Characteristic lindenane sesquiterpenoid dimers and labdane diterpenoids from Chloranthus serratus

Chemical investigation on the roots of Chloranthus serratus (Chloranthaceae) afforded 11 terpenoids, including four lindenane-type sesquiterpenoid dimers (1–4), and seven labdane diterpenoids (5–11). The structures of these terpenoids were established by spectroscopic analysis (MS, ¹H, and ¹³C NMR). Compounds 4–11 were isolated from C. serratus for the first time. The chemotaxonomic significance of the isolated compounds was summarized herein.     

Chemotaxonomic significance of lignans from Serissa japonica (Thunb.) Thunb

Sixteen known lignans were isolated from the 95% alcohol extract of the whole plant of Serissa japonica (Thunb.) Thunb., including nine furofurans (1–9), three tetrahydrofurans (10–12) and four arylnaphthalenes (13–16). In the present report, compounds (+)-epipinoresinol (1), (+)-1-hydroxy-6-epipinoresinol 4,4″-di-O-methyl ether (3), (−)-pinoresinol (4), (+)-8-hydroxypinoresinol (6), pseuderesinol (7), (+)-1-hydroxysyringaresinol (8), (−)-(7′S,8S,8′R)-4,4′-dihydroxy-3,3′,5,5′-tetramethoxy-7′,9-epoxylignan-9′-ol-7-one (10), wikstrone (11), 7'-(+)-oxomatairesinol (12), (+)-cycloolivil (13), (+)-isolariciresinol (14), 5-methoxy-(+)-isolariciresinol (15) and cyclolignans (16) were reported from the Serissa genus for the first time, and compounds (+)-lirioresinol A (2) and (−)-lirioresinol B (5) were firstly isolated from the plant. Their structures were elucidated on the basis of extensive spectroscopic and chemical analyses. Moreover, the chemotaxonomic significance of the isolated compounds is discussed.     

Chemical constituents from Fallopia cynanchoides (Hemsl.) Harald. var. cynanchoides

Fifteen compounds were isolated and elucidated from the alcohol extract of Fallopia cynanchoides by modern phytochemical isolation and spectroscopic methods, and these compounds can be divided into four sterols, a phenol, anthraquinones, a chromone, two stilbenes and three flavonoids. All of these compounds were obtained from this plant for the first time. Chemotaxonomic studies indicated that F. cynanchoides has very close relationships with F. convolvulus and F. aubertii, and the genus Fallopia may have close relationships with the genera Rheum, Fagopyrum, Reynoutria and Polygonum.     

Triterpenoids from Rosa odorata Sweet var. gigantea (Coll.et Hemsl.) Rehd.et Wils and their chemotaxonomic significance

Thirty-three reported compounds were obtained for the first time from Rosa odorata Sweet var. gigantea (Coll.et Hemsl.) Rehd. et Wils and were all identified as triterpenoids. The structure of these compounds was determined by physicochemical constants and spectral analyses (NMR, MS). This is the first report on four compounds (7, 9, 10 and 22) from the family Rosaceae and thirteen compounds (2, 3, 4, 11, 17, 19, 20, 23, 24, 26, 29, 31 and 33) from the genus Rosa. Finally, the chemotaxonomic significance of these compounds is discussed.     

Chemotaxonomic significance of sesquiterpenes and amide derivatives from Chloranthus angustifolius Oliv.

Phytochemical investigation of the aerial parts of Chloranthus angustifolius Oliv. (Chloranthaceae) resulted in the isolation and characterization of seven sesquiterpenes (1–7) and six amide derivatives (8–13). All structures were established based on analysis of their spectroscopic data. This is the first report of compounds 2 and 8–13 from the family Chloranthaceae, and the first report of compounds 3–5 from C. angustifolius. Moreover, the chemotaxonomic significance of these compounds was summarized.     

山东湖北海棠(Malus hupehensis (Pamp.) Rehd.)两新变种

记载了分布于山东省的两个湖北海棠的地理变种,泰山海棠与原变种区别于叶缘锯齿较钝较小,果实紫红色,直径约0.6 cm,花较小,直径不足2 cm;平邑甜茶与原变种区别于叶片较大,平展,锯齿大而钝,叶脉较多,较直行, 花萼齿披针形,长于萼筒。     

湖北海棠DNA的CTAB改良法提取及其SSR反应体系优化

为了利用分子标记技术研究湖北海棠的起源、系统发育和分类问题,本研究对湖北海棠及其近缘种叶DNA的CTAB提取法进行改良,并对SSR体系优化.结果表明,将EDTA用量从20 mmol/L提高到80 mmol/L,加大PVP和RNA酶的用量,有助于提高从湖北海棠叶中提取的DNA质量;利用反复实验优化的SSR体系,可从40对引物中筛选出18对多态性好、条带清晰的湖北海棠SSR引物.本研究筛选出的多态引物,将为探讨湖北海棠的起源、进化和遗传变异等提供基础资料.     

Chemical constituents from Picrasma quassioides (D.Don) Benn. and their network analysis of chemotaxonomic significance

A phytochemical investigation of Picrasma quassioides (D.Don) Benn led to the isolation of seventeen compounds including five coumarins (1–5), six lignans (6–11), two alkaloids (12–13), two phenolic compounds (14–15), one megastigman glycoside (16) and one phenylpropanoid (17). The structures of those compounds were determined by spectroscopy data of NMR spectra. All of the compounds were isolated from P. quassioides for the first time. In this study, in order to discuss the chemotaxonomic significance of those compounds from P. quassioides, network analysis was carried out to determine the chemotaxonomic relationships among the Simaroubaceae family and the other families. The result showed that the Simaroubaceae family and the Rutaceae family, together with the Asteraceae family have some chemotaxonomic relationships.     

Three new terpenoids from Trigonostemon xyphophylloides (Croiz.) L.K. Dai and T.L. Wu

Two new daphnane diterpenoids, trigoxyphins J and K (1 and 2), and one new friedelane triterpene derivative, 3-O-benzoylpluricostatic acid (3), together with thirteen known terpenoids (4–16) were isolated from Trigonostemon xyphophylloides (Croiz.) L.K. Dai and T.L. Wu. Their structures were identified on the basis of physicochemical properties and spectroscopic data. All compounds were evaluated for their cytotoxicity against K562, SGC-7901, and BEL-7402 tumor cell lines, respectively.     

New unsaturated fatty acid and other chemical constituents from the roots of Cola rostrata K. Schum. (Malvaceae)

Phytochemical investigation of the roots of Cola rostrata K. Schum. led to the isolation of a new unsaturated fatty acid, named rostratanic acid (1), together with fourteen known compounds, lignoceric acid, friedelan (7), friedelanone (8), bauerenol (3), lupeol (4), herranone (9), acotatarone A (11), betulinic acid (6), betulin (5), nonanedioc acid (2), arjunolic acid (10) stigmasterol, β−sitosterol, and β−sitosterol-3-O-β-D-glucopyranoside. The structure of the new compound as well as those of the known compounds were established by means of spectroscopic methods: NMR analysis (¹H and ¹³C NMR, ¹H–¹H–COSY, HSQC and HMBC) and high-resolution mass spectrometry (HR-ESI-MS), and by comparison with previously reported data. Two of those known compounds were modified chemically to afford three new derivatives. All those compounds were tested for their cytotoxic activity against the human cervix carcinoma KB-3-1 cells and their antibacterial activity against Escherichia coli, Salmonella enterica, Pseudomonas aeruginosa and Staphylococcus aureus. Although the crude extract gave weak antibacterial activity, none of the isolated compounds showed antibacterial activity, and, only the prenylated derivative showed weak cytotoxicity. In addition, the chemotaxonomic significance of the species Cola rostrata is discussed.     

Rothmanniamide and other constituents from the leaves of Rothmannia hispida (K.Schum.) fagerl. (Rubiaceae) and their chemophenetic significance

The chemical investigation of the CH₂Cl₂/MeOH (1:1) extract of the leaves of Rothmannia hispida (K. Schum.) Fagerl. (Rubiaceae) led to the isolation of a new ceramide rothmanniamide (1) and a naturally isolated alkyl cinnamate derivative n-heptadecyl-4-hydroxy-trans-cinnamate (2), along with fifteen known compounds including lupeol palmitate (3), lupeol (4), a mixture of uvaol (5) and erythrodiol (6), ursolic acid (7), 30-nor-2α,3β-dihydroxyurs-12-ene (8), hederagenin (9), stigmast-22-en-3-ol (10), a mixture of β-sitosterol (11) and stigmasterol (12), stigmast-4,22-dien-3-ol (13), stigmasterol 3-O-β-D-glucoside (14), triacontan-1-ol (15), kaempferol 3-O-β-D-glucopyranoside (16) and D-mannitol (17). Their structures were elucidated with the help of MS and NMR data. Compounds 8, 10 and 15 were isolated for the first time from the Rubiaceae family. The crude extract and the isolates were assessed in vitro for their antileishmanial activity against Leishmania donovani 1 S (MHOM/SD/62/1 S) promastigotes and cytotoxicity on RAW 264.7 macrophage cells. Compounds 7 and 8 exhibited a highly potent antileishmanial activity with IC₅₀ values of 0.88 and 1.75 μg/mL, respectively, with good selectivity indexes (SI > 57). The chemophenetic significance of these compounds is also discussed.     

Flavonoids from the flowers of Adenium obesum (Forssk.) Roem. & Schult., Mandevilla sanderi (Hemsl.) Woodson,and Nerium oleander L. (Apocynaceae)

Twenty-two ornamental flowers from different Adenium obesum, Mandevilla sanderi, and Nerium oleander cultivars/seedlings were analyzed for the presence of anthocyanins, flavonols, and chlorogenic acid using nuclear magnetic resonance (NMR) and mass spectrometry (MS). Cyanidin 3-O-[6-O-(rhamnosyl)-galactoside] and cyanidin 3-O-(galactoside) were identified as the major and minor anthocyanins, respectively, in three A. obesum seedlings that had red and red-purple flowers.Cyanidin 3-O-[2-O-(xylosyl)-galactoside] was identified as the major anthocyanin, whereas cyanidin 3-O-[6-O-(rhamnosyl)-galactoside] and cyanidin 3-O-(galactoside) were identified as the minor anthocyanins in 8 M. sanderi cultivars that had red and red-purple flowers. Cyanidin 3-O-[6-O-(rhamnosyl)-galactoside] and cyanidin 3-O-(galactoside) were identified as the major anthocyanins, whereas cyanidin 3-O-[2-O-(xylosyl)-galactoside] was identified as the minor anthocyanin in 8 N. oleander cultivars with red and red-purple flowers. Low levels of anthocyanins were detected in the N. oleander and M. sanderi cultivars that had white flowers, and there were no anthocyanins detected in the N. oleander cultivars with yellow flowers. Chlorogenic acid and four flavonols, quercetin 3-O-[6-O-(rhamnosyl)-galactoside], quercetin 3-O-[6-O-(rhamnosyl)-glucoside], kaempferol 3-O-(galactoside), and kaempferol 3-O-[6-O-(rhamnosyl)-galactoside], were identified in the flowers from all 22 cultivars/seedlings investigated.     

Cytotoxic,antimicrobial activities,AChE and BChE inhibitory effects of compounds from Tanacetum chiliophyllum (Fisch. & Mey.) Schultz Bip. var. oligocephalum (D.C.) Sosn. and T. chiliophyllum (Fisch. & Mey.) Schultz Bip. var. monocephalum Grierson

Tanacetum L. species traditionally used for insecticidal purposes as well as in folk medicine for their antitumor, antimicrobial, antifungal activities. In our previous study a novel sesquiterpene lactone and triterpene lactone together with 12 known flavonoids, coumarin and a triterpene were isolated from T. chiliophyllum var. oligocephalum and T. chiliophyllum var. monocephalum extracts which have insecticidal and antimicrobial activity. In this study, cytotoxic, antimicrobial activities and acetylcholinesterase (AChE), butyrylcholinesterase (BChE) inhibitory effects of pure compounds isolated from these plants were investigated. The tested compounds showed AChE and BChE inhibition which ranged between 7.20–80.37% and 9.19%–76.99% respectively. The highest AChE and BChE inhibition was observed for ulubelenolide which afforded 80.37% and 76.99% inhibition respectively. The cytotoxic effect of the compounds ranged between 22.34–49.77 μg/mL IC₅₀ values. Highest cytotoxic activity was observed against MCF-7 and HEK 293 cell line by 5–hydroxy-3′,4′,7-trimethoxy flavone and 5-hydroxy-3′,4′,6,7-tetramethoxyflavone that produced 25.80 ± 0.17 and 22.34 ± 0.70 IC₅₀ values respectively. Compounds eupatilin, cirsilineol, 5–hydroxy-3′,4′,7-trimethoxy flavone and ulubelenolide showed significant antimicrobial effect on C. albicans with 7.8 μg/mL MIC. The new compound ulubelenolide afforded high AChE and BChE inhibition as well as high antifungal activity. In our opinion activity of this substance should be evaluated further against other fungal species.     

Antiplasmodial and Cytotoxic Activities of Extract and Compounds from Ozoroa obovata (Oliv.) R. & A. Fern. var. obovata

Ozoroa obovata (Oliv.) R. & A. Fern. var. obovata found in KwaZulu-Natal in South Africa was investigated for phytochemical constituents, and for antiplasmodial and cytotoxic effects. The plant leaves were collected from the University of KwaZulu-Natal (UKZN) arboretum on the Pietermaritzburg Campus, in March 2019. The inhibitory activity against 3D7 Plasmodium falciparum was determined using the parasite lactate dehydrogenase (pLDH) assay and cytotoxicity against HeLa cells was evaluated using the resazurin assay. The bioactive compounds were isolated by chromatographic purification and their structures were established with spectroscopic and spectrometric techniques. The plant leaf extract displayed significant antiplasmodial activity at 50 μg/mL and was also cytotoxic against HeLa cells. Chromatographic purification of the extract led to the isolation of two biflavonoids, four flavonoid glycosides, a steroid glycoside, and a megastigmene derivative. The compounds displayed antiplasmodial and antiproliferative activities at 50 μg/mL but the activity was substantially reduced at 10 μg/mL. The activities and compounds are being reported in O. obovata for the first time.     

Growth of callus and suspension culture cells from cotton varieties (Gossypium hirsutum L.) resistant and susceptible toxanthomonas malvacearum (E. F. Sm.) dows

Summary In vitro conditions are defined for starting and maintaining callus and suspension, cells from two cotton (Gossypium hirsitum L.) varieties, Im 216 and Acala 44, which are resistant and susceptible, respectively, to the bacterial pathogenXanthomonas malvacearum (E. F. Sm.) Dows. A light, friable callus was easily obtained and has been maintained for over 4 years. Whether stems or leaves, the explant source for callus initiation made no difference for growth of callus tissue. Acala 44 callus had a fresh-weight doubling time of 4 to 5 days, and Im 216 callus had a fresh-weight doubling time of 4 to 9 days; however, in suspension culture the fresh-weight doubling times for Im 216 and Acala 44 were 6 days. The pH of the suspension medium dropped to 4.7 during the exponential growth phase and rose to 5.4 at the stationary phase. Attempts to induce root and shoot initiation from these callus cells were unsuccessful; however, greening of the callus tissue did occur. Schenk and Hildebrandt medium was used for both callus and suspension cultures. Inoculation of Im 216 and Acala 44 callus tissues with two races ofX. malvacearum resulted in a resistant and susceptible response, respectively. This research was supported in part by C. S. R. S. Grant 315-16-96 and the Agricultural Experiment Station of Oklahoma State University.     

In vitro propagation of Albizia odoratissima L.F. (Benth.) from cotyledonary node and leaf nodal explants

Summary Cotyledonary node and leaf nodal explants excised from 14-d-old in vitro-grown seedlings of Albizia odoratissima were cultured on a Murashige and Skoog (MS) medium with different concentrations of 6-benzylaminopurine (BAP), N ⁶-(2-isopentenyl) adenine (2-iP) and kinetin, used either solely or in combinations. The highest frequency for shoot regeneration (82.5%), the maximum number of shoots per explant (6.9), and the maximum shoot length (2.55 cm) were obtained from cotyledonary node explants cultured on a MS medium containing 10 μM BAP and 10 μM 2-iP with 30 gl^−1 sucrose. Successful rooting was achieved by placing the microshoots on MS medium with 25 μM indole-3-butyric acid (IBA) for 24h first, then transferring to the same medium without IBA. Of the various substrates tested, vermiculite was best for plant acclimatization, in which 75% of plants survived.     

Flavonoid glycosides from the leaves of Aphananthe aspera (Thunb.) Planch. (Cannabaceae) and their chemotaxonomic significance

From the leaves of Aphananthe aspera (Thunb.) Planch. (Family: Cannabaceae), six flavonol glycosides, such as quercetin 3-O-β-glucopyranoside (1), kaempferol 3-O-β-glucopyranoside (2), quercetin 3-O-rutinoside (3), kaempferol 3-O-rutinoside (4), quercetin 3-O-neohesperidoside (5) and kaempferol 3-O-neohesperidoside (6) were isolated and identified. Structure elucidation of these compounds was performed on the basis of NMR spectral data. All these compounds were isolated for the first time from the genus Aphananthe. Chemotaxonomic significance and distribution of these flavonoid derivatives among the genera of Cannabaceae are explained in detail.     

Phenolic compounds and ecdysteroids of Diplazium esculentum (Retz.) Sw. (Athyriaceae) from Japan and their chemotaxonomic significance

Four phenolic compounds, (2R)-3-(4′-hydroxyphenyl) lactic acid, trans-cinnamic acid (2), protocatechuic acid (3) and rutin (4), and three ecdysteroids, amarasterone A1 (5), makisterone C (6) and ponastrone A (7) were isolated and identified from the young fronds of Diplazium esculentum (Retz.) Sw. (Athyriaceae). The structures of these compounds were elucidated on the basis of NMR spectral data and comparison with literature values. Compounds 1, 2 and 5–7 were isolated for the first time from title plant. Their structure elucidation and chemotaxonomic significance are explained in detail.