A new lanostane-type triterpene from the fruiting bodies of Ganoderma lucidum

A new lanostane-type triterpene, named ganoderic acid LM 2 ( 5 ), was isolated from the fruiting bodies of Ganoderma lucidum . Its structure was characterized as (23S) 7 g , -dihydroxy-3, 11, 15-trioxo-5 f -lanosta-8, 24-dien-26-oic acid by 1D- and 2D-NMR spectra. In addition, a known triterpene, ganoderic acid l ( 4 ), was obtained. Both of them exhibited potent enhancement of ConA-induced mice splenocytes proliferation in vitro .     

赤芝子实体中三萜化学成分的研究

自赤芝[Ganoderma lucidum (Fr.)Karst]的二氯甲烷溶解部分分离得到一个新的三萜内酯化合物,命名为灵芝内酯(ganolactone)。根据光谱(UV,IR,¹HNMR,¹³CNMR,MS和2DNMR)解析,确定其结构为I式。同时还从赤芝子实体中分到三个已知化合物,即灵芝醇A(ganoderiolA,II),灵芝醇B(ganoderiolB,II)和灵芝三醇(ganodermatriolIV)。     

A new ganoderic acid from Ganoderma lucidum mycelia

A new ganoderic acid (GA), 7-O-ethyl ganoderic acid O (GA-O) (1), together with two known compounds, GA-T (2) and GA-Me (3), was isolated and purified from fermented mycelia of Ganoderma lucidum. The structure of the new triterpenoid was elucidated on the basis of the interpretation of extensive spectroscopic data (HR-MS, IR, UV, 1D and 2D NMR) as 3α,15α,22-triacetoxy-7α-ethoxy-5α-lanost-8,24E-dien-26-oic acid. The new compound was found to contain a rare ethoxyl group at C-7. In addition, its cytotoxicity against 95D and HeLa human cancer cell lines was also evaluated.     

Two new triterpenoids from the resin of Boswellia carterii

Two new triterpenoids, 3-oxotirucalla-7,9(11),24-trien-21-oic acid (1) and 18Hα,3β,20β-ursanediol (2), along with 15 known triterpenes, α-amyrin, α-boswellic acid, β-boswellic acid, acetyl α-boswellic acid, acetyl β-boswellic acid, 9,11-dehydro-β-boswellic acid, 9,11-dehydro-α-boswellic acid, acetyl 11α-methoxy-β-boswellic acid, 11-keto-β-boswellic acid, acetyl 11-keto-β-boswellic acid, acetyl α-elemolic acid, 3β-hydroxytirucalla-8,24-dien-21-oic acid, elemonic acid, 3α-hydroxytirucalla-7,24-dien-21-oic acid, and 3α-hydroxytirucall-24-en-21-oic acid, were isolated from the resin of Boswellia carterii Birdw.     

Two new triterpenoids from the resin of Boswellia carterii

Two new triterpenoids, 3-oxotirucalla-7,9(11),24-trien-21-oic acid (1) and 18Hα,3β,20β-ursanediol (2), along with 15 known triterpenes, α-amyrin, α-boswellic acid, β-boswellic acid, acetyl α-boswellic acid, acetyl β-boswellic acid, 9,11-dehydro-β-boswellic acid, 9,11-dehydro-α-boswellic acid, acetyl 11α-methoxy-β-boswellic acid, 11-keto-β-boswellic acid, acetyl 11-keto-β-boswellic acid, acetyl α-elemolic acid, 3β-hydroxytirucalla-8,24-dien-21-oic acid, elemonic acid, 3α-hydroxytirucalla-7,24-dien-21-oic acid, and 3α-hydroxytirucall-24-en-21-oic acid, were isolated from the resin of Boswellia carterii Birdw.     

赤芝子实体中灵芝酸类成分的研究

自赤芝［Ｇａｎｏｄｅｒｍａｌｕｃｉｄｕｍ（Ｆｒ．）Ｋａｒｓｔ．］子实体的二氯甲烷提取物中分离得到一个新的四环三萜化合物，命名为灵芝酸ＤＭ（ｇａｎｏｄｅｒｉｃａｃｉｄＤＭ，Ｉ）。根据光谱（ＵＶ，ＩＲ，１ＨＮＭＲ，１３ＣＮＭＲ，ＭＳ２ＤＮＭＲ）分析，确定其结构为Ｉ式。同时还分离得到二个已知的灵芝酸类化合物，即灵芝酸Ａ（ｇａｎｏｄｅｒｉｃａｃｉｄＡ，Ｉ）和灵芝酸Ｃ（ｇａｎｏｄｅｒｉｃａｃｉｄＣ，ＩＩ）。     

5alpha-reductase inhibitory effect of triterpenoids isolated from Ganoderma lucidum

5alpha-Reductase inhibitory activity-guided fractionation of the EtOH extract of the fruiting body of Ganoderma lucidum (LEYSS.:FR.) KARST. (Ganodermataceae), which is called Reishi, or Mannentake in Japan and Lingzhi in China, led to the isolation of two active compounds which were ganoderic acid DM and 5alpha-lanosta-7,9(11),24-triene-15alpha,26-dihydroxy-3-one with an IC(50) of 10.6 microM and 41.9 microM respectively. A carboxyl group of side chain of ganoderic acid DM is essential to elicit the inhibitory activity because of much less activity of its methyl ester.     

A new lanostane-type triterpene from the fruiting bodies of Ganoderma lucidum

A new lanostane-type triterpene, named ganoderic acid LM2 (5), was isolated from the fruiting bodies of Ganoderma lucidum. Its structure was characterized as (23S) 7beta, -dihydroxy-3, 11, 15-trioxo-5alpha-lanosta-8, 24-dien-26-oic acid by 1D- and 2D-NMR spectra. In addition, a known triterpene, ganoderic acid epsilon (4), was obtained. Both of them exhibited potent enhancement of ConA-induced mice splenocytes proliferation in vitro.     

New terpenes from Salvia palaestina Benth. and Salvia syriaca L. growing wild in Jordan

The novel seco-ursane-type triterpenoid 3β,11α-dihydroxy-17,22-seco-17(28), 12-ursadien-22-oic acid (1) was isolated for the first time from a natural source from two Salvia species growing wild in Jordan, Salvia palaestina Benth. and Salvia syrica L. In addition to compound 1, S. syriaca afforded a new sesquiterpene named syriacine (2). S. palaestina also afforded 15 other known compounds, 6 of which are isolated for the first time from the plant, and these include velutin, hyptadienic acid, cirsilineol, 2α,3β-dihydroxyurs-12-en-28-oic acid, 2α,3α-dihydroxy-24-nor-4(23),12-oleanan-28-oic acid, and 2α,3β,24-trihydroxyurs-12-en-28-oic acid. S. syriaca also afforded 16 other known compounds, 7 of which are isolated for the first time from the plant. These are 1α,3α-dihydroxyolean-9(11),12-diene, maslinic acid, 2α,3β,24-trihydroxyolean-12-en-28-oic acid, 11-oxo-oleanolic acid, 11-oxo-ursolic acid, poriferast-5-en-3,7-diol, and pectolinangenin.     

Anti-inflammatory ergostanes from the basidiomata of Antrodia salmonea

Three new anti-oxidative ergostanes, methyl antcinate L (1), antcin M (2), and methyl antcinate K (3), together with nine additional known compounds, 3-ketodehydrosulphurenic acid, sulphurenic acid, dehydrosulphurenic acid, 3beta,15alpha-dihydroxylanosta-7,9(11),24-trien-21-oic acid, zhankuic acid A, zhankuic acid B, zhankuic acid C, antcin C, and antcin K were isolated from the basidiomata of Antrodia salmonea, a newly identified species of Antrodia (Polyporaceae) in Taiwan. These three new compounds were identified as methyl 3alpha,7alpha,12alpha-trihydroxy-4alpha-methylergosta-8,24(29)-dien-11-on-26-oate (1), 3alpha,12alpha-dihydroxy-4alpha-methylergosta-8,24(29)-dien-11-on-26-oic acid (2), and methyl 3alpha,4beta,7beta-trihydroxy-4alpha-methylergosta-8,24(29)-dien-11-on-26-oate (3) by spectroscopic analysis. We studied their antioxidative potential on the production of reactive oxygen species and nitric oxide (NO) in neutrophils and microglial cells, respectively. Compounds 1-3 displayed potent antioxidative activity with IC50 values of around 2.0-8.8 microM that was partially due to inhibition (6-67%) of NADPH oxidase activity but not through direct radical-scavenging properties. Compounds 1-3 also inhibited NO production with IC50 values of around 1.7-16.5 microM and were more potent than a non-specific NOS inhibitor. We conclude that these three new compounds 1, 2, and 3 exhibit anti-inflammatory activities in activated inflammatory cells.     

海南粗榧内生真菌S26化学成分研究

目的对海南粗榧内生真菌S26发酵液的化学成分进行研究。方法用多种柱色谱技术对化合物进行分离纯化,根据波谱数据和理化性质鉴定化合物的结构。结果从海南粗榧内生真菌S26的发酵液中分离得到6个化合物,分别鉴定为（-）-5-methylmellein（1）、（-）-3,5-dimethyl-8-methoxy-3,4-dihydroisocoumarin（2）、ergosterol peroxide（3）、（3β,5a,8a,22E,24R）-5,8-epidioxy-ergosta-6,9（11）,22-trien-3-ol（4）、22E,24R—ergos—ta-7,22-diene-3β,5α,6β,9α-tetraol（5）、对羟基苯乙醇（6）。结论以上化学成分为从海南粗榧内生真菌中首次分离得到。     

Triterpenoid Acids from Kadsura longipedunculata. Neokadsuranic Acids B and C: Two Novel Triterpenoids with 14 (13 --> 12)abeo-Lanostane Skeletons

Six triterpenoid acids were isolated from the stems of KADSURA LONGIPEDUNCULATA, collected in Kuangxi province. Four of them were new compounds and assigned as (24 Z)-3-oxo-12alpha-acetoxylanosta-8,24-dien-26-oic acid ( 1), (24 Z)-3-oxo-12alpha-hydroxylanosta-8,24-dien-26-oic acid ( 2), (24 Z)-3-oxo-14(13-->12) ABEO-lanosta-8,13(18),24-trien-26-oic acid ( 3), and (24 Z)-3-oxo-13beta-hydroxy-14(13-->12) ABEO-lanosta-8,24-dien-26-oic acid ( 4). Compounds 3 and 4 were named neokadsuranic acids B and C, respectively.     

Terpenoids and steroids from several euphorbiaceae and pinaceae plants]

During the course of a search for biologically active constituents from unexamined plant sources, several biogenetically interesting new di- and tri-terpenes and steroids were isolated from several weeds and shrubs of Euphorbiaceae and the bark, leaves and cones of several Pinaceae trees which had been treated as wastes in the forestry industry. Euphorbia supina contained 3,4-seco-5 alpha- and 5 beta-adian-4(23)-ene-3,5-diols and related oxides, oxygenated fern-8-en-3 beta-ols named supinenolones A-E and unusually migrated oxyfernanes having (9S)- and (9R)-7(8-->9)abeo-9-D:C-friedo-B':A'-neogammacerane skeletons named spirosupinane and neospirosupinane, while E. chamaesyce contained 3,4-seco-oleana-4(23), 18-dien-3-oic acid, 3,4-seco-8 beta H-ferna-4(23),9(11)-dien-3-oic acid and two oxygenated obtusifoliols. The bark of Phyllanthus flexuosus (Euphorbiaceae) contained 11 beta-hydroxy-D:A-friedo-olean-1-en-3-one, lup-20(29)-ene-3 beta, 15 alpha-diol, olean-12-ene-3 beta,15 alpha-diol and olean-12-ene-3 beta,15 alpha,24-triol together with trichadenic acid B for which we revised the structure to 3 beta-hydroxy-D:A-friedo-oleanan-27-oic acid. Two 26-nor-D:A-friedo-olean-14-enes were isolated from P. watsonii. Regarding Pinaceae trees, an unusually migrated abieslactone [(3R, 7S, 9R, 23R)-7-hydroxy-3-methoxy-8-oxo-7(8-->9)abeo-lanost-24-eno-26,23-lactone], named spiroveitchionolide, was isolated from the bark of Abies species, besides nine abieslactone analogues. Two pairs of unusually migrated serratanes, piceanonols A and B and jezananals A and B having novel skeletal systems of 14(13-->12) abeo- and 16(15-->14) abeo-serratanes named piceanane and jezanane, respectively, were also isolated from the stem bark of Picea species, besides three 14 beta,15 beta-epoxyserratanes and two 13 alpha,14 alpha-epoxyserratanes. The leaves of Larix kaempferi contained two deformed abietanes named karamatsuic acid (9,10-seco-9,10 alpha-epoxyabieta-8,11,13-trien-18-oic acid) and larikaempferic acid [9 alpha,13 alpha-epoxy-8-oxo-9(8-->7)abeo-7 beta-abietan-18-oic acid], as well as the cones to contain 8 alpha,12 alpha-epidioxy-15-hydroxyabiet-13-en-18-oic acid, three diepoxy-abietan-18-oic acids and two new dehydroabietic acid analogues. Several of the above compounds exhibited inhibitory effects against tumor-promoting and DNA topoisomerase II activities.     

Aromatase inhibitory activities of standishinal and the diterpenoids from the bark of Thuja standishii

The absolute stereostructure of a novel skeletal diterpene, standishinal (1), from the bark of Thuja standishii was confirmed by X-ray crystallographic analyses of 1 and its p-bromobenzoate derivative. Aromatase inhibitory activities of standishinal, eight known diterpenes, totarol, 12-methoxyabieta-8,11,13-trien-11-ol, 12-hydroxy-6,7-seco-abieta-8,11,13-triene-6,7-dial, trans-communic acid, labda-8(17),13-dien-12 R,15-olid-19-oic acid, 12 S-hydroxylabda-8(17),13(16),14-trien-19-oic acid, 13-oxo-15,16-dinorlabda-8(17),11 E-dien-19-oic acid and 14-oxo-15-norlabda-8 (17),12 E-dien-19-oic acid from the plant, and four synthetic analogs were evaluated using a recombinant human aromatase. Among them, standishinal and its diacetate derivative had significant inhibitory activities.     

Constituents from the fruiting bodies ofGanoderma applanatum and their aldose reductase inhibitory activity

Eight compounds were isolated from the fruiting bodies of Ganoderma applanatum, and were identified as 2-methoxyfatty acids (1), 5-dihydroergosterol (2), ergosterol peroxide (3) 3beta,7beta, 20,23xi-tetrahydroxy-11,15-dioxolanosta-8-en-26-oic acid (4), 7beta,20,23xi-trihydroxy-3,11,15-trioxolanosta-8-en-26-oic acid (5), cerevisterol (6), 7beta,23xi-dihydroxy-3,11,15-trioxolanosta-8,20E (22)-dien-26-oic acid (7), and 7beta-hydroxy-3,11,15,23-tetraoxolanosta-8,20E(22)-dien-26-oic acid methyl ester (8) by spectral analysis. All compounds were isolated for the first time from this fruiting bodies, and their effect on rat lens aldose reductase (RLAR) activity was tested. Among these eight compounds, ergosterol peroxide (3) was found to exhibit potent RLAR inhibition, its IC50 value being 15.4 microg/mL.     

Poriacosones A and B: two new lanostane triterpenoids from Poria cocos

Two new lanostane triterpenoids, poriacosones A (8) and B (9), together with eight known compounds were isolated from the sclerotia of Poria cocos (Schw.) Wolf (Polyporaceae), and identified by spectroscopic analysis, including IR, UV, CD, ESI-TOF-MS, HR-SIMS, 1D-, and 2D-NMR spectra. The structures of the new compounds were established as 3alpha,16alpha-dihydroxy-24-oxolanost-7,9(11)-dien-21-oic acid (8) and 3beta,16alpha-dihydroxy-24-oxolanost-7,9(11)-dien-21-oic acid (9).     

Poriacosones A and B: two new lanostane triterpenoids from Poria cocos

Two new lanostane triterpenoids, poriacosones A (8) and B (9), together with eight known compounds were isolated from the sclerotia of Poria cocos (Schw.) Wolf (Polyporaceae), and identified by spectroscopic analysis, including IR, UV, CD, ESI-TOF-MS, HR-SIMS, 1D-, and 2D-NMR spectra. The structures of the new compounds were established as 3alpha,16alpha-dihydroxy-24-oxolanost-7,9(11)-dien-21-oic acid (8) and 3beta,16alpha-dihydroxy-24-oxolanost-7,9(11)-dien-21-oic acid (9).     

劲直刺桐化学成分研究

采用现代多种色谱技术对劲直刺桐Erythrina strica Roxb枝叶的乙酸乙酯萃取物进行化学成分分离纯化,得到15个化合物,化合物类型涉及倍半萜、三萜、甾体、木脂素等,利用波谱技术和文献对照鉴定它们的结构分别为:loliolide (1),phaseic acid (2),pinnatififidanoid A...     

赤芝孢子粉三萜化学成分研究

自赤芝(Ganoderma lucidum Karst)孢子粉酸性部分分离得到一个新的四环三萜化合物,命名为ganosporeric acid A(1),根据光谱(IR,¹HNMR,¹³CNMR和MS)分析确定其结构为Ⅰ所示。同时还分到四个已知化合物:ganoderic acid B(Ⅱ),ganodefic acid C(Ⅲ),ganoderic acidE(Ⅳ),和ganodermanontriol(Ⅴ)。这些化合物均为首次从赤芝孢子粉中得到。     

Differential effects of ganodermic acid S on the thromboxane A2-signaling pathways in human platelets.

Ganodermic acid S (GAS) [lanosta-7,9(11),24-triene-3beta,15alpha-diacetoxy-26-oic acid], isolated from the Chinese medicinal fungus Ganoderma lucidum (Fr.) Karst (Polyporaceae), exerted a concentration-dependent inhibition on the response of human gel-filtered platelets (GFP) to U46619 (9,11-dideoxy-9alpha,11alpha-methanoepoxyprostaglandin F2alpha), a thromboxane (TX) A2 mimetic. GAS at 2 microM inhibited 50% of cell aggregation. GAS at 7.5 microM inhibited 80% of Ca2+ mobilization, 40% of phosphorylation of myosin light chain and pleckstrin, 80% of alpha-granule secretion, and over 95% of aggregation. GAS also strongly inhibited U46619-induced diacylglycerol formation, arachidonic acid release, and TXB2 formation. An immunoblotting study of protein-tyrosine phosphorylation showed that GAS inhibited the formation of phosphotyrosine proteins at the steps involving the engagement of integrin alphaIIbbeta3 and aggregation. However, GAS did not inhibit U46619-induced platelet shape change or the inhibitory effect of U46619 on the prostaglandin E1-evoked cyclic AMP level in GFP. It is concluded that GAS inhibits platelet response to TXA2 on the receptor-Gq-phospholipase Cbeta1 pathway, but not on the receptor-G1 pathway.