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A new guaianolide from Artemisia
roxburghiana
a

a

a

Phan Minh Giang , Tran Thi Thanh Nhan , Phan Tong Son ,
b

Katsuyoshi Matsunami & Hideaki Otsuka

b

a

Faculty of Chemistry, VNU University of Science, Vietnam
National University, 19 Le Thanh Tong Street, Hanoi, Vietnam
b

Natural Product Research, 2013
Vol. 27, No. 20, 1856–1858, />
A new guaianolide from Artemisia roxburghiana
Phan Minh Gianga*, Tran Thi Thanh Nhana, Phan Tong Sona, Katsuyoshi Matsunamib and
Hideaki Otsukab
a
Faculty of Chemistry, VNU University of Science, Vietnam National University, 19 Le Thanh Tong Street,
Hanoi, Vietnam; bGraduate School of Biomedical Sciences, Hiroshima University, 1-2-3 Kasumi, Minamiku, Hiroshima 734-8553, Japan

Downloaded by [Aston University] at 08:09 04 September 2014

(Received 11 October 2012; final version received 25 December 2012)
A new member of 5a H,6b H,7a H,11a H-guaian-12,6a-olides, 11-epi-8a-hydroxyarborescin, together with a mixture of (24R)- and (24S)-cycloart-25-en-3b,24-diols,
palmitic acid and 1-octacosanol were isolated from the leaves of Artemisia
roxburghiana Bess. (Asteraceae) of Vietnam. Their structures were determined on
the basis of spectroscopic methods.
Keywords: Artemisia roxburghiana; Asteraceae; sesquiterpene lactone; guaianolide

1. Introduction
In the chemistry of Artemisia plants of Asteraceae family, sesquiterpene lactones including
guaianolides, eudesmanolides and germacranolides are the molecules of interest (Kelsey &
Shafizadeh 1979; Tan et al. 1998). The guaiane-type sesquiterpene lactones are recognised as a
diverse group of natural compounds with varied stereochemical and functional groups
(Budeˇsˇ´ınsky´ & Sˇaman 1995). Artemisia roxburghiana Bess. (Vietnamese name: Ngải ru`’ng) is a
subshrub of 50– 100 cm tall and is used to treat fever and intestinal worms (Hayat et al. 2009). As
a part of our study of sesquiterpene lactones from species of the family Asteraceae
A. roxburghiana was investigated. The study showed the accumulation of guaianolides with the
exclusive H-5a, H-6b, H-7a and H-11a stereochemistry in this plant (Phan et al. 2012). In the
search for minor guaianolides, a new guaianolide, 11-epi-8a-hydroxyarborescin (1), together
with a mixture of two known epimeric cycloartane triterpenoids, (24R)- and (24S)-cycloart25-en-3b,24-diols (3), palmitic acid (4) and 1-octacosanol (5) were isolated from the leaves of

9.7) clearly indicated the H-11a orientation (Budeˇsˇ´ınsky´ and Sˇaman 1995). The chemical shifts
of C-11 and C-13 reported for 8a-hydroxyarborescin are dC 40.9 and 16.1, respectively (Wong
& Brown 2002). NOESY spectrum also supported the stereochemical assignments of the
stereocenters of 1 as H-5a, H-6b, H-7a and H-8b on the basis of the correlations between H3-13
(dH 1.28) and H-6b (dH 4.29), between H-5a (dH 2.86) and H-7a (dH 1.99) and between H-8b
(dH 3.86) and H3-13; no correlations were observed between H3-13 and H-5a/H-7a (Figure 1).
Therefore, the structure of 1 was determined to be 11-epi-8a-hydroxyarborescin. A
diastereomeric compound of 1, deacetylglobicin, was isolated from A. absinthium (Lee et al.
1971; Kasamov et al. 1984).

3. Experimental
3.1 General experimental procedures
Optical rotations were measured on a JASCO P-1030 digital polarimeter. FT-IR spectra were
recorded on a Horiba FT-710 spectrophotometer. HR-ESI-TOF-MS spectra were measured on
an Applied Biosystem QSTAR XL mass spectrometer. 1H (500 MHz), 13C NMR and DEPT
(125 MHz) spectra were recorded on a Bruker Avance 500 NMR spectrometer. Silica gels
(0.063 – 0.200 mm, 0.040 – 0.063 mm and 0.015 – 0.040 mm) (Merck, Darmstadt, Germany) were
used for open-CC and flash chromatography. Thin-layer chromatography (TLC) was carried out
on TLC silica gel 60 F254 (Merck, Darmstadt, Germany) and detected by spraying with 1%
vanillin in concentrated H2SO4, followed by heating on a hot plate at 2008C.

3.2 Plant material
The leaves of A. roxburghiana Bess. (Asteraceae) were collected in Ha Giang province, Vietnam
in November 2008. The plant was identified by Mr Nguyen Quoc Binh, a botanist of the Institute
of Biological Resources and Ecology, Vietnam Academy of Science and Technology, Hanoi,
14

O
2


7

H
15

H

11

O
1

12

O

13

H

O
O

1

Figure 1. Structure, NOESY and HMBC correlations of compound 1.

HMBC
NOESY


(NAFOSTED, Hanoi, Vietnam).

References
Budeˇsˇ´ınsky´ M, Sˇaman D. (1995). Carbon-13 NMR spectra of sesquiterpene lactones. Ann Rep NMR Spectrosc.
30:231–475.
Hayat MQ, Khan MA, Ashraf M, Jabeen S. (2009). Ethnobotany of the genus Artemisia L. (Asteraceae) in Pakistan.
Ethnobot Res Appl. 7:147–162.
Kasamov Shz, Abdullaev MD, Yusunov MI, Sidyakin GP, Yagudaev MR. (1984). New guaianolides from Artemisia
absinthium. Chem Nat Compd. 20:754–755.
Kelsey RG, Shafizadeh F. (1979). Sesquiterpene lactones and systematics of the genus Artemisia. Phytochemistry.
18:1591–1611.
Lee KH, Matsueda S, Geissman TA. (1971). Sesquiterpene lactones of Artemisia: new guaianolides from fall growth of
A. douglasiana. Phytochemistry. 10:405–410.
Levy GC. (1976). Topics in carbon-13 NMR spectroscopy. Vol. 2. New York, NY: John Wiley & Sons.
Pei YG, Wu QX, Shi YP. (2007). Triterpenoids and other constituents from Euphorbia humifusa. J Chin Chem Soc.
54:1565–1572.
Phan MG, Tran TTN, Phan TS, Otsuka H, Matsunami K. (2012). Two new sesquiterpene lactones and other chemical
constituents of Artemisia roxburghiana. Biochem Syst Ecol. 45:115–119.
Tan RX, Zheng WF, Tang HQ. (1998). Biologically active substances from the genus Artemisia. Planta Med.
64:295–302.
Wong HF, Brown GD. (2002). Dimeric guaianolides and a fulvenoguaianolide from Artemisia myriantha. J Nat Prod.
65:481–486.