A new chalcone from the aerial roots of Ficus microcarpa

A new flavonoid with chalcone skeleton was isolated from the dried aerial roots of Ficus microcarpa.The structure of the compound was elucidated on the basis of spectral methods including ID and 2D NMR.The new compound showed weak inhibitory effect on nitric oxide production and cytotoxicity against K562 and PC3 ceils.     

Six new ursane- and oleanane-type triterpenes from the aerial roots of Ficus microcarpa

Four new ursane-type triterpenes, 3beta-acetoxy-11alpha-methoxy-12-ursene (1), 3beta-acetoxy-11alpha-ethoxy-12-ursene (2), 3beta-acetoxy-11alpha-hydroperoxy-12-ursene (3), 3beta-hydroxy-11alpha-hydroperoxy-12-ursene (4), and two new oleanane-type triterpenes, 3beta-acetoxy-11alpha-ethoxy-12-oleanene (5), 3beta-acetoxy-111alpha-hydroperoxy-12-oleanene (6), together with 3beta-acetoxy-11alpha-hydroxy-12-ursene (7), 3beta,11alpha-diacetoxy-12-ursene (8), 3beta-acetoxy-11alpha-hydroxy-12-oleanene (9), were isolated from the aerial roots of Ficus microcarpa L. f. Their structures were elucidated by spectroscopic and chemical methods.     

Two new compounds from the heartwood of Dalbergia melanoxylon

Abstract

A new neoflavonoid, named S(+)-3′-hydroxy-4′,2,4,5-tetramethoxydalbergiquinol (1), and a new benzofuran, named (2S,3S)-5-hydroxy-6-methoxy-3-methyl-2-(4′-hydroxyphenyl)-2,3dihydrobenzofuran (4), together with two known neoflavonoids, were isolated from the heartwood of Dalbergia melanoxylon. Their structures were elucidated by a combination of spectroscopic methods and comparison with the literature. Compounds 1–4 were evaluated for inhibitory activity against Staphylococcus aureus ATCC 25923, Escherichia coli ATCC 6538, Salmonella enteri CMCC 50041 and Candida albicans ATCC 289065, which all exhibited inactive or weak activity.     

Six new compounds from the heartwood of Diospyros maritima

Six new compounds, diospyrolide (1), diospyrolidone (2), diethyl (2R)-malate (3), 3-(E)-coumaroylbetulin-28-yl ethyl nonanedioate (4), 3-(E)-coumaroylbetulin-28-yl ethyl succinate (5), and 3-(E)-coumaroylbetulin-28-yl ethyl (2R)-2-hydroxysuccinate (6), have been isolated from the heartwood of Diospyros maritima. Compounds 1 and 2 are novel trinorlupanes, and 4, 5 and 6 are lupane derivatives. Their structures were determined using spectral and chemical methods.     

New cyclopropyl-triterpenoids from the aerial roots of Ficus microcarpa

Four new cyclopropyl-triterpenes, 27-nor-3beta-hydroxy-25-oxocycloartane (1), (22E)-25,26,27-trinor-3beta-hydroxycycloart-22-en-24-al (2), 3beta-acetoxy-15alpha-hydroxy-13,27-cyclours-11-ene (3), 3beta-acetoxy-12alpha-formyloxy-13,27-cycloursan-11alpha-ol (4), together with (23E)-27-nor-3beta-hydroxycycloart-23-en-25-one (5) were isolated from the aerial roots of Ficus microcarpa. Compounds 3 and 4 are rare 13,27-cycloursane-type triterpenes. Their structures were elucidated by spectroscopic and chemical methods.     

Novel triterpenoids from the aerial roots of Ficus microcarpa

Three novel triterpenoids, 3beta-acetoxy-11alpha-hydroxy-11(12-->13)abeooleanan-12-al (1), 3beta-hydroxy-20-oxo-29(20-->19)abeolupane (2), and 29,30-dinor-3beta-acetoxy-18,19-dioxo-18,19-secolupane (3), and the known 4, 5a, and 5b were isolated from the aerial roots of Ficus microcarpa. Their structures were elucidated on the basis of 2D NMR and X-ray diffraction experiments. Compound 1, derived from the oleanane skeleton, has an unusual five-membered C ring. Compounds 2 and 3, derived from the lupane skeleton, have unique skeletons that may arise from the same biogenetic pathway.     

Two Novel Triterpenes from the Leaves of Ficus microcarpa

Two novel triterpenes, 29(20→19)abeolupane‐3,20‐dione ( 4 ) and 19,20‐secoursane‐3,19,20‐trione ( 5 ), besides (3β)‐3‐hydroxy‐29(20→19)abeolupan‐20‐one ( 2 ), lupenone, and α‐amyrone ( 6 ), were isolated from the leaves of Ficus microcarpa and were characterized by spectroscopic means, including 2D‐NMR techniques and chemical methods. Compound 4 is the second derivative having the 29(20→19)abeolupane skeleton, and 5 is a novel skeleton. A biosynthetic pathway to 5 is proposed (Scheme).     

Ficusmicrochlorin A-C, two new methoxy lactone chlorins and an anhydride chlorin from the leaves of Ficus microcarpa

Two new methoxy lactone chlorins ficusmicrochlorin A (1) and ficusmicrochlorin B (2), and one new anhydride chlorin ficusmicrochlorin C (3), along with eight known pheophytins were isolated from the leaves of Ficus microcarpa. Their structures were determined by the extensive 1D- and 2D-NMR techniques. New pheophytin compound was rarely obtained from natural sources. In the past ten years, only three new natural pheophytins were characterized.     

Water-soluble phenylpropanoid constituents from aerial roots of Ficus microcarpa

New water-soluble phenylpropanoid constituents, ficuscarpanoside A, guaiacylglycerol 9-O-beta-D-glucopyranoside, and erythro-guaiacylglycerol 9-O-beta-D-glucopyranoside, along with known guaiacylglycerol, erythro-guaiacylglycerol, 4-methoxy guaiacylglycerol 7-O-beta-D-glucopyranoside, and 3-(4-hydroxy-3-methoxy phenyl) propan-1,2-diol, have been isolated from the aerial roots of Ficus microcarpa. Their structures were elucidated on the basis of 1D and 2D NMR experiments.     

Four new compounds from Neoboletus magnificus

Abstract

Four new compounds, compounds 1, 2, 4, 6, along with two known compounds 3, 5, were isolated from the methanol extract of the fruiting body of Neoboletus magnificus. The structures of compounds were elucidated by HRMS and NMR spectroscopic methods. The in vitro anti-inflammatory activity of the isolated compounds was evaluated.     

Four new compounds from Dendrobium devonianum

Two new phenanthrenes dendrodevonin A and B, two new aliphatic acids dendrodevonic acid A and B, along with ten known compounds, were isolated from the stems of Dendrobium devonianum. The structures of new compounds were elucidated on the basis of MS and NMR spectroscopic data, and single-crystal X-ray diffraction analysis. The cytotoxicities of isolates towards HT-29 cell were discussed, and 4-methoxy-2,7-phenanthrenediol exhibited inhibitory activity compared with other studied compounds.     

Constituents of the Bark of Ficus microcarpa Lf.

The isolation and identification of twenty-eight crystalline components from the bark of Ficus microcarpa L.f. are described. Their structures were determined on the basis of spectral data and values taken from the literature. These compounds include fourteen triterpenoids, one fatty alcohol, eight steroids, one coumarin, one flavane, two 4-hydroxybenzoates, and one carotenoid-like compound.     

A new benzofuran from the heartwood of Dalbergia latifolia

A new benzofuran compound, named 2-[5-hydroxy-4-methoxy-2-(3-p-henyl-trans-allyloxy)benzyl]-5-hydroxy-6-methoxy-3-phenylbenzofuran (1), together with (+)-obtusafuran (2) and isoparvifuran (3), was isolated from the heartwood of Dalbergia latifolia. Their structures were elucidated by a combination of spectroscopic methods and comparison with the literature. Compounds 2 and 3 were obtained from this plant for the first time. Compound 1 exhibited moderated antioxidant effect for scavenging 1,1-diphenyl-2-picryhydrazyl (DPPH) free radical (IC₅₀ = 96.7 ± 8.9 μM).     

A new isoflavonostilbene from the heartwood of Maackia amurensis

A new isoflavonostilbene which has been called maackiasin has been isolated from an ethanolic extract of the heartwood ofMaackia amurensis and its structure has been established by spectral methods. The maackiasin molecule is constructed of fragments of the isoflavone retusin and of 3,3,4,5-tetrahydroxystilbene linked by a diether bond. The dioxane grouping connecting the two fragments is constructed from the hydroxyls at C-7 and C-8 of the isoflavone and the vinyl grouping of the stilbene. Maackiasin is the first representative of a new type of natural polyphenols.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 39–42, January–February, 1986.     

A new drimane from the heartwood of the Japanese yew, Taxus cuspidata

A new drimane sesquiterpenoid was isolated from the heartwood of the Japanese yew, Taxus cuspidata Sieb. et Zucc. Its structure was established as 1beta-acetoxyisodrimeninol (1beta-acetoxy-11,12-epoxy-7-drimen-11-ol, 1). This compound was gradually oxidized to give y-lactone (1beta-acetoxy-8-drimeno-11,12-lactone, 4).     

A new diaryl 1, 2-diketone from the heartwood of Dalbergia latifolia

A new diaryl 1,2-diketone, named 1-(2,5-dihydroxy-4-methoxyphenyl)-2-phenylethane-1,2-dione (1), along with eight known compounds (2–9), were isolated from the heartwood of Dalbergia latifolia. They were identified on the basis of spectral data. Compounds 1–7 were obtained from the Dalbergia genus for the first time. Compounds 8 and 9 were firstly isolated from the plant. Compound 1 exhibited inactive against Staphylococcus aureus ATCC 6538 and Escherichia coli ATCC 21530 with the minimum inhibitory concentrations of 10.0 and 10.0 mg/mL, respectively.     

A new norisoprenoid from the leaves of Ficus pumila

One new norisoprenoid 3,9-dihydroxy dihydro actinidiolide (1), together with eleven known compounds (2–12), were isolated from ethanol extract of the leaves of Ficus pumila collected in Hainan Province, China. Their structures were elucidated by the detailed analysis of comprehensive spectroscopic data. Compounds 1, 2, 4, 5, 8 and 10–12 were isolated from the F. pumila for the first time. All compounds were evaluated for their cytotoxic activity. Compounds 3 and 9 showed weak cytotoxic activity against Hela, MCF-7 and A549 cell lines.     

A new isoflavone from the roots of Ficus auriculata

A new isoflavone, 5,7,4′-trihydroxy-3′-hydroxymethylisoflavone (1), together with three known isoflavones, 3′-formyl-5,4′-dihydroxy-7-methoxyisoflavone (2), ficuisoflavone (3) and alpinumisoflavone (4), were isolated from the roots of Ficus auriculata. Among them, 1 is a rare isoflavone containing 16 carbon atoms on the carbon skeleton. The structure of 1 was elucidated by extensive spectroscopic methods and the known compounds were identified by comparisons with data reported in the literature. All compounds were evaluated for their antibacterial activities against five terrestrial pathogenic bacteria in vitro. Compounds 1–4 showed significant antibacterial activities against various terrestrial pathogenic bacteria with MIC values ranging from 1.30 to 39.93 μM.