Top

Published in:

01-09-2020 | Note

Two new sesquiterpenes from Artemisia annua L.

Authors: Yukiko Takenaka, Satoko Seki, Toyoyuki Nishi, Takao Tanahashi

Published in: Journal of Natural Medicines | Issue 4/2020

Abstract

Investigation of the dried whole plants of Artemisia annua led to the isolation of two new sesquiterpenes, artemanins A (1) and B (2), along with twenty-nine known compounds. The structures of the new compounds were elucidated by spectroscopic and chemical means.

Billia AR, Melillo de Malgalhaes P, Bergonzi MC, Vincieri FF (2006) Simultaneous analysis of artemisinin and flavonoids of several extracts of Artemisia annua L. obtained from a commercial sample and a selected cultivar. Phytomedicine 13:487–493CrossRef

Hien T-T, White NJ (1993) Qinghaosu. Lancet 341:603–608CrossRef

Qinghaosu Antimalaria Cordinating Research Group (1979) Antimalaria studies on Qinghaosu. Chin Med J 92:811–816

Tu Y-Y (2016) Artemisinin-A gift from traditional Chinese medicine to the world (Nobel Lecture). Angew Chem Int Ed 55:10210–10226CrossRef

Brown GD (2010) The biosynthesis of artemisinin (Qinghaosu) and the phytochemistry of Artemisia annua (Qinghao). Molecules 15:7603–7698CrossRef

Wallaart TE, Pras N, Beekman AC, Quax WJ (2000) Seasonal variation of artemisinin and its biosynthetic precursors in plants of Artemisia annua of different geographical origin: proof for the existence of chemotypes. Planta Med 66:57–62CrossRef

Kawamoto H, Sekine H, Furuya T (1999) Production of artemisinin and related sesquiterpenes in Japanese Artemisia annua during a vegetation period. Planta Med 65:88–89CrossRef

Marsaioli AJ, Fujiwara FY, Foglio MA, Sharapin N, Zhang J-S (1994) Proton and carbon-13 NMR and conformation in solution of some amorphanes (Qinghaosu derivatives). Magn Reson Chem 32:583–590CrossRef

Leppard DG, Rey M, Dreiding AS, Grieb R (1974) The structure of arteannuin B and its acid hydrolysis product. Helv Chim Acta 57:602–615CrossRef

10.

Tu Y-Y, Ni M-Y, Zhong Y-R, Li L-N, Cui S-L, Zhang M-Q, Wang X-Z, Ji Z, Liang X-T (1982) Studies on the constituents of Artemisia annua. Part II. Planta Med 44:143–145CrossRef

11.

Brown GD, Liang G-Y, Sy L-K (2003) Terpenoids from the seeds of Artemisia annua. Phytochemistry 64:303–323CrossRef

12.

Nakajima T (1962) Studies on the essential oils of Artemisia annua L. V. Yakugaku Zasshi 82:1323–1326CrossRef

13.

Li H-B, Yu Y, Wang Z-Z, Yang J, Xiao W, Yao X-S (2015) Two new sesquiterpenoids from Artemisia annua. Magn Reson Chem 53:244–247CrossRef

14.

Qin D-P, Pan D-B, Xiao W, Li H-B, Yang B, Yao X-J, Dai Y, Yu Y, Yao X-S (2018) Dimeric cadinane sesquiterpenoid derivatives from Artemisia annua. Org Lett 20:453–456CrossRef

15.

Barberá O, Marco JA, Sanz JF, Sánchez-Parareda J (1986) 3-Methoxyflavones and coumarins from Artemisia incanescens. Phytochemistry 25:2357–2360CrossRef

16.

Raffauf RF, Menachery MD, Le Quesne PWL, Arnold EV, Clardy J (1981) Antitumor plants. 11. Diterpenoid and flavonoid constituents of Bromelia pinguin L. J Org Chem 46:1094–1098CrossRef

17.

Martínez V, Barberá O, Sánchez-Parareda J, Marco JA (1987) Phenolic and acetylenic metabolites from Artemisia assoana. Phytochemisy 26:2619–2624CrossRef

18.

Voirin B (1983) UV spectral differentiation of 5-hydroxy- and 5-hydroxy-3-methoxyflavones with mono-(4′), di-(3′,4′) or tri-(3′,4′,5′) substituted B rings. Phytochemistry 22:2107–2145CrossRef

19.

El-Seedi HR, El-Khodry AE-AA (2002) Flavonoids from Laggera crispata. Afinidad Lix 499:205–210

20.

Ulubelen A, Kerr KM, Mabry TJ (1980) New 6-hydroxyflavonoids and their methyl ethers and glycosides from Neurolaena oaxacana. Phytochemistry 19:1761–1766CrossRef

21.

Chan KK, Giannini DD, Cain AH, Roberts JD, Porter W, Trager WF (1977) Carbon-13 nuclear magnetic resonance studies of coumarin and related compounds. Tetrahedron 33:899–906CrossRef

22.

Banthorpe DV, Brown GD (1989) Two unexpected coumarin derivatives from tissue cultures of Compositae species. Phytochemistry 28:3003–3007CrossRef

23.

Tsukamoto H, Hisada S, Nishibe S (1985) Coumarin and secoiridoid glucosides from bark of Olea africana and Olea capensis. Chem Pharm Bull 33:396–399CrossRef

24.

Yoshikawa M, Shimada H, Saka M, Yoshizumi S, Yamahara J, Matsuda H (1997) Medicinal foodstuffs. V. Moroheiya. (1): Absolute stereostructures of corchoionosides A, B, and C, histamine release inhibitors from the leaves of Vietnamese Corchorus olitorius L. (Tiliaceae). Chem Pharm Bull 45:464–469CrossRef

25.

Umehara K, Hattori I, Miyase T, Ueno A, Hara S, Kagayama C (1988) Studies on the constituents of leaves of Citrus unshiu Marcov. Chem Pharm Bull 36:5004–5008CrossRef

26.

Holland HL, Diakow PRP, Taylor GJ (1978) ¹³C nuclear magnetic resonance spectra of some C-19-hydroxy, C-5,6 epoxy, C-24 ethyl, and C-19-norsteroids. Can J Chem 56:3121–3127CrossRef

27.

Singh AK, Pathak V, Agrawal PK (1997) Annphenone, a phenolic acetophenone from Artemisia annua. Phytochemistry 44:555–557CrossRef

28.

Nishimura K, Takenaka Y, Kishi M, Tanahashi T, Yoshida H, Okuda C, Mizushina Y (2009) Synthesis and DNA polymerase α and β inhibitory activity of alkyl p-coumarates and related compounds. Chem Pharm Bull 57:476–480CrossRef

29.

Meira M, David JM, David JP, Araujo SV, Regis TL, Giulietti AM, de Queiroz LP (2008) Chemical constituents of Ipomoea subincana Meisn. (Convolvulaceae). Quinica Nova 31:751–754CrossRef

30.

Juma BF, Yenese A, Midiwo JO, Waterman PG (2008) Flavones and phenylpropanoids in the surface exudate of Psiadia punctulata. Phytochemistry 57:571–574CrossRef

31.

Sritularak B, Likhiwitayawuld K (2009) New bisbenzyls from Dendrobium falconeri. Helv Chim Acta 92:740–744CrossRef

32.

Ohtani I, Kusumi T, Kashman Y, Kakisawa H (1991) High-field FT NMR application of Mosher’s method. The absolute configurations of marine terpenoids. J Am Chem Soc 113:4092–4096CrossRef

33.

Le DH, Nishimura K, Takenaka Y, Mizushina Y, Tanahashi T (2016) Polyprenylated benzoylphloroglucinols with DNA polymerase inhibitory activity from fruits of Garcinia schomburgkiana. J Nat Prod 79:1798–1807CrossRef

Title: Two new sesquiterpenes from Artemisia annua L.
Authors: Yukiko Takenaka
Satoko Seki
Toyoyuki Nishi
Takao Tanahashi
Publication date: 01-09-2020
Publisher: Springer Singapore
Published in: Journal of Natural Medicines / Issue 4/2020
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-020-01436-3

Keynote webinar | Spotlight on medication adherence

Springer Medicine

Two new sesquiterpenes from Artemisia annua L.

Abstract

Keynote webinar | Spotlight on medication adherence

Springer Medicine

Abstract

Please log in to get access to this content

Other articles of this Issue 4/2020

Caffeic acid and rosmarinic acid contents in genus Perilla

Two new phenylpropanoids from the resin of Styrax tonkinensis (Pierre) Craib ex Hartw

The acrid raphides in tuberous root of Pinellia ternata have lipophilic character and are specifically denatured by ginger extract

Isolation and evaluation of trypanocidal activity of sesquiterpenoids, flavonoids, and lignans in Artemisia sieversiana collected in Mongolia

Physical and chemical characteristics of soils in Ephedra gerardiana and E. pachyclada habitats of Kali Gandaki Valley in Central Nepal

Appetite-enhancing effects of inhaling cinnamon, clove, and fennel essential oils containing phenylpropanoid analogues