Sheng-Zhuo Huang

Three new lanostanoid triterpenes from the fruiting bodies of Ganoderma tropicum

Three new lanostanoid triterpenes, 3β,7β,15β-trihydroxy-11,23-dioxo-lanost-8,16-dien-26-oic acid (1), 3β,7β,15β-trihydroxy-11,23-dioxo-lanost-8,16-dien-26-oic acid methyl ester (2), and 3β,15β-dihydroxy-7,11,23-trioxo-lanost-8,16-dien-26-oic acid methyl ester (3) were isolated from the EtOAc extract of the fruiting bodies of Ganoderma tropicum. Their structures were elucidated on the basis of 1D and 2D NMR spectroscopy as well as MS. The bioassay of inhibitory activity against acetylcholinesterase (AChE) of these isolates was evaluated and compound 2 exhibited definite inhibitory activity against AChE.

Lanostane triterpenoids with cytotoxic activities from the fruiting bodies of Ganoderma hainanense

Twelve lanostane triterpenoids (1–12) including a new one 16α,26-dihydroxylanosta-8,24-dien-3-one (1) were isolated from the fruiting bodies of Ganoderma hainanense. The structure of the new compound was elucidated by 1D and 2D NMR and MS spectroscopic analyses. All isolates were evaluated for their cytotoxicities against human tumor cell lines K-562, SMMC-7721, and SGC-7901 and five compounds (1, 2, 5,7, and 9) showed definite cytotoxicities against K-562 cell line. Meanwhile, compounds 2, 5,7, and 9 exhibited cytotoxic activities against SMMC-7721 and SGC-7901 cell lines.

Lanostanoids with acetylcholinesterase inhibitory activity from the mushroom Haddowia longipes

Nine lanostanoids, together with nine known ones, were isolated from the ethyl acetate extract of the fruiting bodies of the mushroom Haddowia longipes. Their structures were elucidated as 11-oxo-ganoderiol D, lanosta-8-en-7,11-dioxo-3β-acetyloxy-24,25,26-trihydroxy, lanosta-8-en-7-oxo-3β-acetyloxy-11β,24,25,26-tetrahydroxy, lanosta-7,9(11)-dien-3β-acetyloxy-24,25,26-trihydroxy, lanosta-7,9(11)-dien-3β-acetyloxy-24,26-dihydroxy-25-methoxy, 11-oxo-lucidadiol, 11β-hydroxy-lucidadiol, lucidone H and lanosta-7,9(11),24E-trien-3β-acetyloxy-26,27-dihydroxy by analysing their 1D/2D NMR and MS spectra. In addition, bioassays of inhibitory activity against acetylcholinesterase (AChE) of all compounds showed that thirteen compounds possessed inhibitory activity against AChE with the percentage inhibition ranging from 10.3% to 42.1% when tested at 100 μM.

Chrodrimanins K–N and Related Meroterpenoids from the Fungus Penicillium sp. SCS-KFD09 Isolated from a Marine Worm, Sipunculus nudus

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 isopimarane diterpenoids from Excoecaria acerifolia

Three new isopimarane diterpenoids named excoecarins F–H (1–3) were isolated from the EtOAc extract of the Chinese ethnodrug Gua-jing-ban (Excoecaria acerifolia Didr.). Their structures were elucidated by the analysis of spectroscopic data including 1D, 2D NMR and HR-MS. The anti-HIV-1 bioactivity test of 1 and 2 showed weak activity.

Fatty acid synthase inhibitors isolated from Punica granatum L.

The aim of this work is the isolation of fatty acid synthase (FAS) inhibitors from the ethyl acetate extracts of fruit peels of Punica granatum L. Bioassay-guided chemical investigation of the fruit peels resulted in the isolation of seventeen compounds mainly including triterpenoids and phenolic compounds, from which one new oleanane-type triterpene (punicaone) along with fourteen known compounds were isolated for the first time from this plant. Seven isolates were evaluated for inhibitory activities of FAS and two compounds showed to be active. Particularly, flavogallonic acid exhibited strong FAS inhibitory activity with IC50 value of 10.3 µmol L-1.

Terpenoids and their anti-HIV-1 activities from Excoecaria acerifolia

Five new diterpenoids named excocarinols A-E (1-5) including three pimaranes, one cleistanthane, and one nor-beyerane, together with nine known compounds, were isolated from the EtOAc extract of the Chinese ethnodrug Gua-jing-ban (Excoecaria acerifolia Didr.). Their structures were elucidated by the analysis of spectroscopic data including 1D, 2D NMR and HR-MS. The anti-HIV-1 bioassay on the diterpenoids showed that excocarinol A (1) exhibited moderate anti-HIV-1 activity with EC50 5.58 μM and SI (Selection Index) over 112.71.

Chemical Constituents from Cultures of the Fungus Marasmiellus ramealis (Bull.) Singer

A investigacao quimica das culturas do fungo Marasmiellus ramealis resultou na primeira isolacao de onze compostos incluindo dois novos sesquiterpenoides do tipo eudesmano 14(10→1)abeo-eudesmano-13-hidroxil-11-eno, 14(10→1)abeo-eudesmano-11,13-diol, e o novo derivado de meleina (R)-(-)-5-etoxicarbonil meleina. A atividade inibitoria da aceticolinesterase (AChE) dos dois primeiros compostos foi avaliada, que mostraram ser ativos com uma porcentagem de inibicao de 29 e 41%, respectivamente, em uma concentracao de 100 µmol L-1. Chemical investigation on the cultures of the fungus Marasmiellus ramealis resulted in the first isolation of eleven compounds including two new eudesmane-type sesquiterpenoids 14(10→1)abeo-eudesmane-13-hydroxyl-11-ene, 14(10→1)abeo-eudesmane-11,13-diol, and the new mellein derivative (R)-(-)-5-ethoxycarbonyl mellein. The first two compounds were evaluated for their inhibitory activity against acetylcholinesterase (AChE), and proved to be active with a percentage inhibition of 29 and 41%, respectively, at a concentration of 100 µmol L -1 .

Three new sesquiterpenoids from agarwood of Aquilaria crassna.

Three new sesquiterpenoids (1-3), together with two known ones were isolated from the EtOAc extract of agarwood originating from Aquilaria crassna. The new compounds were elucidated on the basis of spectroscopic techniques (UV, IR, MS, 1D and 2D NMR). Compounds 1-5 were isolated from agarwood of A. crassna for the first time. In the acetylcholinesterase inhibition experiment of 2-5, compound 3 showed acetylcholinesterase inhibition activity (IR 42.9±0.6%). Compound 5 expressed antibacterial activities against Staphylococcus aureus and Ralstonia solanacearum with diameter of the inhibition zones of 12.35±0.11mm and 16.90±0.09mm, respectively.

Three New Lanostanoids from the Mushroom Ganoderma tropicum

Three new lanostanoid triterpenes—ganotropic acid (1), 3β,7β,15α,24-tetra-hydroxy-11,23-dioxo-lanost-8-en-26-oic acid (2) and 3β,7β,15α,28-tetrahydroxy-11,23-dioxo-lanost-8,16-dien-26-oic acid (3)—were isolated from the n-BuOH extract of the fruiting bodies of the mushroom Ganoderma tropicum. Their structures were elucidated by 1D and 2D NMR spectroscopy, as well as HR-EI-MS data.