Two New Triterpenes from the Rhizome of Dryopteris crassirhizoma, and Inhibitory Activities of Its Constituents on Human Immunodeficiency Virus-1 Protease

Lee, Ji Suk; Miyashiro, Hirotsugu; Nakamura, Norio; Hattori, Masao

doi:10.1248/cpb.56.711

Cited by 45 publications

(25 citation statements)

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“…1 H-and 13 C-NMR data (Tables 3 and 2, resp.) showed a signal for an additional CHÀO group and a high-field Me signal compared with those of 2b-hydroxy-21bH-hop-22(29)-ene-24-oic acid [8]. In the HMBC spectrum of compound 9, the HÀC (3) 9), suggesting that the MeOCO group was located at C(4) (Fig.…”

Section: )mentioning

confidence: 95%

“…; for structures, see Fig. 1), including 21aH-24-norhopa-4(23),22(29)-diene-3b,6b,7b,11a-tetrol (1), 11a-(acetyloxy)-7b-(benzoyloxy)-21aH-24-norhopa-4(23),22(29)-diene-3b,6b-diol (2), 11a-(acetyloxy)-7b-(caproyloxy)-21aH-24-norhopa-4(23),22(29)-diene-3b,6b-diol (3), 7b-(benzoyloxy)-21aH-24-norhopa-4(23),22(29)-diene-3b,6b,11a-triol (4), 6b-(acetyloxy)-21aH-24-norhopa-4(23), 22(29)-diene-3b,12b-diol (5), 7b-(benzoyloxy)-21aH-24-norhopa-4(23),22(29)-diene3b,6b,11b-triol (6), 6b-(acetyloxy)-7b-(benzoyloxy)-21aH-24-norhopa-4(23),22(29)-diene-3b,11b-diol (7), 6b-(acetyloxy)-12b-(benzoyloxy)-21aH-24-norhopa-4(23), 22(29)-dien-3b-ol (8), methyl 3b,12b-dihydroxy-21aH-hop-22(29)-en-24-oate (9), methyl 6b-(acetyloxy)-3b,11b-dihydroxy-21aH-hop-22(29)-en-24-oate (10), 7b-(benzoyloxy)dammar-20(21)-ene-3b,24x,25-triol (11). Cavalerols A -H (1 -8, resp.)…”

Section: Introduction -Eurycorymbus Cavaleriei (H Le¤ V) Rehder Etmentioning

confidence: 99%

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Eleven New Triterpenes from Eurycorymbus cavaleriei

Cheng

Shen

Zhang

et al. 2010

Helvetica Chimica Acta

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Eleven new triterpenes, cavalerols A -K (1 -11, resp.), ten of which were derivatives of hopane and one was derivative of dammarane, were isolated from the twigs of Eurycorymbus cavaleriei. Their structures were elucidated by spectroscopic methods including 2D-NMR analysis. Cavalerol D (4) and cavalerol F (6), cavalerol B (2), and cavalerol G (7) were two pairs of isomers, and silver ion was introduced for their differentiation by multi-stage tandem mass spectrometry. And nine compounds, except 5 and 10, were tested for quinone reductase (QR) induction activities in vitro, and results showed that compounds 2, 4, and 7 exhibited moderate induction activities with CD values of 8.62, 9.13, and 2.56 mg/ml, respectively, and compounds 6 and 8 showed cytotoxicity against hepa 1c1c7 cell line with IC 50 values of no more than 1 mg/ml.

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Section: )mentioning

confidence: 95%

Section: Introduction -Eurycorymbus Cavaleriei (H Le¤ V) Rehder Etmentioning

confidence: 99%

Eleven New Triterpenes from Eurycorymbus cavaleriei

Cheng

Shen

Zhang

et al. 2010

Helvetica Chimica Acta

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“…Many constituents, including sesquiterpenes, phloroglucins, phenolic glycosides, and sitosterols have been isolated from D. crassirhizoma, D. parallelogramma, D. patula, D. hawaiiensis, D. fuscoatra, D. fragrans, D. abbreviate, D. polylepis, and D. dickinssi [2][3][4][5][6][7][8]. Phloroglucins are characteristic constituents of Dryopteris plants and are of interest to many pharmaceutical scholars due to multiple physiological activities such as antivirus, antitumor, antibacterial, and anti-inflammatory effects [9][10][11][12]. To the best of our knowledge, there is no research on the chemical constituents of D. wallichiana.…”

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A new carbamic acid from Dryopteris wallichiana

2011

Chem Nat Compd

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The genus Dryopteris, belonging to the Dryopteridaceae family, is a cosmopolitan genus comprising approximately 450 species, mostly occurring in temperate forests and mountainous areas of the tropics. China has more than 300 species distributed across the country, 21 of which can be used for medicine [1]. Many constituents, including sesquiterpenes, phloroglucins, phenolic glycosides, and sitosterols have been isolated from D. crassirhizoma, D. parallelogramma, D. patula, D. hawaiiensis, D. fuscoatra, D. fragrans, D. abbreviate, D. polylepis, and D. dickinssi [2-8]. Phloroglucins are characteristic constituents of Dryopteris plants and are of interest to many pharmaceutical scholars due to multiple physiological activities such as antivirus, antitumor, antibacterial, and anti-inflammatory effects [9][10][11][12]. To the best of our knowledge, there is no research on the chemical constituents of D. wallichiana.In the present study, D. wallichiana growing in Xishuangbanna of Yunnan Province was examined. Samples of the aerial parts of D. wallichiana were collected in May 2006, and a voucher specimen was kept at the Herbarium of the Institute of Natural Products, Henan University. The dried aerial parts of D. wallichiana (3.5 kg) were extracted with ethanol (95%) at room temperature. After evaporation of the ethanol, the residue was suspended in water and extracted with petroleum ether, chloroform, and n-butanol. The n-butanol extract (120 g) was subjected to silica gel column chromatography (200-300 mesh, Qingdao Marine Chemical Inc, China) using chloroform-methanol mixtures (I r =10:1 to 8:2) and divided into three fractions by TLC detection. Fraction 1 was subjected repeatedly to column chromatography over silica gel (10-40 P Qingdao Marine Chemical Inc, China), eluting with chloroform-methanol (I r = 10:1) to afford (1,7a-dihydro-1H-inden-2(7aH)-ylidene) methylcarbamic acid (1, 26.2 mg) and 3,7,11,15-tetramethyl-2-hexadecen-1-ol (4, 11.2 mg). Fraction 2 was chromatographed on Sephadex LH-20 using methanol as eluent and then subjected to C-18 eluting with methanol-water (I r = 7:3) to afford 12-ursen-28-oic acid-3-O-E-D-glucopyranoside (2, 19.4 mg) and 12-ursen-3-O-E-D-glucopyranoside (3, 28 mg). Compound 1 was a new compound, and 2 and 3 were isolated and identified from the genus for the first time.Identification of the isolated compounds was performed by comparison of the physical constants and spectral data with those of known compounds [13][14]. Compound 1, obtained as white needles, had the molecular formula C 11 H 13 NO 2 , as deduced from the molecular-ion peak at m/z 192.1034 [M + H] + (calcd 192.1024) in the HR-EI-MS and from 13 C NMR and DEPT analyses. The 13 C NMR spectrum revealed 11 carbon signals that were sorted by DEPT experiments into a carbonyl group (G 172.3), five olefinic methine groups (G 134.3, 126.9 u 2 and 125.3 u 2), an olefinic quaternary carbon atom (G 126.0), two methylene groups (G 49.1 and 45.2), and two methine groups (G 47.0 and 45.2). The signals of two methine protons [G 1.16...

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“…Anti-HIV-1 Protease Activities of Compounds Isolated from Ganoderma Species Our previous publications addressing the development of naturally occurring anti-viral agents, 21,22) indicate that some triterpenes, such as ganoderic acid B and ganoderiol B, 9) N-(3b-hydroxyolean-12-en-28-oyl)-6-aminohexanoic acid, 15) hemiesters of ursolic acid, 23) 3-oxotirucalla-7,24-dien-21-oic acid, 24) 16b-hydroxy-2,3-secolup-20(29)-en-2,3-dioic acid, 25) colossolactone V, 26) and 2-Oacetyldryopteric acid A, 27) potently inhibit HIV-1 PR, which is an essential enzyme for HIV proliferation. 21,22) Here we compared the abilities of 11 triterpenoids isolated from the fruiting body of G. sinense and 11 [ganoderic acid A (15) …”

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confidence: 99%