Biotransformation of cannabinoids using plant tissue culture and their activity

利用植物组织培养对大麻素进行生物转化及其活性

• 批准号: 05671828
• 负责人: SHOYAMA Yukihiro
• 金额: $ 1.34万
• 依托单位: KYUSHU UNIVERSITY
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for General Scientific Research (C)
• 财政年份: 1993
• 资助国家: 日本
• 起止时间: 1993 至 1994
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-05671828/
• 关键词: Cannabinoid; Plant tissue culture; Biotransformation; Glycosidation; Cannabinoid receptor; Binding assay; カンナビジオール; テトラヒドロカンナビノール; 大麻成分配糖体; バインデイングアッセイ; カンナビノール; 植物細胞; カンナビノールグルコシド

The breeding of medicinal plants and the production of naturally occurring biologically active compounds have been investigated by plant tissue culture technique in this laboratory. In this project we started to study the biotransformation of cannabinoids using the plant cell and/or tissue as a plant catalyst in ordsr to create some new cannabinoids for resources of new drugs.Tetrahydrocannabinol (THC), cannabidiol (CBD), cannabidiolic acid (CBDA) and cannabinol (CBN) were incubated individually with the protocorm segment of Pinellia ternata in the medium supplemented with 2,4-D (0.25 mg/l) at 25ﾟC in the dark condition for 1-3 weeks. The biotransformed products were extracted from the protocorm body and the medium, then purified. These structures were elucidated as THC-monoglycoside, CBD-mono and diglycosides, CBDA-monoglycoside and hydroxy-CBDA-monoglycoside, CBN-mono glycoside and hydroxy-CBN-monoglycoside by ^<13>C and ^1HNMR and FAB-MS,respectively. It became evident that THC-monoglycoside and CBN-monoglycoside (Kd>8 ^<mu>M) and CBD-monoglycoside (Kd>20 ^<mu>M) have the affinity with cannabinoid receptor. From these results, the pharmacological activities of three new cannabinoids will be expected.

本实验室采用植物组织培养技术，对药用植物的育种和天然生物活性物质的生产进行了研究。本课题以半夏原球茎切段为材料，在添加2，4-D(0.25 mg/L)的黑暗条件下，分别与四氢大麻酚(THC)、大麻二酚(Cbd)、大麻二酸(CbDA)和大麻酚(Cbn)在25ﾟ℃的黑暗条件下培养1~3周，研究植物细胞和组织作为植物催化剂对大麻素的生物转化作用。从原球茎和培养基中提取转化产物，并进行纯化。经~(13)H-GT；C和~1H核磁共振、FAB-MS鉴定为CbD-单糖苷、CBD-单糖苷、CBDA-单糖苷和羟基-CBDA-单糖苷、CBN-单糖苷和羟基-CBN-单糖苷。可见，THC-单糖苷和CBN-单糖苷(KD&gt；8；lt；Mu&gt；M)和CBD-单糖苷(Kd&gt；20；lt；Mu&gt；M)与大麻素受体具有亲和力。根据这些结果，三种新的大麻素的药理活性将是可望的。

项目成果

Yukihiro Shoyama: "Winged bean and some other vegetefle and medicinal plants in the tropics and subtropics" 日本特殊農産物協会, 59 (1993)

Yukihiro Shoyama：“热带和亚热带的四棱豆和其他一些蔬菜和药用植物”日本特产农产品协会，59（1993）

Yuri Goto: "Determination of tetrahydro cannabirolic acid-carrier protein conjuigate by matrix-assisted laser desorption/ionization Mass spectro-metry" Organic Mass Spectrometry. 29. 618-671 (1994)

Yuri Goto：“通过基质辅助激光解吸/电离质谱测定四氢大麻酚酸载体蛋白缀合物”有机质谱。

Yuri Goto: "Determination of tetrahydro cannabirolic acid-carrier protein conjugate by matrix-assisted Laser desorption/ionization Mass Spectrometry" Organic Mass Spectrometry. 29. 618-671 (1994)

Yuri Goto：“通过基质辅助激光解吸/电离质谱法测定四氢大麻酚酸-载体蛋白缀合物”有机质谱法。

Hiroyuki Tanaka: "Cannabis 21 Biotransformation of cannabinol to its glycosides by in vitro plant tissue" Journal of Natural products. 56. 2068-2072 (1993)

Hiroyuki Tanaka：“Cannabis 21 通过体外植物组织将大麻酚生物转化为其糖苷”《天然产品杂志》。

Yukihiro Shoyama: "Winged been and some other vegetables and medicinal plants in the tropics and subtropics" 日本特殊農産物協会, 59 (1994)

Yukihiro Shoyama：“热带和亚热带的翅菜和其他一些蔬菜和药用植物”日本特产农产品协会，59（1994）