Tags

Type your tag names separated by a space and hit enter

Cucurbitane triterpenoids from the leaves of Momordica charantia, and their cancer chemopreventive effects and cytotoxicities.
Chem Biodivers. 2012 Feb; 9(2):428-40.CB

Abstract

Seventeen cucurbitane-type triterpenoids, 1-17, including six new compounds, (23E)-3β,25-dihydroxy-7β-methoxycucurbita-5,23-dien-19-al (1), (23S*)-3β-hydroxy-7β,23-dimethoxycucurbita-5,24-dien-19-al (6), (23R*)-23-O-methylmomordicine IV (7), (25ξ)-26-hydroxymomordicoside L (8), 25-oxo-27-normomordicoside L (9), and 25-O-methylkaravilagenin D (12), were isolated from a MeOH extract of the leaves of Japanese Momordica charantia. The structures of new compounds were elucidated on the basis of extensive spectroscopic analyses and comparison with literature. Compounds 1-17 were examined for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced with 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, a known primary screening test for inhibitors of tumor promotion. Four compounds, 1, (23E)-3β,7β-dihydroxy-25-methoxycucurbita-5,23-dien-19-al (2), karavilagenin D (11), and 12, showed potent inhibitory effects on EBV-EA induction with IC(50) values in the range of 242-264 mol ratio/32 pmol TPA. In addition, compounds 1 and 11 exhibited inhibitory effects on skin-tumor promotion in an in vivo two-stage mouse skin carcinogenesis test based on 7,12-dimethylbenz[a]anthracene (DMBA) as initiator, and with TPA as a promoter. Furthermore, upon evaluation of the cytotoxic activities of compounds 1-17 against human cancer cell lines, compounds 2, 5-7, 9, and 14 showed potent activities against HL60 cell line, and compound 2 against SK-BR-3 cell line.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Zhang J
College of Science and Technology, Nihon University, 1-8-14 Kanda Surugadai, Chiyoda-ku, Tokyo, Japan.
Huang Y
No affiliation info available
Kikuchi T
No affiliation info available
Tokuda H
No affiliation info available
Suzuki N
No affiliation info available
Inafuku K
No affiliation info available
Miura M
No affiliation info available
Motohashi S
No affiliation info available
Suzuki T
No affiliation info available
Akihisa T
No affiliation info available

MeSH

9,10-Dimethyl-1,2-benzanthraceneAnimalsAntigens, ViralAntineoplastic Agents, PhytogenicApoptosisCarcinogensCell Transformation, NeoplasticGlycosidesHumansMiceMolecular StructureMomordica charantiaPlant LeavesSkin NeoplasmsTetradecanoylphorbol AcetateTriterpenesTumor Cells, Cultured

Pub Type(s)

Journal Article

Language

eng

PubMed ID

22344919

Citation

Zhang, Jie, et al. "Cucurbitane Triterpenoids From the Leaves of Momordica Charantia, and Their Cancer Chemopreventive Effects and Cytotoxicities." Chemistry & Biodiversity, vol. 9, no. 2, 2012, pp. 428-40.
Zhang J, Huang Y, Kikuchi T, et al. Cucurbitane triterpenoids from the leaves of Momordica charantia, and their cancer chemopreventive effects and cytotoxicities. Chem Biodivers. 2012;9(2):428-40.
Zhang, J., Huang, Y., Kikuchi, T., Tokuda, H., Suzuki, N., Inafuku, K., Miura, M., Motohashi, S., Suzuki, T., & Akihisa, T. (2012). Cucurbitane triterpenoids from the leaves of Momordica charantia, and their cancer chemopreventive effects and cytotoxicities. Chemistry & Biodiversity, 9(2), 428-40. https://doi.org/10.1002/cbdv.201100142
Zhang J, et al. Cucurbitane Triterpenoids From the Leaves of Momordica Charantia, and Their Cancer Chemopreventive Effects and Cytotoxicities. Chem Biodivers. 2012;9(2):428-40. PubMed PMID: 22344919.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Cucurbitane triterpenoids from the leaves of Momordica charantia, and their cancer chemopreventive effects and cytotoxicities. AU - Zhang,Jie, AU - Huang,Yan, AU - Kikuchi,Takashi, AU - Tokuda,Harukuni, AU - Suzuki,Nobutaka, AU - Inafuku,Kei-ichiro, AU - Miura,Motofumi, AU - Motohashi,Shigeyasu, AU - Suzuki,Takashi, AU - Akihisa,Toshihiro, PY - 2012/2/21/entrez PY - 2012/2/22/pubmed PY - 2012/6/23/medline SP - 428 EP - 40 JF - Chemistry & biodiversity JO - Chem Biodivers VL - 9 IS - 2 N2 - Seventeen cucurbitane-type triterpenoids, 1-17, including six new compounds, (23E)-3β,25-dihydroxy-7β-methoxycucurbita-5,23-dien-19-al (1), (23S*)-3β-hydroxy-7β,23-dimethoxycucurbita-5,24-dien-19-al (6), (23R*)-23-O-methylmomordicine IV (7), (25ξ)-26-hydroxymomordicoside L (8), 25-oxo-27-normomordicoside L (9), and 25-O-methylkaravilagenin D (12), were isolated from a MeOH extract of the leaves of Japanese Momordica charantia. The structures of new compounds were elucidated on the basis of extensive spectroscopic analyses and comparison with literature. Compounds 1-17 were examined for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced with 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, a known primary screening test for inhibitors of tumor promotion. Four compounds, 1, (23E)-3β,7β-dihydroxy-25-methoxycucurbita-5,23-dien-19-al (2), karavilagenin D (11), and 12, showed potent inhibitory effects on EBV-EA induction with IC(50) values in the range of 242-264 mol ratio/32 pmol TPA. In addition, compounds 1 and 11 exhibited inhibitory effects on skin-tumor promotion in an in vivo two-stage mouse skin carcinogenesis test based on 7,12-dimethylbenz[a]anthracene (DMBA) as initiator, and with TPA as a promoter. Furthermore, upon evaluation of the cytotoxic activities of compounds 1-17 against human cancer cell lines, compounds 2, 5-7, 9, and 14 showed potent activities against HL60 cell line, and compound 2 against SK-BR-3 cell line. SN - 1612-1880 UR - https://www.unboundmedicine.com/medline/citation/22344919/Cucurbitane_triterpenoids_from_the_leaves_of_Momordica_charantia_and_their_cancer_chemopreventive_effects_and_cytotoxicities_ DB - PRIME DP - Unbound Medicine ER -