Chemopreventive potential of Epoxy clerodane diterpene from Tinospora cordifolia against diethylnitrosamine-induced hepatocellular carcinoma

Dhanasekaran, M.; Arul, Albert-Baskar; Ignacimuthu, Savarimuthu; Agastian, Paul; Duraipandiyan, Veeramuthu

doi:10.1007/s10637-008-9181-9

Cited by 59 publications

(43 citation statements)

References 46 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Regenerative effects elicited by andrographolide were the result of decreased activities of serum glutamate pyruvate transaminase, serum glutamate oxalate transaminase, alkaline phosphatase (AP), ornithine carbomoyl transferase and acid phosphatase, all of which are markers of liver damage [138] . A recent investigation by Dhanasekaran et al [139] on the epoxy clerodane diterpene extracted from Tinospora cordifolia proposed increases in the hepatic antioxidant status of Wistar rats administered with DENA to induce HCC. Treatment for 8 wk at a dose of 8 mg/kg per day resulted in reduced incidence, multiplicity and size of hepatic nodules.…”

Section: Diterpenesmentioning

confidence: 99%

Terpenoids as potential chemopreventive and therapeutic agents in liver cancer

Thoppil

Bishayee²

2011

WJH

278

143

View full text Add to dashboard Cite

Despite significant advances in medicine, liver cancer, predominantly hepatocellular carcinoma remains a major cause of death in the United States as well as the rest of the world. As limited treatment options are currently available to patients with liver cancer, novel preventive control and effective therapeutic approaches are considered to be reasonable and decisive measures to combat this disease. Several naturally occurring dietary and non-dietary phytochemicals have shown enormous potential in the prevention and treatment of several cancers, especially those of the gastrointestinal tract. Terpenoids, the largest group of phytochemicals, traditionally used for medicinal purposes in India and China, are currently being explored as anticancer agents in clinical trials. Terpenoids (also called "isoprenoids") are secondary metabolites occurring in most organisms, particularly plants. More than 40 000 individual terpenoids are known to exist in nature with new compounds being discovered every year. A large number of terpenoids exhibit cytotoxicity against a variety of tumor cells and cancer preventive as well as anticancer efficacy in preclinical animal models. This review critically examines the potential role of naturally occurring terpenoids, from diverse origins, in the chemoprevention and treatment of liver tumors. Both in vitro and in vivo effects of these agents and related cellular and molecular mechanisms are highlighted. Potential challenges and future directions involved in the advancement of these promising natural compounds in the chemoprevention and therapy of human liver cancer are also discussed.

show abstract

Section: Diterpenesmentioning

confidence: 99%

Terpenoids as potential chemopreventive and therapeutic agents in liver cancer

Thoppil

Bishayee²

2011

WJH

278

143

View full text Add to dashboard Cite

show abstract

“…The known compounds were identified to be columbin (4) and columbin glucoside (5) by comparing the physical and spectroscopic data in literature. 8,9) Tinospinoside D (1) C-NMR spectroscopic data also indicated the presence of two carbonyl moieties at δ C 173.5 and 174.4, as well as a β-glucopyranosyl moiety with the anomeric resonances at δ H 5.64 (1H, d, J=7.1 Hz) and δ C 100.5, respectively (Tables 1, 2). The β-glucopyranosyl moiety was determined to be in the D-form by GLC analysis of its trimethylsilylthiazolidine derivative after acid hydrolysis of 1.…”

Section: Resultsmentioning

confidence: 94%

“…7) The EtOAc fraction (37.8 g) was subjected to silica gel column chromatography with a gradient of CHCl 3 -MeOH-H 2 O to give five fractions (1)(2)(3)(4)(5). Fraction 4 (10.4 g) was then subject to ODS column chromatography eluting with MeOH-H 2 O (2 : 3).…”

Section: )mentioning

confidence: 99%

See 1 more Smart Citation

Tinospinosides D, E, and Tinospin E, Further Clerodane Diterpenoids from <i>Tinospora sagittata</i>

Huang

et al. 2012

Chem. Pharm. Bull.

View full text Add to dashboard Cite

Chemical investigation on the roots of Tinospora sagittata resulted in the isolation of three novel cis-clerodane diterpenoids, tinospinosides D, E, and tinospin E, together with two known compounds, columbin and columbin glucoside, and their structures were determined by extensive spectroscopic analyses, chemical reactions and computer-assisted calculations. The inhibitory activity of the isolated compounds and their chemical derivatives on nitric oxide production in lipopolysaccharide and interferon-γ activited J774.1 macrophage-like cells was also evaluated.Key words Tinospora sagittata; Menispermaceae; clerodane diterpenoid; nitric oxideThe genus Tinospora (Menispermaceae) has about thirty species, mainly distributing in the tropic area of Asia and Africa, and many of the species have been used in traditional medicines, e.g., T. codifolia has been used in Ayurveda (Indian traditional medicines) as a hepatoprotectant 1) ; the stem of T. sinensis has been used in Traditional Chinese Medicine (TCM) in the treatment of rheumatism and muscle pain; the root of T. capillipes and T. sagittata has been used in TCM to relieve sore throat, expel superficial infection, and stop diarrhea.2) The main chemical constituents of Tinospora species have been reported to be diterpenoids, which has 12-furano cis-clerodane skeleton as their characteristic structure.3-5) As a part of our continuing phytochemical research on Tinospora species, we have previously reported the isolation of three novel clerodane diterpenoids, tinosposinensides A-C, from the stems of T. sinensis, 6) and three novel clerodane diterpenoids, tinospinosides A-C, from the roots of T. sagittata. 7) In a further investigation on the roots of T. sagittata, we herein report the isolation and structural determination of three new clerodane diterpenoids, tinospinoside D (1), tinospin E (2), and tinospinoside E (3) (Fig. 1). The inhibitory activity of these compounds and their chemical derivatives on nitric oxide production in lipopolysaccharide (LPS) and interferon (INF)-γ activited J774.1 macrophage-like cells was also evaluated. Results and DiscussionThe EtOAc fraction from the MeOH extract of roots of T. sagittata was fractionated by repeated column chromatography followed by HPLC purification to afford five compounds 1-5. The known compounds were identified to be columbin (4) and columbin glucoside (5) by comparing the physical and spectroscopic data in literature. 7) Namely, resonances of an epoxy moiety at δ C 54.8 (C-2) and 53.8 (C-3), and an oxyganated quaternary carbon resonance at δ C 83.9 (C-4) were observed in 1, instead of resonances of C-2 oxyganated methine and C-3, 4 olefin in tinospinoside C. The epoxy moiety was assigned at C-2 and C-3 by sequential 1 H-1 H correlation spectroscopy (COSY) correlations between resonances of H-10, H α,β -1, H-2, and H-3, and a heteronuclear multiple bond connectivity (HMBC) correlation from δ H 2.69 (H-10) to δ C 54.8 (C-2) (Fig. 2). The oxylated quaternary carbon resonance at δ C 83.9 was assigned to C-4, by HMBC ...

show abstract

“…Its juice is also used for the treatment of chronic cough [5]. It's use for promoting longevity, enhancing immunomodulatory responses, treating arthritis, diabetes, improving liver function and as a chemopreventive agent has been well documented [6,7]. Recently its efficacy in allergic rhinitis, anti-diabetic potential and prevention of diabetic retinopathy has been assessed using molecular biology tools.…”

Section: Introductionmentioning

confidence: 99%

Phloroglucinol Plays Role in Shoot Bud Induction and In Vitro Tuberization in Tinospora Cordifolia- A Medicinal Plant with Multi- Therapeutic Application

Kumar¹

2015

Adv Tech Biol Med

View full text Add to dashboard Cite

This paper shows the potential of phloroglucinol for In Vitro regeneration and tuberization of microshoots of Tinospora cordifolia. Within a week of nodal explants culture, axillary bud in nodal segments sprouted in all the media investigated including basal MS media without any growth regulators. Maximum response (52.2 per cent) evinced by MS media supplemented with 6.98 µM Kin. The same media produced maximum response for multiple shoot formation out of total shoot bud sprouted fostering average 3 shoots with 3.9 cm shoot length and 4.2 number of leaves per shoot. Effect of PG also investigated for mass multiplication and In Vitro rooting. Basal MS + 6.98 µM Kin + 79.4 µM PG increased shoot bud induction from 52.2 per cent to 84.8 per cent and multiple shoot production per cent from 12.9 to as high as 60.3 percent and also supported maximum number of shoot per explants (7.5). The same treatment promoted highest axillary shoot proliferation in terms of shoot length (3.9 cm) and number of leaves per shoot (4.3). Phloglucinol induced In Vitro tuberization in microshoots. Maximum rooting response observed in ½ MS medium supplemented with 7.4 µM IBA and 793.7 µM PG with 81.1 culture responding taking just 8.7 days to sprout and producing maximum number of roots (3.2) with an average length (3.1 cm). Rooted explants successfully hardened in Soil: Vermicompost: Vermiculite (1:1:1) with 100% success.

show abstract

Chemopreventive potential of Epoxy clerodane diterpene from Tinospora cordifolia against diethylnitrosamine-induced hepatocellular carcinoma

Cited by 59 publications

References 46 publications

Terpenoids as potential chemopreventive and therapeutic agents in liver cancer

Terpenoids as potential chemopreventive and therapeutic agents in liver cancer

Tinospinosides D, E, and Tinospin E, Further Clerodane Diterpenoids from <i>Tinospora sagittata</i>

Phloroglucinol Plays Role in Shoot Bud Induction and In Vitro Tuberization in Tinospora Cordifolia- A Medicinal Plant with Multi- Therapeutic Application

Contact Info

Product

Resources

About