New Sesquiterpene Lactone and Neolignan Glycosides with Antioxidant and Anti-Inflammatory Activities from the Fruits of Illicium oligandrum

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.

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.