天然产物研究与开发 ›› 2023, Vol. 35 ›› Issue (7): 1183-1190.doi: 10.16333/j.1001-6880.2023.7.009

• 研究简报 • 上一篇    下一篇

蜜环菌发酵液及其菌丝体的化学成分研究

罗影子1,2,3,4,黄明进1,2,3,4*,沈寿茂4,苏明智5,于丹丹5,郭跃伟4,5*,覃玉强6,张光文7   

  1. 1贵州大学农学院;2贵州大学石斛研究院;3贵州省药用植物繁育与种植重点(工程)实验室,贵阳 550025;4中国科学院上海药物研究所新药研究国家重点实验室,上海 201203;5中科环渤海(烟台)药物高等研究院,烟台 264117;6贵州创禾源农业科技有限公司,贵阳 550025;7贵州乌蒙腾菌业有限公司,毕节 551700
  • 出版日期:2023-07-31 发布日期:2023-07-31
  • 基金资助:
    贵州省中药材产业发展项目(黔财农[2019]175号,[2020]101号,[2021]145号);贵州创禾源中药产业创新发展项目(创禾源科技合同[2021]001号)

Chemical constituents from Armillaria mellea fermentation broth and its mycelia

LUO Ying-zi1,2,3,4,HUANG Ming-jin1,2,3,4*,SHEN Shou-mao4,SU Ming-zhi5,YU Dan-dan5,GUO Yue-wei4,5*,QIN Yu-qiang6,ZHANG Guang-wen7
  

  1. 1School of Agriculture,Guizhou University;2Dendrobium Research Institute,Guizhou University;3Key Laboratory of Medicinal Plant Breeding and Planting of Guizhou Province,Guiyang 550025,China;4State Key Laboratory of Drug Research,Shanghai Institute of Materia Medica,Chinese Academy of Sciences,Shanghai 201203,China;5Bohai Rim Advanced Research Institute for Drug Discovery,Yantai 264117,China;6Guizhou Chuangheyuan Agricultural Co.,Ltd.,Guiyang 550025,China;7Guizhou Wumengteng Fungi Industry Co.,Ltd.,Bijie 551700,China
  • Online:2023-07-31 Published:2023-07-31

摘要:

蜜环菌(Armillaria mellea)是药用植物天麻(Gastrodia elata)营养生长阶段的共生真菌。为研究蜜环菌的化学成分和生物活性,本实验综合运用MCI树脂、正相硅胶、Sephadex LH-20凝胶及半制备RP-HPLC等色谱分离技术对蜜环菌发酵液及其菌丝体的95%乙醇提取物进行系统分离,得到26个化合物。根据化合物的理化性质和波谱数据,分别鉴定为十四烷酸(1)、α-亚麻酸(2)、油酸(3)、亚油酸(4)、亚油酸乙酯(5)、8(R),11(S-二羟基-9Z12Z-十八烷二烯酸(6)、2-油酰甘油(7)、1-亚油酸甘油酯(8)、二羟丙基-油酸(9)、亚油酸甲酯(10)、甘油1,3-二亚油酸酯(11)、(5Z9Z-17-甲基-非十七烯酸-5,9-二酯(12)、(2S)-α-(9′Z12′Z15′Z-十八碳三烯酸(13)、麦角甾醇(14)、(22E24S-5α,8α-环二氧-6,22-麦角甾二烯-3β醇(15)、对羟基苄基乙基醚(16)、尿嘧啶(17)、环D-脯氨酸-D-异亮氨酸(18)、环D-脯氨酸-D-亮氨酸(19)、环D-脯氨酸-D-苯丙氨酸(20)、脯氨酸(21)、环D-脯氨酸-L-缬氨酸(22)、环D-脯氨酸-D-缬氨酸(23)、4-(2-羟乙基)-5-甲基噁唑(24)、环丙氨酸-缬氨酸(25)、环丙氨酸-脯氨酸(26)。其中,化合物5~131618~26是首次从蜜环菌中分离获得。体外生物活性研究表明化合物1415对LPS诱导的RAW 264.7细胞炎症反应具有抑制作用。

关键词: 蜜环菌, 菌丝体, 化学成分, 抗炎活性

Abstract:

Armillaria mellea is a symbiotic fungus essential for the nutritional growth stage of the medicinal plant Gastrodia elata.To investigate the chemical constitutes and bioactivities of A. mellea,the 95% ethanol extract of A. mellea was repeatedly chromatographed over silica gel,MCI gel,Sephadex LH-20 and reversed-phase (RP)-HPLC,affording twenty-six pure compounds (1-26).Their structures were identified as tetradecanoic acid (1),α-linolenic acid (2),oleic acid (3),linoleic acid (4),ethyl linoleate (5),8(R),11(S)-dihydroxy-9Z,12Z-octadecadienoic acid (6),2-linoleoylglycerol (7),1-monolinolein (8),9-octadecenoic acid-2′,3′-dihydroxy propyl ester (9),methyl linoleate (10),glycerin 1,3-dilinoleate (11),(5Z,9Z)-17-methylnonadeca-5,9-dienoate (12),(2S)-α-(9′Z,12′Z,15′Z)-octadecatrienoic acid (13),ergosta-5,7,22-triene-3β-ol (14),(22E,24S)-5α,8α-epidioxy-24-methyl-cholesta-6,9(11),22-trien-3β-ol (15),p-hydroxybenzylethyl ether (16),uracil (17),cyclo(D)-Pro-(D)-Ile (18),cyclo(D)-Pro-(D)-Leu (19),cyclo(D)-Pro-(D)-Phe (20),proline (21),cyclo(D)-Pro-(L)-Val (22),cyclo(D)-Pro-(D)-Val (23),4-(2-hydroxyethyl)-5-methyloxazole (24),cyclo-(Ala-Val) (25),cyclo-(Ala-Pro) (26),respectively,by comparision of their NMR data and optical rotation values with those reported in the literature. Among them,compounds 5-13,16,and 18-26 were obtained for the first time from A. mellea. In in vitro bioassay,compounds 14 and 15 showed moderate effects against LPS-induced inflammatory responses in RAW 264.7 cells.

Key words: Armillaria mellea, mycelia, chemical constituents, anti-inflammatory

中图分类号:  R284.1