Two new diarylheptanoids from Alnus nitida

Two new diarylheptanoids, trivially named nitidone A and nitidone B, have been isolated from Alnus nitida. The structure elucidation of the compounds was based primarily on 2D-NMR spectroscopic techniques and by comparison with literature data.     

Preparative isolation and purification of antioxidative diarylheptanoid derivatives from Alnus japonica by high-speed counter-current chromatography

This study employed the online HPLC-2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS)(+) bioassay to rapidly determine the antioxidant compounds occurring in the crude extract of Alnus japonica. The negative peaks of the ABTS(+) radical scavenging detection system, which indicated the presence of antioxidant activity, were monitored by measuring the decrease in absorbance at 734 nm. The ABTS(+)-based antioxidant activity profile showed that three negative peaks exhibited antioxidant activity. High-speed counter-current chromatography (HSCCC) was used for preparative scale separation of the three active peaks from the extract. The purity of the isolated compounds was analyzed by HPLC and their structures were identified by (1)H- and (13)C-nuclear magnetic resonance spectrometry (NMR), heteronuclear multiple bond correlation (HMBC), and heteronuclear single quantum correlation (HSQC). Two solvent systems composed of n-hexane/ethylacetate/methanol/water (4:6:4:6, v/v) and of ethyl acetate/methanol/water (1:0.1:1, v/v) were performed in high-speed counter-current chromatography. Consequently, a total of 527 mg of hirsutanonol 5-O-β-D-glucopyranoside, 80.04 mg of 3-deoxohirsutenonol 5-O-β-D-glucopyranoside, and 91.0 mg of hirsutenone were obtained with purity of 94.7, 90.5, and 98.6%, respectively.     

New Diarylheptanoid from the Barks of Alnus japonica Steudel

A new diarylheptanoid glycoside, 1,7-bis-（3,4-dihydroxyphenyl）-5-hydroxyheptane- 3-O-β-D-xylopyranoside （1）, together with nine known diarylheptanoids （2-10） were isolated from the fresh bark of Alnus japonica which is a species of the genus Alnus species, growing throughout Korea.     

New diarylheptanoids from Alpinia pinnanensis

Three new diarylheptanoids, called alpinnanins A-C (1-3), together with two known chalcones, 2',4'-dihydroxy-6'-methoxychalcone and 4',6'-dimethylchalconaringenin, two known flavanones, alpinetin and naringenin 5-O-methyl ether, a known diarylheptanoid, (3S,5S)-trans-3,5-dihydroxy-1,7-diphenyl-1-heptene, stigmasterol and beta-sitosterol as a mixture, and beta-sitosterol 3-O-beta-D-glucopyranoside were isolated from the rhizomes of Alpinia pinnanensis T. L. WU et SENJEN (Zingiberaceae). Their structures were elucidated by spectroscopic analyses.     

New diarylheptanoids from Amomum muricarpum ELMER

Two new diarylheptanoids, designated muricarpones A and B, together with three known diarylheptanoids, 1,7-di-(3',4'-dihydroxyphenyl)-4-hepten-3-one, 1-(3',4'-dihydroxyphenyl)-7-(4'-hydroxyphenyl)-4-hepten-3-one, and 1,7-bis(p-hydroxyphenyl)-4-hepten-3-one, were isolated from the rhizomes of Amomum muricarpum ELMER (Zingiberaceae). Their structures were determined using spectroscopic analyses.     

Three new phenylethanoid glycosides from Caryopteris incana and their antioxidative activity

Three new phenylethanoid glycosides, incanoside C, incanoside D and incanoside E were isolated together with one known glycoside, beta-D-fructofuranosyl-alpha-D-(6-O-[E]-sinapoyl) glucopyranoside from the whole plant of Caryopteris incana (THUNB.) Miq. On the basis of chemical and spectral analyses, the structures of the new compounds were elucidated to be 1-O-(3,4-dihydroxyphenyl)ethyl-O-beta-D-glucopyranosyl(1-->2)-alpha-L- rhamnopyranosyl(1-->3)-4-O-feruloyl-beta-D-glucopyranoside (incanoside C), 1-O-(3-hydroxy-4-methoxyphenyl)ethyl-O-beta-D-glucopyranosyl(1-->2)-alph a-L- rhamnopyranosyl(1-->3)-4-O-feruloyl-beta-D-glucopyranoside (incanoside D) and 1-O-(3methoxy-4-hydroxyphenyl)ethyl-O-beta-D-glucopyranosyl(1-->2) -alpha-L- rhamnopyranosyl(l-->3)-4-O-feruloyl-beta-D-glucopyranoside (incanoside E). The three new phenylethanoid glycosides exhibited radical scavenging activities against DPPH radical and inhibitory activities against the oxidation of linoleic acid.     

Three new diarylheptanoids and their antioxidant property

Three new diarylheptanoids,i.e.,sodium(5S,2E)-1,7-bis(4-hydroxyphenyl)-1-hydroxy-2-hepten-5-sulfonate(1), sodium(5R,2E)-1,7-bis(4-hydroxyphenyl)-1-hydroxy-2-hepten-5-sulfonate (2) and 3,5-diacetoxy-1-(3-methoxy-4,5-dihydroxy- phenyl)-7-(4-hydroxy-3-methoxyphenyl)heptane (3) were isolated from the rhizomes of Zingiber officinale.The structures of the new compounds were elucidated on the basis of spectroscopic methods.The antioxidant activities of 3 were assayed by in vitro models involving DPPH free radicals and superoxide anion radicals.     

Glutinoin, a novel antioxidative ellagitannin from Alnus glutinosa cones with glutinoic acid dilactone moiety

The crude aqueous ethanol extract of the cones of Alnus glutinosa (L.) Gaertn. (Betulaceae; black alder, European alder) was obtained and further partitioned between water and various organic phases. The active water and butanol phases were subjected to assay-guided (DPPH) fractionation using repetitive RP HPLC until individual compounds were isolated. Their antioxidative activities, measured as SC?? values, were evaluated. The chemical structures of the isolated compounds were elucidated with the help of mass spectroscopy, (1)H NMR technique, UV spectroscopy, and chemical approaches. One novel ellagitannin, glutinoin (2), along with two known compounds, pedunculagin (1) and praecoxin D (3), were isolated and found to contribute to antioxidative activity of the A. glutinosa cones extract. The activities (SC??) of 1-3 were evaluated as 0.95 (1), 1.00 (2) and 1.01?μg?mL?1 (3). The scavenging effects of glutinoin (2) and praecoxin D (3) were reported for the first time.     

Two thymol derivatives from the flower buds of Lonicera japonica and their antibacterial activity

A new monoterpenoid, 7-acetyl-8,9-dihydroxy thymol (1), together with a known one 7,8-dihydroxy-9-buyryl thymol (2), were isolated from the dried flower buds of Lonicera japonica Thunb. Their structures were elucidated on the basis of extensive 1D and 2D NMR spectroscopic data analyses. The potential antibacterial effects of these compounds on Staphylococcus aureus, Escherichia coli, Micrococcus luteus, and Bacillus cereus were evaluated. Interestingly, both compounds 1 and 2 exhibited significant antibacterial activities with IC₅₀ values range from 27.64 ± 2.26 to 128.58 ± 13.26 μg/mL.     

Inhibitory activity of diarylheptanoids on farnesyl protein transferase

Diarylheptanoids [curcumin (1), demethoxycurcumin (2), bisdemethoxycurcumin (3), bisdimethoxymethylcurcumin (4), and 1,2-dihydrobis(de-O-methyl)curcumin (5)] were isolated from the methanolic extract of Curcuma longa L. and a new cyclic diarylheptanoid (6) and a known Compound 7 were isolated from fruits of Alnus japonica Steud. Diarylheptanoids (1-3) inhibited farnesyl protein transferase (FPTase) with an IC50 of 29-50 microM. The other compounds very mildly inhibited FPTase, therefore, the inhibitory activity on FPTase very much depends on the structure of diarylheptanoids.     

New Secoiridoid Glucosides from Swertia japonica

Four new secoiridoid glucosides, swertiajaposides C–F ( 1 – 4 , resp.), were isolated from the whole plant of Swertia japonica Makino together with two known compounds, 8‐hydroxy‐10‐hydrosweroside ( 5 ) and senburiside IV ( 6 ). The structures of 1 – 4 were elucidated on the basis of spectroscopic, chemical, and physicochemical evidence.     

Two New Sesquiterpenes from Inula Japonica

Two new sesquiterpenes were isolaed from the aerial patrs of Inula Japonica.Their structures were eluicated as 1β-hydroxy-8β-acetoxyeostic acid methyl ester and 1β-hydroxy-8β-acetoxyisocostic acid mster by spectral methods.     

In vitro and ex vivo antitubercular activity of diarylheptanoids from the rhizomes of Alpinia officinarum Hance

Phytochemical investigation of methanol extract of the rhizomes of Alpinia officinarum Hance afforded four known diarylheptanoids 1,7-diphenylhept-4-en-3-one (1), 5-hydroxy-1,7-diphenyl-3-heptanone (2), 5-hydroxy-7-(4″-hydroxy-3″-methoxyphenyl)-1-phenyl-3-heptanone (3), and 7-(4″-hydroxy-3″-methoxyphenyl)-1-phenyl heptan-3-one (4).The acetate derivative of (4), 7-(4″-actetate-3″-methoxy phenyl)-1-phenyl heptan-3-one (5), was prepared. These diarylheptanoids exhibited promising in vitro and ex vivo antitubercular activity for the first time against dormant Mycobacterium tuberculosis H37Ra with the IC₅₀ values between 0.34–47.69 and 0.13–22.91 μM, respectively. All compounds showed comparable activity against Mycobacterium bovis BCG (dormant phage) and did not show any activity against two gram + ve and two gram –ve bacterial strains. These compounds were also weakly cytotoxic up to 300 μM against three human cancer cell lines THP-1, Panc-1 and A549.     

Two New ent—Kaurane Diterpenoids from Isodon japonica

Two new ent-kauranoids,named maoyecrystals A (1) and B(2),were isolated from the EtOAc extract of the dried leaves of Isodon japonica (Burman f.) Hara collected in Tongbai mountains ,Henan Province,Their structures were determined on the basis of spectral data,especially by 2D NMR.     

New glycosides from the holothurian Cucumaria japonica

Four new compounds have been isolated from the fraction of weakly polar triterpene glycosides of the holothurianCucumaria japonica: cucumariosides A₁-2 (I), A₀-1 (II), A₀-2 (III), and A₀-3 (IV). The structures of these substances have been established by chemical and physical methods.Deceased.Pacific Ocean Institute of Bioorganic Chemistry, Far-Eastern Scientific Center, Russian Academy of Sciences, Vladivostok. Institute of Chemistry of Plant Substances, Uzbekistan Republic Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 242–248, March–April, 1993.     

Three New Atisane Diterpenoids from Spiraea japonica

Three new atisane diterpenoids, spiratisanins A – C ( 1  –  3 , resp.), featuring a phenylacryloxyl substituted ent‐atisane skeleton, were isolated from Spiraea japonica together with two known atisine diterpene alkaloids, spiramine A ( 4 ) and spiradine F ( 5 ). The structures of these new compounds were elucidated as (5β,7α,8α,9β,10α,12α,16β)‐16‐hydroxyatisan‐7‐yl (2E)‐3‐phenylprop‐2‐enoate ( 1 ), (5β,7α,8α,9β,10α,12α,16α)‐16‐hydroxyatisan‐7‐yl (2E)‐3‐phenylprop‐2‐enoate ( 2 ), and (5β,8α,9β,10α,12α,16β)‐16‐hydroxyatisan‐20‐yl (2E)‐3‐phenylprop‐2‐enoate ( 3 ) on the basis of spectroscopic analysis.     

One new and several minor diarylheptanoids from Amomum muricarpum

A new natural diarylheptanoid, designated muricarpin, together with four diarylheptanoids were isolated from the rhizomes of Amomum muricarpum Elmer (Zingiberaceae) growing in Vietnam. Three known compounds, 1,7-bis(3,4-dihydroxyphenyl)heptan-3-yl acetate, 1-(4'-hydroxyphenyl)-7- (3″,4″-dihydroxyphenyl)heptan-3-yl acetate and 1-(3',4'-dihydroxyphenyl)-7-(4″-hydroxyphenyl)-heptan-3-one were isolated for the first time from the genus Amomum, meanwhile (5R)-5-hydroxy-1,7-bis(4-hydroxyphenyl)-heptan-3-one was found for the first time in plants. Their structures were determined using spectroscopic analyses.     

A New Phytotoxic Sesquiterpene from Inula japonica

Chemistry of Natural Compounds - A new eudesmane sesquiterpene, 12-acetoxy-1β,2α-dihydroxyeudesma-4(15),11(13)-diene (1), was isolated from Inula japonica. The chemical structure of...     

New megastigmane and tetraketide from the leaves of Euscaphis japonica

New megastigmane (1) and tetraketide (2) were isolated from the leaves of Euscaphis japonica and the structures were elucidated by means of spectroscopic and chemical evidence.