Flavonoids and Other Constituents from Aletris Spicata and Their Chemotaxonomic Significance

Natural Product Research Formerly Natural Product Letters

ISSN: 1478-6419 (Print) 1478-6427 (Online) Journal homepage: http://www.tandfonline.com/loi/gnpl20

Flavonoids and other constituents from Aletris spicata and their chemotaxonomic significance

Lin-Zhen Li, Meng-Hua Wang, Jian-Bo Sun & Jing-Yu Liang

To cite this article: Lin-Zhen Li, Meng-Hua Wang, Jian-Bo Sun & Jing-Yu Liang (2014) Flavonoids and other constituents from Aletris spicata and their chemotaxonomic significance, Natural Product Research, 28:15, 1214-1217, DOI: 10.1080/14786419.2014.921918

To link to this article: http://dx.doi.org/10.1080/14786419.2014.921918

View supplementary material

Published online: 04 Jun 2014.

Submit your article to this journal

Article views: 156

View related articles

View Crossmark data

Citing articles: 3 View citing articles

Full Terms & Conditions of access and use can be found at http://www.tandfonline.com/action/journalInformation?journalCode=gnpl20

Download by: [City University of Hong Kong Library] Date: 07 January 2017, At: 02:17 Natural Product Research, 2014 Vol. 28, No. 15, 1214–1217, http://dx.doi.org/10.1080/14786419.2014.921918

SHORT COMMUNICATION Flavonoids and other constituents from Aletris spicata and their chemotaxonomic signiﬁcance Lin-Zhen Li, Meng-Hua Wang, Jian-Bo Sun and Jing-Yu Liang*

Department of Natural Medicinal Chemistry, China Pharmaceutical University, #24 Tongjiaxiang, Nanjing 210009, P.R. China (Received 20 March 2014; ﬁnal version received 4 May 2014)

Eleven compounds, including four flavonoids [(2R,3R)-2,3-dihydro-3,5-dihydroxy- 7,40-dimethoxyflavone (1), 5-hydroxy-7,8,40-trimethoxy-flavone (2), amentoflavone (10) and apigenin (11)], two penylpropanoids [sinapaldehyde (3) and 3-methoxy-4- hydroxy-cinnamic aldehyde (4)], three phenolic acids [4-hydroxyl-3,5-dimethoxy- benzaldehyde (5), 4-hydroxyacetophen-one (6) and p-hydroxybenzaldehyde (7)], one furan derivative [5-hydroxymethyl furfural (8)] and one steroid saponin [b-sitosterol-3- O-b-D-glucoside (9)], were isolated and identified from Aletris spicata. Among them, compounds 1–7, 9 and 10 were reported from the genus Aletris for the first time. Furthermore, seven of them (1–6, 10) were obtained from the family Liliaceae for the first time. Chemotaxonomy of the isolated compounds is discussed briefly. Keywords: Aletris spicata; Chemotaxonomy; Nartheciaceae

1. Introduction The genus Aletris L. is composed of 25 species worldwide and mainly distributed in Eastern Asia, West Indies (Bahamas) and Northern America (Sullivan 1973). There are 15 species and 1 variety in China, eight of which are uniquely Chinese (Liang & Turland 2000, Zhao et al. 2006). Aletris spicata (Thunb.) Franch. belongs to this genus and is grown in the east, south and southwest of China as a perennial herb. It possesses a good reputation in the treatment of various human diseases such as bronchitis, whooping cough, mumps and neurosis (Xie et al. 1996). There are a few previous reports on the phytochemical investigations of A. spicata. A literature survey indicated the presence of steroid sapogenins, ﬂavonoids and penylpropanoids (Marker et al. 1940; Akahori et al. 1971; Hao et al. 2012; Huang et al. 2013). There is a great deal of disagreement as to the delimitation of Aletris. First, the genus Aletris was assigned to Liliaceae of Liliales traditionally (Ambrose 1980). However, modern research indicated that the genus and its allies (Lophiola, Metanarthecium, Narthecium and Nietneria) should be removed from Liliaceae to another family, Nartheciaceae of Dioscoreales (APG 2009). Second, the study of Fuse and Tamura revealed that Metanarthecium and Aletris were distantly relative genera (Fuse & Tamura 2000). While Merckx et al. regarded Metanarthecium and Aletris as the same genus and incorporated Metanarthecium in Aletris (Merckx & Bidartondo 2008). These differences manifest the problematic and controversial relationship between Aletris and Metanarthecium within Nartheciaceae.

*Corresponding author. Email: [email protected] q 2014 Taylor & Francis Natural Product Research 1215

2. Results and discussion In this study, 11 compounds, including 4 flavonoids (1, 2, 10, 11), 2 penylpropanoids (3–4), 3 phenolic acids (5–7), 1 furan derivative (8) and 1 steroid saponin (9), were isolated and identified from the herbs of A. spicata. The structures of the isolated compounds were identified on the basis of spectral data and by comparing with those reported in the literature data. They were elucidated as (2R,3R)-2,3-dihydro-3,5-dihydroxy-7,40-dimethoxyflavone (1) (Tsai et al. 1997), 5-hydroxy- 7,8,40-trimethoxy-flavone (2) (Horie et al. 1998), sinapaldehyde (3) (Farah & Samuelsson 1992), 3-methoxy-4-hydroxy-cinnamic aldehyde (4) (Liu et al. 2005), 4-hydroxyl-3,5-dimethoxy- benzaldehyde (5) (Zhao et al. 2012), 4-hydroxyacetophen-one (6) (Li et al. 2011), p- hydroxybenzaldehyde (7) (Zhang et al. 2013), 5-hydroxymethyl furfural (8) (Shen & Mu 1990), b-sitosterol-3-O-b-D-glucoside (9) (El-Alfy et al. 2012), amentoflavone (10) (Markham et al. 1987) and apigenin (11) (Kim et al. 2013), respectively (Figure 1). Among them, compounds 1–7, 9 and 10 were reported from the genus Aletris for the first time; seven of them (1–6, 10) were obtained from the family Liliaceae for the first time. It is well known that steroidal saponins were considered as the major chemical constituents from Liliaceae (Yang et al. 2007). A member of steroidal saponins, b-sitosterol-3-O-b-D- glucoside (9) has been isolated from Aletris spicata in this study. However, compounds 1–7 and 10 were reported from this genus for the first time. Furthermore, seven of these (1–6, 10) were isolated from the family Liliaceae for the first time. These may have contributed greatly to the delimitation of Aletris and support the Angiosperm Phylogeny Group (APG) system classified Aletris into Nartheciaceae of Dioscoreales. To the best of our knowledge, nine sapogenins (metagenin, 3-epi-metagenin, nogiragenin, neonogiragenin, narthogenin, isonarthogenin, meteogenin, neometaogenin and luvigenin) have

been obtained from Metanarthecium (Kitagawa et al. 1976, 1977; Kitagawa & Nakanishi 1981), four sapogenins (diosgenin, isonarthogenin, gentrogenin and bethogenin) and two sterols (b-sitosterol and stigmasterol) have been isolated from Aletris (Marker et al. 1940; Akahori et al. 1971). It is quite obvious that Aletris and Metanarthecium have some parallels as a lot of steroidal saponins have been isolated from both of them, and even share some identical sapogenins such as isonarthogenin. However, they actually differ from each other due to the different types of sapogenins. And in addition, compounds 1–11 isolated from A. spicata have

Figure 1. Chemical constituents of A. spicata. 1216 L.-Z. Li et al. not been reported from Metanarthecium to date. On the basis of phytochemical evidence, it is supported that Aletris excluding Metanarthecium is monophyletic.

3. Conclusion The results indicate that A. spicata has some similar constituents (8, 11) with other species of Dioscoreales plants. Compounds 1–7 and 10 could be marked as the characteristic chemical constituents of the genus Aletris. This study supports the APG that classiﬁed the genus Aletris into the family of Nartheciaceae (Dioscoreales), and Aletris should be paratactic in Nartheciaceae from the chemotaxonomical aspect although it is to some extent similar to Metanarthecium. Further phylogenetic and chemical investigations around the family Nartheciaceae will provide more information and evidence.

Supplementary material Experimental details relating to this article are available online.

Acknowledgements We acknowledge the ﬁnancial support by the National New Drug Innovation Major Project of China (2011ZX09307-002-02).

References Akahori A, Yasuda F, Okanishi T. 1971. Steroidal components of domestic plants. LXIV. Steroidal sapogenins of Aletris spicata. Chem Pharm Bull. 19:2409–2411. Ambrose JD. 1980. A re-evaluation of the Melanthioideae (Liliaceae) using numerical analyses. In: Brickell CD, DF Cutler, Gregory M, editors. Pelaloid monocotyledons. London: Academic Press; p. 65–81. APG. 2009. An update of the Angiosperm Phylogeny Group classification for the orders and families of flowering plants: APG III. Bot J Linn Soc. 161:105–121. El-Alfy TS, Ezzat SM, Sleem AA. 2012. Chemical and biological study of the seeds of Eragrostis tef (Zucc.) Trotter. Nat Prod Res. 26:619–629. Farah MH, Samuelsson G. 1992. Pharmacologically active phenylpropanoids from Senra incana. Planta Med. 58:14–18. Fuse S, Tamura MN. 2000. A phylogenetic analysis of the plastid matK gene with emphasis on Melanthiaceae sensu lato. Plant Biol (Stuttg). 2:415–427. Hao Q, Li R, Yao Y, Li H-Z, Li R-T. 2012. C-glycosylflavone from Aletris spicata. Biochem Syst Ecol. 45:191–193. Horie T, Ohtsuru Y, Shibata K, Yamashita K, Tsukayama M, Kawamura Y. 1998. 13C NMR spectral assignment of the A-ring of polyoxygenated flavones. Phytochemistry. 47:865–874. Huang L, Pan J, Cao P-x, Pan W-d, Liang G-y. 2013. Chemical constituents of Aletris spicata. Chin Tradit Herb Drugs. 44:812–815. Kim AR, Jin Q, Jin H-G, Ko HJ, Woo E-R. 2013. Phenolic compounds with IL-6 inhibitory activity from Aster yomena. Arch Pharm Res. [ahead of print]. Kitagawa I, Nakanishi T. 1981. Saponin and sapogenol. XXX. Furostanol glycosides from Metanarthecium luteo-viride Maxim.: bisdesmosides of furometagenin and furometanarthogenin. Chem Pharm Bull. 29:1299–1311. Kitagawa I, Nakanishi T, Morii Y, Yosioka I. 1976. On the genuine sapogenol of meteogenin, an A-ring aromatized spirostanol from Metanarthecium luteo-viride Maxim. Structure elucidation by means of soil bacterial hydrolysis. Tetrahedron Lett. 17:1885–1888. Kitagawa I, Nakanishi T, Morii Y, Yosioka I. 1977. Soil bacterial hydrolysis leading to genuine aglycone. X. On the structure of a genuine sapogenol of meteogenin, an A-ring aromatized spirostanol from Metanarthecium luteo- viride Maxim. Chem Pharm Bull. 25:2343–2349. Li W, Wang H, Gong T, Chen R. 2011. Chemical constituents from aerial parts of Anabasis aphylla. Chin Tradit Herb Drugs. 42:837–840. Liang SY, Turland NJ. 2000. Aletris Linnaeus in: Flora of China. Beijing: Science Press. Liu D, Pang F, Zhang J, Wang N, Yao X. 2005. Studies on the chemical constituents of Bulbophyllum odoratissimum Lindl. Chin J Med Chem. 15:103–107. Natural Product Research 1217

Marker RE, Turner DL, Shabica AC, Jones EM, Krueger J, Surmatis JD. 1940. Sterols. CVII. Steroidal sapogenins of Aletris, Asparagus and Lilium. J Am Chem Soc. 62:2620–2621. Markham KR, Sheppard C, Geiger H. 1987. Carbon-13 NMR of flavonoids. Part IV. Carbon-13 NMR studies of some naturally occurring amentoflavone and hinokiflavone biflavonoids. Phytochemistry. 26:3335–3337. Merckx V, Bidartondo MI. 2008. Breakdown and delayed cospeciation in the arbuscular mycorrhizal mutualism. Proc Biol Sci. 275:1029–1035. Shen YM, Mu QZ. 1990. New furans from Cirsium chlorolepis. Planta Med. 56:472–474. Sullivan VI. 1973. Biosystematics of Aletris lutea small, Aletris obovata nash, and natural hybrids (Liliaceae). Brittonia. 25:294–303. Tsai Y-C, Chiang S-Y, El-Shazly M, Wu C-C, Beerhues L, Lai W-C, Wu S-F, Yen M-H, Wu Y-C, Chang F-R. 1997. The oestrogenic and anti-platelet activities of dihydrobenzofuroisocoumarins and homoisoflavonoids from Liriope platyphylla roots. Food Chem. 140:305–314. Xie ZW, Fan CS, Zhu ZY. 1996. National collection of chinese herbal medicine. Beijing: People’s Medical Publishing House. Yang CR, Zhang Y, Wang D, Zhang YJ. 2007. Molecular evolution of steroidal saponins in the genus Polygonatum (Convalleriaceae) and their chemotaxonomical significance. Acta Bot Yunnan. 29:591–600. Zhang Y, Chen Q, Liu L-l, Deng S, Qu L, Wang T. 2013. Isolation and identification of chemical constituents from Althaea rosea (Linn.) Cavan. I. J Shenyang Pharm Univ. 30:335–341. Zhao M, Han J, Lu S, Zhang S. 2012. Study on chemical constituents in twigs of Syringa oblata. Chin Tradit Herb Drugs. 43:251–254. Zhao YM, Zhang SR, Bi HY. 2006. Geographical distribution, species diversity and speciation centers of Aletris (Nartheciaceae). Acta Bot Boreal-Occident Sin. 26:2131–2141. 本文献由“学霸图书馆-文献云下载”收集自网络，仅供学习交流使用。

学霸图书馆（www.xuebalib.com）是一个“整合众多图书馆数据库资源，

提供一站式文献检索和下载服务”的24 小时在线不限IP 图书馆。图书馆致力于便利、促进学习与科研，提供最强文献下载服务。

图书馆导航：

图书馆首页文献云下载图书馆入口外文数据库大全疑难文献辅助工具