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Ten schinortriterpenoids with biogenetically related lancischiartane scaffolds, including the first 3-norlancischiartane (1) with unusual configuration inversions occurring at C-1 and C-10, were isolated from Schisandra lancifolia. Unusual ECD curve patterns observed in 6-8 were confirmed to be caused by nondegenerate exciton coupling, suggesting that ECD spectrum empirical comparison should be used with caution in configuration determination. Additionally, structure revision of 2, originally proposed as arisanlactone A, was completed using NMR computation and X-ray diffraction analysis.

A new class of highly oxygenated Schisandra nortriterpenoids, lancolides A-D (1-4), from Schisandra lancifolia, represents the first example of natural products that possess a tricyclo[6.3.0.0(2,11)]undecane-bridged system. Their structures were elucidated by NMR spectra, X-ray diffraction, and quantum chemical calculations. Lancolides A (1) and D (4) had specific antiplatelet aggregation induced by platelet-activating factor (PAF).

Four new highly oxygenated nortriterpenoids, lancifodilactones O-R (1-4), together with six known ones, i.e., 5-10, were isolated from the leaves and stems of Schisandra lancifolia. Their structures were elucidated by spectroscopic analyses, including 1D- and 2D-NMR experiments and mass spectrometry. Compounds 1-3 were evaluated for their cytotoxicity against NB4, A549, SHSY5Y, PC-3, and MCF-7 cell lines. No compounds exhibited significant cytotoxicity, the I(C5)0 values being above 50 mu M.

A new nortriterpenoid, 20-hydroxymicrandilactone D (1) and a novel lignan glycoside, lancilignanside A (2) were isolated from leaves and stems of Schisandra lancifolia, together with three known nortriterpenoids (3-5) and nine known phenolics (6-14). The structures of new compounds 1 and 2 were determined by detailed analysis of their 1D and 2D NMR spectra, and chemical evidences. In addition, compounds 1-2, 6-7, and 9-11 showed anti-human immunodeficiency virus (HIV)-1 activities with 50% effective concentration (EC(50)) in the range of 3.0-99.0 microg/ml. Compound 12 was not bioactive in this assay with EC(50) more than 200 microg/ml.

Three new dibenzocyclooctadiene lignans, schilancifolignans A-C (1-3), together with thirteen known ones, were isolated from the leaves and stems of Schisandra lancifolia. The structures of 1-3 were elucidated by spectroscopic methods, including extensive 1D- and 2D-NMR techniques. Compounds 1-3 were tested for their anti-human immunodeficiency virus-1 activities and showed weak bioactivities.

Eleven triterpene acids including 10 new compounds (kadcoccinic acids A–J, 1–10) were isolated from the stems of Kadsura coccinea. Except for 10, these compounds feature a rearranged lanostane skeleton with a 6/6/5/6 tetracyclic ring system, and compounds 1 and 2 are the first examples of 2,3-seco-6/6/5/6-fused tetracyclic triterpenoids. Their structures were established primarily by spectroscopic and spectrometric methods. Additionally, the absolute configuration of 3 was determined by single-crystal X-ray diffraction. Several of the compounds isolated were tested for their anti-HIV-1 and cytotoxic activities.

A novel bisnortriterpenoid, lancifodilactone A, has been isolated from the leaves and stems of Schisandra lancifolia. Its structure and stereochemistry were determined primarily from ID and 2D NMR spectroscopic data, and were confirmed by a single crystal X-ray analysis. (C) 2003 Elsevier Science Ltd. All rights reserved.

The isolation, structure elucidation and determination of the absolute configuration of six lancifonins are described.

Six unique nortriterpenoids, lancifonins A-F (1-6), were isolated from Schisandra lancifolia. Their absolute configurations were determined by X-ray diffraction and ECD calculation. The conformational analysis of 1 was performed due to the unanticipated changes of Cotton effects in its ECD spectrum. Compounds 5 and 6 possess a unique 7/7 fused carbocyclic core with an internal ester bridge between C-9 and C-14, and 5 exhibited protective activity against H2O2-induced oxidative damage on Caco-2 cells.

Lancolides A (Ia) and D (IIb) show specific antiplatelet aggregation induced by platelet-activating factor (PAF).

Schilancidilactones A (1) and B (2). two novel tetranortriterpenoids possessing an unprecedented skeleton, have been isolated from the stems of Schisandra lancifolia. Their structures were elucidated on the basis of extensive spectroscopic analysis. The relative configurations of 1 were further determined by single-crystal X-ray crystallography. Compounds 1 and 2 were tested for their cytotoxicity against four tumor cell lines NB4, A549, SH-SY5Y, and PC-3, and compound I was further tested for its anti-HIV-1 activity. (C) 2009 Elsevier Ltd. All rights reserved.

Three unique nortriterpenoids, schilancitrilactones A-C (1-3), were isolated from the stems of Schisandra lancifolia . Compound 1 possesses a 5/5/7/5/5/5-fused hexacyclic ring system with a C(29) backbone, while 2 and 3 feature a C(27) skeleton with a 5/7/5/5/5-fused pentacyclic ring system. Their absolute stereochemistries were established by CD and single-crystal X-ray diffraction experiments. Compound 3 showed anti-HIV-1 activity with an EC(50) value of 27.54 μg/mL, and 1 exhibited antifeedant activity at 15.73 μg/cm(2).

Two new neolignans, schilancifolignans D and E (1 and 2), together with eight known ones, were isolated from the leaves and stems of Schisandra lancifolia. The structures of 1 and 2 were elucidated by spectroscopic methods, including extensive 1D and 2D NMR techniques. Compounds 1 and 2 were tested for their anti-HIV-1 activities and cytotoxicity. Both showed significant potential cytotoxic ability and weak anti-HIV-1 activities.

The new nortriterpenoid, 20-hydroxymicrandilactone D (I), and the novel lignan glycoside, lancilignanside A (II) are isolated from the leaves and stems of Schisandra lancifolia along with three known nortriterpenoids and nine known phenolics.

Three new dibenzocyclooctadienes (I), named schilancifolignans A-C, are isolated together with several known lignans from leaves and stems of the title plant.

Two new 18-norschiartane-type schinortriterpenoids, namely wuwezidilactones Q (1) and R (2) were isolated from the stems of Schisandra lancfolia. Their structures were determined on the basis of extensive spectroscopic analysis. The absolute configurations of the new compounds were further determined by ROESY and an empirical comparison of their experimental ECD spectra with literature.

[structures: see text] Lancifodilactone F (1), possessing an unprecedented rearranged pentanortriterpenoid backbone derived from cycloartane, was isolated from the leaves and stems of Schisandra lancifolia (Rehd. et Wils) A. C. Smith. Its structure was established by comprehensive NMR and MS spectroscopic analysis, coupled with single-crystal X-ray experiment. Compound 1 exerted minimal cytotoxicity against C8166 cells (CC50200 microg/mL) and showed anti-HIV activity with EC50 = 20.69 +/- 3.31 microg/mL and a selectivity index6.62.

[structure: see text]. Lancifodilactone G (1), a novel, highly oxygenated nortriterpenoid featuring a partial enol structure and a spirocyclic moiety, was isolated from the medicinal plant Schisandra lancifolia. Its structure and stereochemistry were determined from extensive one- and two-dimensional NMR and mass spectral data, coupled with single-crystal X-ray analysis. Compound 1 exerted minimal cytotoxicity against C8166 cells (CC50 > 200 microg/mL) and showed anti-HIV activity with EC50 = 95.47 +/- 14.19 microg/mL and a selectivity index in the range of 1.82-2.46.