Six new meroterpenoids, chrodrimanins K–N (1–4), including two uncommon chlorinated ones (1 and 2), and verruculides B2 (5) and B3 (6), as well as seven known ones (7–13), were isolated from the fermentation broth of Penicillium sp. SCS-KFD09 isolated from a marine worm, Sipunculus nudus, from Haikou Bay, China. The structures including the absolute configurations of the new compounds were unambiguously elucidated by spectroscopic data, X-ray diffraction analysis, and ECD spectra analysis along with quantum ECD calculations. In addition, the X-ray crystal structures and absolute configurations of two previously reported meroterpenoids, chrodrimanins F (9) and A (11), are described for the first time. Compounds 1, 4, and 7 displayed anti-H1N1 activity with IC50 values of 74, 58, and 34 μM, respectively, while compound 5 showed weak inhibitory activity against Staphylococcus aureus with an MIC of 32 μg/mL.

•Three new compounds were isolated from cultures of the fungus Xylaria polymorpha.•The structures were elucidated by NMR and X-ray diffraction analysis.•Two new compounds showed weak inhibitory activity against acetylcholinesterase.Three new drimane-type sesquiterpenoids named xylariaines A–C (1–3), together with one known analogue (4), were isolated from the ethyl acetate extract of cultures of the fungus Xylaria polymorpha (Pers.: Fr.) Grer. Their structures were elucidated unambiguously by NMR and single-crystal X-ray diffraction analysis. Compounds 1 and 2 exhibited weak anti-acetylcholinesterase activities at a concentration of 50 μg/mL with inhibition ratios of 12.4% and 18.0%, respectively.Download high-res image (119KB)Download full-size image

•Two new nortriterpenoids were isolated from Ganoderma daqingshanense.•Daqingshone B exhibited anti-acetylcholinesterase activity.•Lanostanoids were the main type of triterpenoids in Ganoderma daqingshanense.Two new nortriterpenoids named daqingshones A (1) and B (2), along with two known ganderic acids (3 and 4), were isolated from the fruiting bodies of Ganoderma daqingshanense. Their structures were elucidated by spectroscopic data including MS, 1D and 2D NMR. Compound 2 exhibited weak anti-acetylcholinesterase (AChE) activity with IC50 value of 39.2 μM.Download high-res image (125KB)Download full-size image

•29 lanostane triterpenoids were isolated from Ganorderma alidophilum.•Four of the six previously undescribed lanostanes possess a unique spiro-lactone substructure.•Four compounds showed cytotoxic activity against human tumor cell lines.•Main compound ganoderone A showed moderate cytotoxic activity.To search for active anti-cancer constituents in the fruiting body of Ganoderma calidophilum, we have successfully isolated four previously undescribed spiro-lactone lanostane triterpenoids (spiroganocalitones A-D), two previously undescribed lanostanoids (ganodecalones A and B) together with twenty-three known ones. The structures of the six previously undescribed compounds were elucidated based on 1D, 2D-NMR, and HRMS analyses. Ganoderone A showed moderate cytotoxic activity against K562, BEL7402, and SGC790 cell lines with IC50 values of 7.62, 6.28, and 3.55 μM, respectively.Six previously undescribed lanostanoids including four spiro-lactone lanostane triterpenoids (spiroganocalitones A-D) were isolated from fruiting body of Ganoderma calidophilum, together with twenty-three known ones. Ganoderone A showed moderate cytotoxic activity.Download high-res image (205KB)Download full-size image

Eight new alkaloids, 3β-n-butylstemonamine (1), 8-oxo-3β-n-butylstemonamine (2), 3-n-butylneostemonine (3), 10-epi-3-n-butylneostemonine (4), 8-oxo-oxymaistemonine (5) protostemonine N4-oxide (6), (19S)-hydroxy-21-methoxystemofoline (7), and parvistemonine A (8), were isolated from the roots of Stemona parviflora, together with 17 known alkaloids. The structures of the new alkaloids were elucidated based on a comprehensive spectroscopic data analysis. The absolute configurations of 1–4 were determined by the ECD exciton chirality method and quantum ECD calculations. Protostemonine (10) and stemofoline (12) showed strong nematicidal activity against Panagrellus redivevus, with IC50 values of 0.10 and 0.46 μM, respectively.

⿢Five new compounds were isolated from a marine fungus Penicillium sp. SCS-KFD08.⿢The structures were elucidated by NMR, CD data along with ECD calculation.⿢Two new compounds showed weak inhibitory activity against AChE.Five new compounds named penicillars A⿿E were isolated from the fermentation broth of Penicillium sp. SCS-KFD08 associated with the marine animal Sipunculus nudus from the Haikou bay of China. Their planar structures and absolute configurations were unambiguously elucidated by spectroscopic data, Mo2(OAc)4 induced CD spectrum analysis along with quantum ECD calculation. Among them, compounds 2 and 3, at a concentration of 50 μg/mL, showed weak inhibitory activity against AChE with inhibition rates of 19.5% and 21.3%, respectively.

Thirteen new sesquiterpenoids, including six guaiane type auranticanols A–F (1, 2, and 4–7) and seven carotene type auranticanols G–M (18–24) were isolated from the stems of Daphne aurantiaca Diels., along with fourteen known sesquiterpenoids (3, 8–17, 25–27) and two known tigliane diterpenoids (28, 29), and their structures were elucidated by extensively analyzing their MS and NMR spectroscopic data. A bioassay of anti-HIV activity indicated that compounds 11, 14, 19, and 28 showed definite activities with EC50 values of 2.138, 0.286, 1.773 and 0.000282 μg mL−1 and SI > 93.545, 93.787, 10.243, and 65177.305, respectively.

Daphnauranols A–C (1–3), three new sesquiterpenoids with an unprecedented 5/6/7 ring system, were isolated from the stems of Daphne aurantiaca Diels. Their structures were elucidated on the basis of comprehensive spectroscopic methods including MS and NMR. The absolute configuration of daphnauranol A was further confirmed by single crystal X-ray diffraction (Cu Kα). Their anti-feedant activity was tested, and the fruit fly antifeedant index (AI) were 39.8 ± 7.2%, 29.4 ± 7.2%, and 26.3 ± 6.4%, respectively.

Volvalerenol A (1), an unprecedented type of triterpenoid with a 7/12/7 tricyclic ring system, was obtained from the ethanol extracts of the roots of Valeriana hardwickii. The structure and relative configurations were established by comprehensive analysis of MS and NMR spectroscopic data. The possible biogenetic pathway of 1 was also deduced.