Triterpenes and steroids from the leaves of Aglaia exima (Meliaceae).

A study on the leaves of Aglaia exima led to the isolation of one new and seven known compounds: six triterpenoids and two steroids. Their structures were elucidated and analyzed mainly by using spectroscopic methods; 1D and 2D NMR, mass spectrometry, UV spectrometry and X-ray. All the triterpenoids and steroids were measured in vitro for their cytotoxic activities against eight cancer cell lines; lung (A549), prostate (DU-145), skin (SK-MEL-5), pancreatic (BxPC-3), liver (Hep G2), colon (HT-29), breast (MCF-7) and (MDA-MB-231).

Naucline, a new indole alkaloid from the bark of Nauclea officinalis.

A new indole alkaloid, naucline (1) together with four known alkaloids, angustine (2), angustidine (3), nauclefine (4) and naucletine (5), were isolated from the bark of Nauclea officinalis. The structures of all isolated compounds were elucidated with various spectroscopic methods such as 1D- and 2D- NMR, IR, UV and LCMS-IT-TOF. In addition to that of alkaloid 1, the complete 13C-NMR data of naucletine (5) were also reported.

A triclinic polymorph of (E)-2-(1-hy-droxy-3-phenyl-prop-2-en-1-yl-idene)-4,5-dimeth-oxy-cyclo-pent-4-ene-1,3-dione.

The title compound, C(16)H(14)O(5), is a triclinic polymorph of a previously reported monoclinic structure [Hosseinzadeh et al. (2011 ▶). Acta Cryst.

Anti-acetylcholinesterase, anti-α-glucosidase, anti-leishmanial and anti-fungal activities of chemical constituents of Beilschmiedia species.

Phytochemical investigation of Beilschmiedia alloiophylla has resulted in the isolation of one new alkaloid, 2-hydroxy-9-methoxyaporphine (1), and ten known natural products, laurotetanine (2), liriodenine (3), boldine (4), secoboldine (5), isoboldine (6), asimilobine (7), oreobeiline (8), 6-epioreobeiline (9), β-amyrone (10), and (S)-3-methoxynordomesticine (11). Chemical studies on the bark of B. kunstleri afforded compounds 2 and 4 along with one bisbenzylisoquinoline alkaloid, N-dimethylphyllocryptine (12).

Vasorelaxant effect of isoquinoline derivatives from two species of Popowia perakensis and Phaeanthus crassipetalus on rat aortic artery.

Five bisbenzyl isoquinolines (1-5), three benzyl isoquinolines (6-8), four isoquinoline alkaloids (9-12), and two unclassified compounds (13 and 14) from Popowia perakensis and Phaeanthus crassipetalus were evaluated for their vasorelaxant effect on rat aortic arteries. In aortic rings pre-contracted with phenylephrine (PE, 0.3 μM), some of the bisbenzyl isoquinoline alkaloids, benzyl isoquinoline alkaloids, and isoquinoline alkaloids showed clearly vasorelaxant effects at 30 μM.

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

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.

Whole-mol-ecule disordered (E)-2-(1-hy-droxy-3-phenylprop-2-en-1-yl-idene)-4,5-dimeth-oxycyclo-pent-4-ene-1,3-dione isolated from Lindera oxyphylla (Lauraceae).

In the mol-ecule of the title compound, C(16)H(14)O(5), all non-H atoms are approximately co-planar [maximum atomic deviation = 0.064 (5) Å]. The hy-droxy group is a hydrogen-bond donor to a carbonyl O atom.

N-cyanomethylnorboldine: a new aporphine isolated from Alseodaphne perakensis (Lauraceae).

A phytochemical study of the bark of Alseodaphne perakensis has yielded three aporphine alkaloids: the new compound N-cyanomethylnorboldine (1), and the two known alkaloids N-methyllaurotetanine (2) and norboldine (3). The isolation was achieved by chromatographic techniques and the structural elucidation was performed via spectral methods, notably 1D- and 2D-NMR, UV, IR, and HRFABMS. The vasorelaxation activity of compound 1 has been studied.

Lancifoliaine, a new bisbenzylisoquinoline from the bark of Litsea lancifolia.

A new bisbenzylisoquinoline, lancifoliaine (1), together with seven known alkaloids--N-allyllaurolitsine (2), reticuline (3), actinodaphnine, norboldine, pallidine, cassythicine and boldine--were isolated from the stem bark of Litsea lancifolia (Lauraceae). In addition to that of lancifoliaine, complete ¹³C-NMR data of N-allyl-laurolitsine (2) was also reported. The alkaloidal structures were elucidated by means of high field 1D- and 2D-NMR IR, UV, and LCMS-IT-TOF spectral data.

Antifeedant triterpenoids from the seeds and bark of Lansium domesticum cv Kokossan (Meliaceae).

Two tetranortriterpenoids, kokosanolide A (1) and C (2) were isolated from the seeds and three onoceranoid-type triterpenoids: kokosanolide B (3), 8,14-secogammacera-7,14-diene-3,21-dione (4) and a 1.5:0.5 mixture of 8,14-secogammacera-7,14(27)-diene-3,21-dione (5) and compound 4 were isolated from the bark of kokossan (Lansium domesticum).

Chisomicines A-C, limonoids from Chisocheton ceramicus.

Three new limonoids, chisomicines A-C (1-3), have been isolated from the bark of Chisocheton ceramicus. Their structures were determined by 2D NMR, CD spectroscopic methods, and X-ray analysis. Chisomicine A (1) exhibited NO production inhibitory activity in J774.

Neolamarckines A and B, new indole alkaloids from Neolamarckia cadamba.

Two new indole alkaloids, neolamarckines A and B (1, 2) were isolated from the leaves of Neolamarckia cadamba (Rubiaceae). Structural elucidation of 1 and 2 was performed by combination of 2D-NMR and circular dichroism (CD) spectra, and chemical correlations. Neolamarckine A (1) showed inhibition of inducible nitric oxide synthase (iNOS) dose dependently.

Oppositinines A and B: new vasorelaxant beta-carboline alkaloids from Neisosperma oppositifolia.

A phytochemical study on the bark of Neisosperma oppositifolia (Apocynaceae) yielded two new beta-carboline indole alkaloids, oppositinines A (1) and B (2), together with five known alkaloids, isoreserpiline, isocarapanaubine, vobasine, 10-methoxydihydrocorynantheol-N-oxide, and ochropposinine oxindole. Structural elucidation of 1 and 2 was performed using 2D NMR methods. Oppositinines A (1) and B (2) showed potent vasorelaxant effects on the rat aorta.

Rearranged diterpenoids from the biotransformation of ent-trachyloban-18-oic acid by Rhizopus arrhizus.

In our search for inhibitors of the antiapoptotic protein Bcl-xL, investigation of Xylopia caudata afforded a new diterpenoid, ent-trachyloban-4beta-ol (2), and five known ent-trachylobane or ent-atisane compounds. Only ent-trachyloban-18-oic acid (1) exhibited weak binding activity to Bcl-xL. These compounds exhibited cytotoxicity against KB and HCT-116 cell lines with IC(50) values between 10 and 30 microM.

(6,7-Dimethoxy-4-methylisoquinolinyl)-(4'-methoxyphenyl)-methanone, a new benzylisoquinoline alkaloid from Beilschmiedia brevipes.

The leaves of Beilschmiedia brevipes provided a new benzylisoquinoline alkaloid: (6,7-dimethoxy-4-methylisoquinolinyl)-(4'-methoxyphenyl)-methanone (1) and O,O-dimethylannocherin A (2), a new natural compound which has been synthesized before. Complete 1H- and 13C-NMR data of both compounds were reported. The structures were established through various spectroscopic methods notably 1D- and 2D-NMR, UV, IR and HRESIMS.

14-Hy-droxy-8,14-secogammacera-7-ene-3,21-dione from the bark of Lansium domesticum Corr.

In the title compound (kokosanolide B), C(30)H(48)O(3), the hexa-hydro- and octa-hydro-naphthalen-2-one ring systems are connected through an ethyl-ene fragment, with a C-CH(2)-CH(2)-C torsion angle of 176.2 (2)°. The cyclo-hexene ring adopts a half-chair conformation, while the other six-membered rings adopt distorted chair conformations.

Meranzin hydrate from Muraya paniculata.

The coumarin ring system in the title compound, C(15)H(18)O(5) [IUPAC name: 8-(2,3-dihydr-oxy-3-methyl-butyl)-7-meth-oxy-2H-1-benzopyran-2-one], isolated from Muraya paniculata, is planar (r.m.s.

(20S)-24,25-Dihydr-oxy-20,24-ep-oxy-3,4-secodammar-4(28)-en-3-oic acid from Aglaia smithii.

The title compound, C(30)H(50)O(5), was isolated from the bark of Aglaia smithii. There are two independent mol-ecules in the asymmetric unit that differ in the orientation of the isopropenyl group attached to the cyclo-hexane ring. The cyclo-hexane rings in both mol-ecules adopt chair conformations, whereas the cyclo-pentane and tetra-hydro-furan rings adopt envelope conformations.

(+)-N-(2-hydroxypropyl)lindcarpine: a new cytotoxic aporphine isolated from Actinodaphne pruinosa Nees.

Onenewalkaloid; (+)-N-(2-hydroxypropyl)lindcarpine (1),together with four known aporphine alkaloids, (+)-boldine (2) (+)-norboldine (3), (+)-lindcarpine (4) and (+)-methyllindcarpine (5) were isolated from the stem bark of Actinodaphne pruinosa Nees (Lauraceae). (+)-N-(2-Hydroxypropyl)lindcarpine (1) exhibited cytotoxic activity against P-388 murine leukemia cells with an IC(50 )value of 3.9 microg/mL.

Dunaliine A, a new amino diketone from Desmos dunalii (Annonaceae).

Dunaliine A (1), a new amino diketone, has been isolated from the leaves of Desmos dunalii together with four known dihydrochalcones: 2',4-dihydroxy-4',6'-dimethoxy-3',5'-dimethyldihydrochalcone (2), 2',4-dihydroxy-4',6'-dimethoxydihydrochalcone (3), 2',4-dihydroxy-4',5',6'-trimethoxydihydrochalcone (4) and 2',4-dihydroxy-5'-methyl-4',6'-dimethoxydihydrochalcone (5). The structures of these compounds were established notably by spectral analysis (1D- and 2D- (1)H, (13)C NMR), UV, IR and HRMS.

Grandine A, a new proaporphine alkaloid from the bark of Phoebe grandis.

The stem bark of Phoebe grandis afforded one new oxoproaporphine; (-)-grandine A (1), along with six known isoquinoline alkaloids: (-)-8,9-dihydrolinearisine (2), boldine, norboldine, lauformine, scortechiniine A and scortechiniine B. In addition to that of the new compound, complete 1H- and 13C-NMR data of the tetrahydroproaporphine (-)-8,9-dihydrolinearisine (2) is also reported. The alkaloids' structures were elucidated primarily by means of high field 1D- and 2D-NMR and HRMS spectral data.

8,14-Secogammacera-7,14(27)-diene-3,21-dione-8,14-secogammacera-7,14-diene-3,21-dione (1.5/0.5) from the bark of Lansium domesticum Corr.

The components of the title cocrystal, 1.5C(30)H(40)O(2)·0.5C(30)H(40)O(2), each have two tetra-hydro-deca-lin-type fused rings connected through an ethyl-ene fragment [R-CH(2)-CH(2)-R' torsion angles: 158.

Kokosanolide from the seed of Lansium domesticum Corr.

IN THE TITLE COMPOUND, [SYSTEMATIC NAME: 8,14-secogammacera-7,14(27)-diene-3,21-dione], C(27)H(32)O(9), each of the six-membered rings adopts the common chair conformation. In the crystal, mol-ecules are linked by an O-H⋯O(ester) hydrogen bond into a helical chain.

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

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.