Immunomodulatory constituents from Ascomycetous fungi.

Our screening project, namely, search for new immunomodulatory constituents from Ascomycetous fungi, was guided by the effects on mitogen-induced proliferations of mouse spleen lymphocytes. On the project, the defatted crude extracts from Gelasinospora multiforis, G. heterospora, G.

Diterpenes from Leucas aspera inhibiting prostaglandin-induced contractions.

Investigation of the inhibitory fraction of Leucas aspera on prostaglandin-induced contraction in guinea pig ileum provided four new diterpenes, leucasperones A (1) and B (2) and leucasperols A (3) and B (4), and three new isopimarane glycosides, leucasperosides A, B, and C (5-7), together with the known compounds asperphenamate, maslinic acid, (-)-isololiolide, and linifolioside. The structures of the compounds were determined by detailed spectroscopic analysis. The configurations of 1 and 2 and the acetylated derivatives of 3 and 4 were determined by differential NOE analysis and CD data.

Prostaglandin inhibitory and antioxidant components of Cistus laurifolius, a Turkish medicinal plant.

As Cistus laurifolius has been used traditionally to treat inflammatory and rheumatic disorders, its leaves were tested for prostaglandin (PG) inhibitory and antioxidant activities. The leaf extract showed both activities, i.e.

Nine constituents including six xanthone-related compounds isolated from two ascomycetes, Gelasinospora santi-florii and Emericella quadrilineata, found in a screening study focused on immunomodulatory activity.

Five metabolites tentatively called GS-1 (1)-5 (5) from Gelasinospora santi-florii, and four tentatively called EQ-4 (6), EQ-6 (7)-8 (9) together with 1-4 from Emericella quadrilineata have been isolated in a screening study on immunomodulatory fungal constituents. Among these nine metabolites, EQ-7 and 8 have been unknown. This time, the structures of GS-4 which has previously been isolated, EQ-7, and -8 have been determined to be (4R,4aS,9aR)-1,9a-dihydronidulalin A (4), (4S,4aR,9aR)-4a-carbomethoxy-1,4,4a,9a-tetrahydro-4,8-dihydroxy-6-methylxanthone (8), and 9-hydroxymicroperfuranone (9), respectively, and the six other metabolites have been identified.

Eleven new 2-pyrones from a Fungi Imperfecti, Trichurus terrophilus, found in a screening study guided by immunomodulatory activity.

In a screening study on immunomodulatory fungal constituents, eleven new 2-pyrones tentatively named TT-1 (1), and TT-2-11 (2-11) have been isolated from a Fungi Imperfecti, Trichurus terrophilus, and designated rasfonin (1), and trichurusin B-K (2-11), respectively. Compounds 1-4 exhibited considerably high immunosuppressive activities, and compounds 8-11 have shown moderate ones. The structure-activity relationships of these constituents have also been discussed.

Six immunosuppressive features from an ascomycete, Zopfiella longicaudata, found in a screening study monitored by immunomodulatory activity.

In a screening study on immunomodulatory fungal metabolites, three known anthraquinones, carviolin (roseo-purpurin) (1), 1-O-methylemodin (2), omega-hydroxyemodin (citreorosein) (4), and a new anthraquinone, omega-acetylcarviolin (3), together with a known steroid, ergosta-4,6,8(14),22-tetraen-3-one (5) and a new steroid, 25-hydroxyergosta-4,6,8(14),22-tetraen-3-one (6) were isolated from an Ascomycete, Zopfiella longicaudata, and found to have moderate immunosuppressive activities. The structure-activity relationships of these metabolites are discussed.

Immunomodulatory constituents from an Ascomycete, Chaetomium seminudum.

A screening study focusing on immunomodulatory activity of the EtOAc extract of an Ascomycete, Chaetomium seminudum, has afforded a known epipolythiodioxopiperazine, chetomin (1), together with three new chetomin-related metabolites named chetoseminudins A (2), B (3), and C (4). Among these four metabolites, 1 and 2 have been deduced as the immunosuppressive features of this fungus.

Wrightiamines A and B, two new cytotoxic pregnane alkaloids from Wrightia javanica.

Two new pregnane alkaloids, wrightiamines A (1) and B (2), were isolated from the extract of the tropical Apocynaceous plant Wrightia javanica collected in Thailand, and their structures were elucidated by spectral data. Wrightiamine B (2) was preparaed from 3beta-hydroxy-5alpha-pregnan-20-one to establish the configuration of the C-20 position as S. Wrightiamine A (1) exhibited cytotoxic activity against vincristine-resistant murine leukemia P388 cells.

Separation of Leucas aspera, a medicinal plant of Bangladesh, guided by prostaglandin inhibitory and antioxidant activities.

According to the traditional usage of the plant for antiinflammation and analgesia, Leucas aspera was tested for its prostaglandin (PG) inhibitory and antioxidant activities. The extract showed both activities, i.e.

Six new constituents from an Ascomycete, Chaetomium quadrangulatum, found in a screening study focused on monoamine oxidase inhibitory activity.

A screening study focusing on monoamine oxidase inhibitory activity on the EtOAc extract of an Ascomycete Chaetomium quadrangulatum, which previously gave five unique chromones possessing this activity (chaetoquadrins A-E (1-5)), this time afforded six new constituents termed chaetoquadrins F-K (6-11) in addition to 1-5. The structures of 6-11 have been deduced on the basis of spectral and chemical data, and 7 and 8 have shown appreciable monoamine oxidase inhibitory activity.

New onoceranoid triterpene constituents from Lansium domesticum.

Three new natural onoceranoid triterpenes, lansionic acid (1), 3beta-hydroxyonocera-8(26),14-dien-21-one (2), and 21alpha-hydroxyonocera-8(26),14-dien-3-one (3), were isolated from the fruit peel of Lansium domesticum together with two known triterpenoids (4 and 5), and their structures were elucidated from spectral data. These triterpenoids exhibited mild toxicity against brine shrimp (Artemia salina).

Five new chromones possessing monoamine oxidase inhibitory activity from an ascomycete, Chaetomium quadrangulatum.

Five novel chromones (1,4-benzopyran-4-ones), among which three are tetracyclic and one contains a sulfonyl group, have been isolated from an Ascomycete, Chaetomium quadrangulatum, as monoamine oxidase inhibitory features, and named chaetoquadrins A (1)-E (5).