Anti-Inflammatory and anti-proliferative oleanane-type triterpene glycosides from the vine of Momordica cochinchinensis

Abstract This research isolated two new oleanane-type triterpene glycosides, named mocochinosides A (1) and B (2), together with ten known compounds as chikusetsusaponin IVa ethyl ester (3), momordin Ib (4), momordin IIb (5), momordin II (6), calenduloside G (7), calenduloside H (8), elatoside A (9), elatoside C (10), calendulaglycoside C 6'-O-7-butyl ester (11), and hederagenin 3-O-β-D-glucuronopyranoside (12) and characterized them from the vines of Momordica cochinchinensis. The new structures of both glycosides 1-2 were elucidated by spectroscopic analysis including 2 D NMR and MS, followed by an analysis of their anti-inflammatory and cytotoxic activities. Compounds 1, 4, and 11 showed moderate inhibitions for NO production on RAW264.7 macrophages induced by LPS at IC50 5.41 ∼ 11.28 μM. Compounds 3, 4, and 7 (IC50 8.42 ∼ 19.74 μM) exhibited potential anti-proliferative activities against both of WiDr and MCF-7 human tumor cell lines. GRAPHICAL ABSTRACT

[1]  Xiaobo Li,et al.  New cytotoxic constituents in the water-soluble fraction from Momordicae Semen , 2018, Natural product research.

[2]  Wagner Vilegas,et al.  Chemical metabolome assay by high-resolution Orbitrap mass spectrometry and assessment of associated antitumoral activity of Actinocephalus divaricatus. , 2018, Rapid communications in mass spectrometry : RCM.

[3]  Y. Zhan,et al.  Momordica cochinchinensis Spreng. seed extract suppresses breast cancer growth by inducing cell cycle arrest and apoptosis. , 2015, Molecular medicine reports.

[4]  H. S. Singh,et al.  Assay of Nutritional Composition and Antioxidant Activity of Three Dioecious Momordica Species of South East Asia , 2013, Proceedings of the National Academy of Sciences, India Section B: Biological Sciences.

[5]  F. Debaste,et al.  Impact of limited drying on Momordica cochinchinensis Spreng. aril carotenoids content and antioxidant activity , 2013 .

[6]  Y. Chin,et al.  Anti-gastritis and wound healing effects of Momordicae Semen extract and its active component , 2013, Immunopharmacology and immunotoxicology.

[7]  Shakhnoza S. Azimova,et al.  Momordica cochinchinensis Spreng. , 2012 .

[8]  S. Siriamornpun,et al.  Phytochemicals and antioxidant activity of different fruit fractions (peel, pulp, aril and seed) of Thai gac (Momordica cochinchinensis Spreng). , 2011, Food chemistry.

[9]  Ling Xiao-guang Anti-tumor activity of cochinchina momordica seed extract , 2010 .

[10]  Takashi Suzuki,et al.  Anti-inflammatory, anti-tumor-promoting, and cytotoxic activities of constituents of marigold (Calendula officinalis) flowers. , 2006, Journal of natural products.

[11]  C. Turner,et al.  Fatty acid and carotenoid composition of gac (Momordica cochinchinensis Spreng) fruit. , 2004, Journal of agricultural and food chemistry.

[12]  Zhong-liang Chen,et al.  A New Multiflorane Triterpenoid Ester from Momordica cochinchinensis Spreng , 2001, Natural product letters.

[13]  L. Polito,et al.  Preparation of highly purified momordin II without ribonuclease activity. , 1999, Life sciences.

[14]  K. Ogawa,et al.  Triterpenoid glucuronide saponins from root bark of aralia armata , 1995 .

[15]  N. Murakami,et al.  Elatosides A and B, potent inhibitors of ethanol absorption in rats from the bark of Aralia elata Seem: the structure-activity relationships of oleanolic acid oligoglycosides. , 1993, Chemical & pharmaceutical bulletin.

[16]  R. Faure,et al.  Revised Structures of Triterpenoid Saponins from the Flowers of Calendula officinalis , 1989 .

[17]  Hitoshi Watanabe,et al.  Saponins from roots of Momordica cochinchinensis , 1988 .

[18]  C. Pizza,et al.  Plant metabolites triterpenoid saponins from Calendula arvensis , 1987 .

[19]  H. Itokawa,et al.  Triterpenoids of Akebia quinata callus tissue , 1986 .

[20]  T. Namba,et al.  Studies on nepalese crude drugs. III. On the saponins of Hedera nepalensis K. Koch. , 1985 .

[21]  O. Tanaka,et al.  Saponins from Chinese medicinal plants. (I). Isolation and structures of hemslosides. , 1984, Planta medica.

[22]  L. M. Kogan,et al.  Structures of calendulosides G and H from the roots of Calendula officinalis , 1974, Chemistry of Natural Compounds.