A New Harziane Diterpene, Harziaketal A, and a New Sterol, Trichosterol A, from the Marine-Alga-Epiphytic Trichoderma sp. Z43.

One new diterpene, harziaketal A (1), and one new highly degraded sterol, trichosterol A (2), along with three known compounds, including one diterpene, harzianone (3), and two steroids, (22E,24R)-5α,6α-epoxy-ergosta-8(14),22-dien-3β,7α-diol (4) and isoergokonin B (5), were isolated from the culture of the marine-alga-epiphytic fungus Trichoderma sp. Z43 by silica gel column chromatography (CC), Sephadex LH-20 CC, and preparative thin-layer chromatography (TLC). Their structures and relative configurations were assigned by nuclear magnetic resonance (NMR) and high resolution electrospray ionisation mass spectrometry (HR-ESI-MS) data, and the absolute configuration of 1 was established by X-ray diffraction.

Trichoderols B-G, Six New Lipids from the Marine Algicolous Fungus sp. Z43.

Six new lipids, trichoderols B-G (-), along with a known one, triharzianin B (), were isolated from the culture of sp. Z43 obtained from the surface of the marine brown alga . Their structures and relative configurations were identified by interpretation of 1D/2D NMR and MS data.

Myrochromanol analogues and trichothecene derivatives from the shellfish-derived fungus Albifimbriaverrucaria.

Eight myrochromanol analogues, including three pairs of epimers at C-2 with the myrochromanol scaffold and two examples of myrochromanol with sugar moiety linked at C-4, together with twelve trichothecene derivatives were isolated from the cultures of a shellfish-derived fungus Albifimbria verrucaria CD1-4. Among them, eight compounds named 2-epi-myrochromanol, ent-myrochromanol B, 4-epi-myrochromanol B, 2-epi-myrochromanol A, myrochromanosides A and B, 6',7'-erythro-(2'E,4'Z)-trichoverrol B, 3R,8S-dihyroxyroridin H were previously undescribed fungal metabolites. Their planar structures and relative configurations were established by 1D and 2D NMR, and HR-MS data analysis, and their absolute configurations were determined using the modified Mosher's method and electronic circular dichrosim calculations.

A new lanostane-type triterpenoid from the marine shellfish symbiotic fungus CD7-5.

One new lanostane-type triterpenoid, 3-acetoxy-7,11-dioxolanosta-8,24-dien-21-oic acid (), together with six known analogues (-), were isolated from the cultures of a marine fungus CD7-5, which was derived from the shellfish . Their structures were determined by detailed analysis of spectroscopic data and comparison with the literature reported. The biological activities of these lanostane triterpenoids against marine-derived microalgae, zooplankton, and pathogenic bacteria were also evaluated in this study.

Serum α-Klotho associated with oral health among a nationally representative sample of US adults.

Background: Low klotho is associated with aging-related traits. However, no study has assessed the association between klotho and oral health in a large sample of population. This study aimed to explore the association between serum α-klotho and oral health in US Adults.

Antimicrobial Terpenoids and Polyketides from the Algicolous Fungus RR-dl-2-13.

Four new carotane sesquiterpenoids, byssocarotins A-D (-), two new nor-sesquiterpenoids, byssofarnesin () and byssosesquicarin (), and three new polyketides, byssoketides A and B ( and ) and (8)-paecilocin A (), were obtained from a macroalga-associated strain (RR-dl-2-13) of the fungus . These isolates were identified by a combination of spectroscopic methods, including mass spectroscopy, nuclear magnetic resonance, electronic circular dichroism, and X-ray diffraction. Compounds - greatly contribute to the diversity of rarely occurring 2,15-epoxycarotane sesquiterpenoids, while and are degradation products of farnesane and sesquicarane precursors, respectively.

Cyclopentenone and wickerol derivatives from the marine algicolous fungus A-YMD-9-4.

A new cyclopentenone derivative, 4-hydroxyhypocrenone A, and a new naturally-occurring wickerol derivative, 8-acetoxywickerol A, as well as two known compounds, hypocrenone A and wickerol B, were purified from A-YMD-9-4, an endophytic fungus isolated from the marine red alga . The structures and relative configurations of two new isolates were established by a combination of 1 D/2D NMR, IR, and mass spectroscopic methods, and the absolute configuration of was assigned on the basis of ECD data analyzed by quantum chemical calculations. Compounds and exhibited weak inhibition of one or two marine phytoplankton species.

Sesquiterpenoids and a steroid from the algicolous Trichoderma brevicompactum.

Six new sesquiterpenoids including three bisabolane derivatives, trichobisabolins O, O, and P (1-3), two nerolidol derivatives, trichonerolins A and B (4 and 5), one acorane, trichoacorin A (6), along with one new steroid, isoergokonin B (7), were isolated from the culture of Trichoderma brevicompactum A-DL-9-2 obtained from the inner tissue of the red alga Chondria tenuissima. Their structures and relative configurations were assigned by interpretation of 1D/2D NMR and MS data. As acyclic sesquiterpenoids, compounds 4 and 5 were discovered from Trichoderma for the first time.

Terpenoids from the Marine-Derived Fungus sp. RR-YLW-12, Associated with the Red Alga .

Two new meroterpenoids, aspermeroterpenes D and E ( and ), two new ophiobolin-type sesterterpenoids, the C-18 epimers of 18,19-dihydro-18-methoxy-19-hydroxyophiobolin P ( and ), and two new drimane-type sesquiterpenoids, 3-hydroxystrobilactone A () and 6--strobilactone A (), along with 11 known terpenoids (- and -) were isolated from the cultures of the algicolous fungus sp. RR-YLW-12, derived from the red alga . The structures and relative configurations of new compounds were established by detailed spectroscopic analysis of NMR and HRMS experiments, and the absolute configurations were assigned by X-ray diffraction experiments and comparison of their experimental and calculated ECD spectra.

Antimicrobial bisabolane-type sesquiterpenoids from the deep-sea sediment-derived fungus SD-330.

One new aromatic bisabolene-type sesquiterpenoid (), along with four known analogues () were isolated and identified from the deep-sea sediment-derived fungus SD-330. Their structures were elucidated by NMR, HRESIMS, X-ray crystallographic analysis, and quantum chemical ECD calculations as well as comparison of those data with literature data. Compounds were evaluated for antimicrobial activities against human and aquatic pathogenic bacteria.

Antimicrobial Sesquiterpenoid Derivatives and Monoterpenoids from the Deep-Sea Sediment-Derived Fungus SD-330.

Two new antimicrobial bisabolane-type sesquiterpenoid derivatives, -aspergoterpenin C (compound ) and 7--methylhydroxysydonic acid (), and two new butyrolactone-type monoterpenoids, pestalotiolactones C () and D (), along with a known monoterpenoid pestalotiolactone A () and four known bisabolane sesquiterpenoids (-), were isolated and identified from the deep-sea sediment-derived fungus SD-330. The structures of these compounds were elucidated on the basis of spectroscopic analysis, and the absolute configurations of the new compounds - were determined by the combination of NOESY and TDDFT-ECD calculations and X-ray crystallographic analysis. Additionally, we first determined and reported the absolute configuration of the known monoterpenoid pestalotiolactone A () through the X-ray crystallographic experiment.

Seven chromanoid norbisabolane derivatives from the marine-alga-endophytic fungus Trichoderma asperellum A-YMD-9-2.

An examination of the endophytic fungus Trichoderma asperellum A-YMD-9-2 obtained from the marine red alga Gracilaria verrucosa led to the isolation of seven new chromanoid norbisabolane derivatives, trichobisabolins I-L (1-4) and trichaspsides C-E (5-7). Their structures and relative configurations were established on the basis of spectroscopic techniques, mainly including 1D/2D NMR and MS, and the absolute configuration of 1 was assigned by X-ray crystallographic analysis using Cu Kα radiation. All of these isolates feature a 1,9-epoxy ring system, and 5-7 represent the second occurrence of norbisabolane aminoglycosides.

Cyclonerane Derivatives from the Algicolous Endophytic Fungus A-YMD-9-2.

Seven previously unreported cyclonerane derivatives, namely, 3,7,11-trihydroxycycloneran-10-one, cycloneran-3,7,10,11-tetraol, cycloneran-3,7,11-triol, 11,12,15-trinorcycloneran-3,7,10-triol, 7,10-epoxycycloneran-3,15-diol, 7,10-epoxycycloneran-3,15-diol, and (10)-15-acetoxy-10-cycloneren-3,7-diol, were isolated in addition to the known (10)-cyclonerotriol, (10)-cyclonerotriol, catenioblin C, and chokol E from the culture of A-YMD-9-2, an endophytic fungus obtained from the marine red alga . The structures of previously unreported compounds were established by spectroscopic techniques, including 1D/2D NMR, MS, and IR. The isolation of these new cyclonerane derivatives greatly adds to the structural diversity of unusual cyclonerane sesquiterpenes, and several isolates exhibit potent inhibition against some marine phytoplankton species.

Trichobisabolins A-H, eight new bisabolane derivatives from the marine-alga-epiphytic fungus Trichoderma asperellum Y6-2.

Eight new bisabolane derivatives, trichobisabolins A-H, along with two known ones, (3R,6R,7R)-1,10-bisaboladien-3-ol (9) and (3R,6R,7S)-1,10-bisaboladien-3,6-diol (10) were isolated from the culture of Trichoderma asperellum Y6-2, obtained from the surface of the marine red alga Chondrus ocellatus. Their structures and relative configurations were identified by interpretation of 1D/2D NMR and MS data. Compounds 1-8 were assayed for inhibiting the growth of some marine-derived organisms, including four marine phytoplankton species, one marine zooplankton species, and five pathogenic bacteria.

Two new sesquiterpenoids from the marine-sediment-derived fungus P1-4.

Three cyclonerane sesquiterpenoids, including the known cyclonerodiol (), together with its new derivatives, (10)-12-acetoxy-10-cycloneren-3,7 -diol () and 12-acetoxycycloneran-3,7-diol () were isolated from the cultures of marine-sediment-derived fungus P1-4. The structures of the new compounds ( and ) were elucidated based on extensive spectroscopic methods (1D/2D NMR and HR-MS) and optical rotation analysis.

Diterpenes and Sesquiterpenes from the Marine Algicolous Fungus Trichoderma harzianum X-5.

Six new terpenes, including one harziane diterpene, 3 R-hydroxy-9 R,10 R-dihydroharzianone (1), one proharziane diterpene, 11 R-methoxy-5,9,13-proharzitrien-3-ol (2), three cyclonerane sesquiterpenes, 11-methoxy-9-cycloneren-3,7-diol (3), 10-cycloneren-3,5,7-triol (4), and methyl 3,7-dihydroxy-15-cycloneranate (5), and one acorane sesquiterpene, 8-acoren-3,11-diol (6), were isolated from the culture of Trichoderma harzianum X-5, an endophytic fungus obtained from the marine brown alga Laminaria japonica. Their structures and relative configurations were established by analysis of 1D/2D NMR, HREIMS, and IR data, and the absolute configurations were assigned on the basis of ECD curves or biogenetic considerations. These terpenes possess four different carbon skeletons, and compound 2, with a rarely occurring bicyclic framework, represents a possible precursor of tetracyclic harzianes.

Tricholumin A, a Highly Transformed Ergosterol Derivative from the Alga-Endophytic Fungus Trichoderma asperellum.

Tricholumin A (1) with an unprecedented carbon skeleton was isolated from the fungus Trichoderma asperellum cf44-2, an endophyte from the marine brown alga Sargassum sp. Its structure and relative configuration were identified by extensive 1D/2D NMR and mass spectrometric data, and the absolute configuration was assigned by X-ray diffraction and ECD calculations. Compound 1 represents a highly transformed ergosterol derivative, and it exhibited inhibition of some pathogenic microbes and marine phytoplankton species.

Trichocarotins A-H and trichocadinin A, nine sesquiterpenes from the marine-alga-epiphytic fungus Trichoderma virens.

In addition to CAF-603, 14-hydroxy CAF-603 (trichocarane B), 7-β-hydroxy CAF-603, and trichocarane A, eight new carotane sesquiterpenes, trichocarotins A-H, and one new cadinane sesquiterpene, trichocadinin A, were isolated from the culture of Trichoderma virens Y13-3, obtained from the surface of a marine red alga. Their structures and relative configurations were unambiguously assigned by interpretation of 1D/2D NMR and MS data, and their absolute configurations were established by X-ray diffraction or ECD spectra aided by quantum chemical calculations. These compounds represent two rarely occurring sesquiterpene types from filamentous fungi, and six of them feature potent inhibition against some marine plankton species.

Halogenated and Nonhalogenated Metabolites from the Marine-Alga-Endophytic Fungus cf44-2.

One new bisabolane sesquiterpene, bisabolan-1,10,11-triol (), one new norbisabolane sesquiterpene, 12-nor-11-acetoxybisabolen-3,6,7-triol (), two new naturally occurring monoterpenes, (7)- and (7)-1-hydroxy-3--menthen-9-oic acids ( and ), one new naturally occurring trichodenone, dechlorotrichodenone C (), one new chlorine-containing trichodenone, 3-hydroxytrichodenone C (), one new diketopiperazine, methylcordysinin A (), and one new naturally occurring oxazole derivative, 4-oxazolepropanoic acid (), were isolated from the culture of a marine brown alga-endophytic strain (cf44-2) of . Their structures and relative configurations were determined by extensive 1D/2D NMR and mass spectrometric data, and the absolute configurations of ⁻ were assigned by analysis of the ECD spectra aided by quantum chemical computations. Compounds , , , and showed growth inhibition of some marine phytoplankton species and pathogenic bacteria.

Trichorenins A-C, Algicidal Tetracyclic Metabolites from the Marine-Alga-Epiphytic Fungus Trichoderma virens Y13-3.

Three novel polyketide-like metabolites, trichorenins A-C (1-3), with a unique tetracyclic carbon skeleton were obtained from the culture of Trichoderma virens Y13-3, an epiphyte of the marine red alga Gracilaria vermiculophylla. Their structures and relative configurations were established by analysis of 1D/2D NMR and MS data, and their absolute configurations were unequivocally assigned by X-ray diffraction and ECD spectra aided by quantum chemical calculations. Compounds 1-3 exhibited potent inhibition against two marine phytoplankton species, Chattonella marina and Karlodinium veneficum.

Sesteralterin and Tricycloalterfurenes A-D: Terpenes with Rarely Occurring Frameworks from the Marine-Alga-Epiphytic Fungus Alternaria alternata k21-1.

A new sesterterpene, sesteralterin (1), four new meroterpenes, tricycloalterfurenes A-D (2-5), and a known meroterpene, TCA-F (6), were obtained from the culture extract of an Alternaria alternata strain (k21-1) isolated from the surface of the marine red alga Lomentaria hakodatensis. The structures and relative/absolute configurations of these compounds were identified by spectroscopic analyses, mainly including 1D/2D NMR, ECD, and mass spectra and quantum chemical calculations. Compound 1 represents the first nitidasane sesterterpene naturally produced by fungi, and 2-5 feature a tetrahydrofuran unit rarely occurring in tricycloalternarenes.

Effects of chemical form of sodium on the product characteristics of alkali lignin pyrolysis.

The effects of Na as organic bound form or as inorganic salts form on the pyrolysis products characteristics of alkali lignin were investigated by using thermogravimetric analyzer coupled with Fourier transform infrared spectrometry (TG-FTIR), tube furnace and thermo-gravimetric analyzer (TGA). Results of TG-FTIR and tube furnace indicated that the two chemical forms Na reduced the releasing peak temperature of CO and phenols leading to the peak temperature of the maximum mass loss rate shifted to low temperature zone. Furthermore, organic bound Na obviously improved the elimination of alkyl substituent leading to the yields of phenol and guaiacol increased, while inorganic Na increased the elimination of phenolic hydroxyl groups promoting the formation of ethers.

Three new xanthone derivatives from an algicolous isolate of Aspergillus wentii.

Three new xanthone derivatives, yicathin A (1), yicathin B (2), and yicathin C (3), and three known anthraquinone derivatives, alatinone (4), 1,5-dihydroxy-3-methoxy-7-methylanthraquinone (5), and 5-hydroxy-1,3-dimethoxy-7-methylanthraquinone (6), were isolated from the cultures of Aspergillus wentii pt-1, an endophytic fungus isolated from the marine red alga Gymnogongrus flabelliformis. Their structures were unambiguously elucidated by NMR and mass spectroscopic methods as well as quantum chemical calculations. Compound 2 was active against Escherichia coli, and 3 could inhibit E.