A comprehensive review on the chemical constituents,sesquiterpenoid biosynthesis and biological activities of Sarcandra glabra

Sarcandra glabra(Thunb.)Nakai is a perennial evergreen herb categorised within the Sarcandra Gardner genus under the Chloranthaceae family.Indigenous to tropical and subtropical regions of East Asia and India,this species is extensively distributed across China,particularly in the southern regions(Sichuan,Yunnan,and Jiangxi).In addition to its high ornamental value,S.glabra has a rich history of use in traditional Chinese medicine,evident through its empirical prescriptions for various ailments like pneumonia,dysentery,fractures,bruises,numbness,amenorrhea,rheumatism,and other diseases.Besides,modern pharmacological studies have revealed various biological activities,such as antitumour,anti-bacterial,anti-viral anti-inflammatory and immunomodulatory effects.The diverse chemical constituents of S.glabra have fascinated natural product researchers since the 1900s.To date,over 400 compounds including terpenoids,coumarins,lignans,flavonoids,sterols,anthraquinones,organic acids,and organic esters have been isolated and characterised,some featuring unprecedented structures.This review comprehensively examines the current understanding of S.glabra’s phytochemistry and pharmacology,with emphasis on the chemistry and biosynthesis of its unique chemotaxonomic marker,the lindenane-type sesquiterpenoids.

A review of research on the chemical constituents and pharmacological effects of Elephantopus tomentosus L.

Elephantopus tomentosus,belonging to the genus Elephantopus,is widely distributed in the coastal areas of southern China and tropical regions,used locally as traditional folk medicine.Previous phytochemistry studies on Elephantopus tomentosus led to the isolation of sesquiterpenoids,triterpenoids,flavonoids and other compounds.Research has shown that these compounds possess multiple biological activities,which have attracted great attention of researchers worldwide.This study reviews the chemical constituents and biological activities of the Elephantopus tomentosus in order to better explore and utilize Elephantopus tomentosus.

Carbon-13 Nuclear Magnetic Resonance Spectra of Some Protoilludane Sesquiterpenoid Aromatic Esters from Armillaria mellea (Vahl.ex Fr.) Quel.

The carbon-13 nuclear magnetic resonance spectra of seventeen protoilludane ses- quiterpenoid aromatic esters from the artificially cultured mycelium of Armillaria mellea (Vahl.ex Fr.) Quel.have been analysed and assigned.All the ^(11)CNMR signals of the model compounds melleolide 5 and compounds 8,10,11,13,14,15,and 16 can be assigned on the basis of the multiplicity of the sig- nals in the off-resonance decoupled spectra or INEPT spectra.^(11)C-~1H COSY and long-range ^(13)C-~1H COSY.The assignments of the ^(13)CNMR spectra of other protoilludane sesquiterpenoid aromatic esters were completed by comparison with the model compounds as well as the electronic effects of substi- tuted group on the molecules.The present results indicate that ^(11)CNMR spectroscopy provides an ef- fective method for characterizing the protoilludane sesquiterpenoid aromatic esters.

A New Sesquiterpenoid from Russula lepida

new aristolane sesquiterpenoid named rulepidol was isolated from the fruiting body of Russula lepida Fr. Its structure was elucidated as (1a alpha ,5 alpha ,7 alpha ,7a alpha, 7b alpha)-1, 1a,4,5,6,7,7a, 7b-octahydro-5-hydroxy-1,1,7,7a-tetramethyl-5H-cyclopropa [alpha] naphthalen-2-one mainly by 1D and 2D-NMR techniques.

Eremophilane Sesquiterpenoids from Coleus xanthanthus

A new eremophilane sesquiterpenoid, along with two known ones, was isolated from the ethyl acetate soluble fraction of the aerial part of Coleus xanthanthus C. Y. Wu et Y. C. Huang. Their structures were elucidated as 4,5,11_trimethyl_8,9_seco_1(10),7(11)_eremophiladien_8,12_olid_9_oic acid (1), 2,9_dioxoeuryopsin (2) and 9_oxoeuryopsin (3) by spectral methods. The 1H_NMR and 13 C NMR data of compounds 1, 2 and 3 were unambiguously assigned on the basis of two_dimensional NMR spectroscopy.

Oxyphyllones A and B,novel sesquiterpenes with an unusual 4,5-secoeudesmane skeleton from Alpinia oxyphylla

Two novel 4,5-secoeudesmane sesquiterpenoids, oxyphyllones A （1） and B （2） were isolated from the fruits of Alpinia oxyphylla. Their structures were established by spectroscopic methods including 1D and 21） NMR spectra. These two compounds are the first example of naturally occurring sesquiterpenoids with a 4,5-secoeudesmane skeleton in the family of Zingiberaceae and oxyphyllone A （1） is the first 4,5-secoeudesmane type of 13-norsesquiterpenoid. Compounds 1 and 2 exhibited no cytotoxicities against three cancer cell lines at 10 μg/mL. ？ 2009 Ning Hua Tan. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

Two New Sequiterpenoids from Helicteres angustifolia

A new sesquiterpenoid lactone, 3,6,9-trimethyl-pyrano[2,3,4-de]chromen-2-one (1) and a novel sesquiterpenoid quinone, 6-[2-(5-acetyl-2,7-dimethyl-8-oxo-bicyclo[4.2.0]octa-1,3,5- trien-7-yl)-2-oxo-ethyl]-3,9-dimethylnaphtho[1,8-bc]pyran-7,8-dione (2) together with a known perezone (3) were isolated from the roots of Helicteres angustifolia. The structures were elucidated as mainly on the basis of 1D and 2D NMR spectroscopic data.

Two New Compounds from Schisandra propinqua var.propinqua

Schisanpropinoic acid(1),a new bergamotane sesquiterpenoid,and schisanpropinin(2),a new tetrahydrofuran lignan with a rare epoxyethane unit,were identified from the stems and leaves of Schisandra propinqua var.propinqua.Their structures were determined based on comprehensive spectroscopic and mass spectrometric analysis.The absolute configuration of 1 was determined by X-ray analysis.Compounds 1 and 2 were tested for their cytotoxic activity against five human tumor cell lines.

THE STRUCTURE OF ARMILLARIZIN,A NEW PROTOILLUDANE SESQUITERPENOID AROMATIC ESTER FROM ARMILLARIA MELLEA(VAHL.EX FR)QUEL.

A new protoilludane sesquiterpenoid aromatic ester,named armillarizin (1)has been isolated from the artificially cultured mycelium of Armillaria me- llea(Vahl.ex Fr)Quel.(Tricholomataceae).Its structure was deduced on the ba- sis of spectral analyses.The relative configuration was established from the nuclear Overhauser effects and from the values of ~1H-~1H coupling constants.

Two novel fomannosane-type sesquiterpenoids from the culture of the basidiomycete Agrocybe salicacola

Two novel fomannosane-type sesquiterpenoids,agrocybins H(1)and I(2),together with a known compound illudosin(3),were isolated from the culture broth of the mushroom Agrocybe salicacola.Their structures were elucidated by extensive spectroscopic analysis.The relative stereochemistry of 1 was determined by the use of single crystal X-ray crystallographic diffraction.

Drimane Sesquiterpenoids and Isochromone Derivative from the Endophytic Fungus Pestalotiopsis sp. M-23

Three new drimane sesquiterpenoids(1–3)together with the known 2a-hydroxyisodrimeninol(4),and a new isochromone derivative(5),were obtained from the solid cultures of fungal strain Pestalotiopsis sp.M-23,an endophytic fungus isolated from the leaves of Leucosceptrum canum(Labiatae).Their structures were determined by comprehensive 1D and 2D NMR,and MS analyses.The metabolites were evaluated for their antibacterial activities,and compound 3 showed weak inhibitory activity against Bacillus subtilis.

Integrated multi-omics analysis of developing‘Newhall’orange and its glossy mutant provide insights into citrus fragrance formation

Sesquiterpene valencene is dominant in flavedo tissues of sweet oranges and imparts a unique woody aroma.However,the interaction between the biosynthetic pathways of valencene and other nutritional compounds is less studied.Sesquiterpenoids were significantly accumulated in a previously reported glossy mutant of orange(MT)than the wild type(WT),especially valencene and caryophyllene.In addition,we identified several other pathways with variations at both the transcriptional and metabolic levels in MT.It’s interesting to found those upregulated metabolites in MT,such as eukaryotic lipids,kaempferol and proline also showed strong positive correlation with valencene along with fruit maturation while those down-regulated metabolites,such as phenylpropanoid coumarins and most of the modified flavonoids exhibited negative correlation.We then categorized these shifted pathways into the‘sesquitepenoid-identical shunt’and the sesquitepenoid-opposite shunt’and confirmed the classification result at transcriptional level.Our results provide important insights into the connections between various fruit quality-related properties.

Artemlavanins A and B from Artemisia lavandulaefolia and Their Cytotoxicity Against Hepatic Stellate Cell Line LX2

Two new sesquiterpenoids,artemlavanins A(1)and B(3),together with fifteen known compounds(2 and 4−17)were iso-lated from the EtOH extract of Artemisia lavandulaefolia.The structures of new compounds were elucidated by extensive spectroscopic analyses(HRESIMS,1D and 2D NMR)and ECD calculations.Compound 1 was a sesquiterpenoid lactone possessing a rearranged eudesmane skeleton;compounds 2-5,6-8,9 and 10-12 belonged to the eudesmane,guaiane,oppositane and farnesane sesquiterpenoids,respectively;compounds 13-17 were the phenyl derivatives with a 4-hydroxy-acetophenone moiety.Twelve compounds(1-3,5-7,10-12,14,15 and 17)displayed cytotoxicity against hepatic stellate cell line LX2(HSC-LX2)with IC50 values ranging from 35.1 to 370.3μM.Compounds 2,7,10-12 and 17 exhibited the stronger cytotoxicity than silybin(IC50,169.6μM)with IC50 values of 82.1,35.1,95.0,83.8,81.6 and 90.1μM.Compound 7 as the most active one showed significant inhibition on the deposition of human collagen type I(Col I),human hyaluronic acid(HA)and human laminin(HL)with IC50 values of 10.7,24.5 and 13.3μM.

New Sesquiterpenoids from Hedychium yunnanense gagnep

Two new sesquiterpenoid trialcohol isomers named 1 beta, 4 alpha 11 alpha -trihydroxyeudesmane (1) and Yunnanensehedychetriol (2), were isolated from the fresh rhizomes of Hedychium Yunnanense gagnep. Their structures were elucidated by spectroscopic methods.

Sesquiterpenoids from the Rhizomes of Homalomena occulta

Naturally occurring oplopanane sesquiterpenoids are rarely reported.A phytochemical investigation on the rhizomes of Homalomena occulta(Lours)has resulted in the discovery of six oplopanane sesquiterpenoids(1–6),including four new(1–4)and one 3,5-seco-oplopanane(6),together with three previously reported sesquiterpenoids(7-9).In addition three new oplopananes(2a–4a)were also obtained by chemical transformation.All structures of these sesquiterpenoids were established based on the comprehensive spectroscopic analyses,including NMR,MS,and IR,and comparing with the literatures.

Drimane sesquiterpenoids from a wetland soil-derived fungus Aspergillus calidoustus TJ403-EL05

Soil-derived fungi represent an insufficiently tapped reservoir for discovering new and bioactive natural products(NPs),and despite an ever-increasing number of unknown NPs have been discovered over the past few decades,much of the hidden biosynthetic potential is still in an urgent need to be disclosed.In this research,a chemical inves-tigation was performed on a wetland soil-derived fungus Aspergillus calidoustus TJ403-EL05,leading to the isolation of a total of fourteen drimane sesquiterpenoids(1-14),incorporating three new ones,namely ustusols F-H(1-3).Their structures,comprising absolute configurations,were completely authenticated by widespread spectroscopic data,quantum chemical 13C NMR and ECD calculations,and X-ray crystallography experiments.Compound 14 exhibited moderate anti-inflammatory activity by inhibiting the LPS-induced NO release(IC_(50)=25.6μM).

Two New Oplopanol Esters from Ligularia narynensis

Tow new oplopanol esters were isolated from the roots of Ligularia narynensis. Their structures were eluc idated by spectroscopic methods, especially 2D-NMR techniques.

A geochemical investigation of the free and carbonate-bound organic matter in the clay-sized fraction of argillaceous source rocks and its significance for biogenic interpretation

The molecular composition and biomarker distribution of various occurrences of organic matter in argillaceous source rocks developed in fresh and saline lacustrine environments were revealed by successive treatments of solvent extraction followed by acid hydrolysis using gas chromatography–mass spectrometry. The free fraction obtained by solvent extraction provided abundant geochemical information concerning the sedimentary environment, thermal maturity and biogenic origin, and obvious differences existed between fresh and saline lacustrine source rock samples. Our research results indicate that the carbonate-mineral-bound(CM-bound) fraction released by successive acid hydrolysis could also serve as a significant biogenic indicator, as the bicyclic sesquiterpenoids, indicative of Botryococcus braunii origin, were specifically detected in quite high abundance in the acid-soluble fraction. In addition, the light end hydrocarbons were much better preserved in the acid-soluble fraction, and elemental sulfur was only detected in the CM-bound fraction, suggesting a relatively confined environment for the CM-bound fraction, which thus could preserve additional geochemical information compared to that of the free fraction. The CM-bound fraction also exhibited discernable differences between fresh and saline lacustrine samples. Therefore, it can be concluded that comprehensive analysis of free and CM-bound fractions in the argillaceous source rocks can provide a more authentic and objective interpretation of geologic conditions.

Fischelactone:A novel eremophilane dimer from Ligularia fischeri

A novel eremophilane dimer,named fischelactone（1）,was isolated from the roots of Ligularia fischeri.Complete structural elucidation of this compound was performed by HRESIMS,IR,1D NMR and 2D NMR（;H-;H COSY,HMBC,HMQC and NOESY） data.

Artemyrianins A-G from Artemisia myriantha and Their Cytotoxicity Against HepG2 Cells

Four new sesquiterpenoids,artemyrianins A-D(1-4),and three new norlignans,artemyrianins E-G(5-7),together with five known compounds(8-12),were isolated from the aerial parts of Artemisia myriantha(Asteraceae).The new compounds were established by spectroscopic data analyses(HRMS,IR,1D and 2D NMR),and their absolute configurations were confirmed by the single-crystal X-ray diffraction or ECD calculations.The isolates showed cytotoxicity against HepG2 cells with IC50 values ranging from 33.3 to 145.2μM.