria Botrytis (Pers) Bourdotmentioning

confidence: 99%

Section: Ramaria Botrytis (Pers) Bourdotmentioning

confidence: 99%

Section: Thelephora Ganbajun M Zangmentioning

confidence: 99%

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Bioactive Phytochemical Constituents of Wild Edible Mushrooms from Southeast Asia

et al. 2020

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“…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.…”

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confidence: 99%

A New Pyrrole Alkaloid from Leccinum Extremiorientale

Yang

Huang

et al. 2015

Chem Nat Compd

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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.

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“…During the screening for ER stress protecting effects of the extracts of various mushrooms, we previously reported the protective compounds from the mushrooms Hericium erinaceus, [7][8][9] Termitomyces titanicus, 10 and Leccinum extremiorientale. 11 Moreover, -lactones and phenylpentanols having protective activity against toxicity of tunicamycin (TM) or thapsigargin (TG) from the mushroom Mycoleptodonoides aitchisonii have been reported. 12,13 In the course of our continuing search for ER stress protecting compounds from the mushroom M. aitchisonii, we found active compounds.…”

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Thapsigargin-induced ER stress suppressive compounds from the mushroom Mycoleptodonoides aitchisonii

Choi

Suzuki

Okumura

et al. 2015

Tetrahedron Letters

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Endoplasmic reticulum (ER) is an important organelle for the synthesis, correct folding, post-translation modification and transport of nascent proteins to different destinies. 1,2 ER stress is caused by disturbances in the structure and function of the ER with the accumulation of misfolded proteins and alterations in calcium homeostasis. In case of prolonged or aggravated ER stress, cellular signals leading to cell death are activated 3. ER stress has been reported to cause not only neurodegenerative diseases 3-5 but also some other diseases, such as diabetes, atherosclerosis, or heart and liver disease. 6

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Leccinine A, an endoplasmic reticulum stress-suppressive compound from the edible mushroom Leccinum extremiorientale

Cited by 19 publications

References 22 publications

Bioactive Phytochemical Constituents of Wild Edible Mushrooms from Southeast Asia

Bioactive Phytochemical Constituents of Wild Edible Mushrooms from Southeast Asia

A New Pyrrole Alkaloid from Leccinum Extremiorientale

Thapsigargin-induced ER stress suppressive compounds from the mushroom Mycoleptodonoides aitchisonii

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