Comparison of essential oil components and in vitro anticancer activity in wild and cultivated Salvia verbenaca

The objectives of our research were to study the chemical composition and the in vitro anticancer effect of the essential oil of Salvia verbenaca growing in natural sites in comparison with those of cultivated (Sc) plants. The oil from wild (Sw) S. verbenaca presented hexadecanoic acid (23.1%) as the main constituent, while the oil from Sc plants contained high quantities of hexahydrofarnesyl acetone (9.7%), scarce in the natural oil (0.7%). The growth-inhibitory and proapoptotic effects of the essential oils from Sw and Sc S. verbenaca were evaluated in the human melanoma cell line M14, testing cell vitality, cell membrane integrity, genomic DNA fragmentation and caspase-3 activity. Both the essential oils were able to inhibit the growth of the cancer cells examined inducing also apoptotic cell death, but the essential oil from cultivated samples exhibited the major effects.     

Lipophilic constituents from two processed products and three different parts of Changium smyrnioides Wolff.

This article reports the lipophilic chemical composition of different processed products (Changii Radix, Changii Radix Alba) and parts (root bark, leaf and fruit) of Changium smyrnioides Wolff.. The lipophilic constituents were extracted with petroleum ether in Soxhlet apparatus, subsequently identified and determined by gas chromatography–mass spectroscopy (GC–MS). Yield of lipophilic constituents from Changii Radix (3.65%) was about three times more than Changii Radix Alba's (1.07%), which indicated processing by boiling in water had an impact on the content of lipophilic constituents. Moreover, the major compounds in different processed products and parts were found to be fatty acids and sesquiterpenes. The results are a contribution for the lipophilic chemical composition and can serve as a reference for product development of Changium smyrnioides Wolff..     

Catalytic Asymmetric Construction of α‐Quaternary Cyclopentanones and Its Application to the Syntheses of (−)‐1,14‐Herbertenediol and (−)‐Aphanorphine

A novel and efficient strategy to build α‐benzylic quaternary cyclopentanones with excellent enantioselectivities (up to 96 % ee) and high yields (up to 99 % yield) has been developed, and its application demonstrated by the first catalytic asymmetric total synthesis of (?)‐1,14‐herbertenediol and the formal synthesis of (?)‐aphanorphine.     

A unified,RCM anchored approach to spiro[4.5]decane-based sesquiterpenoids: Collective synthesis of (±)-α & β-vetispirenes, (±)-β-vetivone, (±)-agarospirol and (±)-hinesol

Collective syntheses of five spiro[4.5]decane framework bearing sesquiterpenoids, namely, α & β-vetispirenes, β-vetivone, agarospirol and hinesol as well as formal synthesis of axenol and gleenol from a readily available precursor cyclohexanone-β-ketoester via the intermediacy of a versatile intermediate (2,10-dimethylspiro[4.5]dec-1-en-6-one) have been accomplished in a concise manner.     

Daedaleanols A and B,two new sesquiterpenes from cultures of the basidiomycete Daedalea incana

Two new sesquiterpenes, daedaleanols A (1) and B (2), together with three known sesquiterpenes (3–5), were isolated from cultures of the basidiomycete Daedalea incana. Their structures were elucidated on the basis of extensive spectroscopic means. All compounds were tested for their cytotoxicities against three human cancer cell lines.     

New lignan glycosides from Cissus quadrangularis stems

Phytochemical investigation of Cissus quadrangularis stems led to the isolation of one new phenolic glycoside (1) and two new lignan glycosides (7 &; 8) along with twelve known compounds (2–6 &; 9–15). Their chemical structures were determined on the basis of extensive spectroscopic analysis using 1D, 2D NMR, and mass spectrometric analysis. Among the known compounds, 4–6, 9 and 12 were isolated for the first time from the genus Cissus whereas compounds 10, 11 and 13 for the first time from this plant.     

Two new sesquiterpenes from cultures of the higher fungus Pholiota nameko

Two new sesquiterpenes (1–2), along with one known sesquiterpene (3), were isolated from cultures of the higher fungus Pholiota nameko. The structures of new compounds were elucidated by extensive spectroscopic methods. The known compound was identified by comparing its spectroscopic data with those reported in the literature. All compounds were evaluated for their cytotoxicities against five human cancer cell lines.     

Ligusaginoids A–D,four eremophilane-type sesquiterpenoid dimers and trimers from Ligularia sagitta

Four novel highly oxygenated eremophilane-type sesquiterpenoid dimers and trimers with the unique 6/6/5/5 polycyclic skeleton, designated as ligusaginoids A–D (1–4), were isolated from the aerial parts of Ligularia sagitta. Their structures with absolute configurations were determined by a combined method. Moreover, a plausible biosynthetic pathway of 1–4 was also proposed. These compounds showed weak antibacterial activities.     

Two new sesquiterpenes derivatives from marine fungus Leptosphaerulina Chartarum sp. 3608

Two new sesquiterpenes, leptoterpenes A (1) and B (2) were isolated from the fungus Leptosphaerulina Chartarum sp. 3608, derived from a crinoid. It was the first chemical study on this species. The structures of these compounds were elucidated by spectroscopic methods including NMR and MS spectrometry. The absolute configurations of the new compounds were determined on the basis of the single-crystal X-ray diffraction and electronic circular dichroism data analysis. All compounds were tested for their anti-inflammatory activity and the inhibitory effects on Tyrosyl DNA phosphodiesterase II (TDP2).     

The pseudoguaianolide isoconfertiflorin

The sesquiterpene lactone isoconfertiflorin, C₁₇H₂₂O₅, 1, crystallizes in trigonal space group P3₁ with a = 10.4498(5), c = 12.7516(8) Å, V = 1205.9(2) ų, and Z = 3. It differs from confertiflorin in having an endocyclic C=C bond in the lactone ring, which carries an exocyclic methyl group. The seven-membered ring adopts an approximate twist-chair conformation with C10 lying in the local two-fold axis, and asymmetry parameter C₂ = 5.8°. The cyclopentanone ring has the half-chair conformation with C4 on the local two-fold axis, and C₂ = 0.9°. The lactone ring is almost planar with maximum deviation 0.014(2) Å. Both methyl groups on the 7-membered ring are –oriented. The acetyl group at C8 has an orientation.