Lonijaposides, novel cerebrosides from Lonicera japonica

Six novel cerebrosides, lonijaposides A₁-A₄, B₁ and B₂ (1-6) have been isolated from the flowers of Lonicera japonica. Their structures were established on the basis of 1D, 2D (DEPT, HMQC, HMBC and COSY) NMR, ESI-QTOF-MS/MS and chemical evidence.     

Camptothecins and two new monoterpene glucosides from Ophiorrhiza liukiuensis

Two new monoterpene glucosides, demethylsecologanol and 3'-O-glucosylsenburiside II, were isolated from Ophiorrhiza liukiuensis (Rubiaceae) together with 23 known compounds, including camptothecins and beta-carboline-type alkaloids. Their structures were determined by spectroscopic analysis.     

Hupermine A,a novel C16N2-type Lycopodium alkaloid from Huperzia phlegmaria

A novel C₁₆N₂-type Lycopodium alkaloid consisting of a quinolizidine with a 6-dimethylaminohexyl side chain, hupermine A (1), was isolated from the club moss of Huperzia phlegmaria, and the structure and relative stereochemistry were elucidated on the basis of spectroscopic data.     

Cinachyramine, the novel alkaloid possessing a hydrazone and two aminals from Cinachyrella sp.

The trifluoroacetate salt of cinachyramine (1) was isolated from the Okinawan sponge Cinachyrella sp. This structure was determined by the spectroscopic analysis and the degradation under acidic conditions. Cinachyramine (1) is a novel alkaloid with an unprecedented cage system possessing a hydrazone and two aminals.     

Daphlongeramine A, novel Daphniphyllum alkaloid from Daphniphyllum longeracemosum

A novel Daphyniphyllum alkaloid, Daphlongeramine A (1) with a unique fused octacyclic skeleton, together with a quite recently reported alkaloid Paxdaphnine A (2), were isolated from the fruits of Daphniphyllum longeracemosum. The structures were elucidated on the basis of spectroscopic data.     

Vilmoraconitine, a novel skeleton C19-diterpenoid alkaloid from Aconitum vilmorinianum

A novel C₁₉-diterpenoid alkaloid vilmoraconitine (1) was isolated from the roots of Aconitun vilmorinianum. Its structure was mainly determined by MS, 2D NMR, and X-ray methods. This is the first aconitine-type C₁₉-diterpenoid alkaloid with one three-membered ring at C-8, C-9, and C-10.     

Sauroine—a novel Lycopodium alkaloid from Huperzia saururus

A novel Lycopodium alkaloid, sauroine (7,8-dihydroxylycopodine, 1) was isolated from the aerial parts of the medicinal species Huperzia saururus. The structure and relative stereochemistry of 1 were elucidated on the basis of its spectral data.     

Secu'amamine A, a novel indolizidine alkaloid from Securinega suffruticosa var. amamiensis

A novel indolizidine alkaloid, secu'amamine A (1), was isolated from the leaves and twigs of the medicinal plant, Securinega suffruticosa var. amamiensis together with securinine (2). The structure and relative stereochemistry of 1 was elucidated by spectroscopic data and its absolute configuration was assigned on the basis of the OMe-madelate method.     

Structures of two rare iridoid glucosides from penstemon barbatus

The structures of penstemonoside and penstemoside are described.     

Calyciphylline C, a novel Daphniphyllum alkaloid from Daphniphyllum calycinum

Calyciphylline C (1), a novel Daphniphyllum alkaloid with unprecedented fused-hexacyclic ring system, has been isolated from the leaves of Daphniphyllum calycinum (Daphniphyllaceae), and the structure and relative stereochemistry were elucidated on the basis of spectroscopic data.     

Piperazirum, a novel bioactive alkaloid from Arum palaestinum Boiss.

A novel alkylated piperazine (3α,5α-diisobutyryl-6α-isopropyl-piperazine-2-one, 1) has been isolated from the n-butanol soluble part of the leaves extract of Arum palaestinum Boiss., the chemical structure and the relative stereochemistry of 1 were elucidated on the basis of 1D and 2D NMR spectroscopic data. Piperazirum showed a significant cytotoxicity against cultured tumor cell lines in vitro.     

Hericirine,a novel anti-inflammatory alkaloid from Hericium erinaceum

A novel ergosterol conjunction-type alkaloid, hericirine (1), was isolated from the dried fruiting bodies of Hericium erinaceum. The overall framework of 1 was isolated, and combined with hericerin and ergosterol. Its structure was elucidated based on spectroscopic analysis using 1D and 2D NMR, IR and HRESIMS techniques. We found that hericirine significantly inhibited protein expression of iNOS and COX-2 and reduced NO, PGE₂, TNF-α, IL-6 and IL-1β production in RAW264.7 cells exposed to LPS.     

Oldhamine A, a novel alkaloid from Daphniphyllum oldhami

Oldhamine A, a novel alkaloid with an unusual cyclopentadienyl anion in the fused-pentacyclic skeleton was isolated from the twigs of Daphniphyllum oldhami. The structure of oldhamine A was elucidated based on the spectroscopic data and the single-crystal X-ray diffraction crystallography. It is the first X-ray diffraction of the Daphniphyllum alkaloids with nitrogen-containing two pentacyclic rings. The inter-conversion between cyclopentadienyl anion and conjugated enolic unit was also conducted.     

Myrioneurinol: a novel alkaloid skeleton from Myrioneuron nutans

A new alkaloid, myrioneurinol (1), was isolated from the leaves of Myrioneuron nutans and its structure determined from spectral analysis, including mass spectrometry and 2D NMR. Myrioneurinol (1) presented an unprecedented fused tetracyclic skeleton. The absolute configuration was established by the modified Mosher's method, using (R)- and (S)-9-anthrylmethoxyacetic acid (9-AMAA). A plausible biosynthetic pathway starting from l-lysine via Δ-piperideine was proposed for 1 in comparison with nitraramine biosynthesis and related alkaloids.     

Ancisheynine, a novel naphthylisoquinolinium alkaloid from Ancistrocladus heyneanus

A novel naphthylisoquinoline alkaloid, ancisheynine 1, was isolated from the aerial part of Ancistrocladus heyneanus Wallich ex J. Graham (Ancistrocladaceae). Ancisheynine 1 contained a previously undescribed N-2,C-8′-linkage between the isoquinoline and naphthalene units and its structure was established by spectroscopic methods.     

Cochinchistemonine, a novel skeleton alkaloid from Stemona cochinchinensis

Cochinchistemonine (1), an alkaloid with a novel skeleton, was isolated from the roots of Stemona cochinchinensis collected from northern Vietnam. Its structure was established on the basis of one- and two-dimensional NMR and other spectroscopic studies. The relative configuration was confirmed by single crystal X-ray diffraction experiment.     

Mersilongine, a novel tetracyclic quinolinic alkaloid from Kopsia

A novel quinolinic alkaloid, viz., mersilongine, incorporating a novel tetracyclic carbon skeleton was obtained from a Malayan Kopsia species. The structure was established by spectroscopic analysis and a possible pathway from a mersinine-type precursor is presented.     

Pipermethystine,a novel pyridone alkaloid from piper methysticum

A new alkaloid, pipermethystine, isolated from the leaves of Piper methysticum is shown to be 5-acetoxy-5,6-dihydro-1-(3-phenylpropanoyl)-2(1H)-pyridone (1) by PMR, CMR and mass spectrometry and by its conversion to phenylpropanoic acid and 5-acetoxy-5,6-dihydro-2-(1H)-pyridone (5).     

Structures of two highly oxygenated iridoid glucosides from Globularia alypum

Structures of two acylated iridoid glucosides $\text{1}$ and $\text{6}$ were determined on the basis of chemical transformation and spectroscopic evidence.