New antileishmanial sesquiterpene coumarins from Ferula narthex Boiss

Two new sesquiterpene coumarins, fnarthexone (1) and fnarthexol (2), along with three known coumarin derivatives, conferol (3), conferone (4) and umbelliferone (5), were isolated from the plant Ferula narthex Boiss. The structures of the compounds 1–5 were elucidated using modern spectroscopic techniques. The structure of compound 3 was unambiguously deduced by the single-crystal X-ray diffraction technique. Compounds 1–4 were tested for in vitro leishmanicidal activity and promising results were obtained. Conferol (3) was found to be the most potent with IC₅₀ value of 11.51 ± 0.09 μg/mL.     

Two new compounds from Cryptoporus volvatus

Two new compounds with the aldehyde group, cryptoporusal A (1) and 9-formyl-4-hydroxy-6, 9-dimethyl-1-O-β-D-xylosopyranosyl-8a,9-dihydro-ace-naphthylen-8-one (2), were isolated from the ethyl acetate extract of the fruiting bodies of Cryptoporus volvatus (Pk.) Hubbard. Their structures were elucidated by extensive spectroscopic studies, and comparison with literature data. Furthermore, they were evaluated for their in vivo cytotoxicity against five human cancer cell lines and antioxidant activity. Compound 1 exhibited strong cytotoxicity against HL-60 and both showed high ferric reducing capacity.     

Four new sesquiterpene polyol esters from Celastrus angulatus

Celastrus species, such as Celastrus angulatus, has been demonstrated to be very rich in natural sesquiterpene polyol esters sharing the β-dihydroagarofuran skeleton, some of which showed various biological activities. In this paper, four new sesquiterpene polyol esters, named as angulatins K-N (1–4), along with three known ones, 1β-acetoxy-9β-benzoxy-4α, 6α-dihydroxy-8α, 15-diisobutanoyloxy-2β-(α-methyl)-butanoyloxy-β-dihydroagarofuran, angulatin A, and celangulin III, were isolated from the root bark of C. angulatus. The structures of the new compounds were elucidated by extensive spectroscopic methods, mainly including HR-MS and 1D and 2D NMR techniques.     

Linkiol,a new sesquiterpene from Ferula linkii

A new sesquiterpene ester, linkiol with a daucane skeleton was isolated from Ferula linkii.     

Three new sesquiterpene lactone dimers from Carpesium faberi

Three new 2,4-linked sesquiterpene lactone dimers (SLDs), faberidilactones F-H (1–3), have been isolated from Carpesium faberi. Unlike 1 and 2, 3 was a modified Diels-Alder adduct, characteristic by a 1′-OH and a Δ^5′(6′) double bond. Furthermore, the relative configuration of 1′-OH in 3 was assigned as β-configuration by comparison the experimental NOESY data with those of its two possible epimers. The exo/endo stereochemistry of 1–3 was determined by the spectrographic features of 2,4-linked SLDs that we discovered in our previous works. Compounds 1 and 2 showed potent cytotoxicity against human leukemia (CCRF-CEM) cells with IC₅₀ value of 5.62 and 3.74 μM, respectively.     

Koanolides B-D,new sesquiterpene lactones from Koanophyllon gibbosum

Three new germacrane-type sesquiterpene lactones, koanolides B–D (1-3) have been isolated from the aerial parts of Koanophyllon gibbosum (Asteraceae), along with the previously reported sesquiterpene lactone koanolide A and the flavonoid eupatorin. The structures of the new compounds were elucidated using spectroscopic and spectrometric data analyses, including 1D and 2D NMR, and by comparison with known spectral data. The antiproliferative activities of the new compounds were evaluated in a panel of six representative human solid tumor cell lines and showed GI₅₀ values ranging from 1.3 to 16 μM for the new molecules.     

Polar secondary metabolites of Ferula persica roots

Phytochemical investigation of the methanolic extract of the dried roots of Ferula persica resulted in four sesquiterpene coumarin glycosides, persicaosides A-D, and two known phytosterol glucosides, sitosterol 3-O-beta-glucoside and stigmasterol 3-O-beta-glucoside. The structures of these compounds were elucidated by extensive spectroscopic methods including 1D-((1)H and (13)C) and 2D NMR experiments (DQF-COSY, HSQC, HMBC, and ROESY) as well as ESIMS and TOFMS analyses.     

Two New Sesquiterpene Derivatives from the Tunisian Endemic Ferula tunetana Pom.

A new sesquiterpene ester, tunetanin A ( 1 ), a new sesquiterpene coumarin, tunetacoumarin A ( 2 ), together with eight known compounds, i.e., coladin ( 3 ), coladonin ( 4 ), isosmarcandin ( 5 ), 13‐hydroxyfeselol ( 6 ), umbelliprenin ( 7 ) propiophenone ( 8 ), β‐sitosterol ( 9 ), and stigmasterol ( 10 ), were isolated from the roots of Ferula tunetana. Their structures were elucidated on the basis of extensive spectroscopic methods, including 1D‐ and 2D‐NMR experiments and MS analysis, as well as by comparison with published data. The cytotoxicity of compounds 1 – 7 towards two human colon cancer cell lines, HT‐29 and HCT 116, was evaluated. Compounds 3, 4 , and 6 showed weak cytotoxic activities.     

Ferulsinaic acid, a sesquiterpene coumarin with a rare carbon skeleton from Ferula species

Fractionation of methylene chloride extracts of the resin of Ferula vesceritensis and F. sinaica afforded three sesquiterpene coumarins and a glucose derivative. One of them was a sesquiterpene with a rare carbon skeleton. The structures of these compounds were determined by extensive NMR studies, including DEPT, COSY, NOE, HMQC, and HMBC.     

New antibacterial sesquiterpene aminoquinones from a Vietnamese marine sponge of Spongia sp.

Two new sesquiterpene aminoquinones, langcoquinones A (1) and B (2), together with seven known meroterpenoids (3⿿9), were isolated from the marine sponge Spongia sp. collected in Vietnam. Their structures were determined on the basis of spectroscopic analyses and comparisons with published data. The antibacterial activities of the isolated compounds (1⿿9) were investigated against four bacterial strains. Among these, the new sesquiterpene aminoquinones (1 and 2) and the known related compounds (3, 5, 6, 8, and 9) exhibited significant antibacterial activities against Staphylococcus aureus and Bacillus subtilis, with MICs ranging from 6.25 to 12.5 μM.     

Three new cassane diterpenes from the seeds of Caesalpinia sappan

Three new cassane furanoditerpenes, phanginins N–P (1–3), together with four known ones were isolated from the seeds of Caesalpinia sappan. Their structures were elucidated on the basis of spectroscopic analysis including HRESIMS, 1D and 2D NMR techniques. Evaluation of all the compounds for cytotoxicity against three human cancer cell lines (HepG-2, MCF-7 and HCT-8) showed insignificant results (IC₅₀ > 10 μM).     

Eudesmane-type sesquiterpene derivatives from Laggera alata

Ten eudesmane-type sesquiterpene derivatives (1–10), including six cuauhtemone derivatives (1–6), one di-norsesquiterpene (3-oxo-di-nor-eudesma-4-en-11-oic acid, 7), and three eudesmane glycosides (alatoside F–H, 8–10) were isolated from the whole plants of Laggera alata together with 12 known compounds. Their structures were elucidated on the basis of extensive spectroscopic analysis, acid hydrolysis, and compounds 1 and 7 were studied by single-crystal X-ray diffraction analysis. The absolute configuration of 1 was determined by the application of the modified Mosher’s method. All of the isolated eudesmane-type sesquiterpenes were evaluated for their cytotoxic activities on six human cancer cell lines, but all of the compounds were inactive on the tested cell lines in the concentration of 100 μg/mL.     

Sesquiterpene coumarins from the roots of Ferula assa-foetida.

From the chloroform extract of the roots of Ferula assa-foetida, two sesquiterpene coumarins designated assafoetidnol A and assafoetidnol B were isolated, in addition to six known compounds, gummosin, polyanthin, badrakemin, neveskone, samarcandin and galbanic acid. The structures of the sesquiterpenes new compounds were established by spectroscopic methods.     

Tridysoxyphenols A and B,two new trimeric sesquiterpene phenols from Dysoxylum parasiticum leaves

Two new sesquiterpene phenol trimers, tridysoxyphenols A (2) and B (3), along with two known compounds, namely a sesquiterpene phenol, (+)-7-hydroxycalamenene (1), and a tetralone derivative, 4-hydroxy-4,7-dimethyl-α-tetralone (4), were isolated from the leaves of Dysoxylum parasiticum (Osbeck) Kosterm. The structures of 2 and 3 were elucidated using nuclear magnetic resonance (NMR) spectroscopy, ultraviolet (UV) spectroscopy, infrared (IR) spectroscopy, high-resolution electrospray ionization time-of-flight mass spectrometry (HR-ESI/TOF-MS), and time-dependent density functional theory (TDDFT) calculations of the electronic circular dichroism (ECD) spectroscopic data. No cytotoxic activity was observed for any of the isolated compounds at low concentrations, although compound 1 suppressed the viability of HL60 cells at 119.85 ± 10.03 μM.     

新疆阿魏的胚胎学研究

采用常规石蜡制片技术,对新疆阿魏不同发育时期的花和果实进行了显微切片观察.结果表明:新疆阿魏小孢子母细胞的减数分裂为同时型,小孢子四分体为四面体型和十字交叉型,成熟花粉粒为3-细胞型.雌蕊2心皮合生成2室,中轴胎座,每子房室内产生上、下2个胚珠原基,其中,下方的原基正常发育,而上方的原基停止发育并最终解体,因此,每室仅产生一枚发育正常的倒生胚珠,单珠被,薄珠心,胚囊发育为蓼型;珠被绒毡层和珠孔塞发生于大孢子四分体时期,并于四核胚囊时分化完全,八核胚囊时珠被绒毡层细胞径向延长;3个成熟的反足细胞具双核.胚乳发育为核型,细胞壁较厚,细胞排列紧密,可保护胚免受机械损伤及防止胚失水.胚乳细胞中含有大量PAS染色呈正反应的物质,一些胚乳细胞异常生长形成细胞体积大、核及核仁均较大的巨形细胞.胚胎发生为茄型,四细胞原胚为直线形,十六细胞原胚的顶部由2排各4个细胞组成.成熟种子具胚乳.     

臭阿魏化学成分研究

用95%乙醇提取,溶剂萃取,硅胶柱色谱分离等方法从臭阿魏根中提取分离得到9个化合物,根据NMR,EI-MS等光谱学方法分别鉴定为:badrakemin(1),badrakemin acetate(2),badrakemone(3),feshurin(4),feshurinacetate(5),feterin(6),colladonin(7),孕甾-4-烯-3,20-二酮(8),胡萝卜苷(9)。其中化合物4、5、7、8和9为首次从该植物中分得。     

A pair of new sesquiterpene isomers containing spiro heterocyclic skeleton from plant-derived fungus Botryosphaeria dothidea

A pair of new sesquiterpene isomers containing a spiro heterocyclic skeleton, dothimes A (1) and B (2), together with six known compounds, quindoline (3), (S)-3-(3-indolyl)lactic acid methyl ester (4), dankasterone B (5), dibutyl phthalate (6), (1S,3R,4R,7S)-3,4-dihydroxy-α-bisabolol (7), and p-hydroxybenzaldehyde (8), were isolated from the plant-derived fungus Botryosphaeria dothidea. The structures of all isolated compounds were determined based on extensive spectroscopic analyses, including 1D/2D nuclear magnetic resonance (NMR), and high resolution electrospray ionization mass spectrometry (HRESIMS) data, as well as by comparison with literature reports. Compounds 1 and 2 exhibited inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide (NO) production with IC₅₀ values of 63.66 and 58.29 μM, respectively.     

Three new cucurbitane triterpenoids from Hemsleya penxianensis and their cytotoxic activities

Two new cucurbitane glycosides, hemslepenside A (1) and 16,25-O-diacetyl-cucurbitacin F-2-O-β-d-glucopyranoside (3), one new cucurbitacin, 16-O-acetyl-cucurbitacin F (2), along with three known cucurbitane compounds, were isolated from the roots of Hemsleya penxianensis. The structures of 1–6 were established on the basis of extensive spectroscopic and chemical methods. The isolated compounds were evaluated for their cytotoxic activities against different three human cancer cell lines, with IC₅₀ values in the low microgram range.