Jin-Hai Yu

Cytotoxic diterpenoids from Sapium insigne.

Chemical investigation into the twigs and leaves of Sapium insigne afforded seven new diterpenoids, sapinsignoids A-G (1-7), together with 10 known diterpenoids. The structures of 1-7 were assigned on the basis of detailed spectroscopic analysis and chemical degradation. Compounds 1-4 exhibited significant cytotoxicity against the A-549 tumor cell line (IC(50) 0.2-1.8 μM), while compounds 1-3 showed moderate cytotoxicity against the HL-60 cell line (IC(50) 2.7-6.5 μM).

3-Oxo-axisonitrile-3, a new sesquiterpene isocyanide from the Chinese marine sponge Acanthella sp.

A new sesquiterpene isocyanide, 3-oxo-axisonitrile-3 (1), with a spiro [5,6] decane skeleton (spiroaxane) together with a known related sesquiterpene isonitrile (2), sesquiterpene isothiocyanates (3–8) and two diterpene isonitriles (9, 10) have been isolated from the Chinese marine sponge Acanthella sp. The structure of 1 has been determined on the basis of spectroscopic analysis.

Cipacinoids A-D, Four Limonoids with Spirocyclic Skeletons from Cipadessa cinerascens.

Four limonoids, cipacinoids A-D (1-4), with spirocyclic skeletons were isolated from Cipadessa cinerascens. It is particularly notable that compounds 1-3 had a 17S-configuration for the first time in the limonoid family. Their structures with absolute configurations were assigned by spectroscopic data, X-ray crystallography, and CD analysis. Compound 1 showed moderate protein tyrosine phosphatase 1B (PTP1B) inhibition.

Limonoids with Anti-HIV Activity from Cipadessa cinerascens

Sixteen new limonoids, named ciparasins A-P (1-16), comprising three structural categories of trijugin-type (1-7), cipadesin-type (8-15), and prieurianin-type (16) compounds, as well as 15 known limonoid analogues (17-31), were isolated from Cipadessa cinerascens. Ciparasins E-G (5-7) were found to possess a rare γ-hydroxylbutenolide moiety at C-17. Ciparasins B (2) and P (16) showed significant anti-HIV activities, with EC50 values of 5.5 ± 0.6 (SI >7.2) and 6.1 ± 0.7 (SI >6.5) μM, respectively.

Limonoids and Triterpenoids as 11β-HSD1 Inhibitors from Walsura robusta

Nine new cedrelone-type limonoid derivatives, walsunoids A-I (1-9), and 11 known compounds were isolated from the leaves of Walsura robusta. Walsunoid A (1) is a new degradation product of cedrelone-type limonoids, and walsunoid I (9) is a rare cedrelone-type limonoid amide. Their structures and absolute configurations were determined by spectroscopic data, single-crystal X-ray diffraction, and ECD data analyses. Five compounds showed moderate inhibitory activities against human and/or mouse 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) with IC50 values ranging from 0.69 to 9.9 μM.

New diterpenoids from Sapium discolor

Abstract Chemical fractionation of the ethanolic extract generated from the twigs and leaves of Sapium discolor led to the isolation and identification of four new macrocyclic diterpenoids including three members of the rare casbane family, sapidisins A-C (1–3), and an analog of the cembrane class, sapidisin D (4), a new 3,4-seco ent-kaurane diterpenoid (5), and 18 known phenolic compounds. Their structures were elucidated by comprehensive spectroscopic analyses especially 1D NMR 1H-1H couplings and 2D NMR ROESY data. The discovery of 1–4 from S. discolor provides a clue for further study on the biogenetic evolution of the widely existent tigliane-type diterpenoids in the Sapium species.

Ricinodols A–G: new tetracyclic triterpenoids as 11β-HSD1 inhibitors from Ricinodendron heudelotii

A search for 11β-HSD1 inhibitors from Ricinodendron heudelotii has afforded seven new tetracyclic triterpenoids ricinodols A–G (1–7), along with three known podocarpane-type diterpenoids (8–10). Ricinodols A (1) and B (2) possess a new carbon skeleton with a novel concurrent rearrangement of Me-19 (10 → 9) and Me-30 (14 → 8). Their structures were elucidated by comprehensive spectroscopic analyses and comparison with reported analogues, while the 24R-configuration of those with a 24-OH group was established by an in situ dimolybdenum CD method. Of these isolates, ricinodol E (5) exhibited the best inhibitory activities against both human and mouse 11β-HSD1 with IC50 values of 0.36 ± 0.26 and 0.84 ± 0.18 μM, respectively.

Diterpenes and lignans from Viburnum odoratissimum var. odoratissimum

A new diterpenoid, dehydrovibsanin G (1), a new lignan, (+)-9′-O-senecioyllariciresinol (2), and six known compounds (3–8) were isolated from the branches and leaves of Viburnum odoratissimum var. odoratissimum. The structures of these compounds were elucidated by analysis of spectroscopic data. Both new compounds showed moderate inhibitory activity against human A431 and T47D tumor cell lines.