Two unique pentacyclic steroids with cis C/D ring junction from Xestospongia bergquistia Fromont, powerful inhibitors of histamine release

Shoji, Noboru; Umeyama, Akemi; Shin, Kogyoku; Takeda, Katsuko; Arihara, Shigenobu; Kobayashi, Jun’ichi; Takei, Masao

doi:10.1021/jo00037a009

Cited by 70 publications

(50 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Irradiation of H 3 -18 caused enhancements of H-14, H-20, and H 3 -21, but not of H-17, suggesting a cis -fused C/D ring. The downfield shift (Δ = +10.4 ppm) of C-18 in the 13 C NMR spectrum of 10 , relative to that observed for methyl 4α-methylergost-8,24(28)-dien-3,11-dion-26-oate, was also in agreement with a rare cis C/D ring junction, which has been found in compounds from marine sponges 15–17. Additional smaller carbon signals at δ C 31.8, 45.5, and 16.3 were attributed to the other C-25 epimer.…”

Section: Resultssupporting

confidence: 80%

Camphoratins A−J, Potent Cytotoxic and Anti-inflammatory Triterpenoids from the Fruiting Body of Taiwanofungus camphoratus

Leu

Chen

et al. 2010

J. Nat. Prod.

View full text Add to dashboard Cite

Ten new triterpenoids, camphoratins A-J (1-10), along with 12 known compounds were isolated from the fruiting body of Taiwanofungus camphoratus. Their structures were established by spectroscopic analysis and chemical methods. Compound 10 is the first example of a naturally occurring ergosteroid with an unusual cis-C/D ring junction. Compounds 2-6 and 11 showed moderate to potent cytotoxicity with EC 50 values ranging from 0.3 to 3 μM against KB and KB-VIN human cancer cell lines. Compounds 6, 10, 11, 14-16, 18, and 21 exhibited antiinflammatory NO-production inhibition activity with IC 50 values of less than 5 μM, which was more potent than the nonspecific NOS inhibitor N ω -nitro-L-arginine methyl ester (L-NAME).Taiwanofungus camphoratus (synonym: Ganoderma camphoratum; Antrodia cinnamomea; Antrodia camphorata) (Polyporaceae, Aphyllophorales), is a rare and precious medical fungus in Taiwan and is called a "national treasure of Taiwan".1 Its Chinese name is ZhanKu or Niu-Chang-Chih. The microorganism is parasitic to the inner heart-wood wall of old hollow trunks of Cinnamomum kanehirai Hay. (Lauraceae). The growth rate of natural T. camphoratus in the wild is very slow, and it is difficult to cultivate in a greenhouse, making fruiting bodies expensive to obtain. In traditional Taiwanese folk medicine T. camphoratus has been used as an important health food for treating food, alcohol, and drug intoxication, -methylergost-8,24(28)-diene-3,11-dion-26-oate (21),10 and ergosterol peroxide (22).11 Cytotoxic activity, inhibition of nitric oxide (NO) or reactive oxygen species (ROS) production, and free radical-scavenging activity of the isolates were evaluated in our study. NIH Public Access Results and DiscussionCamphoratin A (1) was obtained as a colorless powder. , suggested a 4-methylergost-8-en-11-one skeleton similar to that of antcin C (16).5 The 3α-OH functionality was deduced by the correlations from H-3 (δ 3.89, 1H, d, J = 1.6 Hz, β-orientation) to C-4 and C-1 and from H 3 -29 to C-3, C-4, and C-5 in the HMBC spectrum of 1. The hydroxy groups attached at C-7 and C-12 were further designated by the correlations from H-7 (δ 4.52, 1H, t, J = 8.4 Hz) to C-6 and C-8 and from H-12 (4.44, 1H, s) to C-13, C-14, and C-17, respectively. The C-25 carboxylic functionality was assigned due to the presence of an HMBC correlation from H-25 (δ 3.45, 1H, q, J = 6.8 Hz) to the carbon resonance at δ 176.9. A comparison of the NMR spectroscopic data of 1 with those of 165 confirmed the above elucidation and unambiguously established the structure of 1. The relative configuration of 1 was determined by the NOE correlations observed in a NOESY experiment. In the NOESY spectrum of 1, H-7 showed NOE enhancements with both H-5 and H-14, suggesting that these protons had α-orientations. Furthermore, NOE correlations between H-3 and H-4 as well as between H-12 and H 3 -18 disclosed that these protons are β-oriented.Camphoratin B (2) was obtained as a colorless syrup. The HRESIMS of 2 gave an [M + Na] + peak at m/z 495.3089 ...

show abstract

Section: Resultssupporting

confidence: 80%

Camphoratins A−J, Potent Cytotoxic and Anti-inflammatory Triterpenoids from the Fruiting Body of Taiwanofungus camphoratus

Leu

Chen

et al. 2010

J. Nat. Prod.

View full text Add to dashboard Cite

show abstract

“…Stemmin C, stemmosides C, D and G-K are characterized by the unusual presence of a C-17 side chain and no substitution in C-12. On the other hand, stemmosides D-J are also characterized by the occurrence of an uncommon 14 [31][32][33][34][35].…”

Section: Chemistrymentioning

confidence: 99%

“…Therefore a dose dependence study was performed to test the effect on the KS cell proliferation in a concentration range 0.1-20 μM for compounds 27, 31-33, 35, 37-54 and 0.001-0.1 μM for compounds 34 and 36. Results indicated that 15-keto-pregnane glycosides (27,(31)(32)(33)35, and 37-39) and 14,15-secopregnane glycosides (40)(41)(42)(43)(44)(45)(46)(47)(48)(49)(50)(51)(52)(53)(54) reduced the VEGF-induced KS cell proliferation in a dose-dependent manner and the highest reduction occurred at concentration of 10 μM. Between secopregnane glycosides argeloside C showed the highest reduction of the VEGF-induced KS cell proliferation at 10 μM (55.3%), while stemmoside D (SmD) was the most effective both of the pregnane and the secopregnane glycosides showing 65% inhibition of the VEGF-induced cell proliferation at 10 μM (Fig.…”

Section: Biological Activitymentioning

confidence: 99%

Solenostemma argel: A Rich Source of Very Unusual Pregnane and 14,15- Secopregnane Glycosides with Antiproliferative Activity

Perrone¹,

Plaza²,

Hamed³

et al. 2008

COC

View full text Add to dashboard Cite

Solenostemma argel Hayne (Asclepiadaceae) is an Egyptian plant whose leaves are commonly used in traditional medicine as a purgative, antipyretic and antispasmodic remedy. From the pericarps, hairy seeds and leaves fifteen new 14,15-secopregnane glycosides, namely argelosides A-J, and nine new 15-ketopregnane glycosides, namely stemmosides C-K, have been isolated. Argelosides A-J show very unusual structures characterized by the opening of ring D between C-14 and C-15, and the occurrence of two ketal functions on C-14 and C-20 generating three five-membered rings with oxygenated functions in positions 16 and 15, respectively. Stemmosides D-J are characterized by the occurrence of an uncommon 14 proton configuration while stemmosides E and F possess in addition a rare enolic function in C-16. Apparently these compounds are the first pregnanes isolated from plants known to have a 15 keto, cis CD ring junction. On the other hand, stemmosides C, D and G-K are the only natural compounds which display an unusual C-17 side chain and no substitution in C-12. On the basis of antitumor and cytotoxic activities reported for pregnane and their glycosides and considering the very unusual structural features of argelosides and stemmosides, the antiproliferative activity of these compounds against Kaposi's sarcoma cells was evaluated. Thus a dose dependence study was performed to test the effects of compounds on the VEGF-induced KS cell proliferation in a concentration range 0.1-20 μM. Results indicated that 15-keto-pregnane glycosides and 14,15-secopregnane glycosides reduced the VEGF-induced KS cell proliferation in a dose-dependent manner and the highest reduction occurred at concentration of 10 μM.

show abstract

“…Additionally, interaction with the IL-8 receptor type A (de Almeida Leone et al 2000), antimicrobial as well as antiviral properties (Rudi et al 2001) have been reported. Recently, steroids with an unusual 14b-configuration attracted attention as anti-inflammatory agents acting on human neutrophil and mast cells (Shoji et al 1992;Keyzers et al 2002). Currently synthetic derivatives (Shen and Burgoyne 2002) of these sterols are under phase II clinical investigations for the treatment of asthma and inflammatory diseases of the skin and eye.…”

Section: Introductionmentioning

confidence: 99%

Isolation and structure elucidation of azoricasterol, a new sterol of the deepwater sponge Macandrewia azorica

Gross

Reitner

König

2004

Naturwissenschaften

View full text Add to dashboard Cite

Chemical investigation of the deepwater sponge Macandrewia azorica, collected from the flanks of the Gettysburg and Ormonde Sea Mount, North Atlantic, from a depth of 600 m, has led to the isolation of a new sterol with an unusual side chain (1), along with S-methylergothioneine (2). The structures of compounds 1 and 2 were established by employing spectroscopic techniques (NMR, MS, UV, IR and polarimetry). This is the first report of metabolites of a sponge belonging to the genus Macandrewia.

show abstract

Two unique pentacyclic steroids with cis C/D ring junction from Xestospongia bergquistia Fromont, powerful inhibitors of histamine release

Cited by 70 publications

References 0 publications

Camphoratins A−J, Potent Cytotoxic and Anti-inflammatory Triterpenoids from the Fruiting Body of Taiwanofungus camphoratus

Camphoratins A−J, Potent Cytotoxic and Anti-inflammatory Triterpenoids from the Fruiting Body of Taiwanofungus camphoratus

Solenostemma argel: A Rich Source of Very Unusual Pregnane and 14,15- Secopregnane Glycosides with Antiproliferative Activity

Isolation and structure elucidation of azoricasterol, a new sterol of the deepwater sponge Macandrewia azorica

Contact Info

Product

Resources

About