Sesquiterpenoids from Illicium difengpi and their Chemotaxonomic Significance https://doi.org/10.26538/tjnpr/v1i4.

Main Article Content

Chun-tong Li
Cui Tong
Xiang Li
Zhi-jun Wu
Wan-sheng Chen

Abstract

Illicium difengpi (family Illiciaceae) is a known medicinal plant used in Ancient Chinese medicines for the treatment of diseases and infections. The purpose of the present study was to investigate the chemical constituents of the stem bark of Illicium difengpi and determine their chemotaxonomic significance. The stem barks of I. difengpi were purchased from Caitongde Pharmacy and authenticated by Professor Lian-na Sun. The 80 % ethanol extract was fractionated with silica gel column chromatography (C.C.) and compounds were isolated with ODS C.C., silica gel (SiO2) C.C. and preparative/semipreparative HPLC from the fractions. The chemical structures were elucidated by NMR spectroscopy and mass spectrometry, as well as the comparison of spectra data with that reported in the literature. The present phytochemical investigation on Illicium difengpi led to the isolation and characterization of 13 sesquiterpenoids, including five eudesmanes, three cadinanes, two bullatanes and three other types of sesquiterpenoids. All compounds except compound 2 were isolated from this species for the first time. In addition, compounds 1, 3, 4, 5, 7, 8, 11 and 13 have not been reported in any species of the genus Illicium and the family Illiciaceae. Sesquiterpenoid compounds from I. difengpi may have the potential to produce new insights into the historical debate concerning the systematic position and
phylogenetic relationship of the genus Illicium

Downloads

Download data is not yet available.

Article Details

How to Cite
Li, C.- tong, Tong, C., Li, X., Wu, Z.- jun, & Chen, W.- sheng. (2017). Sesquiterpenoids from Illicium difengpi and their Chemotaxonomic Significance: https://doi.org/10.26538/tjnpr/v1i4. Tropical Journal of Natural Product Research (TJNPR), 1(4), 158-162. https://tjnpr.org/index.php/home/article/view/314
Section
Articles

How to Cite

Li, C.- tong, Tong, C., Li, X., Wu, Z.- jun, & Chen, W.- sheng. (2017). Sesquiterpenoids from Illicium difengpi and their Chemotaxonomic Significance: https://doi.org/10.26538/tjnpr/v1i4. Tropical Journal of Natural Product Research (TJNPR), 1(4), 158-162. https://tjnpr.org/index.php/home/article/view/314

References

Oh IC, Denk T, Friis EM, Evolution of Illicium (Illiciaceae): Mapping morphological characters on the molecular tree. Plant Syst Evol. 2003; 240:175-209.

Chinese Pharmacopoeia Commission. Chinese Pharmacopoeia (2015 edition): Book I. Beijing: China Medical Science Press; 2015. 123 p.

Liu P, Liu XC, Dong HW, Liu ZL, Du SS, Deng ZW. Chemical composition and insecticidal activity of the essential oil of illicium pachyphyllum fruits against two grain storage insects. Molecules 2012; 17:14870-14811.

Wang GW, Hu WT, Huang BK, Qin LP. Ultrasonic nebulization extraction coupled with on-line gas chromatography for determination of trans-anethole in spices. J Ethnopharmacol. 2011; 136:10-20.

Gholivand MB, Nasrabadi MR, Chalabi H. Determination of essential oil components of star anise (Illicium verum) using simultaneous hydrodistillation-static headspace liquid-phase microextraction-gas chromatography mass spectrometry. Anal Lett. 2009; 42:1382-1397.

Liu YN, Su XH, Huo CH, Xhang XP, Shi QW, Gu YC. Chemical Constituents of Plants from the Genus Illicium. Chem Biodivers. 2009; 6:963-989.

Zhuang PY, Zhang GJ, Wang XJ, Zhang Y, Yu SS, Ma SG, Liu YB, Qu J, Li Y, Xu S, Lü HN, Chen X, Li L, Si YK, Zhang Dl. Prenylated C6–C3 compounds from the roots of Illicium henryi. Phytochemistry 2013; 86:176-183.

Dong CF, Liu L, Li XN, Guan ZY, Huo HR, Wang YF. Sesquineolignans and Terpene-Sesquineolignans: AntiAcetylcholinesterase Constituents from Illicium simonsii. Planta Med. 2013; 79:338-347.

Isao K, Yukari Y, Satomi S, Miki S, Yang CS. Phenylpropanoids from the Barks of Illicium difengpi. Chem Pharm Bull. 1992; 40:2461-2464.

Fang L, Du D, Ding GZ, Si YK, Yu SS, Liu Y, Wang WJ, Ma SG, Xu S, Qu J, Wang JM, Liu YX. Neolignans and glycosides rom the stem bark of Illicium difengpi. J Nat Prod. 2010; 73:818-824.

Huang P, Yang M, Lai MX, Zheng XZ, Nisimasa S, Naknisi C. Chemical Constituents of Illicium difengpi Bark. Acta Pharm Sin. 1996; 31:278-

Isao K, Yukari Y, Satomi S, Miki S, Yumi I, Yang CS. Neolignans and a phenylpropanoid glucoside from Illicium difengpi. Phytochemistry

; 32:1573-1577.

Fang L, Wang XJ, Ma SG, Yu SS. A new sesquiterpene lactone and a new aromatic glycoside from Illicium difengpi. Acta Pharm Sin B 2011; 1:178-183.

Huang P, Nishi M, Zheng XZ, Lai MX, Naknishi T. Chemistry constituents of Illicium difengpi. Acta Pharm Sin 1997; 32:704-707.

Rui HK, Ji WL. The chemical constituents of essential oils from Illicium difengpi. Guihaia 1992; 12:381-383.

Wang JL, Yang CS, Da WR. GC-MS analysis on essential oils from Illicium difengpi fruit. Zhongguo Zhongyao Zazhi 1994 ; 19 : 422-423.

Chu SS, Wang CF, Du SS, Liu SL, Liu ZL. Toxicity of the essential oil of Illicium difengpi stem bark and its constituent compounds towards two grain storage insects. J Insect Sci. 2011; 11:152.

Aman D, Ermias D., Olov S. Furanosesquiterpenes from Commiphora sphaerocarpa and related adulterants of true myrrh. Fitoterapia 2002; 73:48-55.

Albert TB, David JG. Sesquiterpene Alcohols from Hedychium spicatum var. Acuminatum. J Nat Prod. 1987; 50:732-734.

Zhang HJ, Tan GT, Bernard DS, Andrew DM, Nguyen VH, Nguyen MC, Doel S, John MP, Harry HSF. New Sesquiterpenes from Litsea verticillata. J Nat Prod. 2003; 66:609-615.

Fumihiro N, Katsuhiro K, Yuko H, Shigeru t, Yoshinori A. EntVerticillane-type diterpenoids from the Japanese liverwort Jackiella javanica. Phytochemistry 2005; 66:1662-1670.

Isao K, Zheng C, Byeng WS, Motomasa K, Yoshimasa K. Marine Natural Products. XVII. Nephtheoxydiol, a New Cytotoxic Hydroperoxy-Germacrane Sesquiterpene, and Related Sesquiterpenoids from an Okinawan Soft Coral of Nephthea sp. (Nephtheidae). Chem Pharm Bull. 1987; 35:124-135.

Tsui WY, Geoffrey DB. Sesquiterpenes from Baeckea frutescens. J Nat Prod. 1996; 59:1084-1086.

Luo MH, Lei LF, Lin HH. Studies on chemical constituents from rhizomes of Hedychium chrysoleucum. Chin J Chin Mat Med. 2009; 34:180-183.

Jung KY, Kim DS, Oh SR, Lee IS, Lee JJ, Lee HK, Shin DH, Kim EH, Cheong CJ. Sesquiterpene components from the flower buds of Magnolia fargesii. Arch Pharm Res. 1997; 20:363-367.

Yoshiyasu F, Naomi S, Mitusaki K. Isodunnianin: A New Sesquiterpene Enhancing Neurite Outgrowth in Primary Culture of Fetal Rat Cerebral Hemisphere from Illicium tashiroi. Planta Med. 1993; 59:181-182.

Li RT, Zhao AH, Sheng YH, Na Z, Sun HD. Chemical constituents from Schisandra plena. J Asian Nat Prod Res. 2005; 7:847-852.

Sung TV, Steffan B, Steglich W, Klebe G, Adam G. Sesquiterpenoids from the roots of Homalomena aromatica. Phytochemistry 1992; 31:3515-3520.

Hu YM, Liu C, Cheng KW, Sung HY, Williams LD, Yang ZL, Ye WC. Sesquiterpenoids from Homalomena occulta affect osteoblast proliferation, differentiation and mineralization in vitro. Phytochemistry 2008; 69:2367-2373.

Parmar VS, Jain SC, Gupta S, Talwar S, Rajwanshi VK, Kumar R, Azim A, Malhotra S, Kumar N, Jain R, Sharma NK, Tyagi OD. Polyphenols and alkaloids from piper species. Phytochemistry 1998; 48:1069-1078.

Lee J, Kim NH, Nam JW, Lee YM, Jang DS, Kim YS, Nam SH, Seo EK, Yang MS, Kim JS. Scopoletin from the flower buds of Magnolia fargesii inhibits protein glycation, aldose reductase, and cataractogenesis Ex Vivo. Arch Pharm Res.2010; 33:1317-1323.

Schühly W, Skarbina J, Kunert O, Nandi OI, Bauer R. Chemical Characterization of Magnolia biondii (Flos Magnoliae, Xin Yi). Nat Prod Commun. 2009; 4:231-234.

Smith AC. The families Illiciaceae and Schisandraceae. Sargentia 1947; 7:156-209.

Bailey IW, Nast CG. Morphology and relationships ofIllicium, Schisandra andKadsura I. Stem and leaf. J Arnold Arbor 1948; 29:77-89.

Sy LK, Richard MKS, Geoffrey DB. Marasmane sesquiterpenes from the basidiomycete Clitocybe hydrogramma. Phytochemistry 1997; 44:1099-1101.

Zhao L Q, Luo YM. Terpenoids and their chemotaxonomic signigicance in Illicium. Guihaia 2007; 2:272-276.

Lin Q. Taxonoma of Genus Illicium Linn. Bull Bot Res. 2001; 21:161-174.

Lin Q. Taxonoma of Genus Illicium Linn. Bull Bot Res. 2001; 21:322-334.

Liu JF, Zhang XM, Shi Y, Zhang Q, Ma YB, Chen JJ. Chemical constituents in stems and leaves of Illicium simonsii. Chin Tradit Herbal Drugs 2012; 43:51-54