Abstract
Seven new secoiridoids, swertianglide (1) and swertianosides A−F (2–7), together with fifteen known compounds, were isolated from the whole plants of Swertia angustifolia. Their structures were elucidated on the basis of extensive spectroscopic analyses ([α]D, UV, IR, MS, 1D- and 2D-NMR). Fourteen compounds were evaluated for their anti-hepatitis B virus (HBV) activities on the Hep G 2.2.15 cell line in vitro. Compound 2, an unusual secoiridoid glycoside dimer, showed significant activities inhibiting the secretion of HBsAg (IC50 0.18 mM, SI 3.11) and HBeAg (IC50 0.12 mM, SI 4.67).
Key words
secoiridoids - swertianglide - swertianosides A–F -
Swertia angustifolia
- Gentianaceae - anti-HBV activity
References
-
1 Ho T N. Flora of China. Volume 62 Beijing: Science Press; 1988: 344
-
2 Yang Y C. Zangyaozhi. Qinghai: People of Qinghai Press; 1992: 104
-
3 State Pharmacopoeia Committee .Chinese Pharmacopoeia, 2010 edition. Beijing: China Medical Pharmaceutical Science and Technology Publishing House; 2010: 182
-
4
Geng C A, Jiang Z Y, Ma Y B, Luo J, Zhang X M, Wang H L, Shen Y, Zuo A X, Zhou J, Chen J J.
Swerilactones A and B, anti-HBV new lactones from a traditional Chinese herb: Swertia mileensis as a treatment for viral hepatitis.
Org Lett.
2009;
11
4120-4123
-
5
Geng C A, Zhang X M, Shen Y, Zuo A X, Liu J F, Ma Y B, Luo J, Zhou J, Jiang Z Y, Chen J J.
Swerilactones C and D, anti-HBV new lactones from a traditional Chinese herb: Swertia mileensis.
Org Lett.
2009;
11
4838-4841
-
6
Geng C A, Wang L J, Zhang X M, Ma Y B, Huang X Y, Luo J, Guo R H, Zhou J, Shen Y, Zuo A X, Jiang Z Y, Chen J J.
Anti-hepatitis B virus active lactones from the traditional Chinese herb: Swertia mileensis.
Chem Eur J.
2011;
17
3893-3903
-
7
Geng C A, Zhang X M, Ma Y B, Luo J, Chen J J.
Swerilactones L–O, secoiridoids with C12 and C13 skeletons from Swertia mileensis.
J Nat Prod.
2011;
74
1822-1825
-
8
Geng C A, Zhang X M, Ma Y B, Jiang Z Y, Luo J, Zhou J, Wang H L, Chen J J.
Swerilactones E–G, three unusual lactones from Swertia mileensis.
Tetrahedron Lett.
2010;
51
2483-2485
-
9
Geng C A, Zhang X M, Ma Y B, Jiang Z Y, Liu J F, Zhou J, Chen J J.
Three new secoiridoid glycoside dimers from Swertia mileensis.
J Asian Nat Prod Res.
2010;
6
542-548
-
10 Jia M R, Li X W. ZhongGuo MinZu YaoZhi Yao. Bejing: China Medical Science Press; 2005: 591
-
11
Ghosal S, Sharma P V, Jaiswal D K.
Chemical constituents of Gentianaceae. XXIII: tetraoxygenated and pentaoxygenated xanthones and xanthone O-glucosides of Swertia angustifolia Buch.-Ham.
J Pharm Sci.
1978;
67
55-60
-
12
Dhoubhadel S P, Wagley P P, Pradhan S D.
A new xanthone glycoside from Swertia angustifolia Buch.-Ham. ex. D. Don.
Indian J Chem Sect B.
1980;
19?B
929-930
-
13
Acharya H P, Gewali M B, Manandhar M D, MacKelvey R D.
Phytochemical studies on Swertia chirata and Swertia angustifolia.
J Nepal Chem Soc.
1997;
16
23-26
-
14
Lou Y H, Nie R L.
Studies on iridoid glycosides from Swertia angustifolia.
Acta Pharm Sin.
1992;
2
125-129
-
15
Mulholladn D A, Langlois A, Randrianarivelojosia M, Derat E, Nuzillard J M.
The structural elucidation of a novel iridoid derivative from Tachiadenus longiflorus (Gentianaceae) using the LSD programme and quantum chemical computations.
Phytochem Anal.
2006;
17
87-90
-
16
Zhou L, Li X K, Miao F, Yang M L, Yang X J, Sun W, Yang J.
Further studies on the chemical constituents of Chinese folk medicine Gentiana apiata N.E.Br.
J Asian Nat Prod Res.
2009;
11
345-351
-
17
Duan C H, Shi B J, Wu L H, Chou G X, Wang Z T.
Chemical constituents of Gentiana waltonii.
Chin J Nat Med.
2007;
5
417-420
-
18
Nie R L, He R Y.
The erythrocentaurin and swermirin from Swertia mileensis.
Acta Bot Yunn.
1982;
6
325-328
-
19
Suhr J H, Arends P, Jensen B.
Gentiolactone, a secoiridoid dilactone from Gentiana purpurea.
Phytochemistry.
1978;
17
135-138
-
20
Van der Nat J, Van der Sluis W G, Labadie R P.
Gentiogenal, a new antimicrobial iridoid derived from gentiopicrin (gentiopicroside).
Planta Med.
1982;
45
161-162
-
21
Wang Z G, Tang S H, Ma C M, Toyooka N, Kida H, Kawasaki M, Hattori M.
Determination of novel nitrogen-containing metabolites after oral administration of swertiamarin to rats.
J Tradit Med.
2008;
25
29-34
-
22
Guiso M, Tassone G, Nicoletti M, Serafini M, Bianco A.
Chemotaxonomy of iridoids in Linaria vulgaris.
Nat Prod Res.
2007;
21
1212-1216
-
23
Luo L H, Nie R L.
Iridoid glycosides from Swertia angustifolia.
Acta Pharm Sin.
1992;
27
125-129
-
24
Ray S, Majumder H K, Chakravarty A K, Mukhopadhyay S, Gil R R, Cordell G A.
Amarogentin, a naturally occurring secoiridoid glycoside and a newly recognized inhibitor of topoisomerase I from Leishmania donovani.
J Nat Prod.
1996;
59
27-29
-
25
Zhou Y, Di Y T, Gesang S, Peng S L, Ding L S.
Secoiridoid glycosides from Swertia mileensis.
Helv Chim Acta.
2006;
89
94-102
-
26
Kikuzaki H, Kawasaki Y, Kitamura S, Nakatani N.
Secoiridoid glucosides from Swertia mileensis.
Planta Med.
1996;
62
35-38
-
27
Rodriguez S, Wolfender J L, Hakizamungu E, Hostettmann K.
An antifungal naphthoquinone, xanthones and secoiridoids from Swertia calycina.
Planta Med.
1995;
61
362-364
Prof. Ji-Jun Chen
State Key Laboratory of Phytochemistry and Plant Resources in West China
Kunming Institute of Botany
Chinese Academy of Sciences
132 Lanhei Road
Kunming 650201
PR China
Telefon: +86 87 15 22 32 65
Fax: +86 87 15 22 71 97
eMail: chenjj@mail.kib.ac.cn
