Pyrrololactam alkaloids with IL-6 inhibitory activities from the sponge Phakellia fusca collected in the South China Sea.

Sixteen undescribed pyrrololactam alkaloids, including five 2-bromopyrrole-ε-lactam (1a, 1b, 4a, 4b and 5), two 3-bromopyrrole-ε-lactam (9 and 10), eight pyrrole-ε-lactam (2a-3 and 6a-8), and one pyrrole-δ-lactam alkaloids (11), along with three previously reported compounds (12-14) were isolated from the marine sponge Phakellia fusca collected in the South China Sea. The planar structures were determined by NMR and MS analyses, while the absolute configurations were clearly elucidated by comparing the experimental and calculated ECD spectra. Compounds 2a, 2b, 4a-7b, 10, 12 and 13 exhibited anti-inflammatory activity in inhibiting the production of inflammatory cytokines IL-6 in LPS-induced RAW264.

Tagpyrrollins A and B and Tagpyrrollidone A: Three Pyrrole Steroid Analogues with AKR1B1-Targeting Inhibitory Activity from the Sponges and .

Pyrrole alkaloids (PAs) are a diverse class of natural products with complex carbon frameworks and broad bioactivities that are usually derived from marine sponges. and are two independent sponges collected from the South China Sea in 2013 and 2018, respectively. We discovered PAs are common constituents in both two sponges; more specifically, produces pyrrole-imidazole alkaloids, and contains pyrrolidone alkaloids.

Arenarialins A-F, Anti-inflammatory Meroterpenoids with Rearranged Skeletons from the Marine Sponge .

Six new sesquiterpene quinone/hydroquinone meroterpenoids, arenarialins A-F (-), were isolated from the marine sponge collected from the South China Sea. Their chemical structures and absolute configurations were determined by HRMS and NMR data analyses coupled with DP4+ and ECD calculations. Arenarialin A () features an unprecedented tetracyclic 6/6/5/6 carbon skeleton, whereas arenarialins B-D (-) possess two rare secomeroterpene scaffolds.

Dysambiol, an Anti-inflammatory Secomeroterpenoid from a sp. Marine Sponge.

An unusual secomeroterpenoid, dysambiol (), was isolated from a sp. marine sponge collected from the South China Sea. Dysambiol features an unprecedented secomeroterpene scaffold with a rare lactone bridge.

Aspergetherins A-D, New Chlorinated Biphenyls with anti-MRSA Activity from the Marine Sponge Symbiotic Fungus Aspergillus terreus 164018.

Aspergetherins A-D (1-4), four new chlorinated biphenyls, were isolated from the rice fermentation of a marine sponge symbiotic fungus Aspergillus terreus 164018, along with seven known biphenyl derivatives (5-11). The structures of four new compounds were determined by a comprehensive analysis of the spectroscopic data, including HR-ESI-MS and 2D NMR data. All 11 isolates were evaluated for their anti-bacterial activity against two strains of methicillin-resistant Staphylococcus aureus (MRSA).

A Series of New Pyrrole Alkaloids with ALR2 Inhibitory Activities from the Sponge .

Twelve new and four known alkaloids including five different structural scaffolds were isolated from the sponge collected in the South China Sea. Compound is the first identified precursor metabolite of the classic 5/7/5 tricyclic skeleton with unesterified guanidine and carboxyl groups, compounds - and - belong to the spongiacidin-type pyrrole imidazole alkaloids (PIAs). - and -configurations of the spongiacidin-type PIAs often appeared concomitantly and were distinguished by the chemical shift analysis of C NMR spectra.

New Spiro-Sesquiterpenoids from the Marine Sponge Myrmekioderma sp.

Three new spiro-sesquiterpenoids, myrmekiones A-C (1-3), were isolated from the marine sponge Myrmekioderma sp. collected from the South China Sea. The structures of 1-3 were experimentally illuminated though comprehensive NMR spectra, X-ray diffraction analysis and calculated ECD.

Guaiane sesquiterpenes from the gorgonian collected in the South China Sea.

Echinoflorine (1), a new dimethylamino-substituted guaipyridine alkaloid with a novel γ-lactone-cyclohepta[]pyridine fused skeleton, and three new guaiane sesquiterpene lactones, echinofloranolides A-C (2-4), together with eight known guaiane sesquiterpenes were isolated from the gorgonian collected in the South China Sea. Their structures were elucidated by 1D and 2D NMR, HRESIMS, calculated ECD and DP4+ probability analyses.

Dolabellane Diterpenes and Elemane Alkaloids from the Soft Coral Collected in the South China Sea.

Five new dolabellane diterpenes, clavularinlides A-E (-), and four new racemic elemane alkaloids, clavulacylides A-D (-), together with one known compound (), were isolated from the soft coral collected in the South China Sea. Their structures were elucidated by 1D and 2D NMR, HRESIMS, calculated ECD, and DP4+ probability analyses. Compounds - showed anti-inflammatory activity in the zebrafish assay.

Lemnalemnanes A-C, Three Rare Rearranged Sesquiterpenoids from the Soft Corals and sp.

Three novel sesquiterpenoids, lemnalemnanes A-C (-), were obtained from marine soft corals and sp. Their structures were determined by 1D/2D NMR spectroscopy, HRESIMS, single-crystal X-ray diffraction analysis (Cu Kα), Mosher's method, and ECD quantum chemistry calculations. Lemnalemnane A () possessed an intriguing basket-like structure with a spiro[bicyclo[3.

Cytotoxic Manoalide-Type Sesterterpenes from the Sponge Collected in the South China Sea.

Thirteen new linear terpenes, including 11 rare acyclic manoalide derivatives (-), one polyprenylphenol derivative (), and one polyprenylbenzaldehyde derivative (), together with three known compounds (-) were isolated from the sponge collected in the South China Sea. The planar structures were resolved by NMR and MS analyses, while the absolute configurations were fully elucidated by NOESY experiments, combined with experimental and calculated ECD spectra, acetal formation, empirical rules of H and C NMR shifts, DP4+ probability analyses, and Mosher's method. Compounds -, , and demonstrated cytotoxic activities against several human cancer cell lines with IC values ranging from 2 to 10 μM.

Lemnardosinanes A-I: New Bioactive Sesquiterpenoids from Soft Coral sp.

Two rearranged nardosinane sesquiterpenoids with novel carbon skeletons, lemnardosinanes A () and B (), and seven new nardosinane-related sesquiterpeniod lemnardosinanes C-I (), together with a known compound 6,7-seco-13-nornardosinan (), were isolated from the soft coral sp. collected from Xisha Islands of the South China Sea. Their structures were elucidated by comprehensive spectroscopic analyses, Mosher's method, Mo(OAc)-induced circular dichroism experiment, and quantum chemical calculations.

Isolation and Identification of Three New Sterigmatocystin Derivatives from the Fungus Aspergillus versicolor Guided by Molecular Networking Approach.

Molecular networking approach was applied for the targeted isolation of new sterigmatocystin derivatives, sterigmatocystins A-C, from the marine sponge-derived fungus Aspergillus versicolor. Sterigmatocystin A features a rare 6/6/6/6/5 polycyclic system. The structures of sterigmatocystins A-C, including absolute configurations, were determined on the basis of spectroscopic data and ECD calculations.

Clavukoellians G-K, New Nardosinane and Aristolane Sesquiterpenoids with Angiogenesis Promoting Activity from the Marine Soft Coral sp.

The chemical examination of the marine soft coral sp., collected at the Xisha islands in the South China Sea, resulted in the isolation of four new nardosinane-type sesquiterpenoids, namely clavukoellians G-J (-), and one new aristolane sesquiterpene, namely clavukoellian K (), together with five known compounds, -. The structure elucidation of the isolated natural products was based on various spectroscopic techniques including HRESIMS and NMR, while their absolute configurations were resolved on the basis of comparisons of the ECD spectra with the calculated ECD data.

Sesquiterpenoids from the soft coral sp.

Two new neolemnane-type sesquiterpenoids lemnolins A () and B (), together with one known tricyclic sesquiterpenoid () were isolated from the South China Sea soft coral sp. The structures were elucidated by comprehensive spectroscopic analysis and ECD analysis. Compound displayed antiviral activity against influenza A (H1N1) virus .

Bishomoscalarane Sesterterpenoids from the Sponge Collected in the South China Sea.

Granulosane A (), a new C bishomoscalarane sesterterpenoid with a rare 6/6/6/8 tetracyclic skeleton, together with eight additional new C bishomoscalarane sesterterpenes (, -) and five new C 20,24-bishomo-25-norscalarane sesterterpenes (-), were isolated from the marine sponge collected in the South China Sea. Their structures were elucidated by extensive spectroscopic analysis and quantum chemical calculation methods. Compound showed antiproliferative activities against two cancer cell lines.

Agelanemoechine, a Dimeric Bromopyrrole Alkaloid with a Pro-Angiogenic Effect from the South China Sea Sponge .

One new dimeric bromopyrrole alkaloid, agelanemoechine, with an unprecedented imidazo [1,5-] azepin nucleus together with one known dimeric bromopyrrole alkaloid sceptrin were isolated from the marine sponge . The structure elucidation and absolute configuration assignments were determined by extensive spectroscopic analyses and the comparison of experimental and calculated ECD. Agelanemoechine showed strong pro-angiogenic activity in zebrafish.

Cytotoxic sesquiterpenoid quinones from South China Sea sponge sp.

A new sesquiterpene, (+)-19-methylaminoavarone (), together with six known compounds (-), were isolated from the Xisha Islands marine sponge sp. The structures were elucidated based on their spectroscopic data. We revised the carbon spectrum data of the compound .

Terpenoids from the South China Sea soft coral .

A rare sinulariane-type norcembranoid sinulariadiolide B () with a unique cyano group, and a eunicellin-based diterpenoid multifloralin (), along with two known related analogues, sinulariadiolide () and sclerophytin E (), were isolated from the extract of the South China Sea soft coral . Their structures were elucidated on the basis of detailed spectroscopic analysis and by comparison with previously reported data. Compounds and showed potent antifouling activity against barnacle .

Combinational protective therapy for spinal cord injury medicated by sialic acid-driven and polyethylene glycol based micelles.

Spinal cord injury (SCI) leads to immediate disruption of neuronal membranes and loss of neurons, followed by extensive secondary injury process. Treatment of SCI still remains a tremendous challenge clinically. Minocycline could target comprehensive secondary injury via anti-inflammatory, anti-oxidant and anti-apoptotic mechanisms.

Clavukoellians A-F, Highly Rearranged Nardosinane Sesquiterpenoids with Antiangiogenic Activity from Clavularia koellikeri.

Six new nardosinane-type sesquiterpenoids, clavukoellians A-F (1-6), together with one new neolemnane-type sesquiterpene, 4- O-deacetylparalemnolin D (7), were isolated from the marine soft coral Clavularia koellikeri. The structures of compounds 1-7 were elucidated by NMR spectroscopy, ECD analysis, and quantum chemical calculation methods. Compounds 1 and 7 demonstrated significant antiangiogenic activities in wound healing assays on HUVECs.

Two new compounds from the marine sponge derived fungus .

Two new compounds ( and ) were isolated from the marine sponge derived fungus by using various column chromatography techniques. Their structures were elucidated by extensive analysis of spectroscopic data and quantum chemical calculation. Compound exhibited moderate activity against PTP1B with 2.

Aplysinopsin-type and Bromotyrosine-derived Alkaloids from the South China Sea Sponge Fascaplysinopsis reticulata.

Seven pairs of new oxygenated aplysinopsin-type enantiomers, (+)- and (-)-oxoaplysinopsins A‒G (1‒7), two new bromotyrosine-derived alkaloids, subereamollines C and D (18 and 19), together with ten known compounds (8‒17) were isolated from the Xisha Islands sponge Fascaplysinopsis reticulata. The planar structures were determined by extensive NMR and MS spectroscopic data. Each of the optically pure enantiomers was achieved by chiral HPLC separation.

Metabolites from the Paracel Islands Soft Coral cf. .

Five new oxygenated sesquiterpenes, molestins A⁻D (, ⁻) and -gibberodione (), three new cyclopentenone derivatives, -sinulolides C, D, and F ((+)-⁻(+)-), one new butenolide derivative, -sinulolide H ((+)-), and one new cembranolide, molestin E (), together with 14 known related metabolites (⁻, (⁻)-⁻(⁻)-, (±)-, (⁻)-, ⁻) were isolated from the Paracel Islands soft coral cf. . The structures and absolute configurations were elucidated based on comprehensive spectroscopic analyses, quantum chemical calculations, and comparison with the literature data.