Min Fan

New cytotoxic and anti-inflammatory compounds isolated from Morus alba L.

Six Diels–Alder adducts (1–6) and nine prenylated flavanones (7–15) were isolated from the root bark of Morus alba L. Among them, soroceal B (1) and sanggenol Q (7) were new compounds. Their structures were elucidated on the basis of extensive spectroscopic methods, including 1D and 2D NMR techniques. Compounds 1–3, 9, 10, 12, 13 and 15 exhibited cytotoxic activity against five human tumour lines and compound 2 inhibited significantly selective cytotoxic activities towards HL-60 and AGS cells with IC50 of 3.4 and 3.6 μM. Compounds 3, 5, 9 and 12 exhibited moderate inhibitory activity against nitric oxide production in LPS-activated RAW264.7.

New neo-clerodane diterpenoids with neurotrophic activity from the aerial parts of Salvia tiliifolia

Five new neo-clerodane diterpenoids, tiliifolins A-E (1-5), along with ten known ones, were isolated from the aerial part of Salvia tiliifolia. Their structures were proposed based on 1D and 2D NMR spectroscopic data analysis. All new compounds were evaluated for their neurotrophic activity on PC12 cells and cytotoxicity against five human cancer cell lines (HL-60, A-549, SMMC-7721, MCF-7, and SW480), and compound 5 showed statistically significant neuroprotective effect in vitro assay.

Guaiane-Type Sesquiterpenoids from Alismatis Rhizoma and Their Anti-inflammatory Activity

Twelve guaiane-type sesquiterpenoids, including four new ones, 10-O-methyl-orientalol A (1), 10-O-ethyl-alismoxide (2), 3β,4β-expoxy-chrysothol (3), orientalol G (4), and a new norsesquiterpenoid, orientalol H (5), were isolated from Chinese Alismatis Rhizoma, the dried rhizome of Alisma orientale. The structures of new compounds were elucidated on the basis of spectroscopic data. Moreover, the inhibition of lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 cells of all compounds was tested.

Four new fawcettimine-related alkaloids from Phlegmariurus squarrosus

Four new fawcettimine-related alkaloids (1–4), together with 17 known ones, were isolated from club moss Phlegmariurus squarrosus. Notably, compound 1 was the derivative of lycoflexine with an unprecedented additional methyl group at C-17. Their structures were determined by extensive spectroscopic analysis, including 1D and 2D NMR, and HR-MS, as well as by comparison with the literature data. All new compounds were tested for their β-site amyloid precursor protein (APP)-cleaving enzyme 1 (BACE1) and acetylcholinesterase (AChE) inhibitory activities.

Two New Anti-Proliferative C18-Norditerpenes from the Roots of Podocarpus macrophyllus

Activity‐guided fractionation strategy was used to investigate chemical constituents from the roots of Podocarpus macrophyllus. Successfully, two new norditerpenes, 2β‐hydroxymakilactone A (1) and 3β‐hydroxymakilactone A (2), along with ten known analogues (3 – 12) were isolated. The structures of 1 and 2 were elucidated by spectroscopic analysis including 1D‐, 2D‐NMR, and HR‐ESI‐MS data. The previously reported structure of 2,3‐dihydro‐2α‐hydroxypodolide was revised as 2,3‐dihydro‐2β‐hydroxypodolide (3) by spectroscopic analysis, and was further confirmed by X‐ray crystallographic analysis. Cytotoxic activities of all isolated compounds against five human solid tumour cell lines (AGS, HeLa, MDA‐MB‐231, HepG‐2, and PANC‐1) were evaluated. All of them exhibited anti‐proliferative activities (IC50 = 0.3 – 27 μm), except for 10. Compounds 1, 4, 5, 6, and 8 exhibited potent inhibitory activities with IC50 < 1 μm against HeLa and AGS cells.

Three new Lycopodium alkaloids from Lycopodium japonicum

Abstract Three new Lycopodium alkaloids (1–3), together with 15 known alkaloids, were isolated from club moss Lycopodium japonicum. Their structures were determined by extensive spectroscopic analysis, including 1D and 2D NMR spectra. Compound 1 has an unusual β-oriented methyl group substituted at C-15 and an α-hydroxy cyclopentenone moiety. All new alkaloids were evaluated for the inhibition of T-type calcium channel.

Vibsane-Type Diterpenoids from Viburnum odoratissimum and Their Cytotoxic and HSP90 Inhibitory Activities

Four new vibsane‐type diterpenoids, vibsanol I (1), 15‐hydroperoxyvibsanol A (2), 14‐hydroperoxyvibsanol B (3), 15‐O‐methylvibsanin U (4), and a new natural product, 5,6‐dihydrovibsanin B (5), as well as six known analogues, were isolated from the twigs and leaves of Viburnum odoratissimum. Their structures were elucidated by spectroscopic analyses and chemical derivatization method. All compounds showed different levels of cytotoxicity against five cell lines (HL‐60, A‐549, SMMC‐7721, MCF‐7, and SW480). Remarkably, 14,18‐O‐diacetyl‐15‐O‐methylvibsanin U (4a) showed significant cytotoxicity against HL‐60, A‐549, SMMC‐7721, MCF‐7, and SW480, with IC50 values of 0.15 ± 0.01, 0.69 ± 0.01, 0.41 ± 0.02, 0.75 ± 0.03, and 0.48 ± 0.03 μm, respectively. In addition, vibsanin K (10) was identified as a HSP90 inhibitor with an IC50 value of 19.16 μm.

Protostane-Type Triterpenoids from Alisma orientale

Twenty‐eight protostane triterpenoids, including a new degraded one (1), nine new ones (2 – 10), and two new natural ones (11 and 12), have been isolated from the dried rhizomes of Alisma orientale. Alisol R (1) was the first 20,21,22,23,24,25,26,27‐octanorprotostane triterpenoid. The absolute configurations of 25‐methoxyalisol F (2) and 16β‐hydroperoxyalisol B 23‐acetate (3) were determined by X‐ray diffraction analysis. In addition, alismaketone‐B 23‐acetate (28) showed potent vasorelaxant activity on endothelium‐intact thoracic aorta rings precontracted with KCl.

Five new Lycopodium alkaloids from the aerial parts of Phlegmariurus henryi.

A series of new Lycopodium alkaloids, namely 1-epi-malycorin A (1), 1-epi-17S-hydroxymalycorin A (2), 6α-hydroxyphlegmariurine A (3), 2S,4R-dihydroxyfawcettimine (4), and 16-hydroxylycodine (5), together with 24 known ones, have been isolated from the club moss Phlegmariurus henryi. The structures of the new compounds were determined by extensive spectroscopic analysis, including 1D and 2D NMR, as well as X-ray crystallographic analysis. Among them, the absolute configurations of 1, 2, and 4 and the structure of 3 were confirmed on the basis of the single-crystal X-ray diffraction analysis. 1-Epi-17S-hydroxymalycorin A (2) was a unique C19N-type Lycopodium alkaloid consisting of a serratinine skeleton with 1,2-propanediol unit. 2S,4R-dihydroxyfawcettimine (4) was a 2,4-dihydroxy derivative of fawcettimine. 16-Hydroxylycodine (5) was the oxidative product of lycodine with an unusual hydroxymethyl group at C-15. All new compounds were evaluated for in vitro acetylcholinesterase (AChE) inhibitory activity and cytotoxicity against four human cancer cell lines.

Three new iridoids from two Viburnum species

Three new iridoids, 10-deacetyl suspensolide A aglycone (1), 7-deacetyl suspensolide A aglycone (2), and 7,10-dideacetyl suspensolide A aglycone (3), were isolated from two species of Viburnum. Their structures were elucidated on the basis of spectroscopic methods, including 1D and 2D NMR techniques. Compound 2 exhibited moderate anti-inflammatory activity against NO production in LPS-stimulated RAW 264.7 cells with IC50 of 17.2 μM.