Artemisia annua Chinese name Qing hoa su English

Artemisia annua Chinese name: Qing hoa su English: wormwood, sweet wormwood

Artemisia annua

Crystals of artemisinin isolated from A. annua Aug. 19, 2005

Artemisinin 94 105. 7 172. 3

Dept-135, and C-13 NMR Spectra of Artemisinin 12 a 10 C 12 a Artemisinin C 12 12 C 3 C 10 3 X

d 172. 6 ppm C-10 105. 9 and 79. 9 C-3 and C-12 a 94. 1 (C-12), 50. 5 (C-5 a) and 45. 3 (C-8 a) C-3 C-10 C-12 a C-12 C-13 NMR spectrum of the crude Et. OH ext of A. annua

Aug. 19, 2005

Aug. 19, 2005 Dihydroepideoxyareannuin B Confirms presence of Active ingredient in the Tea Artemisinin 1. Et. OH Ext 2. Artemisinin 3. Tea (5 g) 1 2 3

Dihydro-epideoxyarteannuin B Constituents other than Artemisinin

Quantitative Aspects Artemisinin Levels in A. annua grown in Vietnam Stages of the growth of the plant • • • Vegetative growth 5 -8 months (from sown seeds) Mass formation of buds (9 months) Full blooming (10 months) • Artemisinin highest in 5 -months old plant (0. 86%) • Content then drops to 0. 4% and • Post flowering as low as 0. 16% Essential oil: 1. 9% (v/w) just before flowering Source: Planta Medica, 1993 (I. d. 16624)

J. Nat. Prod. , 68 (1), 133 -149, 2005. Quantitative 1 H NMR: Development and Potential of a Method for Natural Products Analysis Guido F. Pauli, *Birgit U. Jaki, and David C. Lankin. College of Pharmacy, University of Illinois at Chicago, Illinois 60612 Abstract: Based on a brief revision of what constitutes state-of-the-art "quantitative experimental conditions" for 1 H quantitative NMR (q. HNMR), this comprehensive review contains almost 200 references and covers the literature since 1982 with emphasis on natural products. It provides an overview of the background applications of q. HNMR in natural products research, new methods such as decoupling and hyphenation, and analytical potential and limitations, and compiles information on reference materials used for and studied by q. HNMR. The dual status of natural products, being single chemical entities and valuable biologically active agents that need to be purified from complex matrixes, results in an increased analytical demand when testing their deviation from the singleton composition ideal. The outcome and versatility of reported applications lead to the conclusion that q. HNMR is currently the principal analytical method to meet this demand. Considering both 1 D and 2 D 1 H NMR experiments, q. HNMR has proved to be highly suitable for the simultaneous selective recognition and quantitative determination of metabolites in complex biological matrixes. This is manifested by the prior publication of over 80 reports on applications involving the quantitation of single natural products in plant extracts, dietary materials, and materials representing different metabolic stages of (micro)organisms. In summary, q. HNMR has great potential as an analytical tool in both the discovery of new bioactive natural products and the field of metabolome analysis.

1 H NMR of Artemisinin

Top: 8 month plant extract 77 -75 I Bottom: Artem. Ref. DHCL

Expansion of H-12 region of 77 -75 I Ref. 2 mg 0. 0087 mmol From ratio Artem. mmol = 0. 019 Hence Artem. Wt = 5. 47 mg Artem % = 0. 6% H-12

2 month plant extract 77 -76 C Ref. 2 mg 0. 0087 mmol Integral Ratio 1: 1 Calcd Artem. mmol =. 009 Hence Artem. Wt = 2. 5 mg Artem % = 0. 3%

Artemisinin Caffeine DHCL 1 mg 282 MW 2 mg 194 MW 2 mg 230 MW 0. 0035 mmol 0. 0100 mmol 0. 0087 mmol Artemi/Caf. Integral Ratio. 037/1 Therefore Artemi = 0. 37 x 0. 01 = 0. 0037 mmol Mass of Artemi. = 0. 0037 x 282 = 1. 04 mg = 1 mg Artemi/DHCL Integral Ratio 0. 37/0. 8 = 0. 46 Therefore Artemi = 0. 46 x 0. 0087 = 0. 004 mmol Mass of Artemi. = 0. 004 x 282 = 1. 1 mg = 1 mg Conclusion: Actual Artemi. Added 1 mg Found by QHNMR 1 mg

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