Tenacigenin B

The cytotoxic and tyrosine kinase inhibitory properties of C21 steroids and iridoids from the tubers of Alocasia cucullata.[Pubmed:27120176]

J Nat Med. 2016 Jul;70(3):602-9.

Ten steroids and iridoids were isolated from the tubers of Alocasia cucullata (Lour.) G. Don. Among them, alocasgenin A (1) and alocasgenoside B-C (2-3) were new compounds and the aglycone of compound 1, obtained from the acid hydrolysis of 1, was named alocasgenol (1a). Also, for the first time, Tenacigenin B (4), 17beta-tenacigenin-B (5), 3-O-6-deoxy-3-O-methyl-beta-D-allopyranosyl-(1-->4)-beta-D-oleandropyranosyl-tena cigenin C (6), marsdenoside A-B (7-8) and tenacigenoside A-B (9-10) were isolated from the genus Alocasia. The chemical structures were elucidated by the extensive analysis of spectral data and compared with the literature. By evaluation of the cytotoxic and tyrosine kinase inhibition, compounds 1-10, 1a and compound 2 showed significant growth inhibition against two tumour cell lines, MGC-803 and HT-29, while compounds 1, 1a, 3, 6 and 8 presented moderate inhibition. Furthermore, compound 2 had the inhibitory property against the enzyme activity biochemically.

Simultaneous determination of six C21 steroids of Xiao-Ai-Ping injection in rat plasma by LC-MS/MS.[Pubmed:24037806]

Biomed Chromatogr. 2014 Feb;28(2):223-30.

Xiao-Ai-Ping injection (XAPI) is a traditional Chinese medicine that has been widely used to treat cancer. Modern pharmacological studies have demonstrated that C21 steroids are the main active compounds in XAPI. In this study, a sensitive and specific liquid chromatography tandem mass spectrometry (LC-MS/MS) method was developed and validated the first time for simultanenous determination of three isomeric pregnane genins (17beta-Tenacigenin B, Tenacigenin B and tenacigenin A) and their corresponding glycosides (tenacigenoside A, tenacissoside F and marsdenoside I) from XAPI in rat plasma. A simple liquid-liquid extraction technique was used after the addition of dexamethasone acetate as internal standard. The chromatography separation of analytes was achieved on an Agilent Zorbax Eclipse XDB-C18 column (3.5 microm, 150 x 3 mm i.d.) using methanol-water as mobile phase in a gradient elution program. Detection was performed in multiple reaction monitoring mode using electrospray ionization in the negative ion mode. The method showed satisfactory linearity over a concentration range 5.00-2000.00 ng/mL for Tenacigenin B, tenacigenin A, marsdenoside I and tenacissoside F (r(2) > 0.99), 10.00-4000.00 ng/mL for 17beta-Tenacigenin B and tenacigenoside A (r(2) > 0.99). Intra- and inter-day precisions (valued as relative standard deviation) were <9.00% and accuracies (as relative error) in the range -6.31 to 7.23%. Finally, this validated method was successfully applied to the pharmacokinetic study of XAPI after intravenous administration to rats.

Tenacigenin B derivatives reverse P-glycoprotein-mediated multidrug resistance inHepG2/Dox cells.[Pubmed:18512984]

J Nat Prod. 2008 Jun;71(6):1049-51.

Tenacissimoside A (1) and 11alpha-O-benzoyl-12beta- O-acetylTenacigenin B (2), two derivatives of Tenacigenin B (3) from the plant Marsdenia tenacissima, reversed multidrug resistance in P-glycoprotein (Pgp)-overexpressing multidrug-resistant cancer cells. The sensitivity of HepG2/Dox cells to the antitumor drugs doxorubicin, vinblastine, puromycin, and paclitexel was increased by 18-, 10-, 11-, and 6-fold by 20 microg/mL (or 25 microM) of 1 and 16-, 53-, 16-, and 326-fold by 20 microg/mL (or 39 microM) of 2, respectively. A preliminary mechanistic study has suggested that 1 might modulate Pgp-mediated multidrug resistance through directly interacting with the Pgp substrate site.