Literature DB >> 22098611

Cytotoxic withanolide constituents of Physalis longifolia.

Huaping Zhang1, Abbas K Samadi, Robert J Gallagher, Juan J Araya, Xiaoqin Tong, Victor W Day, Mark S Cohen, Kelly Kindscher, Rao Gollapudi, Barbara N Timmermann.   

Abstract

Fourteen new withanolides, 1-14, named withalongolides A-N, respectively, were isolated from the aerial parts of Physalis longifolia together with eight known compounds (15-22). The structures of compounds 1-14 were elucidated through spectroscopic techniques and chemical methods. In addition, the structures of withanolides 1, 2, 3, and 6 were confirmed by X-ray crystallographic analysis. Using a MTS viability assay, eight withanolides (1, 2, 3, 7, 8, 15, 16, and 19) and four acetylated derivatives (1a, 1b, 2a, and 2b) showed potent cytotoxicity against human head and neck squamous cell carcinoma (JMAR and MDA-1986), melanoma (B16F10 and SKMEL-28), and normal fetal fibroblast (MRC-5) cells with IC₅₀ values in the range between 0.067 and 9.3 μM.

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Year:  2011        PMID: 22098611      PMCID: PMC3253737          DOI: 10.1021/np200635r

Source DB:  PubMed          Journal:  J Nat Prod        ISSN: 0163-3864            Impact factor:   4.050


  18 in total

1.  Withaferin A, a cytotoxic steroid from Vassobia breviflora, induces apoptosis in human head and neck squamous cell carcinoma.

Authors:  Abbas K Samadi; Xiaoqin Tong; Ridhwi Mukerji; Huaping Zhang; Barbara N Timmermann; Mark S Cohen
Journal:  J Nat Prod       Date:  2010-09-24       Impact factor: 4.050

Review 2.  Withanolides and related ergostane-type steroids.

Authors:  E Glotter
Journal:  Nat Prod Rep       Date:  1991-08       Impact factor: 13.423

3.  Antiproliferative activity of withanolides against human breast cancer cell lines.

Authors:  Rubén P Machin; Adriana S Veleiro; Viviana E Nicotra; Juan C Oberti; José M Padrón
Journal:  J Nat Prod       Date:  2010-05-28       Impact factor: 4.050

Review 4.  Natural withanolides: an overview.

Authors:  Li-Xia Chen; Hao He; Feng Qiu
Journal:  Nat Prod Rep       Date:  2011-02-23       Impact factor: 13.423

5.  Cholinesterase-inhibiting withanolides from Ajuga bracteosa.

Authors:  Naheed Riaz; Abdul Malik; Sarfraz Ahmad Nawaz; Pir Muhammad; M Iqbal Choudhary
Journal:  Chem Biodivers       Date:  2004-09       Impact factor: 2.408

6.  Withanolides from Withania aristata and their cytotoxic activity.

Authors:  Gabriel G Llanos; Liliana M Araujo; Ignacio A Jiménez; Laila M Moujir; Jesús T Vázquez; Isabel L Bazzocchi
Journal:  Steroids       Date:  2010-06-11       Impact factor: 2.668

7.  Withanolide derivatives from the roots of Withania somnifera and their neurite outgrowth activities.

Authors:  Jing Zhao; Norio Nakamura; Masao Hattori; Tomoharu Kuboyama; Chihiro Tohda; Katsuko Komatsu
Journal:  Chem Pharm Bull (Tokyo)       Date:  2002-06       Impact factor: 1.645

8.  2,3-Dihydrowithaferin A-3beta-O-sulfate, a new potential prodrug of withaferin A from aeroponically grown Withania somnifera.

Authors:  Ya-ming Xu; Marilyn T Marron; Emily Seddon; Steven P McLaughlin; Dennis T Ray; Luke Whitesell; A A Leslie Gunatilaka
Journal:  Bioorg Med Chem       Date:  2008-11-12       Impact factor: 3.641

9.  Microbial transformations of natural antitumor agents. 23. Conversion of withaferin-A to 12 beta- and 15 beta-hydroxy derivatives of withaferin-A.

Authors:  J Fuska; J Prousek; J Rosazza; M Budesinsky
Journal:  Steroids       Date:  1982-08       Impact factor: 2.668

10.  Withanolides from Jaborosa laciniata.

Authors:  Adriana M Cirigliano; Adriana S Veleiro; Rosana I Misico; María C Tettamanzi; Juan C Oberti; Gerardo Burton
Journal:  J Nat Prod       Date:  2007-09-21       Impact factor: 4.050

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  16 in total

1.  Withanolides are potent novel targeted therapeutic agents against adrenocortical carcinomas.

Authors:  Chitra Subramanian; Huaping Zhang; Robert Gallagher; Gary Hammer; Barbara Timmermann; Mark Cohen
Journal:  World J Surg       Date:  2014-06       Impact factor: 3.352

2.  New withanolides with TRAIL-sensitizing effect from Physalis pubescens L.

Authors:  Li-Xia Chen; Gui-Yang Xia; Hao He; Jian Huang; Feng Qiu; Xiao-Lin Zi
Journal:  RSC Adv       Date:  2016-05-26       Impact factor: 3.361

3.  Withanolides from Jaborosa caulescens var. bipinnatifida.

Authors:  Huaping Zhang; Cong-Mei Cao; Robert J Gallagher; Victor W Day; Gloria Montenegro; Barbara N Timmermann
Journal:  Phytochemistry       Date:  2013-12-05       Impact factor: 4.072

4.  Analysis of Major Withanolides in Physalis longifolia Nutt. by HPLC-PDA.

Authors:  Cong-Mei Cao; Kelly Kindscher; Robert J Gallagher; Huaping Zhang; Barbara N Timmermann
Journal:  J Chromatogr Sci       Date:  2014-12-02       Impact factor: 1.618

5.  Minor withanolides of Physalis longifolia: structure and cytotoxicity.

Authors:  Huaping Zhang; Hashim Motiwala; Abbas Samadi; Victor Day; Jeffrey Aubé; Mark Cohen; Kelly Kindscher; Rao Gollapudi; Barbara Timmermann
Journal:  Chem Pharm Bull (Tokyo)       Date:  2012       Impact factor: 1.645

6.  Synthetic high-density lipoprotein nanoconjugate targets neuroblastoma stem cells, blocking migration and self-renewal.

Authors:  Chitra Subramanian; Peter T White; Rui Kuai; Avinaash Kalidindi; Valerie P Castle; James J Moon; Barbara N Timmermann; Anna Schwendeman; Mark S Cohen
Journal:  Surgery       Date:  2018-05-09       Impact factor: 3.982

7.  Antiproliferative withanolides from Datura wrightii.

Authors:  Huaping Zhang; Joseph Bazzill; Robert J Gallagher; Chitra Subramanian; Patrick T Grogan; Victor W Day; Kelly Kindscher; Mark S Cohen; Barbara N Timmermann
Journal:  J Nat Prod       Date:  2012-12-19       Impact factor: 4.050

8.  Screening of promising chemotherapeutic candidates from plants against human adult T-cell leukemia/lymphoma (II): apoptosis of antiproliferactive principle (24,25-dihydrowithanolide D) against ATL cell lines and structure-activity relationships with withanolides isolated from solanaceous plants.

Authors:  Daisuke Nakano; Kenji Ishitsuka; Hiroo Katsuya; Naoko Kunami; Rumiko Nogami; Yuka Yoshimura; Michika Matsuda; Mio Kamikawa; Ryota Tsuchihashi; Masafumi Okawa; Tsuyoshi Ikeda; Toshihiro Nohara; Kazuo Tamura; Junei Kinjo
Journal:  J Nat Med       Date:  2012-09-09       Impact factor: 2.343

Review 9.  Antiproliferative withanolides from several solanaceous species.

Authors:  Huaping Zhang; Cong-Mei Cao; Robert J Gallagher; Barbara N Timmermann
Journal:  Nat Prod Res       Date:  2014-05-28       Impact factor: 2.861

10.  Synthesis and Cytotoxicity of Semisynthetic Withalongolide A Analogues.

Authors:  Hashim F Motiwala; Joseph Bazzill; Abbas Samadi; Huaping Zhang; Barbara N Timmermann; Mark S Cohen; Jeffrey Aubé
Journal:  ACS Med Chem Lett       Date:  2013-11-14       Impact factor: 4.345

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