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Eleven undescribed cembrane-type diterpenoids, named litoamentenes A-K (1-11), were isolated from the soft coral Litophyton amentaceum collected from the South China Sea. Their structures were elucidated by extensive analysis of spectroscopic data, comparison with the literature data, single crystal X-ray diffraction, quantum chemical calculations and TDDFT-ECD calculations. This is the first systematic investigation of L. amentaceum. In particular, compounds 1-3 are cembrane-type norditerpenoids that lack isopropyl side chains. Compound 6 is a cembrane-type norditerpenoid without a methyl group at C-4, the first natural product identified with this carbon skeleton. Compounds 6, 9 and 10 showed modest cytotoxicity against several human cancer cell lines with IC 50 values ranging from 3.99 to 14.56 μM., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier Ltd. All rights reserved.)

The angucylines are a family of aromatic polyketides featuring a tetracyclic benz[a]anthraquinone skeleton. This class of polycyclic aromatic polyketides are exclusively associated with actinomycetes and can undergo many modifications such as oxidation, ring cleavage, glycosylation and dimerization. Here we report the discovery of a new ether-linked benz[a]anthraquinone heterodimer, named mycolatone (1), from a grasshopper-derived actinomycete, Amycolatopsis sp. HCa1. The structure of mycolatone (1) was determined by comprehensive two-dimensional NMR analysis, high-resolution electrospray ionization mass spectrometry and biogenetic consideration. This new heterodimeric molecule is structurally derived from the dimerization of two tetracyclic angucylines, 2-hydroxy-5-O-methyltetragomycin and PD116779, through an ether bond between C-8 and C-8'. This new structural feature enrich the structural diversity of angucylines. Additionally, the surface tension activity and cytotoxic activities of 1 against human cervical cancer cell line (Hela), human gastric adenocarcinoma cell line (SGC-7901) and human lung adenocarcinoma cell line (SPC-A-1) were evaluated., (Copyright © 2021 Elsevier B.V. All rights reserved.)

Eight new complex flavanones with a novel linkage, cryptoyunnanones A-H ( 1 - 8 ), together with four known α-pyrones, were isolated from the leaves and twigs of Cryptocarya yunnanensis . The structures of 1 - 8 including their absolute configurations were characterized by spectroscopic data analysis and single-crystal X-ray crystallography. Plausible biosynthetic pathways for the formation of compounds 1 - 8 were proposed. Compounds 1 - 4 exhibited cytotoxicity against HCT-116, MDA-MB-231, and PC-3 cancer cells with IC 50 values from 6.4 to 9.1 μM.

Twelve new [11]-chaetoglobosins, chaetopseudeurins A-L ( 1 - 12 ), were identified from the fermentation of the endophytic fungus Pseudeurotium bakeri P1-1-1. Their structures with absolute configurations were elucidated by detailed interpretation of NMR spectroscopy, mass spectrometry, and single-crystal X-ray diffraction. Compounds 2 and 5 - 7 exhibited significant cytotoxicities against seven human cancer cell lines, with IC 50 values ranging from 4.7 ± 1.0 to 12.2 ± 0.7 μM, and induced G2/M cell cycle arrest and apoptosis in MCF-7 and A427 cells dose dependently. Western blot analysis showed that compound 2 induced apoptosis of MCF-7 cells via the Bcl-2/caspase-3/PARP pathway.

Chemical investigation on the solid rice culture of Chaetomium globosum D38, an endophytic fungus derived from Salvia miltiorrhiza, has afforded two new 19,20-seco-chaetoglobosins, salchaetoglobosins A (1) and B (2), along with three known analogues, chaetoglobosins E (3), Fex (4), and V b (5). Their structures and absolute configurations were elucidated by a set of spectroscopy and single-crystal X-ray crystallography. Compounds 1-5 were evaluated for their cytotoxic activities against HCT-116 (colorectal carcinoma) and PC3 (prostate cancer) cells, as well as the NO production inhibitory effects in LPS-stimulated RAW264.7 cells., (Copyright © 2021. Published by Elsevier B.V.)

Six rocaglaol derivatives were isolated from Dysoxylum gotadhora, and those compounds showed good cytotoxic activity with IC 50 values ranging from 10 to 350 ng/mL against five different cancer cells. Obviously, further total synthesis of rocaglaol derivatives for medical chemistry study is of great significance. Then, twenty six rocaglaol derivatives including 25 new compounds were designed, synthesized, and evaluated for their cytotoxic activities against three human cancer cell lines: human colon cancer cells (HCT116), colorectal cancer stem cells (P6C), and human red leukocyte leukemia cells (HEL), using MTT assay. Most of derivatives showed good cytotoxic activities, with the lowest IC 50 being 3.2 nM for HEL cells, which was 169 times stronger than that of the positive control (doxorubicin). Further mechanism study indicated that 11k could significantly suppress MAPK pathway in HCT116 cells, which may responsible for induction of apoptosis and cell cycle arrest., (Copyright © 2021. Published by Elsevier B.V.)

Two new 1,3-benzodioxole derivatives, leucandioxoles A and B ( 1 - 2 ), together with two known related compounds ( 3 - 4 ), have been isolated from the South China Sea sponge Leucandra sp. The structures of all compounds were clearly elucidated on the basis of spectroscopic analyses and compared with the literatures. The cytotoxicity against A549, Hep G2, MDA-MB-231, and HeLa cell lines of 1 - 4 were evaluated. Only compound 1 exhibited moderate activity against MDA-MB-231 cells with the IC 50 value of 7.98 ± 0.74  μ M.

Six julichrome derivatives including a new monomeric julichrome named as julichrome Q 10 ( 1 ), and previous reported julichrome Q 6 ( 2 ), julichrome Q 6.6 ( 4 ), julichrome Q 3.5 ( 5 ), julichrome Q 5.6 ( 6 ), julichrome Q 2.3 ( 7 ), along with a diketopiperazine gliotoxin ( 3 ) were isolated from a soil derived strain Streptomyces sp. The structures of these compounds were identified by HR-ESI-MS, UV, IR and NMR methods. The isolated compounds were tested for their in vitro cytotoxicity against human hepatocarcinoma HepG-2 and SMMC-7721 cell lines, human breast cancer MCF-7 and MDA-MB-231 cell lines, and human normal heptical LO2 cell line. Gliotoxin ( 3 ) showed the most cytotoxic activity against the tested tumor cell lines, with IC 50 values ranging from 0.11 to 1.45 μM. Julichrome Q 6.6 ( 4 ) displayed selective cytotoxic activity against SMMC-7721, MCF-7 and MDA-MB-231 cell lines.

Phytochemical investigation on the nonpolar extracts of P. acidus leaves afforded three new cleistanthane diterpenoids, named phyllanacidins A-C (1-3), in addition to three known ones (4-6). Among them, compounds 2 and 3 represent the first examples of 17-nor cleistanthane diterpenoids. Their structures including absolute configurations were elucidated on the basis of extensive spectroscopic data and single crystal X-ray diffraction analysis. All the isolated cleistanthane diterpenoids were evaluated for their cytotoxic activities against five human cancer cell lines. Compounds 4-6 exhibited moderate cytotoxicity with IC 50 values ranging from 16.11 to 30.82 μM., (Copyright © 2020 Elsevier B.V. All rights reserved.)

Three new mycophenolic acid derivatives, penicacids E-G (1-3), together with three known analogues, mycophenolic acid (4), 4'-hydroxy-mycophenolic acid (5) and mycophenolic methyl ester (6), were isolated from a marine-derived fungus Penicillium parvum HDN17-478 from a South China Sea marine sediment sample. The structures of compounds 1-3 were elucidated by HRMS, NMR, and Mosher's method. Among them, compounds 1 and 2 were the first examples of mycophenolic acid analogs with a double bond at C-3'/C-4' position. The cytotoxicity of 1-6 was evaluated against the HCT-116, BEL-7402, MGC-803, SH-SY5Y, HO-8910 and HL-60 cell lines, and compounds 4 and 6 showed potent cytotoxicity with IC 50 values ranging from 1.69 to 12.98 μmol·L -1 ., (Copyright © 2020 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.)

Two new polyoxygenated cyclohexenes (1-2), one new benzoate derivative (3), and one new dineolignan (4) together with one known neolignan (5) were isolated from whole plants of Piper pleiocarpum. The structures of these compounds were determined by extensive spectroscopic methods including 1D, 2D NMR, HR-ESI-MS, and by comparison with the literature. The 13 C NMR spectra of the known compound 5 were completely assigned for the first time. All isolated compounds (1-5) were evaluated for their cytotoxic activities against five human cancer cell lines (including A-549, SMMC-7721, HL-60, MCF-7, and SW-480), Only compound 4 showed inhibitory activity against MCF-7 cell line with IC 50 value of 18.24 ± 0.69 μM., (Copyright © 2020 Elsevier B.V. All rights reserved.)

Two new hydroperoxy steroids, namely, xidaosteroids A and B (1 and 2), along with five known related compounds 3-7, were isolated from the South China Sea gorgonian Rumphella sp.. Their structures were established by extensive spectroscopic analyses and comparison of the spectral data with those reported in the literature. In bioassay, compound 3 showed weak cytotoxicities against SNU-398 and Capan-1 cells., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2019 Elsevier Inc. All rights reserved.)

Four new alkaloids, melodinines W 1 -W 4 (1-4), together with twenty one known alkaloids (5-25) were isolated from Melodinus henryi. The structures with absolute configurations were elucidated by extensive MS and NMR spectroscopic methods, as well as the single crystal X-ray diffraction and ECD calculations. All compounds were evaluated for their cytotoxicities to five human cancer cell lines. Many compounds showed certain cytotoxicities to five human cancer cell lines with an IC 50 range of 1.4-29.4 μM., (Copyright © 2019 Elsevier B.V. All rights reserved.)

A new benzylated alkamide, N -(3,4-dimethoxybenzyl)-9 Z -oleamide ( 1 ), along with two known ones ( 2 and 3 ) were isolated from the roots of Lepidium meyenii collected from Lijiang, Yunnan Province of China. Their structures were elucidated by extensive spectroscopic analyses and the new compound further confirmed by a one-step synthesis. All the isolated alkamides were evaluated for their cytotoxicity against five human cancer cell lines. However, no significant activities were detected at concentrations up to 40  μ M.

Three newly isolated ergosterols, psathergosterols A-C (1-3), together with two known ones (4 and 5), have been isolated from cultures of the basdiomycete Psathyrella candolleana. Their structures with the absolute configuration were elucidated by means of spectroscopic methods and the single crystal X-ray diffraction. Compounds 2-4 exhibited certain cytotoxicities to five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, SW480)., (Copyright © 2019 Elsevier B.V. All rights reserved.)

Five new monoterpenoid indole alkaloids, melotenuines A-E (1-5), along with 18 known indole alkaloids, were isolated from the twigs and leaves of Melodinus tenuicaudatus. The structures of the new alkaloids were determined by a combination of MS, NMR and ECD analysis. Melotenuine A (1) represents the first example of aspidosperma-meloscandonine type bisindole alkaloids characterized by a methylene bridge between the two monomers, while melotenuine B (2) possessed a rare eburnamine-melsocandonine skeleton. All of the new indole alkaloids were evaluated for in vitro cytotoxicities against five human cancer cell lines. Among them, alkaloid 4 showed specific cytotoxicity against HL-60 cell line with IC 50 value (5.15 ± 0.16 μM) comparable with that of positive control., (Copyright © 2019 Elsevier B.V. All rights reserved.)

Chemical investigation on CH 2 Cl 2 extract of the marine sponge Leucetta chagosensis , collected from the South China Sea, afforded two new 5,6-epoxysterols, 5α,6α-epoxycholesta-8(14),22( E )-diene-3 β ,7 α -diol ( 1 ) and (24 R )-24-ethyl-5α,6α-epoxycholesta-8(14),22( E )-diene-3 β ,7 α -diol ( 2 ) along with ten known related steroid analogs ( 3 - 12 ). Their structures were elucidated on the basis of NMR spectroscopic analyses, and comparison with the literature. All isolates were tested for cytotoxicity against three tumor cell lines only known compounds 11 and 12 exhibited notable cytotoxic activity against A549 (IC 50 : 3.0 and 5.6 μM), PC9 (2.0 and 15.6 μM), and MCF-7 (9.4 and 11.8 μM) cell lines, respectively.

A new bisindole alkaloid, melosuavine I (1) possessing an aspidosperma-aspidosperma dimeric skeleton, was isolated from the leaves of Melodinus suaveolens. The structure with absolute configuration of 1 was elucidated by a combination of MS, NMR and computational methods. MTT assays indicated that 1 exhibited significant cytotoxicity on human breast cancer BT549 cells with an IC 50 value of 0.89 μM. Further study showed that 1 inhibited BT549 cell proliferation by inducing apoptosis through activation of caspase 3 and p53, and down-regulation of Bcl-2., (Copyright © 2019 Elsevier B.V. All rights reserved.)

Four new polyhydroxylated steroids lobophysterols A-D (1-4), together with two known related compounds sarcophytosterol (5) and klyflaccisteroid B (6), were isolated from the South China Sea soft coral Lobophytum sp. Their structures were elucidated on the basis of spectroscopic analysis and by comparison with those reported in the literature. In bioassay, compound 4 showed weak cytotoxicities against HT-29, SNU-398, and Capan-1 cells., (Copyright © 2018 Elsevier Inc. All rights reserved.)

Four new diterpenoids scapanacins A-D (1-4) including one kaurane and three clerodane derivatives, along with eleven known compounds (9-15), were isolated from the Chinese liverwort Scapania carinthiaca J.B. Jack ex Lindb. Their structures were determined based on extensive spectroscopic analyses, and electronic circular dichroism (ECD) calculations. Vasorelaxant activity assays of the clerodane-type diterpenoids 2, and 4-8 revealed that they relaxed 3 rd -order rat mesenteric arterioles pre-contracted with norepinephrine (NE). Further assays with scapanacin D (4) confirmed that the vasodilatation was mediated through inhibition of Ca 2+ influx via voltage-dependent Ca 2+ channels (VDCs), and this Ca 2+ channel blocking effect was also confirmed by inhibiting the extracellular Ca 2+ influx in MOVAS cells. Besides, very little decrease of the relaxant activity caused by 4 on endothelium-denuded mesenteric arterioles with NE also suggested the vasodilatation was mainly produced by inhibiting Ca 2+ -induced contraction of smooth muscle. In addition, cytotoxicity testing showed that compounds 1 and 9 with α,β-unsaturated ketone exhibited inhibitory activities against a small panel of human cancer cell lines., (Copyright © 2018 Elsevier Ltd. All rights reserved.)

Phytochemical investigation on the stems of Schisandra glaucescens resulted into the isolation of three new lanostane triterpenoids, 12-hydroxyschiglausin B (1), 12-hydroxykadsuphilactone B (2), and 20R-hydroxyschinalactone C (3). Structural elucidation of all the compounds was accomplished by spectral methods. The isolated compounds were tested in vitro for cytotoxic activities. As a result, triterpenoids 1 and 2 showed cytotoxic activities for all six tested tumor cell lines with IC 50 values less than 15 μM.

A new diphenyl ether (1) as well as 20 other compounds were identified from the fermentative extracts of marine-derived fungi Phoma sp. CZD-F11 (Compounds 1-8) and Aspergillus sp. CZD-F18(Compounds 9-21). Their structures were elucidated on the basis of extensive spectroscopic analysis. The broth extracts of the fungi exhibited very good anticancer activity against H1975 cells with 5.62 and 25.8% viability at concentration of 10 μg/mL for Phoma sp. CZD-F11 and Aspergillus sp. CZD-F18, respectively. The inhibitory activity of all compounds against PC-3 cell lines, BRD4 and aromatase were evaluated. The results showed compound 7 exhibited moderate anticancer activity with 66.1% inhibition against PC-3 cell lines at the concentration of 10 μg/mL. Compound 7 and 8 exhibited favourable BRD4 inhibitory activity with 78.5 and 76.4% inhibition at the concentration of 10 μg/mL.

Water-soluble polysaccharides from Umbilicaria tornata (UTP) were purified and preliminarily characterized. The antioxidant and antitumor activities of crude UTP and two purified fractions (UTP-1 and UTP-2) were evaluated using in vitro experiments. The results showed that the molecular weights of UTP-1 and UTP-2 were 84.86 and 28.66 kDa, respectively. Both UTP-1 and UTP-2 were composed of glucose and xylose, with their molar ratios being 1.3:0.9 and 0.9:4.6, respectively. In addition, crude UTP, UTP-1 and UTP-2 showed dose-dependent DPPH and hydroxyl radical scavenging and reducing activities. However, crude UTP exhibited stronger antioxidant activity than UTP-1 and UTP-2, particularly in terms of DPPH radicals. Crude UTP and the two purified fractions inhibited the growth of HeLa, HepG2, A375, MCF-7, SGC7901 and Caco2 cancer cells in vitro. Compared with UTP-1 and UTP-2, crude UTP presented significantly higher antitumor activity in vitro against HeLa and HepG2 cells (p < 0.05). These findings provide a scientific basis for the deeper exploration and resource development of U. tornata.

Three new drimane sesquiterpenoids, 12-hydroxyalbrassitriol (1), drim-8(12)-en-6β,7α, 9α,11-tetraol (2), and drim-68(12)-dien-9α,11-diol (3), along with one known analog albrassitriol (4), were isolated from cultures of the tin mine tailings-associated fungus Penicillium sp. The new structures were determined on the basis of extensive spectroscopic analyses. All compounds were tested for their cytotoxicities against five human cancer cell lines.

The new heterodimeric botryane ethers hypocriols A-F (1-6) and the known compounds 4β-acetoxy-9β,10β,15α-trihydroxyprobotrydial (7), dihydrobotrydial (8), 10-oxodehydrodihydrobotrydial (9), and dehydrobotrydienol (10) were isolated from the solid cultures of an insect-associated fungus Hypocrea sp. The structures of 1-6 were elucidated primarily by NMR experiments. The absolute configuration of 1 was assigned using the modified Mosher method and electronic circular dichroism (ECD) calculations, whereas those for 3-5, and 2 and 6 were deduced via ECD calculations and circular dichroism data, respectively. Compounds 1-6 appear to be the first heterodimeric botryane ethers and showed antiproliferative effects against a small panel of four human tumor cell lines.

Oryzaeins A-D (1-4), four new isocoumarin derivatives, along with five known ones (5-9) were isolated from solid cultures of an endophytic fungus Aspergillus oryzae. Their structures were elucidated by detailed spectroscopic analysis and by comparison with reported data of related derivatives. Among them, compounds 1 and 2 represent the first examples of isocoumarins possessing an unusual 2-oxopropyl group and a rare 3-hydroxypropyl group. Compounds 1 and 2 displayed moderate anti-tobacco mosaic virus activities with inhibition rates of 28.4% and 30.6%, respectively, at the concentration of 20 µM. The new compounds showed moderate inhibitory activities against several human tumor cell lines with IC50 values in the range of 2.8-8.8 µM. Supporting information available online at http://www.thieme-connect.de/products., (Georg Thieme Verlag KG Stuttgart · New York.)

Four new Amaryllidaceae alkaloids, named lycoranines C-F (1-4), together with seven known ones (5-11) were isolated from the bulbs of Lycoris radiata. Their structures with absolute configurations were elucidated by nuclear magnetic resonance, high-resolution electrospray ionization mass spectrometry, circular dichroism spectra, modified Mosher's method, and molecular modeling calculation. Compounds 6, 7, 10, and 11 exhibited a potent inhibitory effect on A549 and LoVo cells with IC50 values ranging from 3.97 ± 0.36 to 17.37 ± 1.57 µM., (Georg Thieme Verlag KG Stuttgart · New York.)

A pair of novel bisheterocyclic quinoline-imidazole alkaloids, (+)- and (-)-spiroreticulatine (1), were isolated from the South China Sea sponge Fascaplysinopsis reticulata. The structures and absolute configurations were elucidated by comprehensive spectroscopic analysis, single-crystal X-ray diffraction, and quantum chemical calculation methods. Spiroreticulatine is the first example of a sponge-derived natural spiro quinoline-imidazole alkaloid that may derive from tryptophan and 1,3-dimethylurea. Compound 1 showed inhibitory activity on IL-2 production but inactive against normal tumor cell lines.

Ten new cytochalasan alkaloids, termed armochaetoglobins A-J (1-10), and four known chaetoglobosins (11-14) were isolated from a methanol extract of Chaetomium globosum TW1-1, a fungus isolated from the medicinal terrestrial arthropod Armadillidium vulgare. Their structures were elucidated by a combination of spectroscopy, single-crystal X-ray crystallography, and ECD calculations. Armochaetoglobins A-E (1-5) represented the first examples of seco-chaetoglobosins arising from an oxidative cleavage of C-19 and C-20. Among these compounds, armochaetoglobin A (1) features an unusual pyrrole ring. The cytotoxic activities of 2-10 were evaluated, and armochaetoglobin H (8) showed moderate inhibitory activities against five human cancer cell lines, with IC50 values ranging from 3.31 to 9.83 μM.

Neonectrolides B-E (4-7), four new oxaphenalenone ketals incorporating the new furo[2,3-b]isochromeno[3,4,5-def]chromen-11(6aH)-one skeleton, were isolated from the fermentation extract of the ascomycete fungus Neonectria sp. in an in-depth investigation guided by HPLC fingerprint and a cytotoxicity assay. The previously identified oxaphenalenone spiroketal neonectrolide A (1) and its putative biosynthetic precursors (2 and 3) were also reisolated in the current work. The structures of 4-7 were primarily elucidated by interpretation of NMR spectroscopic data, and the absolute configurations were deduced by electronic circular dichroism calculations. Compound 6 showed cytotoxic effects against four of the six human tumor cell lines tested. Biosynthetically, compounds 4-7 could be derived via the Diels-Alder reaction cascades starting from derivatives of the co-isolated metabolites 2 and 3.

Ten new ergosteroids, gloeophyllins A-J (1-10), have been isolated from the solid cultures of Gloeophyllum abietinum. The absolute configurations of 1, 2, and 9 were determined by X-ray crystallographic analysis. Compound 1 has a rare C-nor-D-homosteroid skeleton. Compound 9 possesses an unusual ergostane skeleton having a 10-oxabicyclo [4.3.1] decane moiety replacing 6/5 fused C/D rings. Compound 10 represents the first ergosteroid featuring the cleavage of a C8-C14 bond. The cytotoxicity of 1-10 was tested against the human cancer cell lines K562 and HCT116. The biosynthetic pathway for 1-10 is postulated.

Three new citrinin analogues, penicitols A-C (1-3), and one new xanthone derivative, penixanacid A (4), together with four known biogenetically related compounds (5-8), were discovered from the extract of a mangrove-derived fungus, Penicillium chrysogenum HND11-24. The structures of penicitols A-C and penixanacid A were established through analysis of extensive spectroscopic data. Their cytotoxic activity against HeLa, BEL-7402, HEK-293, HCT-116, and A549 cell lines was evaluated.

Two new 3,4-seco-lanostane-type triterpenes, named as 15α-hydroxy-3,4-seco-lanosta-4(28),8,24-triene-3,21-dioic acid (1), 5α-hydroxy-3,4-seco-lanosta-4(28),8,24-triene-3,21-dioic acid 3-methyl ester (2), and one new lanostane triterpene 15α-acetoxylhydroxytrametenolic acid (3) together with a known one versisponic acid D (4) were isolated from the fruiting bodies of Laetiporus sulphureus var. miniatus. Their structures were determined on the basis of extensive spectroscopic methods and comparison with reported data. All four compounds were evaluated for their cytotoxicities against five human cancer cell lines; however, none exhibited inhibitory effects.

Two new triterpenoids, (24E)-9α,11α-epoxy-3β-hydroxylanosta-7,24-dien-26-al (1) and (22Z,24Z)-13-hydroxy-3-oxo-14(13 → 12)abeo-lanosta-8,22,24-trien-26,23-olide (2) were isolated from dried fruiting bodies of fungus Ganoderma lucidum. The structures of these two new compounds were elucidated on the basis of extensive spectroscopic analyses. Compound 1 possessed a lanostane skeleton, while compound 2 was based on a rare 14 (13 → 12)abeo-lanostane skeleton with a 26,23-olide moiety. Both of them were evaluated for their antifungal and cytotoxic activities. Neither of them displayed obvious inhibition on Candida albicans and five human cancer cell lines.

One new diketopiperazine heterodimer, asperazine A (1), and eight known compounds, asperazine (2), cyclo(d-Phe-l-Trp) (3), cyclo(l-Trp-l-Trp) (4), 4-(hydroxymethyl)-5,6-dihydro-pyran-2-one (5), walterolactone A (6), and campyrones A-C (7-9), were isolated from an endophytic fungus Aspergillus niger. Their structures were determined unequivocally on the basis of extensive spectroscopic data analysis. This is the first report of the presence of compound 3 as a natural product. Cytotoxicity test against human cancer cell lines PC3, A2780, K562, MBA-MD-231, and NCI-H1688 revealed that compounds 1 and 2 had weak activities.

A new daphnane diterpenoid, venenatin (1), along with six known compounds, was isolated from the aerial parts of Excoecaria venenata. The structure of 1 was elucidated on the basis of extensive spectroscopic analysis. Compound 1 exhibited growth inhibitory effect on human leukaemia HL-60 cell line with IC50 value of 28.10 μM.

Two new sesquiterpenoids (phellinuins H and I), together with five known compounds, were isolated from cultures of mushroom Phellinus sp. Their structures were elucidated based on comparison of nuclear magnetic resonance and MS data and those reported in the literature. All of these compounds were tested for cytotoxicity against five cancer cell lines (HL-60, SMMC-721, A-549, MCF-7, and SW-480).

In this research, the chemical composition and anticancer and antioxidant activity of the new medicinal mushroom Ganoderma tsugae var. jannieae CBS-120304 were evaluated. The chemical composition assay includes amounts of total carbohydrates and proteins, amino acids, fatty acids, micro- and macroelements, and vitamins. The investigated medicinal mushroom seemed to be a rich source of nutritional components. Mycelium accumulated more than 2-fold more total protein compared with the fruiting body and reached 37% and 16% of dry weight, respectively. Carbohydrate content in the fruiting body seemed to be conspicuously higher than in the mycelium (50% of dry weight) and reached 80% of dry weight. Quantification of the identified fatty acids indicated that, in general, palmitic acid, oleic acid, and linoleic acid were the major fatty acids. Toxic elements, such as silver, arsenic, cadmium, and mercury, were found only in trace amounts in mycelium and were not detected in the fruiting body. Furthermore, the 1,1-diphenyl-2-picrylhydrazyl free radical scavenging assay was used to evaluate antioxidant activity. The highest radical scavenging activity was 9.0 mg/mL (65.9%) by ethanol extract. In addition, mycelial extracts were tested to inhibit MCF7 breast cancer cells. Ganoderma tsugae var. jannieae ethyl acetate extract (GTEAE) extract showed high potential by inhibiting reporter activity by more than 70%. Results demonstrated that GTEAE had a strong effect on inhibitory protein κΒα level in the higher concentration used (200 gg/mL), which could be compared with the effect of parthenolide. Furthermore, GTEAE demonstrated strong inhibition of IκΒα phosphorylation.

One new ergostane-type steroid, (12β,15β,22R,23S,24S)-22,25-epoxy-12,15,23-trihydroxyergost-4,6,8(14)-trien-3-one (1), three new phthalide derivatives, 5-(2',3'-epoxy-3',3'-dimethylpropoxy)-7-methoxy-6-methylphthalide (2), (2')-(Z)-5-(3'-hydroxymethyl-3'-methylallyloxy)-7-methoxy-6-methylphthalide (3), and 5-(3',3'-dimethylallyloxy)-7-hydroxy-6-methylphthalide (4), along with one known phthalide derivative, 5-(3',3'-dimethylallyloxy)-7-methoxy-6-methylphthalide (5), were isolated from cultures of the basidiomycete Albatrellus confluens. The structures of the new compounds were established on the basis of extensive spectroscopic data (IR, MS, 1D, and 2D NMR) analyses. All compounds were evaluated for their cytotoxic activities on five tumor cell lines.

Three new aaptamine derivatives (1-3), together with six known related compounds (4-9), have been isolated from the South China Sea sponge Aaptos aaptos. The structures of all compounds were unambiguously elucidated on the basis of spectroscopic analyses. Compounds 1, 4, 5, 7, and 9 showed cytotoxic activities against HeLa, K562, MCF-7, and U937 cell lines with IC50 values in the range of 0.90-12.32 μM.

Talaflavuterpenoid A (1), a new nardosinane-type sesquiterpene, was isolated from the wetland soil-derived fungus Talaromyces flavus BYD07-13, and its structure was elucidated on the basis of HR-MS, NMR, and X-ray diffraction analysis. The absolute configuration of 1 was established by comparing the experimental electronic circular dichroism (ECD) spectrum with the calculated ECD spectra. Its cytotoxic effects on five human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW480), and antimicrobial activity against Escherichia coli, Staphylococcus aureus, Candida albicans, and Aspergillus niger were evaluated. This is the first report of the presence of nardosinane-type sesquiterpene in Talaromyces sp.

Nine new aaptamine derivatives (1-9), together with three known related compounds (10-12), have been isolated from the South China Sea sponge Aaptos aaptos. The structures of all compounds were unambiguously elucidated on the basis of spectroscopic analyses. Structurally, compound 1 possesses a piperidinyl group fused to a demethyl(oxy)aaptamine moiety, whereas compounds 3-6 share an imidazole-fused 1H-benzo[de][1,6]naphthyridin-2(4H)-one skeleton. The cytotoxic activities of the compounds were evaluated against various human cancer cell lines, and compounds 2, 8, 11, and 12 showed potent cytotoxicities against HL60, K562, MCF-7, KB, HepG2, and HT-29 cells, with IC50 values in the range of 0.03 to 8.5 μM.

Six new disulfide-bridged diketopiperazine derivatives, brocazines A-F (1-6), along with one known analogue (7), were isolated and identified from the cytotoxic extract of Penicillium brocae MA-231, a fungus obtained from the fresh tissue of the marine mangrove plant Avicennia marina. The structures of these compounds were established on the basis of detailed interpretation of NMR and mass spectroscopic data. X-ray crystallographic analysis confirmed the structure of 1 and established the structure and absolute configuration of 5, while the absolute configurations for compounds 1, 4, and 6 were deduced by comparison of the CD data with those of 5. Compounds 1, 2, 5, and 6 showed cytotoxic activities against several tumor cell lines.

Three new nortriterpenes, ganoboninketals A-C (1-3), featuring rearranged 3,4-seco-27-norlanostane skeletons and highly complex polycyclic systems were isolated from the medicinal mushroom Ganoderma boninense. The structures of the new metabolites were established by spectroscopic methods. The absolute configurations in 1-3 were assigned by electronic circular dichroism (ECD) calculations. Compounds 1-3 showed antiplasmodial activity against Plasmodium falciparum with IC50 values of 4.0, 7.9, and 1.7 μM, respectively. Compounds 1 and 3 also displayed weak cytotoxicity against A549 cell line with IC50 values of 47.6 and 35.8 μM, respectively. Compound 2 showed weak cytotoxicity toward HeLa cell line with an IC50 value of 65.5 μM. Compounds 1-3 also presented NO inhibitory activity in the LPS-induced macrophages with IC50 values of 98.3, 24.3, and 60.9 μM, respectively.

Five new 9,11-secosteroids 1, 2, and 4-6, and seven known analogs, 3 and 7-12, with the same steroid skeleton, (5αH)-3β,6α,11-trihydroxy-9,11-secocholest-7-en-9-one, were isolated from the South China Sea gorgonian Subergorgia suberosa. Among them, 2/3 and 4/5 are C(24)-epimeric mixtures, and 6/7 is an (E)/(Z) mixture of (C(24)C(28)). Their structures and relative configurations were elucidated by using comprehensive spectroscopic methods including NOESY spectra. The absolute configuration of the steroidal nucleus was established by the modified Mosher method applied to 10 and on the basis of a common biogenesis for all of these compounds. All isolated compounds, 1-12, and five synthetic acetylated derivatives, 12a-12e, were evaluated for their cytotoxicities in vitro. Compounds 4/5, 11, 12, and 12b-12d showed cytotoxic activities against K562 cell line with the IC50 values ranging from 1.09 to 8.12 μM., (Copyright © 2014 Verlag Helvetica Chimica Acta AG, Zürich.)

Hawaiinolides A-D (1-4), four new secondary metabolites including three cleistanthane (1, 3, and 4) and one cassane (2) type of diterpene lactones, were isolated from the crude extract of Paraconiothyrium hawaiiense, a fungus entomogenous to the Septobasidium-infected insect Diaspidiotus sp. The structures of 1-4 were elucidated by nuclear magnetic resonance experiments, and 1 and 3 were further confirmed by X-ray crystallography. The absolute configuration of 1 was assigned via single-crystal X-ray diffraction analysis using Cu Kα radiation, whereas that of 2-4 was deduced via the circular dichroism data. Compound 1 showed significant cytotoxicity against a small panel of five human tumor cell lines, A549, T24, HeLa, HCT116, and MCF-7.

Cercosporenes A-F (1-6, respectively), six new guanacastane diterpenes, including a homodimer (5) and a heterodimer (6), were isolated from the crude extract of the fungus Cercospora sp., endophytic to the medicinal plant Fallopia japonica. The structures of 1-6 were elucidated by nuclear magnetic resonance experiments, and 4 and 5 were further confirmed by X-ray crystallography. The absolute configuration of 1 and 3 was assigned by electronic circular dichroism calculations, whereas that of 6 was deduced by the application of the circular dichroism exciton chirality method. In addition to its cytotoxicity against a panel of five human tumor cell lines, HeLa, A549, MCF-7, HCT116, and T24, heterodimer 6 also induced autophagy in HCT116 cells.

Four new briarane diterpenoids, junceellolides M-P (1-4), were isolated together with seven known analogs (5-11) from the South China Sea gorgonian, Junceella gemmacea. The structures of these compounds were elucidated by detailed spectroscopic analysis and comparison with the reported data. The absolute configuration of compounds 1-3 were determined based on an ECD experiment, while the absolute configuration of compound 4 was genetically determined. All the compounds were isolated for the first time from J. gemmacea. These compounds showed no growth inhibitory activity against A549, MG63 and SMMC-7721 cell lines in an in vitro bioassay.

Three new thiodiketopiperazines, named phomazines A-C (1-3), along with 10 known analogues (4-13), were isolated from the fermentation broth of an endophytic fungus, Phoma sp. OUCMDZ-1847, associated with the mangrove plant Kandelia candel. The structures including the absolute configurations of the new compounds were unambiguously elucidated by spectroscopic, X-ray crystallographic, and Mosher's methods along with quantum ECD and (13)C NMR calculations. Compounds 2, 4, 5, 11, and 12 showed cytotoxicities against the HL-60, HCT-116, K562, MGC-803, and A549 cell lines with IC50 values in the range 0.05 to 8.5 μM.

Three new bisabolane sesquiterpenoids, inonotic acid A (1), 3-O-formyl inonotic acid A (2), inonotic acid B (3), and one new drimane sesquiterpenoid 3α,6β-dihydroxycinnamolide (4), were isolated from the fruiting bodies of mushroom Inonotus rickii. Their structures were elucidated by means of extensive spectroscopic methods. Compound 4 had moderate inhibitory activity on human colon cancer SW480 (IC50 = 20.4 μmol).