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Fulltext (+)-Kunstlerone, a new antioxidant neolignan from the Leaves of Beilschmiedia kunstleri gamble

Mollataghi A, Hadi AH, Awang K, Mohamad J, Litaudon M, Mukhtar MR

Molecules, 2011 Aug 04;16(8):6582-90.

PMID: 21818061 DOI: 10.3390/molecules16086582

A new neolignan, 3,4-dimethoxy-3',4'-methylenedioxy-2,9-epoxy-6,7-cyclo-1,8-neolign-11-en-5(5H)-one, which has been named (+)-kunstlerone (1), together with six known alkaloids: (+)-norboldine (2), (+)-N-methylisococlaurine (3), (+)-cassythicine (4), (+)-laurotetanine (5), (+)-boldine (6) and (-)-pallidine (7), were isolated from the leaves of Beilschmiedia kunstleri. The structures were established through various spectroscopic methods notably 1D- and 2D-NMR, UV, IR and LCMS-IT-TOF. (+)- Kunstlerone (1) showed a strong antioxidant activity, with an SC(50) of 20.0 µg/mL.

Fulltext (-)-Kunstleramide, a new antioxidant and cytotoxic dienamide from the bark of Beilschmiedia kunstleri gamble

Mollataghi A, Hadi AH, Cheah SC

Molecules, 2012 Apr 05;17(4):4197-208.

PMID: 22481540 DOI: 10.3390/molecules17044197

A new dienamide, (2E,4E)-7-(3',4'-dimethoxyphenyl)-N-ethyl-6-(R)-hydroxyhepta- 2,4-dienamide, named (-)-kunstleramide (1), were isolated from the bark of Beilschmiedia kunstleri Gamble together with one neolignan: (+)-kunstlerone (2) and seven known alkaloids: (+)-nornuciferine (3), (-)-isocaryachine (4), (+)-cassythicine (5), (+)-laurotetanine (6), (+)-boldine (7), noratherosperminine (8), (+)-N-demethylphyllocaryptine (9). Their structures were established from spectroscopic techniques, most notably 1D- and 2D-NMR, UV, IR, OR, circular dichroism (CD) spectra and LCMS-IT-TOF. (-)-Kunstleramide (1) exhibited very poor dose-dependent inhibition of DPPH activity, with an IC₅₀ value of 179.5 ± 4.4 μg/mL, but showed a moderate cytotoxic effect on MTT assays of A375, A549, HT-29, PC-3 and WRL-68 with EC₅₀ values of 64.65, 44.74, 55.94, 73.87 and 70.95 µg/mL, respectively.

Fulltext (20R)-24-Bromo-5β-cholane

Ketuly KA, A Hadi AH, Ng SW

Acta Crystallogr Sect E Struct Rep Online, 2009;65(Pt 5):o1124.

PMID: 21583934 DOI: 10.1107/S1600536809014585

In the title compound (5S,8R,9R,10R,13S,14S,17R,20R)-24-bromo-5β-cholane, C(24)H(41)Br, the fused-chair conformation of the cyclo-hexane A/B ring junction is cis with a 5β-H configuration.

Fulltext (20R,24R,25S)-3α,7α,12α,27-Tetra-acet-oxy-24,26-ep-oxy-5β-cholestane

Ketuly KA, A Hadi AH, Ng SW

Acta Crystallogr Sect E Struct Rep Online, 2009;65(Pt 5):o1026.

PMID: 21583846 DOI: 10.1107/S160053680901188X

In the title anhydro-scymnol tetra-acetate, C(35)H(54)O(9), the fused chair conformation of the cyclo-hexane A/B ring junction is cis with a 5β-H configuration. The compound has a trimethyl-ene oxide ring at position 24,26 and four acetate groups at the 3α,7α,12α,27 positions.

Fulltext (20S)-22-Acetoxymethyl-6β-meth-oxy-3α,5-dihydro-3'H-cyclo-propa[3α,5]-5α-pregnane

Ketuly KA, A Hadi AH, Ng SW

Acta Crystallogr Sect E Struct Rep Online, 2009;65(Pt 7):o1486.

PMID: 21582787 DOI: 10.1107/S1600536809020674

In the title steroid derivative, C(25)H(40)O(3), the fused cyclo-propane unit that corresponds to a part of the A ring has a β-configuration and the associated cyclo-pentane ring an envelope-shaped conformation.

Fulltext (20S)-22-Iodo-methyl-6β-meth-oxy-3α,5-dihydro-3'H-cyclo-propa[3α,5]-5α-pregnane

Ketuly KA, A Hadi AH, Ng SW

Acta Crystallogr Sect E Struct Rep Online, 2009;65(Pt 5):o1125.

PMID: 21583935 DOI: 10.1107/S1600536809014597

In the title steroid derivative, C(23)H(37)IO, the fused cyclo-propane unit that comprises part of the A ring has a β-configuration, and the associated cyclo-pentane ring has an envelope conformation.

Fulltext (8S,9R,10S,11S,13S,14S,16S,17R)-4,4-Dichloro-16β-methyl-3,20-dioxo-17,21-bis-(propano-yloxy)-5β,8β-epoxy-pregna-1,9-diene

Ketuly KA, A Hadi AH, Ng SW

Acta Crystallogr Sect E Struct Rep Online, 2009;65(Pt 9):o2220.

PMID: 21577621 DOI: 10.1107/S1600536809028293

The title compound, C(28)H(34)Cl(2)O(7), is a derivative of the glucocorticoid steroid beclomethasone dipropionate. It features an expoxide linkage [angle at oxygen = 96.6 (2)°]. The dichlorocyclohexenone ring adopts an envelope conformation, with the C atom bearing the two Cl substituents representing the flap. The dichloro-methyl C atom deviates by 0.471 (4) Å from the plane defined by the other five atoms, whose maximum r.m.s. deviation is 0.04 Å.

Fulltext 17-(5-Ethyl-6-methyl-heptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetra-deca-hydro-1H-cyclo-penta[a]phenanthrene-3,7-diol from Chisocheton tomentosus (Meliaceae)

Najmuldeen IA, Hadi AH, Awang K, Mohamad K, Ng SW

Acta Crystallogr Sect E Struct Rep Online, 2008;64(Pt 11):o2163.

PMID: 21581023 DOI: 10.1107/S1600536808033163

The asymmetric unit of the title compound, C(29)H(50)O(2), contains two mol-ecules; one mol-ecule is linked to the other by two O-H⋯O hydrogen bonds, whereas only one of the hydr-oxy groups of the second mol-ecule is involved in hydrogen bonding. This gives rise to a chain that runs along the a axis of the monoclinic unit cell.

Fulltext 17-Deoxoestrone [estra-1,3,5(10)-trien-3-ol]-methanol (3/1)

Ketuly KA, Hadi AH, Ng SW, Tiekink ER

Acta Crystallogr Sect E Struct Rep Online, 2011 May 1;67(Pt 5):o1160-1.

PMID: 21754468 DOI: 10.1107/S1600536811013651

Three independent mol-ecules of the title estrone derivative and a mol-ecule of methanol comprise the asymmetric unit of the title compound [systematic name: 13-methyl-6,7,8,9,11,12,13,14,15,16-deca-hydro-cyclo-penta-[a]phenanthren-3-ol-meth-an-ol (3/1)], 3C(18)H(24)O·CH(3)OH. Two of the estrone mol-ecules exhibit 50:50 disorder (one displays whole-mol-ecule disorder and the other partial disorder in the fused five- and six-membered rings) so that five (partial) mol-ecular conformations are discernable. The conformation of the six-membered ring abutting the aromatic ring is close to a half-chair in all five components. The conformation of the six-membered ring fused to the five-membered ring is based on a chair with varying degrees of distortion ranging from minor to significant. Two distinct conformations are found for the five-membered ring: in four mol-ecules, the five-membered ring is twisted about the bond linking it to the six-membered ring, and in the other, the five-membered ring is an envelope with the quaternary C atom being the flap atom. The crystal packing features O-H⋯O hydrogen bonding whereby the four mol-ecules comprising the asymmetric unit are linked into a supra-molecular chain along the b axis.

Fulltext 2,7-Dihydr-oxy-3,6-dimethoxy-phenanthrene from Dehaasia longipedicellata

Mukhtar MR, Nafiah MA, Awang K, A Hadi AH, Ng SW

Acta Crystallogr Sect E Struct Rep Online, 2008;64(Pt 6):o1135.

PMID: 21202644 DOI: 10.1107/S1600536808014451

The hydr-oxy groups in the title compound, C(16)H(14)O(4), are each hydrogen bonded to the adjacent meth-oxy O atom; one of the two hydr-oxy groups is additionally linked to the O atom of the meth-oxy group of another mol-ecule, forming a linear chain.

Fulltext 2-Bromo-beclometasone dipropionate

Ketuly KA, A Hadi AH, Ng SW

Acta Crystallogr Sect E Struct Rep Online, 2009;65(Pt 8):o1822.

PMID: 21583524 DOI: 10.1107/S1600536809025987

In the crystal structure of 2-bromo-beclometasone dipropionate [systematic name: (8S,9R,10S,11S,13S,14S,16S,17R)-2-bromo-9α-chloro-11-hydr-oxy-10,13,16-trimethyl-3-oxo-17-[2-(propion-yloxy)acet-yl]-6,7,8,9,10,11,12,13,14,15,16,17-dodeca-hydro-3H-cyclo-penta-[a]phenanthren-17-yl propionate], C(28)H(36)BrClO(7), the six-membered ring with the 1,4-diene-3-one composition is planar (r.m.s. deviations = 0.03 and 0.04 Å for the two independent mol-ecules), whereas the remaining six-membered rings have chair conformations. Each of the independent mol-ecules self-associates via O-H⋯O(propionate) hydrogen bonding, generating a supra-molecular chain running along the b axis. The crystal is twinned, with the monoclinic unit cell emulating an orthorhomic crystal system; the major twin component constitutes approximately 60%.

Fulltext 3-Iodo-8β,9α,14α-estra-1,3,5(10)-trien-17-one

Ketuly KA, A Hadi AH, Ng SW

Acta Crystallogr Sect E Struct Rep Online, 2009;65(Pt 6):o1195.

PMID: 21583067 DOI: 10.1107/S1600536809014603

In the title compound, C(18)H(21)IO, the cyclo-hexane ring adopts a chair conformation, whereas the cyclo-pentane ring and the ten-membered tetra-line portions each adopt an envelope conformation. For the five-membered ring, the methine C atom deviates by 0.638 (4) Å (r.m.s. of the four other atoms is 0.005 Å) and for the ten-membered ring, the methine C atom constituting the flap deviates by 0.671 (3) Å (r.m.s. of the other nine atoms is 0.066 Å).

Fulltext 3-Methyl-5α-cholest-2-ene

Ketuly KA, Hadi AH, Ng SW, Tiekink ER

Acta Crystallogr Sect E Struct Rep Online, 2010;66(Pt 9):o2265.

PMID: 21588624 DOI: 10.1107/S160053681003117X

In the title cholestane derivative, C(28)H(48) [systematic name: (1S,2S,7R,10R,11R,14R,15R)-2,5,10,15-tetra-methyl-14-[(2R)-6-methyl-heptan-2-yl]tetra-cyclo-[8.7.0.0(2,7).0(11,15)]hepta-dec-4-ene], the cyclo-hexene ring adopts a half-chair conformation. The parent 5α-cholest-2-ene and the equivalent fragment of the title compound are almost superimposable (r.m.s. deviation = 0.033 Å).

Fulltext 3β-Acet-oxy-6-hy-droxy-imino-cholestane

Ketuly KA, Hadi AH, Ng SW, Tiekink ER

Acta Crystallogr Sect E Struct Rep Online, 2011 Apr 1;67(Pt 4):o773-4.

PMID: 21754066 DOI: 10.1107/S1600536811007306

Two independent mol-ecules comprise the asymmetric unit of the title cholestane derivative, C(29)H(49)NO(3) {systematic name: (3S,8S,9S,10R,13R,14S,17R)-17-[(1R)-1,5-dimethyl-hex-yl]-6-hy-droxy-imino-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetra-deca-hydro-1H-cyclo-penta-[a]phenanthren-3-yl ace-tate}. The major differences between the mol-ecules relate to the relative orientations of the terminal acetyl [C-C-O-C torsion angles = -158.8 (3) and -81.7 (3)°] and alkyl groups [C-C-C-C = 168.9 (3) and 65.8 (4)°]. In the crystal, the independent mol-ecules associate via pairs of O-H⋯N hydrogen bonds, forming dimeric aggregates. Supra-molecular layers in the ab plane are mediated by C-H⋯O inter-actions.

Fulltext 4-(3,4-Dihydro-β-carbolin-1-yl)pyrimidin-2-amine

Mukhtar MR, Zainal Abidin A, Awang K, A Hadi AH, Ng SW

Acta Crystallogr Sect E Struct Rep Online, 2009;65(Pt 3):o594.

PMID: 21582249 DOI: 10.1107/S160053680900600X

The mol-ecule of accanthomine A, C(15)H(13)N(5), is approximately planar, with the indolyl fused-ring and the pyrimidyl ring being twisted by 31.7 (1)° The amino group of the five-membered ring is an intramolecular hydrogen-bond donor to a nitro-gen acceptor of the pyrimide ring. The amino group of the pyrimide ring is a hydrogen-bond donor to the N atoms of adjacent mol-ecules. These hydrogen-bonding inter-actions give rise to a layered network with a 4.8(2) topology.

Fulltext 5,22-Stigmastadien-3β-yl p-toluene-sulfonate

Ketuly KA, Hadi AH, Khaledi H, Tiekink ER

Acta Crystallogr Sect E Struct Rep Online, 2010;66(Pt 6):o1336.

PMID: 21579426 DOI: 10.1107/S1600536810016661

The asymmetric unit of the title compound {systematic name: (3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methyl-hept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodeca-hydro-1H-cyclo-penta-[a]phenanthren-3-yl p-toluene-sulfonate}, C(36)H(54)O(3)S, comprises two independent mol-ecules that differ significantly in terms of the relative orientations of the peripheral groups; the conformation about the C=C bond of the side chain is E. In the crystal, mol-ecules associate into linear supra-molecular chains aligned along the a axis via C-H⋯O inter-actions.

Fulltext 6-[(E)-3,7-Dimethyl-octa-2,6-dien-yl]-5,7-dihydr-oxy-8-(2-methyl-butano-yl)-4-phenyl-2H-chromen-2-one from Mesua kunstleri King (Kosterm)

Chan G, Awang K, A Hadi AH, Ng SW

Acta Crystallogr Sect E Struct Rep Online, 2008;64(Pt 7):o1332.

PMID: 21202956 DOI: 10.1107/S1600536808018151

The title compound, C(30)H(34)O(5), crystallizes with two symmetry-independent mol-ecules in the asymmetric unit. In the crystal structure, the two independent mol-ecules are disposed about a pseudo-center of inversion. An intra-molecular O-H⋯O hydrogen bond is observed in each independent mol-ecule. The crystal structure is stabilized by C-H⋯O hydrogen bonds.

Fulltext 9α-Bromo analog of beclometasone dipropionate monohydrate

Ketuly KA, A Hadi AH, Ng SW

Acta Crystallogr Sect E Struct Rep Online, 2009;65(Pt 8):o1821.

PMID: 21583523 DOI: 10.1107/S1600536809025975

In the crystal structure of (8S,9R,10S,11S,13S,14S,16S,17R)-9α-bromo-11-hydr-oxy-10,13,16-trimethyl-3-oxo-17-[2-(propion-yloxy)acet-yl]-6,7,8,9,10,11,12,13,14,15,16,17-dodeca-hydro-3H-cyclo-penta-[a]phenanthren-17-yl propionate monohydrate, C(28)H(37)BrO(7)·H(2)O, which has a 9α-Br atom in place of the 9α-Cl atom of monohydrated beclometasone dipropionate, one six-membered ring is planar (r.m.s. deviation = 0.02 Å) owing to its 1,4-diene-3-one composition, whereas the two other six-membered rings each have a chair conformation. The organic mol-ecule and water mol-ecules engage in hydrogen-bonding inter-actions, generating a helical chain running along the c axis of the ortho-rhom-bic unit cell.

Fulltext A Phenylbutenoid Dimer, cis-3-(3',4'-Dimethoxyphenyl)-4-[(E)-3''',4'''-Dimethoxystyryl] Cyclohex-1-ene, Exhibits Apoptogenic Properties in T-Acute Lymphoblastic Leukemia Cells via Induction of p53-Independent Mitochondrial Signalling Pathway

Anasamy T, Abdul AB, Sukari MA, Abdelwahab SI, Mohan S, Kamalidehghan B, et al.

Evid Based Complement Alternat Med, 2013;2013:939810.

PMID: 23710242 DOI: 10.1155/2013/939810

The current study was designed to evaluate the in vitro cytotoxicity effect of a phenylbutenoid dimer, cis-3-(3',4'-dimethoxyphenyl)-4-[(E)-3 (‴) ,4 (‴) -dimethoxystyryl]cyclohex-1-ene (ZC-B11) isolated from the rhizome of Zingiber cassumunar on various cancer cell line, and normal human blood mononuclear cells, and to further investigate the involvement of apoptosis-related proteins that leads, to the probable pathway in which apoptosis is triggered. Cytotoxicity test using MTT assay showed selective inhibition of ZC-B11 towards T-acute lymphoblastic leukemia cells, CEMss, with an IC50 value of 7.11 ± 0.240 μ g/mL, which did not reveal cytotoxic effects towards normal human blood mononuclear cells (IC50 > 50 μ g/mL). Morphology assessments demonstrated distinctive morphological changes corresponding to a typical apoptosis. ZC-B11 also arrested cell cycle progression at S phase and causes DNA fragmentation in CEMss cells. Decline of mitochondrial membrane potential was also determined qualitatively. In the apoptosis-related protein determination, ZC-B11 was found to significantly upregulate Bax, caspase 3/7, caspase 9, cytochrome c, and SMAC and downregulate Bcl-2, HSP70, and XIAP, but did not affect caspase 8, p53, and BID. These results demonstrated for the first time the apoptogenic property of ZC-B11 on CEMss cell line, leading to the programmed cell death via intrinsic mitochondrial pathway of apoptosis induction.

Fulltext Acute toxicity and gastroprotection studies of a new schiff base derived copper (II) complex against ethanol-induced acute gastric lesions in rats

Hajrezaie M, Golbabapour S, Hassandarvish P, Gwaram NS, A Hadi AH, Mohd Ali H, et al.

PLoS One, 2012;7(12):e51537.

PMID: 23251568 DOI: 10.1371/journal.pone.0051537

BACKGROUND: Copper is an essential element in various metabolisms. The investigation was carried out to evaluate acute gastroprotective effects of the Copper (II) complex against ethanol-induced superficial hemorrhagic mucosal lesions in rats.

METHODOLOGY/PRINCIPAL FINDINGS: Rats were divided into 7 groups. Groups 1 and 2 were orally administered with Tween 20 (10% v/v). Group 3 was orally administered with 20 mg/kg omeprazole (10% Tween 20). Groups 4-7 received 10, 20, 40, and 80 mg/kg of the complex (10% Tween 20), respectively. Tween 20 (10% v/v) was given orally to group 1 and absolute ethanol was given orally to groups 2-7, respectively. Rats were sacrificed after 1 h. Group 2 exhibited severe superficial hemorrhagic mucosal lesions. Gastric wall mucus was significantly preserved by the pre-treatment complex. The results showed a significant increase in glutathione (GSH), superoxide dismutase (SOD), nitric oxide (NO), and Prostaglandin E2 (PGE(2)) activities and a decrease in malondialdehyde (MDA) level. Histology showed marked reduction of hemorrhagic mucosal lesions in groups 4-7. Immunohistochemical staining showed up-regulation of Hsp70 and down-regulation of Bax proteins. PAS staining of groups 4-7 showed intense stain uptake of gastric mucosa. The acute toxicity revealed the non-toxic nature of the compound.

CONCLUSIONS/SIGNIFICANCE: The gastroprotective effect of the Copper (II) complex may possibly be due to preservation of gastric wall mucus; increase in PGE(2) synthesis; GSH, SOD, and NO up-regulation of Hsp70 protein; decrease in MDA level; and down-regulation of Bax protein.

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