13C-2H correlation NMR spectroscopy studies of the in vivo transformations of natural products from Artemisia annua

Phytochemistry Reviews

Volumn 2, Issue 1-2, 2003, Pages 45-59

  Brown, G D ^a,b  

^a UNIVERSITY OF READING   (United Kingdom)

^b UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

13C 2H correlation spectroscopy; Artemisia annua; Artemisinin; Autoxidation; Biogenesis; Dihydroartemisinic acid; Isotopic labelling; Natural product; Two dimension nuclear magnetic resonance (NMR)

Indexed keywords

ANTIMALARIAL AGENT; ARTEMISIA ANNUA EXTRACT; ARTEMISININ; CARBON 13; DEUTERIUM; DICHLOROMETHANE; DIHYDROARTEMISINIC ACID; DIHYDROARTEMISININ DERIVATIVE; FLAVONOID; HYDROPEROXIDE; NATURAL PRODUCT; SESQUITERPENE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTEMISIA ANNUA; AUTOOXIDATION; BIOGENESIS; BIOSYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CHROMATOGRAPHY; CONFERENCE PAPER; CORRELATION ANALYSIS; DEUTERON NUCLEAR MAGNETIC RESONANCE; METABOLITE; PLANT PRODUCT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY;

ARTEMISIA; ARTEMISIA ANNUA;

EID: 0347614987     PISSN: 15687767     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:PHYT.0000004199.43295.64     Document Type: Conference Paper

References (19)

1. Bax A & Morris GA (1981) An improved method for heteronuclear chemical shift correlation by two-dimensional NMR. J. Mag. Res. 42: 501-505.
2. 1H decoupling. J. Mag. Res. 59: 223-236.
3. Brown GD (1992) Two new compounds from Artemisia annua J. Nat. Prod. 55: 1756-1760.
4. 13C NMR. J. Biol. Chem. 277: 7799-7807.
5. 1H spin-spin coupling constants. J. Mag. Res. 28: 145-148.
6. Haynes RK & Vonwiller SC (1997) From qinghao, marvelous herb of antiquity to the antimalarial trioxane qinghao - and some remarkable new chemistry. Ace. Chem. Res. 30: 73-79.
7. Ho KF (2000) The Biogenesis of Artemisinin (Chapter 4). M. Phil. Dissertation, The University of Hong Kong, Hong Kong.
8. 13C: application to polycyclic aromatic hydrocarbon anions. Mag. Res. Chem. 39: 489-494.
9. Kim NC & Kim SU (1992) Biosynthesis of artemisinin from 11,12-dihydroartemisinic acid. J. Korean Agric. Chem. Soc. 35: 106-109.
10. Liu JM, Ni MY, Fan YF, Tu YY, Wu ZH, Wu YL & Zhou WS (1979) Artemisinin. Acta Chim. Sin. 37: 129-141.
11. Saunders JKM & Hunter BK (1988) Modern NMR spectroscopy. Oxford University Press, Oxford, England.
12. 2H spin-spin coupling: elimination of solvent signals and analysis of partially deuterated systems. J. Mag. Res. 52: 511-514.
13. Sy LK & Brown GD (1998) Three sesquiterpenes from Artemisia annua. Phytochemistry 48: 1207-1211.
14. Sy LK, Haynes R & Brown GD (1998) A novel endoperoxide and related sesquiterpenes from Artemisia annua which are possibly derived from allylic hydroperoxides. Tetrahedron 54: 4345-1356.
15. Sy LK & Brown GD (2001) Deoxyarteannuin B, dihydro-deoxyarteannuin B and trans-5-hydroxy-2-isopropenyl-5-methylhex-3-en-1-ol from Artemisia annua. Phytochemistry 58: 1159-1166.
16. Sy LK, Zhu NY & Brown GD (2001) Syntheses of dihydroartemisinic acid and dihydro-epi-deoxyarteannuin B incorporating a stable isotope label at the 15-position for studies into the biosynthesis of artemisinin. Tetrahedron 57: 8495-8510.
17. Sy LK & Brown GD (2002) The mechanism of the spontaneous autoxidation of dihydroartemisinic acid. Tetrahedron 58: 897-908.
18. Waalart TE, van Uden W, Lubberink HGM, Woerdenbag HJ, Pras N & Quak WJ (1999) Isolation and identification of dihydroartemisinic acid from Artemisia annua and its possible role in the biosynthesis of artemisinin. J. Nat. Prod. 62: 430-433.
19. van Zijl PCM (1987) The use of deuterium as a nucleus for locking, shimming, and measuring NMR at high magnetic fields. J Mag. Res. 75: 335-344.