Isolation and identification of dihydroartemisinic acid from Artemisia annua and its possible role in the biosynthesis of artemisinin

被引:115
作者
Wallaart, TE [1 ]
van Uden, W [1 ]
Lubberink, HGM [1 ]
Woerdenbag, HJ [1 ]
Pras, N [1 ]
Quax, WJ [1 ]
机构
[1] Univ Groningen, Dept Pharmaceut Biol, Ctr Pharm, Groningen Inst Drug Studies, NL-9713 AV Groningen, Netherlands
来源
JOURNAL OF NATURAL PRODUCTS | 1999年 / 62卷 / 03期
关键词
D O I
10.1021/np980370p
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Dihydroartemisinic acid (2) was isolated as a natural product from Artemisia annua in a 66% yield, and its structure was confirmed by H-1 and C-13 NMR spectroscopy. Compound 2 could be chemically converted to artemisinin (4) under conditions that may also be present in the living plant. The results suggest that the conversion of 2 into 4 in the living plant might be a nonenzymatic conversion.
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收藏
页码:430 / 433
页数:4
相关论文
共 27 条
[1]   ON THE CONVERSION OF DIHYDROARTEMISINIC ACID INTO ARTEMISININ [J].
ACTON, N ;
ROTH, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) :3610-3614
[2]   BIOSYNTHESIS OF ARTEMISINIC ACID IN ARTEMISIA-ANNUA [J].
AKHILA, A ;
RANI, K ;
THAKUR, RS .
PHYTOCHEMISTRY, 1990, 29 (07) :2129-2132
[3]   BIOSYNTHESIS OF ARTEMISININ IN ARTEMISIA-ANNUA [J].
AKHILA, A ;
THAKUR, RS ;
POPLI, SP .
PHYTOCHEMISTRY, 1987, 26 (07) :1927-1930
[4]   THE EPIDEMIOLOGY OF DRUG-RESISTANT MALARIA [J].
BJORKMAN, A ;
PHILLIPSHOWARD, PA .
TRANSACTIONS OF THE ROYAL SOCIETY OF TROPICAL MEDICINE AND HYGIENE, 1990, 84 (02) :177-180
[5]   ION SPRAY INTERFACE FOR COMBINED LIQUID CHROMATOGRAPHY/ATMOSPHERIC PRESSURE IONIZATION MASS-SPECTROMETRY [J].
BRUINS, AP ;
COVEY, TR ;
HENION, JD .
ANALYTICAL CHEMISTRY, 1987, 59 (22) :2642-2646
[6]   LOCALIZATION OF ARTEMISININ AND ARTEMISITENE IN FOLIAR TISSUES OF GLANDED AND GLANDLESS BIOTYPES OF ARTEMISIA-ANNUA L [J].
DUKE, MV ;
PAUL, RN ;
ELSOHLY, HN ;
STURTZ, G ;
DUKE, SO .
INTERNATIONAL JOURNAL OF PLANT SCIENCES, 1994, 155 (03) :365-372
[7]   FLORAL MORPHOLOGY OF ARTEMISIA-ANNUA WITH SPECIAL REFERENCE TO TRICHOMES [J].
FERREIRA, JFS ;
JANICK, J .
INTERNATIONAL JOURNAL OF PLANT SCIENCES, 1995, 156 (06) :807-815
[8]   ECONOMIC-PROSPECTS FOR A NEW ANTIMALARIAL DRUG [J].
FOSTER, S .
TRANSACTIONS OF THE ROYAL SOCIETY OF TROPICAL MEDICINE AND HYGIENE, 1994, 88 :55-56
[9]   ISOLATION OF SECRETORY-CELLS FROM PLANT GLANDULAR TRICHOMES AND THEIR USE IN BIOSYNTHETIC-STUDIES OF MONOTERPENES AND OTHER GLAND PRODUCTS [J].
GERSHENZON, J ;
MCCASKILL, D ;
RAJAONARIVONY, JIM ;
MIHALIAK, C ;
KARP, F ;
CROTEAU, R .
ANALYTICAL BIOCHEMISTRY, 1992, 200 (01) :130-138
[10]   EXTRACTION OF ARTEMISININ AND ARTEMISINIC ACID - PREPARATION OF ARTEMETHER AND NEW ANALOGS [J].
HAYNES, RK ;
VONWILLER, SC .
TRANSACTIONS OF THE ROYAL SOCIETY OF TROPICAL MEDICINE AND HYGIENE, 1994, 88 :23-26