Seven guaiane-type sesquiterpenoids, a new compound 6-formyl-5-isopropyl-3-hydroxymethyl-7-methyl-1H-indene (1), a new natural product 5-isopropyl-3, 7-dimethyl-1H-indene-1-one (2), along with five known compounds: guaiazulene (3), 4-formyl-7-isopropyl-10-methylazulene (4), sesquiterpene ketolactone (5), alismoxide (6) and guaia-1 (5), 6-diene (7), were isolated from gorgonian Muriceides collaris collected in South China Sea. Their structures were elucidated on the basis of extensive spectroscopic analysis [MS, IR, 1H NMR, 13C NMR (DEPT), HMQC, HMBC, NOESY] and by comparison of the spectral data with those of the literatures.
Animals ; Anthozoa ; chemistry ; Azulenes ; China ; Sesquiterpenes ; chemistry ; isolation & purification ; Sesquiterpenes, Guaiane

A sesquiterpene synthase (AsSS4) full-length open reading frame (ORF) cDNA was cloned from wounded stems of Aquilaria sinensis by RT-PCR method. The result showed that the ORF of AsSS4 was 1,698 bp encoding 565 amino acids. Prokaryotic expression vector pET28a-AsSS4 was constructed and transformed into E. coli BL21 (DE3) pLysS. Recombinant AsSS4 protein was obtained after induction by IPTG and SDS-PAGE analysis with a MW of 64 kD. Enzymatic reactions using farnesyl pyrophosphate showed that recombinant AsSS4 protein purified by Ni-agarose gel yielded five sesquiterpene compounds, cyclohexane, 1-ethenyl-1-methyl-2, 4-bis(1-methylethenyl)-, β-elemene, α-guaiene, α-caryophyllene and δ-guaiene. This paper reported the first cloning and functional characterization of AsSS4 gene from A. sinensis, which will establish a foundation for future studies on the molecular mechanisms of wound-induce agarwood formation in A. sinensis
Alkyl and Aryl Transferases ; biosynthesis ; genetics ; Azulenes ; Cloning, Molecular ; DNA, Complementary ; Escherichia coli ; Open Reading Frames ; Polyisoprenyl Phosphates ; Recombinant Proteins ; biosynthesis ; Sesquiterpenes ; metabolism ; Sesquiterpenes, Guaiane ; Thymelaeaceae ; enzymology ; genetics

As an important member of metabotropic glutamate receptors (mGluR), metabotropic glutamate receptor 1 (mGluR1) plays an important role in the signal transduction of central nervous system. Selective mGluR1 antagonists can block the signaling pathway activated by mGluR1 and exert a series of physiological actions including analgesia, antianxiety, antidepression, etc. Currently, the discovery and modification of selective mGluR1 antagonists have become a hot research focus. This paper reviews the structural catalogs of selective mGluR1 antagonists and their structure-activity relationships in the last decade.
Analgesics ; chemical synthesis ; chemistry ; pharmacokinetics ; pharmacology ; Animals ; Benzimidazoles ; chemical synthesis ; chemistry ; pharmacokinetics ; pharmacology ; Blood-Brain Barrier ; Cycloheptanes ; chemical synthesis ; chemistry ; pharmacokinetics ; pharmacology ; Heterocyclic Compounds, 3-Ring ; chemical synthesis ; chemistry ; pharmacokinetics ; pharmacology ; Pain Measurement ; Pyrimidines ; chemical synthesis ; chemistry ; pharmacokinetics ; pharmacology ; Receptors, Metabotropic Glutamate ; antagonists & inhibitors ; chemistry ; Signal Transduction ; drug effects ; Structure-Activity Relationship ; Thiazoles ; chemical synthesis ; chemistry ; pharmacokinetics ; pharmacology

Five sesquiterpenoids were isolated from 90% ethanol extract of Croton yunnanensis by silica gel,Sephadex LH-20 column chromatography,as well as prep-HPLC methods. Based on MS,1 D and 2 D NMR spectral analyses,the structures of the five compounds were identified as 11-methoxyl alismol(1),6β,7β-epoxy-4α-hydroxyguaian-10-ene(orientalol C,2),multisalactone D(3),arvestonol(4),and 4,5-dihydroblumenol A(5). Compound 1 was a new guaiane-type sesquiterpenoid. Compounds 2-4 were isolated from the Croton genus for the first time,and compound 5 was obtained from this plant for the first time.
Croton ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Sesquiterpenes ; Sesquiterpenes, Guaiane

Guaiane-type sesquiterpenoids are a class of terpenoids with [5,7] ring-fused system as the basic skeletal structure composed of three isoprene units, which are substituted by 4,10-dimethyl-7-isopropyl. According to the difference in functional groups and degree of polymerization, they can be divided into simple guaiane-type sesquiterpenoids, sesquiterpene lactones, sesquiterpene dimers, and sesquiterpene trimers. Natural guaiane-type sesquiterpenoids are widely distributed in plants, fungi, and marine organisms, especially in families such as Compositae, Zingiberaceae, Thymelaeaceae, Lamiaceae, and Alismataceae. Guaiane-type sesquiterpenoids have good antibacterial, anti-inflammatory, anticancer, and neuroprotective effects. In this paper, the novel guaiane-type sesquiterpenoids isolated and identified in recent 10 years(2013-2022) and their biological activities were reviewed in order to provide refe-rences for the research and development of guaiane-type sesquiterpenoids.
Humans ; Molecular Structure ; Sesquiterpenes, Guaiane ; Asteraceae/chemistry* ; Sesquiterpenes

To study the chemical constituents in the non-alkaloid part of stems of Dendrobium nobile. The macroporous adsorption resin, MCI, silica gel, RP-C_(18), and Sephadex LH-20 gel, preparative thin layer chromatography, and preparative high-performance liquid chromatography(HPLC) were used to isolate and purify the compounds. The structures of the compound were determined according to the spectra data, physicochemical properties, and relevant references. A total of 8 compounds were isolated from D. nobile, which were soltorvum F(1), p-hydroxyphenylpropionic acid(2), vanillic acid(3), p-hydroxybenzoic acid(4), N-trans-cinnamic acid acyl-p-hydroxybenzene ethylamine(5),(+)-(1R,2S,3R,4S,5R,6S,9R)-2,11,12-trihydroxypicrotoxane-3(15)-lactone(6), dendronobilin H(7), soltorvum E(8). Compound 1 was a novel compound, named as soltorvum F. Compound 8 was isolated from Dendrobium species for the first time.
Dendrobium/chemistry* ; Molecular Structure ; Sesquiterpenes, Guaiane ; Sesquiterpenes/chemistry*

Three compounds were isolated from the extract of Taxus cuspidta Sibe et Zucc with the column chromatography on silica gel and preparative HPLC methods. Their structures were identified according to the physicochemical properties and spectral analysis, and they were identified as (E)-1-methoxy-2-O-(p-coumaroyl)-myo-inositol (1), 2-deacetoxy-7beta, 9a, 10beta-trideacetyltaxinine J (2) and (3aS, 4aR, 6S, 8S, 8aS, 9R, 10R, 10aS)-benz[f]azulene-6, 8, 9, 10 (3H)-terol, 3a, 4, 4a, 5, 6, 7, 8, 8a, 9, 10-decahydro-10a-(1-hydroxyl-1-methylethyl)-1, 8a-dimethyl-5-methylene (3). Among them, compound 1 was a new compound, and compounds 2, 3 were two novel natural products.
Azulenes ; chemistry ; isolation & purification ; Coumarins ; chemistry ; isolation & purification ; Inositol ; analogs & derivatives ; chemistry ; isolation & purification ; Molecular Structure ; Plants, Medicinal ; chemistry ; Taxoids ; chemistry ; isolation & purification ; Taxus ; chemistry

In the present study, two new trinor-guaiane sesquiterpenes, named clavuridins B (1), and A (2), along with three known sesquiterpenes (3-5), were isolated from the Xisha soft coral Clavularia viridis. Their structures and absolute configurations were determined on the basis of spectroscopic analysis, X-ray diffraction analysis with Cu Kα radiation and by comparison with related model compounds. Compounds 1 and 3-5 were evaluated for their cytotoxic activity.
Animals ; Anthozoa ; chemistry ; Biological Products ; chemistry ; pharmacology ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Sesquiterpenes, Guaiane ; chemistry ; isolation & purification ; pharmacology

OBJECTIVETo investigate the efficiency, safety, and possible mechanisms of Qingre Buyi Decoction (QBD) in the treatment of acute radiation proctitis (ARP).

METHODSThis study was a single center, prospective, single blind, randomized, and placebo-controlled clinical trial. A total of 60 patients with ARP was equally and randomly distributed into the control group (conventional treatment) and the combination group (conventional treatment plus QBD). The changes of main Chinese medicine clinical symptoms and signs, including stomachache, diarrhea, mucous or bloody stool before and after treatment, and their adverse reactions were observed after the two-week treatment. Also, D-lactate and diamine oxidase (DAO) levels, hepatic and renal function were measured. Cure rates, effective rates, and recurrence rates were compared between the two groups.

RESULTSThe blood levels of both DAO and D-lactate were significantly decreased in the combination group as compared with those in the control group (P<0.05 or P<0.01). All main clinical symptoms and signs were alleviated more significantly in the combination group (P<0.01). The main symptom scores also were significantly decreased after treatment in the control group (P<0.01), except those for mucous or bloody stool (P>0.05). Compared to the control group, the improvements of stomachache, diarrhea, defecation dysfunction, and stool blood in the combination group were significantly better (P<0.05 or P<0.01). For the combination group, the curative rate, effective rate, and recurrence rate was 76.67%, 16.67%, and 6.67%, respectively. On the other hand, for the control group, the rate was 53.33%, 16.67%, and 30.00%, respectively. The total curative effect was significantly better in the combination group than in the control group (P<0.05). However, the recurrence rate was similar between the two groups (P>0.05). The hepatic and renal function remained normal in both groups (P>0.05). In addition, no severe adverse event was found in both groups.

CONCLUSIONSAddition of QBD to the conventional treatment can effectively alleviate the damage of intestinal mucosal barrier function and improve all main clinical symptoms and signs of the ARP. The combination of conventional treatment with Chinese herbal medicine QBD is effective and safe for ARP.

Acute Disease ; Adult ; Aged ; Anti-Inflammatory Agents ; administration & dosage ; Azulenes ; administration & dosage ; Drug Therapy, Combination ; Drugs, Chinese Herbal ; administration & dosage ; adverse effects ; therapeutic use ; Female ; Gastrointestinal Agents ; administration & dosage ; Glutamine ; administration & dosage ; Humans ; Integrative Medicine ; methods ; Male ; Middle Aged ; Norfloxacin ; administration & dosage ; Pain ; complications ; Proctitis ; complications ; drug therapy ; Sesquiterpenes ; administration & dosage ; Silicates ; administration & dosage ; Single-Blind Method ; Treatment Outcome

Endothelins secreted from keratinocytes are intrinsic mitogens and melanogens of human melanocytes in UVB-induced hyperpigmentation. To elucidate the cellular mechanism of antimelanogenic activity of bamboo extract, the effects of three ingredients of bamboo extract on endothelin 1 (ET-1) -induced Ca2+ mobilization were investigated in cultured human melanocytes. ET-1 receptors in human melanocytes were characterized by using specific antagonist, and ET-1 was found to increase intracellular Ca2+ concentration ([Ca2+]i) by activating ET-B receptor. SM709 (1, 2-O-diferulyl-glycerol), an ingredient of bamboo extract, inhibited ET-1-induced [Ca2+]i increase in a concentration- and time-dependent manner, although another ingredients SM707 and SM708 had no effect on ET-1-induced [Ca2+]i increase in human melanocytes. SM709 (100 microM), however, did not affect [Ca2+]i increase induced by thapsigargin and caffeine, suggesting that SM709 has no effect on the Ca2+ store in melanocytes. Furthermore, SM709 did not affect [Ca2+]i increase induced by LPA or ATP, known as G protein-mediated PLC activators like ET-1. Taken together, it is suggested that SM709 antagonizes ET-1-induced transmembrane signaling through ET-B receptor, which maybe a possible underlying mechanism of antimelanogenic activity of bamboo extract in human melanocytes.
Adenosine Triphosphate ; Caffeine ; Endothelin-1 ; Endothelins ; Humans* ; Hyperpigmentation ; Keratinocytes ; Melanocytes* ; Mitogens ; Thapsigargin