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Three new sugar alcohol conjugated acyclic sesquiterpenes, cosmosporasides F-H ( 1 - 3 ), were isolated from the fermented cultures of Fusarium oxysporum SC0002. Their structures were elucidated by extensive analysis of spectroscopic data, including 1 H- 13 C long-range coupling constants ( J C,H ). Their antibacterial, cytotoxic and anti-inflammatory activities were evaluated.

Falandi is a common strawberry (Fragaria × ananassa Duch.) cultivar in southern China. Further study of the chemical constituents in Falandi fruit led to the isolation of nine norsesquiterpenoids and three triterpenoids. Falandioside D (1) and falandins A (2) and B (3) were new norsesquiterpenoids, and the others excluding tormentic acid (11) were found in strawberry for the first time. Compounds 1 and 11 exhibited potent α-glucosidase inhibitory activity with the half maximal inhibitory concentration (IC50) values of 565.0 and 27.4 μM in comparison to acarbose (619.9 μM). Compounds 3, 7 (blumenol C glucoside), and 11 showed cytotoxicity against human nasopharyngeal carcinoma cell line CNE1 with the IC50 values of 57.6, 56.4, and 36.0 μM, respectively. Among new compounds, 1 showed 2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radical cation scavenging capacity (IC50=36.2 μM). These results suggested that non-phenolic constituents were also involved in the antidiabetic, antitumour, and antioxidant effects of strawberry fruit., (Copyright © 2016 Elsevier Ltd. All rights reserved.)

Five new highly oxygenated α-pyrone merosesquiterpenoids, ochraceopones A-E (1-5), together with one new double bond isomer of asteltoxin, isoasteltoxin (6), and two known asteltoxin derivatives, asteltoxin (7) and asteltoxin B (8), were isolated from an Antarctic soil-derived fungus, Aspergillus ochraceopetaliformis SCSIO 05702. Their structures were determined through extensive spectroscopic analysis, CD spectra, quantum mechanical calculations, and X-ray single-crystal diffraction. Ochraceopones A-D (1-4) are the first examples of α-pyrone merosesquiterpenoids possessing a linear tetracyclic carbon skeleton, which has not been previously described. All the isolated compounds were tested for their antiviral, cytotoxic, antibacterial, and antitubercular activities. Among these compounds, ochraceopone A (1), isoasteltoxin (6), and asteltoxin (7) exhibited antiviral activities against the H1N1 and H3N2 influenza viruses with IC50 values of >20.0/12.2 ± 4.10, 0.23 ± 0.05/0.66 ± 0.09, and 0.54 ± 0.06/0.84 ± 0.02 μM, respectively. A possible biosynthetic pathway for ochraceopones A-E (1-5) was proposed.

Two new quinone sesquiterpenes named myrothecols G and H (1 and 2), a pair of C-1' diastereomers of 13-hydroxyl penicilliumin A, were isolated from the mycelia solid cultures of Myrothecium sp. SC0265. Their structures, including the absolute configurations, were established on the basis of the spectroscopic data combining with the theoretical conformational analysis. The cytotoxic activities of 1 and 2 were tested against a panel of human tumor cell lines.

Six new quinone sesquiterpenes, myrothecols A-F (1-6), and hymenopsin B (7) were isolated from cultures of Myrothecium sp. SC0265 by bioassay-guided fractionation. Their structures were elucidated on the basis of 1D and 2D NMR and MS data. The absolute configurations of the new compounds were assigned by CD/TDDFT calculations, and that of and hymenopsin B was confirmed by X-ray diffraction analysis. Compounds 1-5 and hymenopsin demonstrated cytotoxic activity against human carcinoma A549, HeLa, and HepG2 cells. Compounds 1-5 also exhibited antibacterial activity against Staphylococcus aureus and Bacillus cereus.

The allelopathic effects of different parts of the plant Xanthium italicum Moretti were evaluated by conducting bioassays against two dicot plants, amaranth (Amaranthus mangostanus L.) and lettuce (Lectuca sativa L.), and two monocot plants, wheat (Triticum aestivum Linn) and ryegrass (Lolium multiforum). Leaf and fruit extract possessed the strongest biological activity, killing all seeds of four test species at 0.05 g/mL concentration. Fruits were chosen for further investigation because of their high biomass. This led to the isolation and identification of a phytotoxin-Xanthinosin-a known sesquiterpene lactone. Xanthinosin significantly affected seedling growth of all test species at 160 µM concentration. Cultivating seeds in 800 μM xanthinosin solution resulted in a great decrease in seedling growth of all test species, especially for the two dicot plants, amaranth and lettuce, whose root length was inhibited by 78% and 89%, respectively. By comparison, the numbers were 69% lower for wheat, and 66% for ryegrass, two monocot plants. When treated with 4 mM xanthinosin solution, seed germination of all test plants was almost completely inhibited. The possibility of utilizing xanthinosin as an eco-friendly herbicide was discussed.

Three new sesquiterpenes including a rearranged hirsutane, dichomitol (1), an aromadendrane, 2beta,13-dihydroxyledol (2), and a 1,10-seco-2,3-seco-aromadendrane, dichomitone (3), were isolated from mycelial solid cultures of Dichomitus squalens. Their structures were elucidated by spectroscopic methods, and their nematicidal activities against Bursaphelenchus xylophilus were assessed.

Two new illudane sesquiterpenes, paneolic acid and paneolilludinic acid, along with a known antibiotic diterpene, pleuromutilin, were isolated from the mycelial solid cultures of Panaeolus retirugis. Their structures were elucidated on the basis of spectroscopic analysis. Both compounds exhibited antibacterial activity against Staphylococcus aureus, and paneolic acid showed cytotoxicity to HL60 cell with an IC50 of 18.9 microg/ml.

Four new sesquiterpene dilactones, mikamicranolide (1), 11 beta,13-dihydromikamicranolide (2), 3 alpha-hydroxy-11 beta,13-dihydrodeoxymikanolide (3), and 2 beta,3 beta-dihydroxy-11 beta,13-dihydrodeoxymikanolide (4), were isolated from the whole plants of Mikania micrantha. Their structures were elucidated on the basis of spectroscopic analysis. Compounds 1 and 2 possess an unusual rearranged 12,8-germacranolide sesquiterpene skeleton.

Highlights: [•] Six phenolics and two sesquiterpenes were isolated from litchi pericarp. [•] Their structures were identified by spectroscopic methods. [•] Five compounds were new and the others were reported from litchi for the first time. [•] Five phenolics showed antioxidant activity in FRAP and DPPH assays. [Copyright &y& Elsevier]

The fruit of Clausena lansium (wampee) is popular in southern China and warm areas of the world. Our chemical study on the fruit yielded three jasmonoid glucosides, 12-β- d -glucopyranosyloxy-6- epi -7-isocucurbic acid-1,6-lactone ( 1 ), 12-β- d -glucopyranosyloxyjasmonic acid ( 2 ) and 12-hydroxyjasmonic acid ( 3 ), two sesquiterpenes, (+)-curcumen-12-oic acid ( 4 ) and (+)-( E )-α-santalen-12-oic acid ( 5 ), two coumarins, xanthotoxol ( 6 ) and indicolactone ( 7 ), in addition to 3,4-dihydroxybenzoic acid ( 8 ), 5-hydroxymethylfuraldehyde ( 9 ), isopropyl β- d -glucopyranoside ( 10 ) and stigmasterol ( 11 ). Their structures were determined by spectroscopic methods. Compound 1 was a new metabolite and the others excluding 6 were reported from the species for the first time. Compounds 1 – 7 were evaluated for antioxidant and antibacterial activities. Among them, compound 6 showed antioxidant activity in ferric reducing antioxidant power (FRAP) and DPPH radical scavenging assays as well as antibacterial activity against Staphyloccocus aureus and Shigella dysenteriae , while compound 5 was active against Bacillus cereus . [ABSTRACT FROM AUTHOR]

Abstract: Two new sesquiterpene glucosides, litchiosides A (1) and B (2), were obtained along with pumilaside A (3) and funingensin A (4) from lychee (Litchi chinensis Sonn.) seed. Their structures were elucidated on the basis of spectroscopic and chemical evidence. The in vitro antitumour activity of compounds 1–4 against A549, LAC, Hela, and Hep-G2 cell lines was determined using the MTT colourimetric assay. Pumilaside A (3) exhibited significant activity against all the tested cell lines with IC50 values of 0.012–6.29μM, and funingensin A (4) showed moderate activity against Hep-G2 cells (IC50 =39.27μM), while litchiosides A (1) and B (2) were found to be inactive. [Copyright &y& Elsevier]