Structures and biological activities of the triterpenoids and sesquiterpenoids from Alisma orientale

Phytochemistry

Volumn 131, Issue , 2016, Pages 150-157

  Ma, Qingjuan ^a   Han, Li ^a   Bi, Xiaoxu ^a   Wang, Xingbo ^a   Mu, Yu ^a   Guan, Peipei ^a   Li, Liya ^a   Huang, Xueshi ^a  

^a NORTHEASTERN UNIVERSITY   (China)

Author keywords

Alisma orientale; Alismataceae; Anti inflammatory activity; Antibacterial activity; Cytotoxicity; Sesquiterpenoid; Triterpenoid

Indexed keywords

ALISOL A; ALISOL A 24-ACETATE; ALISOL B 23-ACETATE; ALISOL F; ALPHA GLUCOSIDASE; ANTIINFECTIVE AGENT; CHOLEST 4 EN 3 ONE; HERBACEOUS AGENT; NITRIC OXIDE; SESQUITERPENE; TRITERPENE;

ALISMA; BACILLUS SUBTILIS; BIOSYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; HUMAN; ISOLATION AND PURIFICATION; MACROPHAGE; METABOLISM; MICROBIAL SENSITIVITY TEST; RHIZOME; STAPHYLOCOCCUS AUREUS;

ALISMA; ALPHA-GLUCOSIDASES; ANTI-BACTERIAL AGENTS; BACILLUS SUBTILIS; CHOLESTENONES; DRUGS, CHINESE HERBAL; HUMANS; MACROPHAGES; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; NITRIC OXIDE; RHIZOME; SESQUITERPENES; STAPHYLOCOCCUS AUREUS; TRITERPENES;

EID: 84989184548     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2016.08.015     Document Type: Article

References (25)

1. Blay, G., Garcia, B., Molina, E., Pedro, J.R., Syntheses of (+)-alismoxide and (+)-4-epi-alismoxidem. J. Org. Chem. 71 (2006), 7866–7869.
2. Chen, D.Q., Feng, Y.L., Tian, T., Chen, H., Yin, L., Zhao, Y.Y., Lin, R.C., Diuretic and anti-diuretic activities of fractions of Alismatis rhizoma. J. Ethnopharmacol. 157 (2014), 114–118.
3. Feng, Y.L., Chen, H., Tian, T., Chen, D.Q., Zhao, Y.Y., Lin, R.C., Diuretic and anti-diuretic activities of the ethanol and aqueous extracts of Alismatis rhizoma. J. Ethnopharmacol. 154 (2014), 386–390.
4. Fong, W.F., Wang, C., Zhu, G.Y., Leung, C.H., Yang, M.S., Cheung, H.Y., Reversal of multidrug resistance in cancer cells by Rhizoma alismatis extract. Phytomedicine 14 (2007), 160–165.
5. Han, C.W., Kwun, M.J., Kim, K.H., Choi, J.Y., Oh, S.R., Ahn, K.S., Lee, J.H., Joo, M., Ethanol extract of Alismatis rhizoma reduces acute lung inflammation by suppressing NF-κB and activating Nrf2. J. Ethnopharmacol. 46 (2013), 402–410.
6. Huang, Y.T., Huang, D.M., Chueh, S.C., Teng, C.M., Guh, J.H., Alisol B acetate, a triterpene from Alismatis rhizoma, induces Bax nuclear translocation and apoptosis in human hormone-resistant prostate cancer PC-3 cells. Cancer Lett. 231 (2006), 270–278.
7. Hunter, R.A., Storm, W.L., Coneski, P.N., Schoenfisch, M.H., Inaccuracies of nitric oxide measurement methods in biological media. Anal. Chem. 85 (2013), 1957–1963.
8. Hu, X.Y., Guo, Y.Q., Gao, W.Y., Zhang, T.J., Chen, H.X., Two new triterpenes from the rhizomes of Alisma orientalis. J. Asian Nat. Prod. Res. 10 (2008), 481–484.
9. Jin, H.G., Jin, Q.L., Kim, A.R., Choi, H., Lee, J.H., Kim, Y.S., Lee, D.G., Woo, E.R., A new triterpenoid from Alisma orientale and their antibacterial effect. Arch. Pharm. Res. 35 (2012), 1919–1926.
10. Kitagawa, I., Zui, Z., Son, B.W., Kobayashi, M., Kyoqoku, Y., 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. 35 (1987), 124–135.
11. Li, L., Xu, J., Mu, Y., Han, L., Liu, R., Cai, Y., Huang, X., Chemical characterization and anti-hyperglycaemic effects of polyphenol enriched longan (Dimocarpus longan Lour.) pericarp extracts. J. Funct. Foods 13 (2015), 314–322.
12. Mai, Z.P., Zhou, K., Ge, G.B., Wang, C., Huo, X.K., Dong, P.P., Deng, S., Zhang, B.J., Zhang, H.L., Huang, S.S., Ma, X.C., Protostane triterpenoids from the rhizome of Alisma orientale exhibit inhibitory effects on human carboxylesterase 2. J. Nat. Prod. 78 (2015), 2372–2380.
13. Matsuda, H., Kageura, T., Toguchida, I., Murakami, T., Kishi, A., Yoshikawa, M., Effects of sequiterpenes and triterpenes from the rhizome of Alisma orientale on nitric oxide production in lipopolysaccharide-activated macrophages: absolute stereostructures of alismaketones-B 23-acetate and -C 23-acetate. Bioorg. Med. Chem. Lett. 9 (1999), 3081–3086.
14. Nakajima, Y., Satoh, Y., Katsumata, M., Tsujiyama, K., Ida, Y., Shoji, J., Terpenoids of Alisma orientale rhizome and the crude drug Alismatis rhizome. Phytochemistry 36 (1994), 119–127.
15. Peng, G.P., Lou, F.C., Terpenoids of Alisma orientalis Juzep. Nat. Prod. Res. Dev. 13 (2001), 1–4.
16. Peng, G.P., Zhu, G.Y., Lou, F.C., Terpenoids from Alisma orientalis Juzep III. Nat. Prod. Res. Dev. 14 (2002), 7–10.
17. Peng, G.P., Tian, G., Huang, X.F., Lou, F.C., Guaiane-type sesquiterpenoids from Alisma orientalis. Phytochemistry 63 (2003), 877–881.
18. Sakui, N., Kuroyanagi, M., Ishitobi, Y., Sato, M., Ueno, A., Biotransformation of sesquiterpenes by cultured cells of Curcuma zedoaria. Phytochemistry 31 (1992), 143–147.
19. Tian, T., Chen, H., Zhao, Y.Y., Traditional uses, phytochemistry, pharmacology, toxicology and quality control of Alisma orientale (Sam.) Juzep: a review. J. Ethnopharmacol. 158 (2014), 373–387.
20. Weyerstahl, P., Marschall, H., Splittgerber, U., Wolf, D., Analysis of the polar fraction of Haitian vetiver oil. Flavour Frag. J. 15 (2000), 153–173.
21. Xu, J., Zhang, P., Ma, Z., Guo, Y., Zhao, X., Wei, K., Two carabrane-type sesquiterpenes from Vladimiria souliei. Phytochem. Lett. 2 (2009), 204–206.
22. Yoshikawa, M., Hatakeyama, S., Tanaka, N., Fukuda, Y., Murakami, N., Yamahara, J., Orientalols A, B and C, sesquiterpenoids constituents from Chinese Alismatis rhizoma, and revised structures of alismol and alismoxide. Chem. Pharm. Bull. 40 (1992), 2582–2584.
23. Yoshikawa, M., Hatakeyama, S., Tanaka, N., Fukuda, Y., Yamahara, J., Murakami, N., Crude drugs from aquatic plants I. on the constituents of Alismastis rhizoma. (1). Absolute stereostructures of alisols E 23-acetate, F, and G, three new protostane-type triterpenes from Chinese Alismatis rhizoma. Chem. Pharm. Bull. 41 (1993), 1948–1954.
24. Yang, J.L., Liu, L.L., Wang, B.G., Shi, Y.P., Secondary metabolites from Grateloupia turuturu and their chemotaxonomic significance. Biochem. Syst. Ecol. 38 (2010), 850–852.
25. Zhao, M., Goedecke, T., Gunn, J., Duan, J., Che, C., Protostane and fusidane triterpenes: a mini-review. Molecules 18 (2013), 4054–4080.