A New Sesquiterpene from the Roots of Chloranthus multistachys

Chemistry of Natural Compounds - A new sesquiterpene, 1β-hydroxy-4(5),7(8),11(12)-triene-6,9-dione-7,8-furanoeudesmane (1), was isolated from the root extract of Chloranthus multistachys C....     

Terpenoids from Roots of Chloranthus spicatus

Five new terpenoids, including four eudesmane‐type sesquiterpenoids, 1 – 4 , and one labdane‐type diterpenoid, 6 , together with ten known compounds, were isolated from the roots of Chloranthus spicatus. The structures and their relative configurations were mainly established by 1D‐ and 2D‐NMR spectra, and MS experiments.     

Two new polyhydroxysterols produced by Fusarium solani,an endophytic fungus from Chloranthus multistachys

A highly antagonistic endophytic fungus, designated strain CL39, was originated from the leaves of Chloranthus multistachys collected in Wulong of Chongqing municipality of China in November 2015. The strain was identified as Fusarium solani based on morphological characteristics, 5.8S gene and internal transcribed spacer sequence analysis. Two new compounds, 2β, 9α-dihydroxy-5α-methoxyergosta-7, 22-diene (1), 2β, 6β-dihydroxy-5α-methoxyergosta-7, 22-diene (2) have been isolated from the culture broth of the strain. Structures of the new compounds were elucidated by detailed analysis of their spectroscopic data aided by the comparison with reported data of related derivatives, and found to belong to the polyhydroxylated steroids with a hydroxyl at C-2 instead of C-3, a rare structure among the steroids. The extract of this strain and all isolated compounds were evaluated for their antagonistic activities.     

New Sesquiterpenes from Chloranthus japonicus

Chemical investigation of the roots of Chloranthus japonicus Sieb . has resulted in the isolation and characterization of four new eudesmane‐type sesquiterpenes including two new sesquiterpene cinnamates, along with one new and two known sesquiterpene dimers. Their structures were established by spectroscopic means and by comparison with the respective literature values.     

A new tetrahydrophenanthrene from Chloranthus henryi

<正>A new tetrahydrophenanthrene named henryin A(1) was isolated from the leaves of Chloranthus henryi.Its structure was determined to be(S)-4,6,9-trimethyl-5,6,7,8-tetrahydrophenanthrene-1,2-diol on the basis of IR,MS,1D and 2D NMR spectral.     

Terpenoids from endophytic fungi

This work reviews the production of terpenoids by endophytic fungi and their biological activities, in period of 2006 to 2010. Sixty five sesquiterpenes, 45 diterpenes, five meroterpenes and 12 other terpenes, amounting to 127 terpenoids were isolated from endophytic fungi.     

Terpenoids from Turraeanthus species

Chemical investigation of the root bark of Turraeanthus mannii and the stem of T. longipes resulted in the isolation of two new diterpenes, 13-methyl-labda-8(17)-en-15-oic acid (1) and 13-(hydroxymethyl)-14-hydroxy-ent-labda-8(17)-en-15-oic acid (2), along with two known diterpenes, 19-hydroxy-ent-labda-8(17),13-dien-15,16-olide (3) and 19-acetoxy-ent-labda-8(17),13-dien-15,16-olide (4), and the phytosterol, stigmasterol. The structure elucidation of the new compounds has been achieved using spectroscopic techniques.     

Terpenoids from Loxocalyx urticifolius

Two new diterpenoids, loxocalyxin A ( 1 ) and 13‐epiloxocalyxin A ( 2 ), and two new sesquiterpenoids, loxocalyxins B and C ( 3 and 4 , resp.), together with three known compounds, were isolated from the MeOH extract of the whole plant of Loxocalyx urticifolius Hemsl . The structures of the new compounds were established by means of spectroscopic analysis including one‐ and two‐dimensional NMR spectroscopy. All new structures were confirmed by X‐ray crystallographic analysis. Their absolute configurations were established.     

Terpenoids from Croton regelianus

Two new terpenoids, the bisnorditerpene rel‐(5β,8α,10α)‐8‐hydroxy‐13‐methylpodocarpa‐9(11),13‐diene‐3,12‐dione ( 1 ) and the guaiane sesquiterpene rel‐(1R,4S,6R,7S,8aR)‐decahydro‐1‐(hydroxymethyl)‐4,9,9‐trimethyl‐4,7‐(epoxymethano)azulen‐6‐ol ( 2 ), together with seven known compounds, were isolated from Croton regelianus var. matosii. The structures of the isolated compounds were determined by HR‐ESI‐TOF and a combination of 1D‐ and 2D‐NMR experiments.     

Two new sesquiterpenes from Chloranthus japonicus Sieb

Two new sesquiterpenes, namely, 1β,10β-dihydroxy-eremophil-7(11), 8-dien-12,8-olide (1) and 8,12-epoxy-1β-hydroxyeudesm-3,7,11-trien-9-one (2), together with three known sesquiterpenoids, shizukolidol (3), 4α-hydroxy-5α(H)-8β-methoxy-eudesm-7(11)-en-12,8-olide (4), and neolitacumone B (5), and two known monoterpenes, (3R,4S,6R)-p-menth-1-en-3,6-diol (6) and (R)-p-menth-1-en-4,7-diol (7), were isolated from the whole plant of Chloranthus japonicus Sieb. Their structures were elucidated on the basis of spectroscopic data analysis and comparison with those of related known compounds. Compounds 4–7 were isolated from this plant for the first time.     

Cadinane and Eudesmane Sesquiterpenoids from Chloranthus henryi

Chemical investigation of the leaves and stems of Chloranthus henryi resulted in the isolation and characterization of the three new cadinane‐type sesquiterpenes 1 – 3 and of the new eudesmane‐type sesquiterpene 4 , together with three known compounds. Among the new compounds, the two cadinane‐type sesquiterpenes 1 and 2 possess an unusual aromatic ring B in their molecule. These structures were established on the basis of spectroscopic evidence. In addition, antitumor activities of the isolates were also evaluated.     

Terpenoids from Two Dicranopteris Species

Two new compounds, (6S,13S)‐6‐{[β‐D ‐glucopyranosyl‐(1→4)‐α‐L ‐rhamnopyranosyl]oxy}cleroda‐3,14‐dien‐13‐ol ( 1 ) and kadsuric acid 3‐methyl ester ( 2 ), together with nine known compounds, (6S,13E)‐6‐{[β‐D ‐glucopyranosyl‐(1→4)‐α‐L ‐rhamnopyranosyl]oxy}cleroda‐3,13‐dien‐15‐ol ( 3 ), (6S,13S)‐6‐[6‐O‐acetyl‐β‐D ‐glucopyranosyl‐(1→4)‐α‐L ‐rhamnopyranosyl]oxy}‐13‐{[α‐L ‐rhamnopyranosyl‐(1→4)‐β‐D ‐fucopyranosyl]oxy}cleroda‐3,14‐diene ( 4 ), (6S,13S)‐6‐{[6‐O‐β‐D ‐glucopyranosyl‐(1→4)‐α‐L ‐rhamnopyranosyl]oxy}‐13‐{[α‐L ‐rhamnopyranosyl‐(1→4)‐β‐D ‐fucopyranosyl]oxy}cleroda‐3,14‐diene ( 5 ), 15‐hydroxydehydroabietic acid ( 6 ), 15‐hydroxylabd‐8(17)‐en‐19‐oic acid ( 7 ), junicedric acid ( 8 ), (4β)‐kaur‐16‐en‐18‐oic acid ( 9 ), (4β)‐16‐hydroxykauran‐18‐oic acid ( 10 ), and (4β,16β)‐16‐hydroxykauran‐18‐oic acid ( 11 ) were isolated from the fronds of Dicranopteris linearis or D. ampla. Their structures were established by extensive 1D‐ and 2D‐NMR spectroscopy. Compounds 1 and 3 – 8 showed no anti‐HIV activities.     

Terpenoids from Eupatorium fortunei Turcz

Four new terpenoids, namely, rel‐(1R,2S,3R,4R,6S)‐p‐menthane‐1,2,3,6‐tetrol ( 1 ), rel‐(1R,2R,3R,4S,6S)‐p‐menthane‐1,2,3,6‐tetrol ( 2 ), 9‐hydroxythymol 3‐O‐angelate ( 3 ), and (3β,20R)‐20‐hydroxylanost‐25‐en‐3‐yl palmitate ( 4 ), together with fourteen known compounds, were isolated from the AcOEt part of the MeOH extracts of Eupatorium fortunei. In addition, two other monoterpenoids, ‘acetone thymol‐8,9‐diyl ketal’ ( 19 ) and 8‐methoxy‐9‐hydroxythymol 3‐O‐angelate ( 20 ) were also obtained which were probably artifacts but have never been reported in the literature. The structures of the new compounds, including their relative configurations, were established by an extensive study of their spectral data, especially 1D‐ and 2D‐NMR. The cytotoxic activity of the new compounds against human hepatoma (SMMC‐7721), human leukemia (HL‐60), and human hepatocyte (LO₂) cells was investigated.     

Cytotoxic Terpenoids from Turraea pubescens

Three new triterpenoids, turrapubesols A–C ( 1 – 3 ), and one new sesquiterpenoid, 1α,4α‐dihydroxyeudesman‐11‐ene ( 4 ), along with 12 known terpenoids were isolated from Turraea pubescens. The structures of the terpenoids were established on the basis of extensive spectroscopic analyses and by a chemical transformation. The previous assignment of the NMR data for guaidiol ( 5 ) was corrected. Some of the triterpenoids exhibited cytotoxicity against the P‐388 cell line.     

Four New Eudesmane Sesquiterpenoid Lactones from Chloranthus serratus

Four new eudesmane sesquiterpenoids endowed with an α,β‐unsaturated γ‐lactone five‐membered ring, serralactones A–D ( 1 – 4 , resp.), along with seven known sesquiterpenoids, were isolated from the whole plant Chloranthus serratus. Their structures and relative configurations were established on the basis of extensive spectroscopic analyses.     

Three New Terpenoids from Pinus yunnanensis

A new abietatrienoid, 15‐methoxydidehydroabietic acid ( 1 ), a new ring B‐seco abietatrienoid, 10‐hydroxy‐9,10‐secoabieta‐8,11,13‐trien‐18‐oic acid ( 2 ), and a new tetracyclic triterpenoid, pinusyunnanol ( 3 ), together with five known compounds, were obtained from the twigs and needles of Pinus yunnanensis. The structures of the new compounds were elucidated by means of extensive spectroscopic analyses.