Bungsteroid A: One Unusual C₃₄ Pentacyclic Steroid Analogue from Zanthoxylum bungeanum Maxim

Abstract

Bungsteroid A (1), possessing an unreported carbon skeleton, was isolated from the pericarps of Zanthoxylum bungeanum Maxim. It represents the first carbon skeleton of a C34 steroid analogue featuring a unique 6/6/6/6/5-fused pentacyclic skeleton, which has been determined by spectroscopic methods, quantum-chemical 13C NMR, ECD calculations, and calculations of optical rotations. Bungsteroid A showed the antiproliferative effects against HepG2, MCF-7, and HeLa cell lines with the IC50 values of 56.3 ± 1.1, 64.2 ± 0.9, and 74.2 ± 1.3 μM, respectively.

Narjatamolide, an Unusual Homoguaiane Sesquiterpene Lactone from Nardostachys jatamansi

“…The absolute configuration of 1 was confirmed by the quantum-mechanical time-dependent density functional theory (TDDFT) calculations. , The theoretically calculated ECD spectrum of 1 showed a negative Cotton effect at 214 (Δε −5.17), which was consistent with the experimental CD spectrum at 220 (Δε −7.73) (Figure ). Moreover, colorless columnar crystals were yielded in a dichloromethane (CH 2 Cl 2 ) solution at room temperature.…”

“…Compound 1 was screened for antiproliferative effects against BEL-7402, HepG2, and Huh-7 hepatocellular carcinoma cell lines and HeLa cervical cancer cell lines, which exhibited the inhibition with the IC 50 values of 5.67 ± 1.43, 21.84 ± 1.62, 25.5 ± 3.14, and 15.46 ± 0.69 μM, respectively. The effect of 1 in different concentrations on morphology of BEL-7402 cell lines under microscope showed that 1 induced cell death in a dose-dependent manner (Supporting Information).…”

“…N. jatamansi showed anticancer and antidiabetic activities and has been used for the treatment of numerous disorders including epilepsy, hysteria, and convulsions, and sesquiterpenes are considered as the bioactive components . As part of our screening of bioactive natural compounds, , an extract of the roots and rhizomes of N. jatamansi was investigated. Chemical investigation yielded an unusual homoguaiane sesquiterpene lactone narjatamolide ( 1 ), which was the first sesquiterpene lactone reported from N. jatamansi (Figure ).…”

Synthesis and crystal structures of D-annulated pentacyclic steroids: looking within and beyond AR signalling in prostate cancer

“…[1][2][3][4][5][6][7][8][9] A variety of steroids are widely used as anticancer, anti-inflammatory, immunosuppressive, progestational, diuretic, anabolic and contraceptive agents as well as in other applications. [10][11][12][13][14][15][16][17] Certain structural modifications of the rigid tetracyclic steroidal skeleton induced changes of biological response, providing compounds with pronounced biological activity. Pentacyclic steroids are among them and belong to an important class of natural products, which, depending on the fifth cycle condensation position, can both maintain hormonal properties and completely suppress them.…”

“…Pentacyclic steroids are among them and belong to an important class of natural products, which, depending on the fifth cycle condensation position, can both maintain hormonal properties and completely suppress them. [17][18][19][20][21][22][23] There are many examples of pentacyclic steroidal derivatives of pharmacological and biological importance. [24][25][26][27][28] However despite the diversity of biological activity exhibited by pentacyclic steroids, their syntheses are often hard and multistep.…”