Anatolioside E: A New Acyclic Monoterpene Glycoside from Viburnum orientale

A new open-chain monoterpene glycoside, anatolioside E ( 1 ), was isolated from the leaves of Viburnum orientale in addition to three known acyclic monoterpene glycosides, betulalbusides A ( 2 ) and B ( 3 ), and 2(E)-2,6-dimethyl-2,7-octadien-1,6-diol-6-O-β-D -glucopyranoside( 4 ). The structure of anatolioside E ( 1 ) was elucidated on the basis of chemical and spectral data as 6-O-[β-D -glucopyransoyl-(1?? → 6?″)-2-(E), 6(R), 2,6-dimethyl-6-hydroxy-2,7-octadienoyl-(1?″ → 2″″)-β-D -glucopyranosyl-(1″″ → 6?)-2-(E), 6(R), 2,6-dimethyl-6-hydroxy-2,7-octadienoyl-(1? → 4″)-α-L -rhamnopyranosyl-(1″″ → 2′)-β-D -glucopyranosyl]linalool.     

A Novel Monoterpene Glycoside from Swertia mileensis

A novel monoterpene glycoside, mileenside, was isolated from Swertia mileensis by repeated normal and reverse phase silica gel chromatography and its structure was elucidated mainly based on spectral evidence.     

Two Novel Monoterpene Alkaloid Dimers from Incarvillea arguta

Two novel monoterpene alkaloid dimers, named argutanes A and B ( 1 and 2 , resp.), together with the known alkaloid boschniakine ( 3 ), were isolated from the roots of Incarvillea arguta. The structures were elucidated on the basis of 1D‐ and 2D‐NMR, as well as HR‐ESI‐MS data.     

Dissectol A,A Novel Monoterpene Glycoside from Incarvillea dissectifoliola

Dissectol A,a novel monoterpene glycoside was isolated from the methanol part of the 95% EtOH extract of Incarvillea dissecfoliola and its structure was determined by 1D and 2D NMR data.     

虎眼万年青单萜内酯新成分的分离及结构鉴定

对虎眼万年青氯仿提取物进行柱层析分离,得到一种单萜内酯(Loliolide)化合物(6-羟基-4,4,7 a-三甲基-5,6,7,7 a-四氢-4H-苯并呋喃-2-酮),用红外光谱和核磁共振波谱确定了该化合物的结构,并用电喷雾多级串联质谱对化合物的裂解机理进行了研究.通过比旋光度和核磁共振氢谱确定了化合物的立体构型.     

A Novel Secobetulinic Acid 3,4‐Lactone from Viburnum aboricolum

Bio‐assay‐guided fractionation of the CHCl₃‐soluble extract from the leaves of Viburnum aboricolum led to the isolation of a novel secobetulinic acid 3,4‐lactone, viburolide (=(6β)‐4,6‐dihydroxy‐3,4‐secolup‐20(29)‐ene‐3,28‐dioic acid 3,4‐lactone; 1 ). This is the first lupane‐type compound possessing such a lactone skeleton from natural products. Its structure was elucidated by spectral analysis and comparison with 6‐dehydroxy‐20,29‐dihydroviburolide ( 6 ) prepared from benzyl betulinate ( 2 ). Compound 6 was found to inhibit androgen‐independent human prostate cancer cells (PC‐3) with an IC₅₀ of 12.3 μM .     

Iridoids from Viburnum cylindricum

Two new iridoids, methyl (+)‐rel‐(1R,3S,4R,5R,8R,9R)‐1,3,4,5,8,9‐hexahydro‐8‐hydroxy‐3‐methoxy‐2H‐1a,2‐dioxacyclopent[cd]indene‐4‐carboxylate ( 1 ) and methyl (+)‐rel‐(1R,3S,4S,5R,8R,9R)‐1,3,4,5,8,9‐hexahydro‐8‐hydroxy‐3‐methoxy‐2H‐1a,2‐dioxacyclopent[cd]indene‐4‐carboxylate ( 2 ), were isolated from Viburnum cylindricum along with 14 known compounds. Their structures were determined by spectroscopic analyses. This type of iridoids bearing a MeO group at C(3) was discovered for the first time.     

Monoterpene alkaloids from Argylia radiata

Argylia radiata (L.) D. Don (Bignoniaceae) represents an important source of secondary metabolites, largely unexplored. The paper presents the isolation from the plant root of two new monoterpene alkaloids, 10-acetoxy-actinidine and 4-nor-7,8-dehydro-10-hydroxy-skytanthine, whose structures were elucidated by Mass spectrometry and 1H-NMR data.     

Monoterpene glycosides from Indigofera hetrantha

Monoterpene glycosides have been isolated from the ethyl acetate soluble fraction of Indigofera hetrantha and their structures assigned to be 3,7-dimethyl-2(E),6-octadien-5-one-1-O-beta-D-6-O-acetylglucopyranoside (1) and 3,7-dimethyl-2(E), 6-octadien-5-one-1-O-[-beta-D-6'-O-acetylglucopyra-nosyl (1' --> 6')-beta-D-glucopyranoside] (2), on the basis of spectroscopic analysis including 1D and 2D NMR techniques. Compounds 1 and 2 displayed moderate inhibitory potential against the enzyme lipoxygenase.     

Iridoid glucosides from Viburnum chinshanense

The phytochemical study of the aerial parts of Viburnum chinshanense Graebn., a species growing in Western and Central China, led to the isolation of six iridoid glucosides: the novel 10,2'-diacetylpatrinoside, 1, and the known 2'-acetyldihydropenstemide, 2'-trans- p-coumaroyl-dihydropenstemide, 2'-acetylpatrinoside, decapetaloside, and patrinoside. In addition, amentoflavone and rosarin were also isolated.     

Iridoid glucosides from Viburnum sargenti

The phytochemical study of aerial parts of Viburnum sargenti Koehne, a species spontaneous in Mongolia and Northern China, led to the isolation of three iridoid glucosides of Valeriana-type: the novel 7,10,2'-triacetylsuspensolide F, 1, and the known viburtinoside IV and V. In addition, (+)-epicatechin was also isolated.     

Vibsane-type diterpenes from Taiwanese Viburnum odoratissimum

Two new eleven-membered and three new seven-membered vibsane-type diterpenes, named vibsanin L (1) and 14-hydroxyvibsanin F (2), and vibsanin I (3), 14R*,15-epoxyvibsanin C (4) and 14S*,15-epoxyvibsanin C (5) respectively, have been isolated from Viburnum odoratissimum collected in Taiwan. Their structures have been elucidated by spectroscopic analyses and comparison of Nuclear magnetic resonance method (NMR) data with those of the previously reported vibsane-type diterpenes. High performance liquid chromatography (HPLC) analyses indicated that the methanol extract of V. odoratissimum collected in Taiwan contained no neovibsanines, characteristic chemicals occurring in V. awabuki.     

Three New Monoterpene Glucosides from Lamium amplexicaule

Three new monoterpene glucosides, lamiuamplexosides A–C ( 1 – 3 ), along with thirteen known glucosides, were isolated from the whole plant of Lamium amplexicaule L. The structures of 1 – 3 were elucidated on the basis of spectroscopic, chemical, and physicochemical evidence.     

Six New Dammarane Triterpenoids from Viburnum cylindricum

One new dammarane triterpenoid, cylindrictone A ( 1 ), as well as five new nor‐dammarane triterpenoids cylindrictone B–F ( 2 – 6 ) were isolated from the leaves of Viburnum cylindrium, together with three known compounds 3β‐hydroxy‐hexanordammaran‐20‐one ( 7 ), 3α‐hydroxyoctanordammar‐12‐en‐17‐one ( 8 ), and neoalsogenin B ( 9 ). Their structures were identified by extensive NMR‐spectroscopic (especially 2D‐NMR) and mass‐spectrometric experiments, and the structure of 3 was further confirmed by a single‐crystal X‐ray analysis. The compounds exhibited no activity against human promyelocytic leukemia HL60 cell.     

Seven New Phenolic Glucosides from Viburnum cylindricum

Seven new phenolic glucosides, 2′‐O‐acetylhenryoside ( 1 ), 2′,3′‐di‐O‐acetylhenryoside ( 2 ), 2′,6′‐di‐O‐acetylhenryoside ( 3 ), 2′,3′,6′‐tri‐O‐acetylhenryoside ( 4 ), 2′,3′,4′,6′‐tetra‐O‐acetylhenryoside ( 5 ), 2‐[(2,3‐di‐O‐acetyl‐β‐D ‐glucopyranosyl)oxy]‐6‐hydroxybenzoic acid ( 6 ), and 6‐hydroxy‐2‐[(2,3,4,6‐tetra‐O‐acetyl‐β‐D ‐glucopyranosyl)oxy]benzoic acid ( 7 ), were isolated from the leaves and stems of Viburnum cylindricum, along with 26 known compounds (henryoside=2‐(β‐D ‐glucopyranosyloxy)‐6‐hydroxybenzoic acid [2‐(β‐D ‐glucopyranosyloxy)phenyl]methyl ester). The structures of the new compounds were established on the basis of chemical and spectroscopic evidences.     

Chemical Composition of Essential Oils from Hedyosmum orientale

Chemistry of Natural Compounds -     

Monoterpene glucosides from Ziziphora clinopodioides (Labiatae)

Three new monoterpene glucosides, ziziphoroside A (1), B (2), and C (3), together with fifteen known compounds were isolated from the whole herb of Z. clinopodioides. The structures of new compounds were determined primarily from 1D-, 2D-NMR and circular dichroism (CD) spectroscopic analyses. The isolated compounds were evaluated for their inhibitory activity against nitric oxide (NO) production by lipopolysaccharide (LPS) and interferon (IFN)-γ activated macrophages, RAW 264.7. Shizonepetoside A (8) and flavones (11, 12, 13) showed potent inhibitory activity against NO production.