Download PDF
Planta Med 2012; 78(17): 1873-1877
DOI: 10.1055/s-0032-1327785
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

New Alkaloids and Cytotoxic Principles from Sinomenium acutum

Jing-Jy Cheng
1   National Research Institute of Chinese Medicine, Taipei, Taiwan
4   Institute of Biophotonics, National Yang-Ming University, Taipei, Taiwan
,
Tung-Hu Tsai
2   Institute of Traditional Medicine, National Yang-Ming University, Taipei, Taiwan
,
Lie-Chwen Lin
1   National Research Institute of Chinese Medicine, Taipei, Taiwan
3   Graduate Institute of Integrated Medicine, China Medical University, Taichung, Taiwan
› Author Affiliations
Further Information

Publication History

received 30 April 2012
revised 29 August 2012

accepted 06 September 2012

Publication Date:
11 October 2012 (online)

    Permissions and Reprints

Abstract

Two new alkaloids, 2-demethyl-oxypalmatine (1) and 5-ethoxycarbonylsinoracutine (2), were isolated from the rhizomes of Sinomenium acutum, along with thirty-four known compounds. Cytotoxicity of the isolated compounds was examined for the MCF-7, H460, HT-29, and CEM human cancer cell lines. Dauriporphine (16), 6-O-demethylmenisporphine (17), bianfugecine (18), menisporphine (19), and 6-O-demethyldauriporphine (20) showed differential effects in their cytotoxic activity on the target cancer cell lines. Significant angiogenesis inhibitions of 16 and 19 were also observed.

Key words

Sinomenium acutum - Menispermaceae - 2-demethyl-oxypalmatine - 5-ethoxycarbonylsinoracutine - cytotoxicity - angiogenesis

Supporting Information

 

  • References

  • 1 Juangsu New Medical College. Zhong Yao Da Ci Dian (dictionary of Chinese materia medica), Vol. 1. Shanghai: Shanghai Scientific and Technological Publishers; 1977: 1234-1236
    Google Scholar
  • 2 Tomita M, Okamoto Y, Kikuchi T, Osaki K, Nishikawa M, Kamiya K, Sasaki Y, Matoba K, Goto K. Studies on the alkaloids of menispermaceous plants. CCLIX. Alkaloids of Menispermum dauricum DC. Structures of acutumine and acutumidine. Chem Pharm Bull 1971; 19: 770-791
    CrossrefPubMedGoogle Scholar
  • 3 Ichikawa K, Kinoshita T, Itai A, Iitaka Y, Sankawa U. Isolation of (−)-stepholidine, an alkaloid of antiserotonergic-like activity from Sinomenium acutum . Heterocycles 1984; 22: 2071-2077
    CrossrefPubMedGoogle Scholar
  • 4 Jin HZ, Wang XL, Wang HB, Wang YB, Lin LP, Ding J, Qin GW. Morphinane alkaloid dimers from Sinomenium acutum . J Nat Prod 2008; 71: 127-129
    CrossrefPubMedGoogle Scholar
  • 5 Bao GH, Qin GW, Wang R, Tang XC. Morphinane alkaloids with cell protective effects from Sinomenium acutum . J Nat Prod 2005; 68: 1128-1130
    CrossrefPubMedGoogle Scholar
  • 6 Wang X, Jin H, Li Z, Qin G. 8-demethoxyrunanine from Sinomenium acutum . Fitoterapia 2007; 78: 593-595
    CrossrefPubMedGoogle Scholar
  • 7 Liu L, Buchner E, Beitze D. Amelioration of rat experimental arthritis by treatment with the alkaloid sinomenine. Int J Immunopharmacol 1996; 18: 529-543
    CrossrefPubMedGoogle Scholar
  • 8 Candinas D, Mark W, Kaever V, Miyatake T, Koyamada N, Hechenleitner P, Hancock WW. Immunomodulatory effects of the alkaloid sinomenine in the high responder ACI-to-Lewis cardiac allograft model. Transplantation 1996; 62: 1855-1860
    CrossrefPubMedGoogle Scholar
  • 9 Nishida S, Satoh H. In vitro pharmacological actions of sinomenine on the smooth muscle and the endothelial cell activity in rat aorta. Life Sci 2006; 79: 1203-1206
    CrossrefPubMedGoogle Scholar
  • 10 Fatokun AA, Stone TW, Smith RA. Hydrogen peroxide-induced oxidative stress in MC3 T3-E1 cells: the effects of glutamate and protection by purines. Bone 2006; 39: 542-551
    CrossrefPubMedGoogle Scholar
  • 11 Bao GH, Wang XL, Tang XC, Chiu P, Qin GW. Sinoracutine, a novel skeletal alkaloid with cell-protective effects from Sinomenium acutum . Tetrahedron Lett 2009; 50: 4375-4377
    CrossrefPubMedGoogle Scholar
  • 12 Kashiwaba N, Morooka S, Ono M, Toda J, Suzuki H, Sano T. Alkaloidal constituents of the leaves of Stephania cepharantha cultivated in Japan: structure of Cephasugine, a new Morphinane alkaloid. Chem Pharm Bull 1997; 45: 545-548
    CrossrefPubMedGoogle Scholar
  • 13 Pinho PMM, Pinto MMM, Kijjoa A, Pharadai K, Diaz JG, Herz W. Protoberberine alkaloids from Coscinium fenestratum . Phytochemistry 1992; 31: 1403-1408
    CrossrefPubMedGoogle Scholar
  • 14 Furuya T, Nakano M, Yoshikawa T. Biotransformation of (RS)-reticuline and morphinan alkaloids by cell cultures of Papaver somniferum . Phytochemistry 1978; 17: 891-893
    CrossrefPubMedGoogle Scholar
  • 15 Sugimoto Y, Babiker HAA, Inanaga S, Kato M, Isogai A. Oxoisoaporphines from Menispermum dauricum . Phytochemistry 1999; 52: 1431-1436
    CrossrefPubMedGoogle Scholar
  • 16 Kunitomo J, Satoh M, Shingu T. Structure and synthesis of menisporphine, a new type of isoquinoline alkaloid. Alkaloids of Menispermum dauricum DC. Tetrahedron 1983; 39: 3261-3266
    CrossrefPubMedGoogle Scholar
  • 17 Kunitomo JI, Miyata Y. Further evidence for the structure of bianfugecone. Heterocycles 1986; 24: 437-440
    CrossrefPubMedGoogle Scholar
  • 18 Nozaka T, Morimoto I, Ishino M, Okitsu T, Kondoh H. Mutagenic principles in Sinomeni Caulis et Rhizoma. I. The structure of a mutagenic alkaloid, N-demethyl-N-formyldehydronuciferine, in the neutral fraction of the methanol extract. Chem Pharm Bull 1987; 35: 2844-2848
    CrossrefPubMedGoogle Scholar
  • 19 Stuart KL, Cava MP. The proaporphine alakaloids. Chem Rev 1968; 68: 321-338
    CrossrefPubMedGoogle Scholar
  • 20 Berthelot K, Buret D, Guerin B, Delay D, Negrel J, Delmotte FM. Vir-gene-inducing activities of hydroxycinnamic acid amides in Acrobacterium tumefaciens . Phytochemistry 1998; 49: 1537-1548
    CrossrefPubMedGoogle Scholar
  • 21 Cutillo F, DʼAbrosca B, DellaGreca M, Marino CD, Golino A, Previtera L, Zarrelli A. Cinnamic acid amides from Chenopodium album: effects on seeds germination and plant growth. Phytochemistry 2003; 64: 1381-1388
    CrossrefPubMedGoogle Scholar
  • 22 Gupta M, Manickam M, Sinha SC, Sinha-Bagchi A, Ray AB. Withanolides of Datura metel . Phytochemistry 1992; 31: 2423-2426
    CrossrefPubMedGoogle Scholar
  • 23 Kinjo J, Higuchi H, Fukui K, Nohara T. Lignoids from Albizziae Cortex. II. A biodegradation pathway of Syringaresinol. Chem Pharm Bull 1991; 39: 2952-2955
    CrossrefPubMedGoogle Scholar
  • 24 Matsuura S, Iinuma M. Lignan from calyces of Diospyros kaki . Phytochemistry 1985; 24: 626-628
    CrossrefPubMedGoogle Scholar
  • 25 Takasugi M, Anetai M, Katsui N, Masamune T. Occurrence of vomifoliol, dehydrovomifoliol, and dihydrophaseic acid in the root of kidney bean (Phaseoulus vulgaris). Chem Lett 1973; 24: 245-248
    PubMedGoogle Scholar
  • 26 Galbraith MN, Horn DHS. Structures of the natural products blumenols A, B, and C. J Chem Soc Chem Commun 1972; 113-114
    PubMedGoogle Scholar
  • 27 Sefton MA, Skouroumounis GK, Massy-Westropp RA, Williams PJ. Norisoprenoids in Vitis vinifera white wine grapes and the identification of a precursor of damascenone in these fruits. Australian J Chem 1989; 42: 2071-2084
    CrossrefPubMedGoogle Scholar
  • 28 Fang SD, Berry DE, Lynn DG, Hecht SM, Campbell J, Lynn WS. The chemistry of toxic principles from Maytenus nemerosa . Phytochemistry 1984; 23: 631-634
    CrossrefPubMedGoogle Scholar
  • 29 Wang XL, Liu BR, Wang JR, Chen CK, Qin GW, Lee SS. Two new morphinane alkaloids from Sinomenium acutum . J Asian Nat Prod Res 2011; 13: 523-528
    CrossrefPubMedGoogle Scholar
  • 30 Hsieh TJ, Chia YC, Wu YC, Chen CY. Chemical constituents from the stems of Mahonia japonica . J Chin Chem Soc 2004; 51: 443-446
    PubMedGoogle Scholar
  • 31 Valencia E, Weiss I, Firdous S, Freyer AJ, Shamma M. The isoindolobenzazepine alkaloids. Tetrahedron 1984; 40: 3957-3962
    CrossrefPubMedGoogle Scholar
  • 32 Pinho PMM, Pinto MMM, Kijjoa A, Pharadai K, Diaz JG, Herz W. Protoberberine alkaloids from Coscinium fenestratum . Phytochemistry 1992; 31: 1403-1407
    CrossrefPubMedGoogle Scholar
  • 33 Jiang T, Zhou L, Zhang W, Qu D, Xu X, Yang Y, Li S. Effects of sinomenine on proliferation and apoptosis in human lung cancer cell line NCI-H460 in vitro . Mol Med Rep 2010; 3: 51-56
    PubMedGoogle Scholar
  • 34 Min YD, Choi SU, Lee KR. Aporphine alkaloids and their reversal activity of multidrug resistance (MDR) from the stems and rhizomes of Sinomenium acutum . Arch Pharm Res 2006; 29: 627-632
    CrossrefPubMedGoogle Scholar
  • 35 Miyamura M, Nohara T, Tomimatsu T, Nishiokat I. Seven aromatic compounds from bark of Cinnamomum cassia . Phytochemistry 1983; 22: 215-218
    CrossrefPubMedGoogle Scholar