Constituents of High Altitude Himalayan Herbs, Part V. A New Diterpenoid Quinone from Salvia hians

Khetwal, K. S.; Pathak, Rekha; Vashisht, Anil; Pant, Namita

doi:10.1021/np50085a015

Cited by 11 publications

(6 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Chemically, tanshinones are 20-norditerpenes with an abietane-type skeleton containing a quinone moiety in the C-ring. Over 50 tanshinones have so far been identified in S. militiorrhiza and other Salvia species. ,,,− In the present work, we report that Perovskia abrotanoides Kar. (Lamiaceae) is a new, rich source of tanshinones.…”

Section: Introductionmentioning

confidence: 49%

See 1 more Smart Citation

Leishmanicidal, Antiplasmodial, and Cytotoxic Activity of Novel Diterpenoid 1,2-Quinones from Perovskia abrotanoides: New Source of Tanshinones

et al. 2001

View full text Add to dashboard Cite

Cryptotanshinone (1), a quinoid diterpene with a nor-abietane skeleton, and three new natural products, 1beta-hydroxycryptotanshinone (2), 1-oxocryptotanshinone (3), and 1-oxomiltirone (4), were isolated from roots of the Iranian medicinal plant Perovskia abrotanoides. Their structures were established using homo- and heteronuclear two-dimensional NMR experiments, supported by HRMS. The total amount of tanshinones isolated from dry roots of Perovskia abrotanoides was about 1.5%. The compounds exhibited leishmanicidal activity in vitro (IC(50) values in the range 18-47 microM). These findings provide a rationale for traditional use of the roots in Iran as a constituent of poultices for treatment of cutaneous leishmaniasis. The isolated tanshinones also inhibited growth of cultured malaria parasites (3D7 strain of Plasmodium falciparum), drug-sensitive KB-3-1 human carcinoma cell line, multidrug-resistant KB-V1 cell line, and human lymphocytes activated with phytohaemagglutinin A (IC(50) values in the range 5-45 microM). The toxicity of tanshinones toward the drug-sensitive KB-3-1 and the multidrug-resistant KB-V1 cells was the same, indicating that the compounds are not substrates for the P-glycoprotein drug efflux pump.

show abstract

Section: Introductionmentioning

confidence: 49%

“…Over 50 tanshinones have so far been identified in S. militiorrhiza and other Salvia species. 10,14,25,[31][32][33][34][35][36][37][38][39][40] In the present work, we report that Perovskia abrotanoides Kar. (Lamiaceae) is a new, rich source of tanshinones.…”

Section: Introductionmentioning

confidence: 92%

Leishmanicidal, Antiplasmodial, and Cytotoxic Activity of Novel Diterpenoid 1,2-Quinones from Perovskia abrotanoides: New Source of Tanshinones

et al. 2001

View full text Add to dashboard Cite

show abstract

“…Quantitative Analysis Tanshinones are widespread in the genus Salvia and about 50 tanshinones have so far been identified in S. miltiorrhiza and other Salvia species. [27][28][29][30][31][32][33][34][35] For quantitative analysis, peak areas were used to calculate the amount of cryptotanshinone present in different plant material as compared to the standard. The calibration plot was linear.…”

Section: Resultsmentioning

confidence: 99%

Isolation and Quantitative Analysis of Cryptotanshinone, an Active Quinoid Diterpene Formed in Callus of <i>Salvia miltiorrhiza</i> B<small>UNGE</small>

Mulabagal

Nalawade

et al. 2003

Biological & Pharmaceutical Bulletin

View full text Add to dashboard Cite

Effect of N(6)-benzyladenine (BA) on tanshinone formation in callus cultures of Salvia miltiorrhiza was examined in an attempt to increase the productivity of the medicinal compound, cryptotanshinone. Primary callus was induced by culturing leaf explants on Murashige and Skoog's (MS) basal medium supplemented with 1.0 mg l(-1) of 2,4-dichlorophenoxyacetic acid (2,4-D) in darkness. The callus proliferated further on MS basal medium containing 1.0 mg l(-1) 2,4-D and 0.5 mg l(-1) BA and was analyzed for cryptotanshinone by high performance liquid chromatography (HPLC). The HPLC results indicated that it contained small amounts of cryptotanshinone (0.26+/-0.05 mg/g dry wt). Omission of 2,4-D from the medium resulted in a marked increase in the content of cryptotanshinone in callus. The HPLC analysis revealed that the content of cryptotanshinone in the callus cultured on the MS basal medium supplemented with 0.1, 0.2, 0.5, 1.0, and 2.0 mg l(-1) of BA was significantly higher than the marketed crude drug (processed underground parts of S. miltiorrhiza). Maximum yield of cryptotanshinone (4.59+/-0.09 mg/g dry wt) was observed in the callus cultured on MS basal medium supplemented with 0.2 mg l(-1) BA for 60 d. Cryptotanshinone was isolated from callus through silica gel column chromatography followed by preparative TLC and characterized based on NMR and mass spectral data.

show abstract

“…The other two novel norabietane derivatives (3 and 4) had orthoquinoid structures with aromatic A and B rings and are among the first examples of this type of norditerpene. 27 The HREIMS of multiorthoquinone (3) showed a molecular formula of C 20 H 20 O 3 (m/z 308.1422), indicating 11 degrees of unsaturation, of which two were accounted for by the presence of two quinoid carbonyl groups and three by a tricyclic skeleton, and the remaining six degrees of unsaturation indicated the presence of six double bonds. The IR and 13 C NMR spectra showed the presence of quinoid carbonyl groups at 1680 and 1654 cm -1 and at δ 183.1 and 181.4, respectively.…”

Section: Resultsmentioning

confidence: 99%

Norditerpenoids and Diterpenoids from Salvia multicaulis with Antituberculous Activity

1997

View full text Add to dashboard Cite

From the roots of Salvia multicaulis, four new aromatic norditerpenoids, multicaulin (1), 12-demethylmulticauline (2), multiorthoquinone (3), and 12-demetylmultiorthoquinone (4), two new abietane diterpenoids, 12-methyl-5-dethydrohorminone (5) and 12-methyl-5-dehydroacetylhorminone (6), as well as a new pimarane diterpenoid, salvipimarone (7), were isolated. Also obtained in this investigation were the known compounds alpha-amyrin, hinokione, horminone, lupeol, manool, 1-oxoferruginol, 18-oxoferruginol, pisiferal, and sempervirol. The structures of compounds 1-7 were established by 1D and 2D NMR techniques and by chemical methods. The antituberculous activity of 1-7 was tested against Mycobacterium tuberculosis strain H37Rv, and all compounds were found to be significantly active, with 2 and 4-6 being the most potent substances. Six of these novel compounds were evaluated against a number of additional bacterial cultures.

show abstract

Constituents of High Altitude Himalayan Herbs, Part V. A New Diterpenoid Quinone from Salvia hians

Cited by 11 publications

References 0 publications

Leishmanicidal, Antiplasmodial, and Cytotoxic Activity of Novel Diterpenoid 1,2-Quinones from Perovskia abrotanoides: New Source of Tanshinones

Leishmanicidal, Antiplasmodial, and Cytotoxic Activity of Novel Diterpenoid 1,2-Quinones from Perovskia abrotanoides: New Source of Tanshinones

Isolation and Quantitative Analysis of Cryptotanshinone, an Active Quinoid Diterpene Formed in Callus of <i>Salvia miltiorrhiza</i> B<small>UNGE</small>

Norditerpenoids and Diterpenoids from Salvia multicaulis with Antituberculous Activity

Contact Info

Product

Resources

About