Anti-proliferative, apoptotic induction, and anti-migration effects of hemi-synthetic 1′S-1′-acetoxychavicol acetate analogs on MDA-MB-231 breast cancer cells

Nine analogs of 1′S-1′-acetoxychavicol acetate (ACA) were hemi-synthesized and evaluated for their anticancer activities against seven human cancer cell lines. The aim of this study was to investigate the anti-proliferative, apoptotic, and anti-migration effects of these compounds and to explore the plausible underlying mechanisms of action. We found that ACA and all nine analogs were non toxic to human mammary epithelial cells (HMECs) used as normal control cells, and only ACA, 1′-acetoxyeugenol acetate (AEA), and 1′-acetoxy-3,5-dimethoxychavicol acetate (AMCA) inhibited the growth of MDA-MB-231 breast cancer cells with a half-maximal inhibitory concentration (IC50) value of 30.0 μM based on 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay results, and were selected for further investigation. DNA fragmentation assays showed that these three compounds markedly induced apoptosis of MDA-MB-231 cells. Western blot analysis revealed increased expression levels of cleaved PARP, p53, and Bax, while decreased expression levels of Bcl-2 and Bcl-xL were seen after treatment, indicating that apoptosis was induced via the mitochondrial pathway. Moreover, ACA, AEA, and AMCA effectively inhibited the migration of MDA-MB-231 cells. They also downregulated the expression levels of pFAK/FAK and pAkt/Akt via the integrin β1-mediated signaling pathway. Collectively, ACA and its hemi-synthetic analogs, AEA and AMCA are seen as potential anticancer agents following their abilities to suppress growth, induce apoptosis, and inhibit migration of breast cancer cells

Anthraquinones with Antiplasmodial Activity from the Roots of

molecule

Methyl 3-acet­oxy-3-dehydroxy­ursolate

Four of the five six-membered rings of the title penta­cyclic triterpene, C33H52O4, adopt chair conformations; the fifth, which has a C=C double bond, adopts an approximate envelope conformation

Methyl 3-dehydr­oxy-3-oxoursolate

Four of the five six-membered rings of the title penta­cylic triterpene, C31H48O3, adopt chair conformations; the fifth, which has a C=C double bond, adopts an approximate envelope conformation

[1R-(1α,2α,4α,5β,6α,7α)]-4-Benzoyl­oxymethyl-5,6-dihy­droxy-3,8-dioxa­tricyclo­[5.1.0.02,4]octan-5-yl acetate (3-deacetyl­crotepoxide) from Kaempferia rotunda Val.

The title compound, C16H16O7, isolated from Kaempferia rotunda rhizomes, features a six-membered cyclo­hexane ring that adopts a twisted-boat conformation owing to the presence of two adjacent epoxide attachments that lock in four of the six axial positions. The CH3CO2– and HO– substituents occupy equatorial positions. However, the bond angles at the ring carbon connected to the C6H5CO2CH2– substituent deviate signifcantly from the idealized tetra­hedral angles as the carbon atom is part of an epoxide ring. In the crystal, the molecules are linked into chains by O—H⋯O hydrogen bonds

Cardiovascular Activity of Labdane Diterpenes from Andrographis paniculata in Isolated Rat Hearts

The dichloromethane (DCM) extract of Andrographis paniculata Nees was tested for cardiovascular activity. The extract significantly reduced coronary perfusion pressure by up to 24.5 ± 3.0 mm Hg at a 3 mg dose and also reduced heart rate by up to 49.5 ± 11.4 beats/minute at this dose. Five labdane diterpenes, 14-deoxy-12-hydroxyandrographolide (1), 14-deoxy-11,12-didehydroandrographolide (2), 14-deoxyandrographolide (3), andrographolide (4), and neoandrographolide (5), were isolated from the aerial parts of this medicinal plant. Bioassay-guided studies using animal model showed that compounds, (2) and (3) were responsible for the coronary vasodilatation. This study also showed that andrographolide (4), the major labdane diterpene in this plant, has minimal effects on the heart

(E)-3-(2H-1,3-Benzodioxol-5-yl)-1-(7-hy­droxy-5-meth­oxy-2,2-dimethyl­chroman-8-yl)prop-2-en-1-one

The reaction of 5,6-(2,2-dimethyl­chromane)-2-hy­droxy-4-meth­oxy­acetophenone and 3,4-methlene­dioxy­benzaldehyde affords the title chalcone derivative, C22H22O6. The two benzene rings are connected through a —C(=O)—CH=CH— (propenone) unit, which is in an E conformation; the ring with the hy­droxy substitutent is aligned at 6.2 (1)° with respect to this unit, whereas the ring with the methyl­enedi­oxy substituent is aligned at 8.2 (1)°. The dihdral angle between the rings is 14.32 (7)°. The hy­droxy group engages in an intra­molecular hydrogen bond with the carbonyl O atom of the propenone unit, generating an S(5) ring

(E)-1-(2-Hy­droxy-4,6-dimeth­oxy­phen­yl)-3-(4-meth­oxy­phen­yl)prop-2-en-1-one from Kaempferia rotunda Val.

The planar –CH=CHC(=O)– fragment (r.m.s. deviation = 0.074 Å) in the title compound, C18H18O5, connects the planar hy­droxy­dimeth­oxy­phenyl (r.m.s. deviation = 0.039 Å) and meth­oxy­lphenyl (r.m.s. deviation = 0.021 Å) parts. The central fragment forms a dihedral angle of 13.7 (1)° with the hy­droxy­dimeth­oxy­phenyl part and 32.0 (1)° with the meth­oxy­phenyl part. The hy­droxy group forms an intra­molecular hydrogen bond to the carbonyl O atom

N′-{2-[2-(3-Methoxyphenyl)ethenyl]phenyl}acetamide

In the title compound, C17H17NO2, the phenyl­ene rings are bent with respect to the carbon–carbon double bond [dihedral angle between rings = 39.6 (1)°]. The acetamido group is twisted out of the plane of the aromatic ring [dihedral angle = 44.2 (1)°] in order to form an N–H⋯O hydrogen bond to the acetamido group of an adjacent mol­ecule, generating a zigzag chain running along the c axis