RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000058.xml
Planta Med 2014; 80(13): 1113-1117
DOI: 10.1055/s-0034-1382956
DOI: 10.1055/s-0034-1382956
Original Papers
Isolation and Cytotoxic Effect of Anthraquinones from Morinda umbellata
Weitere Informationen
Publikationsverlauf
received 29. Januar 2014
revised 03. Juli 2014
accepted 09. Juli 2014
Publikationsdatum:
19. August 2014 (online)
Abstract
Four new anthraquinones, 1,6-dihydroxy-2-methoxymethylanthraquinone (1), 6-hydroxy-7-methoxy-2-methoxymethylanthraquinone (3), 3,6-dihydroxy-7-methoxy-2-methylanthraquinone (4), and 6-hydroxy-2-methoxymethylanthraquinone (8), together with 12 known anthraquinones and 6 other known compounds, were isolated from the EtOAc extract of Morinda umbellata. Among the isolated compounds, 1, rubiadin (14), and, 3-hydroxy-2-hydroxymethylanthraquinone (16) exhibited significant cytotoxicities against HepG2 cells, with GI50 values of 4.4, 3.6, and 4.8 µM, respectively.
Key words
Morinda umbellate - Rubiaceae - 1,6-dihydroxy-2-methoxymethyl-anthraquinone - 6-hydroxy-7-methoxy-2-methoxymethylanthraquinone - 3,6-dihydroxy-7-methoxy-2-methylanthraquinone - 6-hydroxy-2-methoxymethylanthraquinone - cytotoxicity-
References
- 1 Yang TYA. Morinda L. In: Editorial Committee of the Flora of Taiwan, editor Flora of Taiwan. 2nd edition, Volume IV. Taipei: Department of Botany, National Taiwan University; 1998: 299-301
- 2 Juangsu New Medical College. Zhong Yao Da Ci Dian (Dictionary of Chinese Materia Medica). Shanghai: Shanghai Scientific and Technological Publishers; 1977: 807
- 3 Ismail NH, Lajis NH, Ali AM, Aimi N, Kitajima M, Takayama H. Anthraquinones from Morinda elliptica. Phytochemistry 1997; 45: 1723-1725
- 4 Ee GC, Wen YP, Sukari MA, Go R, Lee HL. A new anthraquinone from Morinda citrifolia roots. Nat Prod Res 2009; 23: 1322-1329
- 5 Kamiya K, Satake T, Tanaka Y, Kamiya K, Satake T, Endang H, Umar M. New anthraquinone and iridoid from the fruits of Morinda citrifolia . Chem Pharm Bull 2005; 53: 1597-1599
- 6 He QW, Wang G, Feng T, He QW, Liu JK. Two new phenylpropanoids and one propanoate from Morinda citrifolia . J Asian Nat Prod Res 2011; 13: 238-241
- 7 Cimanga K, Bruyne TD, Lasure A, Li Q, Pieters L, Claeys M, Berghe DV, Kambu K, Tona L, Vlietinck A. Flavonoid O-glycosides from the leaves of Morinda morindoides . Phytochemistry 1995; 38: 1301-1303
- 8 Guo SP, Song QS, Xiang W, Xiang W, Zhang HJ. Antimicrobial anthraquinones from Morinda angustifolia . Fitoterapia 2008; 79: 501-504
- 9 Sittie AA, Lemmich E, Olsen CE, Hviid L, Kharazmi A, Nkrumah FK, Christensen SB. Structure-activity studies: in vitro antileishmanial and antimalarial activities of anthraquinones from Morinda lucida . Planta Med 1999; 65: 259-261
- 10 Chang P, Chen CF. Isolation and characterization of antitumor anthraquinones from Morinda umbellata . Chin Pharm J 1995; 47: 347-353
- 11 Wu YB, Han T, Jiao L, Qin LP, Sun LN, Wu YB, Zhang QY, Zheng CJ, Wu JZ. Antiosteoporotic activity of anthraquinones from Morinda officinalis on osteoblasts and osteoclasts. Molecules 2009; 14: 573-583
- 12 Hamabe W, Harada S, Kamiya K, Murakami R, Satake T, Tokuyama S. Chemical constituents of Morinda citrifolia roots exhibit hypoglycemic effects in streptozotocin-induced diabetic mice. Biol Pharm Bull 2008; 31: 935-938
- 13 Núñez Montoya SC, Agnese AM, Cabrera JL. Anthraquinone derivatives from Heterophyllaea pustulata . J Nat Prod 2006; 69: 801-803
- 14 Schripsema J, Ramos-Valdivia A, Verpoorte R. Robustaquinones, novel anthraquinones from an elicited Cinchona robusta suspension culture. Phytochemistry 1999; 51: 55-60
- 15 Huang WH, Yu SH, Li YB, Jiang JQ. Two new anthraquinones from Hedyotis diffusa . J Asian Nat Prod Res 2008; 10: 467-471
- 16 Itokawa H, Mihara K, Takeya K. Studies on a novel anthraquinone and its glycosides isolated from Rubia cordifolia and R. akane . Chem Pharm Bull 1983; 31: 2353-2358
- 17 Cameron DW, Schütz PE. Oxidation and reduction of some methoxy-anthracenes and their derivatives. J Chem Soc C 1967; 2121-2125
- 18 Ali M, Akhtar MSM, Mir SR, Singh O. New anthraquinones from Rubia cordifolia roots. Indian J Chem B 2006; 45: 1945-1950
- 19 Wijnsma R, Verpoorte R, Mulder-Krieger T, Svendsen AB. Anthraquinones in callus cultures of Cinchona ledgeriana . Phytochemistry 1984; 23: 2307-2312
- 20 Jang DS, Jeong IH, Kim JS, Lee YM, Yoo NH, Cho JH, Kim JH. Anthraquinones from the roots of Knoxia valerianoides inhibit the formation of advanced glycation end products and rat lens aldose reductase in vitro . Arch Pharm Res 2010; 33: 209-214
- 21 Fox BW, Hadfield JA, Zhang X. Preparation of naturally occurring anthraquinones. Synthetic Commun 1996; 26: 49-62
- 22 Houghton P, Fang R, Techatanawat I, Steventon G, Hylands PJ, Lee CC. The sulphorhodamine (SRB) assay and other approaches to testing plant extracts and derived compounds for activities related to reputed anticancer activity. Methods 2007; 42: 377-387