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DOI: 10.1055/s-2007-967189
© Georg Thieme Verlag KG Stuttgart · New York
New Sesquiterpene Lactone and Neolignan Glycosides with Antioxidant and Anti-Inflammatory Activities from the Fruits of Illicium oligandrum
Publication History
Received: November 11, 2006
Revised: February 27, 2007
Accepted: March 13, 2007
Publication Date:
26 April 2007 (online)
![](https://www.thieme-connect.de/media/plantamedica/200705/lookinside/thumbnails/10.1055-s-2007-967189-1.jpg)
Abstract
Phytochemical investigations of the fruits of Illicium oligandrum resulted in a new sesquiterpene lactone, 3β-benzoyloxy-10-deoxyfloridanolide (1), and three new neolignan glycosides, including two dihydrobenzofuran neolignan glycosides, (7R,8S)-9-O-β-D-xylopyranosyl-9′-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyldihydrodehydrodiconiferyl alcohol (2) and (7R,8S)-9-O-shikimoyl-4-O-β-D-glucopyranosyldihydrodehydrodiconiferyl alcohol (3) and one 8-O-4′ neolignan glycoside, (7S,8R)-1-[4-O-(β-D-glucopyranosyl)-3-methoxyphenyl]-2-[4-(3-hydroxypropyl)-2,6-dimethoxyphenoxy]-1,3-propanediol (4), together with three known sesquiterpene lactones (5 - 7) and two known neolignan glycosides (8 and 9). Their structures were elucidated on the basis of 1D, 2D NMR, HR-MS and chemical evidence. Compounds 3 and 4 showed moderate antioxidant activity with the inhibitory rates 13.30 % and 9.30 % at 1.0 × 10-5 M, respectively. Compounds 3 and 9 exhibited anti-inflammatory activity with the inhibitory rates 67.0 % and 51.0 % at 1.0 × 10-5 M, respectively.
Key words
Illicium oligandrum - Illiciaceae - sesquiterpene lactones - neolignan glycosides - antioxidant activity - anti-inflammatory activity
References
- 1 Kouno I, Shimamoto S, Jiang Z H, Tanaka T. Prenylated C6-C3 compounds from root bark of Illicium anisatum . Phytochemistry. 1997; 46 1389-92.
- 2 Kouno I, Iwamoto C, Kameda Y, Tanaka T, Yang C S. A new triphenyl-type neolignan and a biphenylneolignan from the bark of Illicium simonsii . Chem Pharm Bull. 1994; 42 112-4.
- 3 Yokoyama R, Huang J M, Yang C S, Fukuyama Y. New seco-prezizaane-type sesquiterpenes, jiadifenin with neurotrophic activity and 1,2-dehydroneomajucin from Illicium jiadifengpi . J Nat Prod. 2002; 65 527-31.
- 4 Schmidt T J, Schmidt H M, Müller E, Peters W, Fronczek F R, Truesdale A. et al . New sesquiterpene lactones from Illicium floridanum . J Nat Prod. 1998; 61 230-6.
- 5 Lennart N, Lundgren T P, Theander O. Dilignol glycosides from needles of Picea abies . Phytochemisty. 1981; 20 1967-9.
- 6 Lemiere G, Gao M, Alex D G. 3′,4-O-Methycedrusin: synthesis, resolution and absolute configuration. J Chem Soc Perkin Trans. 1995; 1 1775-9.
- 7 Zhang Z Z, EISohly H N, Li X C, Khan S I, Broedel S E, Raulli R E. et al . Phenolic compounds from Nymphaea odorata . J Nat Prod. 2003; 66 548-50.
- 8 Braga A CH, Zacchino S, Baddano H, Gonzalez S M, Ruveda A E. 13C-NMR spectral and conformational analysis 8-O-4 neolignans. Phytochemistry. 1984; 23 2025-8
- 9 Matsuda N, Kikuchi M. Studies on the constituents of Lonicera species. X. Neolignan glycosides from the leaves of Lonicera gracilipes Var. glandulosa Maxim. Chem Pharm Bull. 1996; 44 1676-9.
- 10 Kouno I, Hashimoto M, Enjoii S, Takahashi M, Kaneto H, Yang C S. Isolation of neoanisatin derivatives from the pericarps of Illicium majus with other constituents. Chem Pharm Bull. 1991; 39 1773-8.
- 11 Kouno I, Kawano N. New pseudoanisatin-like sesquiterpene lactones from the bark of Illicium dunnianum . J Chem Soc Perkin Trans. 1988; 1 1537-9.
- 12 Kauno I, Irie H, Kawano N. The structures of pseudoanisatin and its novel base-catalysed rearrangement product. J Chem Soc Perkin Trans. 1984; 1 2511-5.
- 13 Schmidt T J. Novel seco-prezizaane sesquiterpenes from North America Illicium species. J Nat Prod. 1999; 62 684-7.
- 14 Zhao P P, Li B M, He L Y. Studies on the method of determination of combined sugars in glycosides. Acta Pharm Sin. 1987; 22 70-4.
- 15 Oshima R, Kumanotani J. Determination of configuration of monosaccharides by HPLC diastereoiso meric 1-deoxy-1-(N-acetyl-α-methylbenzylamino) alditol acetates. Chem Lett 1981: 943-6.
- 16 Dai S J, Wu Y, Wang Y H, He W Y, Chen R Y, Yu D Q. New Diels-Alder type adducts from Morus Macroura and their anti-oxidant activities. Chem Pharm Bull. 2004; 52 1190-3.
- 17 Zhong M, Cheng G F, Wang W J, Guo Y, Zhu X Y, Zhang J T. Inhibitory effect of resveratrol on interleukin 6 release by stimulated peritoneal macrophages of mice. Phytomedicine. 1999; 6 79-84.
- 18 Zhang M, Yao Q, Sun B H, Zhou Y X. Inducement and production of tumor necrosis factor by murine peritoneal macrophage. J Immunol (Chinese). 1991; 7 254-7.
Shi-Shan Yu
Key Laboratory of Bioactive Substance and Resources Utilization of Chinese Herbal Medicine
Ministry of Education
Institute of Materia Medica
Chinese Academy of Medical Sciences and Peking Union Medical College
Beijing 100050
People’s Republic of China
Phone: +86-10-6316-5324
Fax: +86-10-6301-7757
Email: yushishan@imm.ac.cn