Sesquiterpenoid Compounds from Curcuma kwangsiensis

Two previously undescribed guaiane‐type sesquiterpenes ( 1 and 2 ), a pair of new salvialane‐type sesquiterpenes ( 3a and 3b ), together with 11 known compounds were isolated and purified from the rhizomes of Curcuma kwangsiensis. Their structures were elucidated by the extensive spectroscopic data (1D‐ and 2D‐NMR) analysis. All the isolated compounds were assessed for their anti‐neuroinflammatory activity by inhibiting the nitric oxide (NO) production in lipopolysaccharide (LPS)‐activated murine BV‐2 microglial cells in vitro assay, and the isolates 3 and 11 showed anti‐neuroinflammatory activity with IC₅₀ values of 1.85 and 20.05 μm , respectively.     

Novel Zierane‐ and Guaiane‐Type Sesquiterpenes from the Root of Melicope denhamii

Two novel zierane‐type sesquiterpenes, named melicodenones A and B ( 1 and 2 , resp.), and three new guaiane‐type sesquiterpenes, named melicodenones C–E ( 3 – 5 ), were isolated from the root of Melicope denhamii (Seem. ) T. G. Hartley together with zierone ( 6 ). Their structures were established by extensive NMR‐spectroscopic analyses. Compounds 1 – 6 were tested for cytotoxicity using human colon cancer DLD‐1 cells, and melicodenone A ( 1 ) was found to exhibit moderate activity.     

New sesquiterpenes from Pleocarphus revolutus

Six new sesquiterpenes of the guaiane and isopatchoulenone types have been isolated from the Chilean plant Pleocarphus revolutus. Of these, the compound hydroxy-isopatchoulenone and related esters showed cytotoxicity towards TLX5 mouse mammary lymphoma cells.     

Japonicones A–D,bioactive dimeric sesquiterpenes from Inula japonica Thunb.

Four new dimeric sesquiterpene lactones japonicones A?D (1?4), comprised by eudesmane and guaiane sesquiterpenes, were isolated from the aerial part of Inula japonica Thunb. The structures and stereochemistry of 1?4 were elucidated by use of 2D NMR spectroscopic techniques, X-ray crystallography and modified Mosher method. Japonicone A (1) showed the most potent cytotoxicities against four tumor cell lines, A549, LOVO, CEM and MDA-MB-435.     

New Sesquiterpenes from Aspergillus terreus Thom

Four neutral sesquiterpenes were isolated from the culture filtrate of of Aspergillus terreus THOM NO. 14 which produces two sesquiterpene antibiotics, terrecyclic acid A and terrecyclol. On the basis of spectroscopic data the structures of four neutral sesquiterpenes were elucidated. One of these is quadrone, a known antitumor substance, but isoquadrone, 8-hydroxyquadrone and 6-hydroxyisoquadrone are new sesquiterpenes. Although terrecyclic acid A exhibits antimicrobial and antitumor activities, these four scarcely show these activities.     

Cyclohexenone Derivative and Drimane Sesquiterpenes from the Seagrass-Derived Fungus Aspergillus insuetus

One new cyclohexenone derivative ( 1 ), and two undescribed drimane sesquiterpenes ( 2 and 3 ), together with another seven known drimane sesquiterpenes were isolated from a seagrass-derived fungus Aspergillus insuetus SYSU6925. Structures of these metabolites were elucidated by comprehensive spectroscopic analysis, including NMR analysis, mass spectrometry, and ECD calculations. Compounds 1 – 3 , 5 and 7 displayed weak to moderate antifungal activities towards four phytopathogenic fungi, with Minimum inhibition concentration (MIC) values range from 50 to 200 μg/mL. Compound 1 , a rare cyclohexenone derivative with n-propyl group exhibited more potent inhibitory activities (MIC, 50 μg/mL) against F. oxysporum than positive control (Triadimefon). Compounds 2 and 3 also exhibit potent anti-inflammatory activities by inhibiting the production of nitric oxide (NO) in RAW264.7 cells with IC₅₀ values of 21.5±1.1 and 32.6±1.16 μM, respectively.     

Eremophilane Sesquiterpenes and Benzene Derivatives from the Endophyte Microdiplodia sp. WGHS5

Three new eremophilane sesquiterpenes phomadecalins G−I ( 1 – 3 ) and two new benzene derivatives microdiplzenes A and B ( 12 and 13 ), together with nine known eremophilane sesquiterpenes ( 4 – 11 and 14 ) were isolated from an endophytic fungus, Microdiplodia sp. WGHS5. Their structures were elucidated by the interpretation of HR-ESI-MS and NMR data; meanwhile, the absolute configurations of new compounds were determined on the base of ECD calculations. All compounds were evaluated for the antimicrobial activities and antiproliferative effect on human gastric cancer cell lines (BGC-823).     

Two New Steroids from an Endophytic Fungus Phomopsis sp.

Two new steroids, (14β,22E)‐9,14‐dihydroxyergosta‐4,7,22‐triene‐3,6‐dione ( 1 ) and (5α,6β,15β,22E)‐6‐ethoxy‐5,15‐dihydroxyergosta‐7,22‐dien‐3‐one ( 2 ), together with three known steroids, calvasterols A and B ( 3 and 4 , resp.), and ganodermaside D ( 5 ), were isolated from the culture broth of an endophytic fungus Phomopsis sp. isolated from Aconitum carmichaeli. The structures of these compounds were elucidated on the basis of spectroscopic analysis, and their inhibitory activities against six pathogenic fungi were evaluated. Most of the compounds showed moderate or weak antifungal activities in a broth‐microdilution assay.     

Chemical constituents from the fungus Stereum sp. YMF1.04183

The chemical constituents of the basidiomycete Stereum sp. YMF1.04183 were studied. Three new sesquiterpenes, stereumenes A–C (1–3), were isolated and identified from the EtOAc extract of Stereum sp. YMF1.04183 culture broth. Stereumene B showed weak nematicidal activity against Caenorhabditis elegans.     

Terpenes from the Soft Corals of the Genus Sarcophyton: Chemistry and Biological Activities

This review covers structural diversity and biological activities of terpenes from soft corals of the genus of Sarcophyton, reported from 1995 to July, 2011. During this period, besides undefined species, 16 species of the genus Sarcophyton, from different geographical areas, had been chemically examined. Two hundred and five terpenes had been isolated from this genus, including eleven sesquiterpenes, 165 diterpenes, 29 biscembranoids, some of which had novel skeletons. They exhibited various biological features, such as antifeedant, anti‐inflammatory, antiviral, and antifouling activities.     

Enantiomeric Neolignans and a Sesquiterpene from Solanum erianthum and Their Absolute Configuration Assignment

One pair of new C‐8–C‐3′/C‐7–O–C‐4′ linked neolignan enantiomers ( 1a / 1b ) and one new guaiane sesquiterpene ( 2 ) first featuring the 1(2),9(10)‐conjugated double bond were isolated from the stems of Solanum erianthum (Solanceae). Their structures were characterized on the basis of extensive spectroscopic analyses, especially from their 2D nuclear magnetic resonance (NMR) spectra. The absolute configurations of 1a / 1b were rigorously elucidated by electronic circular dichroism (ECD) experiments combined with the reversed helicity rule for the 2,3‐dihydrobenzo[b]furan chromophore, and compound 2 is the first report on the sterochemical assignment of a guaiane sesquiterpene by using the allylic axial chirality rule for the conjugated diene chromophore in combination with the calculated ECD spectrum. Chirality 28:259–263, 2016. © 2016 Wiley Periodicals, Inc.     

Three New Constituents with Anti-Inflammatory and Antimicrobial Activities in Vitro from the Roots of Capsicum annuum L.

Three new compounds, including two new sesquiterpenes ( 1–2 ), named Annuumine E−F, and one new natural product, 3-hydroxy-2,6-dimethylbenzenemethanol ( 3 ), together with seventeen known compounds ( 4–20 ) were isolated from the ethanol extract of the roots of Capsicum annuum L. Among them, five compounds ( 4 , 5 , 9 , 10 and 20 ) were isolated from this plant for the first time. The structures of new compounds ( 1–3 ) were determined via detailed analysis of the IR, HR-ESI-MS and 1D and 2D NMR spectra. The anti-inflammatory activities of the isolated compounds were evaluated by their ability to reduce NO release by LPS-induced RAW 264.7 cells. Notably, compound 11 exhibited moderate anti-inflammatory activity (IC₅₀=21.11 μM). Moreover, the antibacterial activities of the isolated compounds were also evaluated.     

Two New Butenolides Produced by an Actinomycete Streptomyces sp.

Two new butenolides, (4S)‐4,10‐dihydroxydodec‐2‐en‐1,4‐olide ( 1 ) and (4S)‐4,8,10‐trihydroxy‐10‐methyldodec‐2‐en‐1,4‐olide ( 2 ), together with three known compounds, MKN‐003B ( 3 ), MKN‐003C ( 4 ), and cyclo(Ala‐Leu) ( 5 ), were isolated from the culture broth of a bacterium of the genus Streptomyces derived from soil environment. The structures of these compounds were elucidated on the basis of spectroscopic analysis. The inhibitory activities of the butenolides against eight pathogenic fungi were evaluated. All of the butenolides showed moderate‐or‐weak antifungal activities in a broth microdilution assay.     

Chemical constituents from Teucrium viscidum

A new guaiane sesquiterpenoid (1), two known guaiane sesquiterpenoids (2 and 3), and eleven known compounds (4–14), were isolated from Teucrium viscidum. Their structures were identified by spectroscopic analyses and by comparison of their spectral data with those reported in the literature. The absolute configuration of lipidiol (2) was determined by single-crystal X-ray diffraction analysis with Cu Kα radiation. Compounds 12 and 13 were isolated as natural products for the first time. All compounds were isolated from T. viscidum for the first time.     

Chemical and Pharmacological Studies of the Plants from Genus Celastrus

The plants of genus Celastrus, distributed in Asia, have been used as natural insecticides and folk medicines to treat fever, chill, joint pain, edema, rheumatoid arthritis, and bacterial infection in China for a long time. This contribution reviews the chemical constituents, 1 – 144 , isolated from the plants in genus Celastrus in the past few decades, and their biological activities. The compounds listed are sesquiterpenes (β‐agarofurans), diterpenes, triterpenes, alkaloids, and flavonoids.     

The recurvatianes: a suite of oxygenated guaiane sesquiterpenes from Perezia recurvata

Six guaiane sesquiterpenes recurvatiane A-F, including the previously known recurvatiane E and xanthomicrol, were isolated from the Andean Perezia recurvata and their structures determined by spectroscopic evidence. The absolute stereochemistry of recurvatiane A was established by derivatization with (R)- and (S)-α-methoxy-α-phenylacetic acids (MPA). The suite of guaiane-based metabolites here reported, which we have named recurvatianes A-F, provide an example of a pathway by which molecular diversity is generated by the occurrence of specific oxidation reactions in the late biosynthetic steps of the frame structure.     

Production,Isolation and Pharmacological Studies of AI-77s

Two potent gastroprotective substances against experimental gastric ulcers in rats induced by stress and five of their analogues were isolated from the culture broth of bacterial strain AI-77 which was classified taxonomically as Bacillus pumilus. Physico-chemical properties and pharmacological activities of the seven compounds were examined and compared with each other.     

Antifungal trichothecene sesquiterpenes obtained from the culture broth of marine-derived Trichoderma cf. brevicompactum and their structure-activity relationship

Two new trichothecene sesquiterpenes, trichobreols D (1) and E (2), were isolated from the culture broth of marine-derived Trichoderma cf. brevicompactum together with trichobreol A (3). The structures of 1 and 2 were assigned on the basis of their spectroscopic data. Compound 1 inhibited the growth of two yeast-like fungi, Candida albicans and Cryptococcus neoformans, with equivalent MIC values (6.3 μg/mL), while 2 gave MIC values of 12.5 and 25 μg/mL, respectively. The antifungal activities of five semisynthetic derivatives (4–8) prepared from 3 were evaluated and compared to investigate the preliminary structure-activity relationship.     

Repraesentins D,E and F,New Plant Growth Promoters from Lactarius repraesentaneus

Three new plant growth regulatory sesquiterpenes were isolated from the Lactarius repraesentaneus fungus. Their structures were elucidated to be lactarane sesquiterpenes, namely repraesentins D (1) and E (2), and a protoilludane-related sesquiterpene, namely repraesentin F (3). Repraesentin E (2) showed the strongest promotion activity, 164% at 3.6 μM, of the three compounds toward the radicle elongation of lettuce seedlings.     

The genus Laggera (Asteraceae) – Ethnobotanical and Ethnopharmacological Information,Chemical Composition as well as Biological Activities of Its Essential Oils and Extracts: A Review

Most species of the genus Laggera are often used in traditional and folk medicines for the treatment of jaundice, inflammation, leukemia, removing phlegm, bronchitis and bacterial diseases. The essential oils obtained from Laggera plants are rich sources of oxygenated monoterpenes and sesquiterpenes. Among oxygenated monoterpenes, aromatic ether 2,5‐dimethoxy‐p‐cymene is the most abundant and dominant compound of many essential oils of the Laggera species. Till today, to the best of our knowledge, chemical compounds of the essential oils and/or extracts of only eight Laggera species were reported from different countries. Thus, this review presents the chemical compositions and biological activities of the essential oils of these plants studied in thirteen countries. In addition, it discusses the reported ethnobotanical and ethnopharmacological information as well as biological activities of the extracts and some of the isolated compounds of Laggera plants species.