Chemical constituents of the Gorgonian Dichotella fragilis (Ridleg) from the South China Sea

Two new steroidal glycosides, fragilioside A (1) and fragilioside B (2), along with five known compounds (3-7) were isolated from the gorgonian Dichotella fragilis (Ridleg) collected from the South China Sea. The structures of the new compounds (1 and 2) were elucidated by comprehensive analysis of spectral data, especially 2D NMR. The brine shrimp lethality and antifouling activity of the isolated compounds were also evaluated.     

Studies on the metabolism of gomisin A (TJN-101). II. Structure determination of biliary and urinary metabolites in rat

After oral administration of gomisin A (1) to rats, the bile and urine were collected and treated with beta-glucuronidase and arylsulfatase. Seven metabolites, met B (2), met A-III (3), met E (4), met D (5), met F (6), met G (7), and met H (8) were isolated from the bile treated with the enzymes. Eight metabolites 2-8, and met A-II (9) were isolated from the urine treated with the enzymes. A major metabolite 2, and two minor metabolites 3 and 9 were identified as met B, met A-III, and met A-II, respectively, which are oxidative products of 1 formed by rat liver S9 mix. The structures of five new metabolites 4-7, and 8 were determined on the basis of chemical and spectral studies.     

Three new nardosinane Type Sesquiterpenes from an Indonesian Soft Coral Nephthea sp

Three new sesquiterpenes, 2-deoxy-7-O-methyllemnacarnol (1), 2-deoxy-12 alpha-ethoxy-7-O-methyllemnacarnol (2), and 2-deoxy-12 alpha-methoxy-7-O-methyllemnacarnol (3), were isolated from a soft coral Nephthea sp. collected in Indonesia, together with five known sesquiterpenes. The structures of the new compounds were assigned on the basis of their spectroscopic data.     

New triterpenoid saponins from fruits specimens of Panax japonicus collected in Kumamoto and Miyazaki prefectures (1)

Seven new dammarane-type triterpenoid saponins, chikusetsusaponin FK1 (1), chikusetsusaponin FK2 (2), chikusetsusaponin FK3 (3), chikusetsusaponin FK4 (4), chikusetsusaponin FK5 (5), chikusetsusaponin FK6 (6), and chikusetsusaponin FK7 (7), and eleven known triterpenoid saponins, ginsenoside Rb3 (9), ginsenoside Rc (10), chikusetsusaponin VI (11), ginsenoside Re (12), ginsenoside Rg1 (13), pseudo-ginsenoside RS1 (14), notoginsenoside R1 (15), chikusetsusaponin L5) (17), chikusetsusaponin L10 (18), chikusetsusaponin IVa (19), and chikusetsusaponin V (20), were isolated from the fruits of Panax japonicus C. A. MEYER, collected in Kumamoto prefecture, Japan, and two new dammarane-type triterpenoid saponin, chikusetsusaponin FK5 (5) and chikusetsusaponin FM1 (8), and five known triterpenoid saponins, ginsenoside Rb3 (9), ginsenoside Rc (10), ginsenoside Re (12), ginsenoside Rg1 (13), and floralquinquenoside E (16), were isolated from the fruits of P. japonicus C. A. MEYER, collected in Miyazaki prefecture, Japan. The structures of new chikusetsusaponins were elucidated on the basis of chemical and physicochemical evidences.     

Constituents of Pongamia pinnata isolated in a screening for activity to overcome tumor necrosis factor-related apoptosis-inducing ligand-resistance

In a search for natural products with activity to overcome tumor necrosis factor-related apoptosis-inducing ligand (TRAIL)-resistance, we performed the bioassay-guided fractionation of a semi mangrove, Pongamia pinnata, collected from Bangladesh, and isolated a new compound, (2S)-(2″,3″:7,8)-furanoflavanone (1), along with six known flavonoids (2-7). Two of the compounds significantly overcame TRAIL-resistance in human gastric adenocarcinoma (AGS) cell lines.     

New triterpene constituents, foliasalacins A(1)-A(4), B(1)-B(3), and C, from the leaves of Salacia chinensis

Four dammarane-type, three lupane-type, and an oleanane-type triterpenes named foliasalacins A(1) (1), A(2) (2), A(3) (3), A(4) (4), B(1) (5), B(2) (6), B(3) (7), and C (8) were isolated from the leaves of Salacia chinensis LINN. collected in Thailand. The structures of new triterpene constituents (1-8) were characterized on the basis of chemical and physiochemical evidence.     

Flavones and rosmarinic acid from Salvia limbata

The genus Salvia (Lamiaceae) contains more than 50 shrub species in Iran, and Salvia limbata C.A. Meyer grows widely in the north and central parts of the country. Six flavones and rosmarinic acid were isolated from the ethyl acetate and methanol extracts of the flowered aerial parts of S. limbata collected from Semnan province. The separation process was carried out using several chromatographic methods. Structural elucidation was based on NMR data, in comparison with those reported in the literature. The isolated compounds were identified as ladanein (1), salvigenin (2), luteolin 7-methyl ether (3), cirsiliol (4), eupatorin (5), luteolin 7-O-glucoside (6) and rosmarinic acid (7). Some of these flavonoids have been reported to show antibacterial and cytotoxic activities.     

南海海绵Axinyssa aplysinoides的化学成分研究(三)

从南海海绵Ａｘｉｎｙｓｓａ　ａｐｌｙｓｉｎｏｉｄｅｓ中分离得到两个小分子化合物 Ｃ７Ｈ６Ｏ２和 Ｃ５Ｈ６Ｎ５Ｏ５。利用 ＩＲ、ＵＶ、ＮＭＲ、ＭＳ等分析手段确定了它的结构 为对羟基苯甲醛和胸腺嘧啶。     

New triterpenoid saponins from fruit specimens of Panax japonicus collected in Toyama prefecture and Hokkaido (2)

Four new dammarane-type triterpenoid saponins, chikusetsusaponin FT(1) (1), chikusetsusaponin FT(2) (2), chikusetsusaponin FT(3) (3), chikusetsusaponin FT(4) (4), and six known triterpenoid saponins, chikusetsusaponin FK(4) (8), chikusetsusaponin FK(5) (9), chikusetsusaponin FK(2) (10), chikusetsusaponin FK(3) (11), chikusetsusaponin LN(4) (12), and chikusetsusaponin IVa (14), were isolated from the fruits of Panax japonicus C. A. MEYER, collected in Toyama prefecture, Japan, and five new dammarane-type triterpenoid saponins, chikusetsusaponin FT(1) (1), chikusetsusaponin FT(3) (3), chikusetsusaponin FT(4) (4), chikusetsusaponin FH(1) (5), chikusetsusaponin FH(2) (6), and eight known triterpenoid saponins, ginsenoside Re (7), chikusetsusaponin FK(5) (9), chikusetsusaponin FK(2) (10), chikusetsusaponin FK(3) (11), chikusetsusaponin LN(4) (12), 28-desglucosylchikusetsusaponin IVa (13), chikusetsusaponin IVa (14), and chikusetsusaponin V (15), were isolated from the fruits of P. japonicus C. A. MEYER, collected in Hokkaido, Japan. The structures of new chikusetsusaponins were elucidated on the basis of chemical and physicochemical evidences.     

Saponins of plants of Panax species collected in Central Nepal, and their chemotaxonomical significance. III

Panax pseudo-ginseng subsp. pseudo-ginseng has a carrot like root with a small rhizome. It was shown that the saponin composition of roots and rhizomes of this subspecies collected in Tibet and China was extremely poor. From the roots and rhizomes collected in Central Nepal, (specimen-PNct), only a small amount of an oleanolic acid saponin, beta-D-glucopyranosyl-oleanolate (2) was isolated together with a polyacetylene-alcohol, panaxynol (3). In another specimen (specimen-PNs), also collected in Central Nepal, two oleanolic acid saponins, stipleanoside R2 (4) and chikusetsusaponin IV (5) were detected. No dammarane saponin was identified in either specimen. P. pseudo-ginseng subsp. himalaicus (Subsp-H) has a big rhizome with a small round root. From rhizomes and roots of this subsp. collected in Central Nepal (specimen-HNct), a fairly large amount of dammarane saponins, ginsenosides-Rb1 (6), -Rd (7), -Re (9) and -Rg1 (10), gypenoside XVII (8), notoginsenoside-R1 (11), majonoside-R2 (12) and pseudo-ginsenoside-F11 (13) were isolated, while no oleanane saponin (oleanolic acid saponin) was identified in this subsp. Based on the present and previous studies, medicinal evaluation and chemogeographical correlation of Himalayan Panax spp. are discussed.     

Bis-allylic Reactivity of the Funicolides, 5,8(17)-diunsaturated briarane diterpenes of the sea pen Funiculina quadrangularis from the tuscan archipelago,leading to 16-nortaxane derivatives

Funicolides A–C ( 1–3 ), D ( 5 ), and E ( 7 ) and 7-epifunicolide A ( 4 ), new 5,8(17)-diunsaturated briarane diterpenes, as well as the known analogue brianthein W ( 6 ), were isolated from the pennatulacean coral Funiculina quadrangularis (PALLAS , 1766) collected in the Tuscan archipelago. Easy degradation under oxidative and/or basic conditions served to assign the ester groups at C(2) or C(14), while revealing bis-allylic reactivity at C(7) with formation of 16-nortaxane derivatives.     

Absolute structures of new megastigmane glycosides, foliasalaciosides E(1), E(2), E(3), F, G, H, and I from the leaves of Salacia chinensis

Following the investigation of foliasalaciosides A(1), A(2), B(1), B(2), C, and D, seven new megastigmane glycosides named foliasalaciosides E(1)-I (1-7), together with four known constituents, were isolated from the leaves of Salacia chinensis LINN. collected in Thailand. The absolute stereostructures of the new compounds were characterized on the basis of chemical and physicochemical evidence, including the application of the modified Mosher's method.     

A new compound, jolynamine, from marine brown alga Jolyna laminarioides

A new compound, jolynamine (1), was isolated from the marine brown alga Jolyna laminarioides collected from the coast of Karachi, Pakistan. In addition, four known compounds, namely saringosterol (2), loliolide (3), methyl-4-hydroxybenzoate (4) and propyl-4-hydroxybenzoate (5), were isolated for the first time from the marine brown alga Iyengaria stellata, and two known compounds, namely 3,4,5-trimethylaniline (6) and harmine (7), were isolated for the first time from the marine brown alga Melanothamnus afaqhusainii. Compound 6 is synthetically known but was isolated for the first time from a natural source. The structures of these compounds were elucidated with the help of powerful spectroscopic techniques. Furthermore, the methanolic extracts of both algae showed anti-microbial activities against various bacteria and fungi.     

Urinary metabolites of genistein administered orally to rats.

In a study on the metabolism of flavonoids, the isoflavone genistein was administered orally to rats. Urine samples were collected and treated with beta-glucuronidase and arylsulfatase. Genistein and its metabolites, 4',5,7-trihydroxyisoflavanone (M1), 4',7-dihydroxyisoflavan (M2), and p-ethylphenol (M3) were isolated from the urine following treatment with enzymes. The structures of M1, M2, and M3 were determined on the basis of chemical and spectral data.     

Two new terpenoids from endophytic fungus Periconia sp. F-31

Two new terpenoids, (+)-(3S,6S,7R,8S)-periconone A (1) and (-)-(1R,4R,6S,7S)-2-caren-4,8-olide (2), have been isolated from an endophytic fungus Periconia sp., which was collected from the plant Annona muricata. Their structures were elucidated on the basis of extensive spectroscopic analyses. In the in vitro assays, the two compounds showed low cytotoxic activities against six human tumor cell lines (HCT-8, Bel-7402, BGC-823, A549, A2780 and MCF-7) with IC(50)>10(-5) M.     

Two new paeciloxocins from a mangrove endophytic fungus Paecilomyces sp.

Paeciloxocins A and B (2-(1-hydroxy-3-methylbutyl)- and 2-(1-acetoxy-3-methylbutyl)- 11-hydroxy-9-methyl-1-methoxy-5H,7H-dibenzo[b,g]-1,5-dioxocin-5-ones), viz., two new metabolites, were isolated from the mangrove fungus Paecilomyces sp. collected from the Taiwan Strait. Their structures were elucidated by spectral methods. Paeciloxocin A exhibited strong cytotoxicity against the hepG2 cell line.     

(1)H and (13)C NMR assignments for five anthraquinones from the mangrove endophytic fungus Halorosellinia sp. (No. 1403)

We report the unambiguous assignments of the (1)H and (13)C NMR spectra of two new natural products, namely, 1,4,5,6,7,9-hexahydroxy-2-methoxy-7-methyl-5beta,9beta,8abeta, 6alpha,10aalpha-hexahydroanthracen-10 (10aH)-one (1) and 1,4,6-trihydroxy-2-methoxy-7-methylanthracene-9, 10-dione (2), together with three known anthraquinones. These compounds were all isolated from the marine endophytic fungus No. 1403 collected from the South China Sea. Compounds 3 and 4 were isolated from the marine fungus for the first time. The structures were elucidated by the spectroscopic methods 1D and 2D NMR including COSY, HMQC, HMBC and NOE, and HREIMS. In our cytotoxicity assays, compound 5 showed cytotoxicity toward KB and KBv-200 cells with IC(50) of 1.40 and 2.58 microg/ml, respectively. In addition, the plausible biogenic relationship of compounds 1, 2, 3 and 4 is discussed.     

A new flavonoid and other constituents from Centaurea nicaeensis All. var. walliana M

A new flavone glucoside, apigenin 4'-(6″-methylglucuronide) (1), together with six known compounds, cirsilineol, jaceosidin, melitensin, apigenin, apigenin 7-(6″-methylglucuronide) and prunasin, were isolated from the ethanolic extract of the aerial parts of Centaurea nicaeensis All. var. walliana M. (Asteraceae) collected from Souk-Ahras, eastern Algeria. The structures were established by spectral analysis, mainly HRESI-MS, UV and 2D-NMR experiments (COSY, HSQC and HMBC).     

A new dehydroaporphine alkaloid from Papaver fugax

A new dehydroaporphine alkaloid (-)-6a,7-dehydrofloripavidine has been isolated from the aerial parts of Papaver fugax Poir. (Papaveraceae) collected from Erzurum (Eastern Anatolia). (-)-Floripavidine (aporphine) and (-)-mecambrine (proaporphine) were isolated as major alkaloids. Other bases present were (+)-salutaridine (promorphinane) and argentinine (phenanthrene). The presence of argentinine has been shown for the first time in the Papaveraceae.     

冬凌草中的新对映-贝壳杉烷二萜化合物

对河南省济源地区产冬凌草[Isodon rubescens(Hemsl.)Hara]再次进行了深入 的研究，从其叶的乙酸乙酯提取物中分离得到了16个化合物，其中1和2为两个新的 7，20-环氧-对映-贝壳杉烷类二萜化合物，其结构通过波谱分析确定为16（S）-羟 甲基-1α，6β，7β，11β-甲羟基-7α，20-环氧-对映-贝壳杉烷-15-酮（1）和 16（R）-羟甲基-1α，6β，7β，14β-四羟基-7α，20-环氧-对映-贝壳杉烷-15- 酮（2），分别命名为冬凌草已素（1）和庚素（2）；其余的已知化合物分别鉴定 为lasiodonin（3），冬凌草甲素（oridonin，4），乙素（ponicidin），丙素（ rubescensin C），丁素（rubescensin D），牛尾草丙素（rabdoternin C），荛 花香茶菜乙素（wikstroemioidin B），enmenol-1α-O-β-D-glucoside， enmenol，胡麻素（pedalitin），水杨酸，乌索酸，β-谷甾醇和胡萝卜甙。