Wrightiamines A and B, Two New Cytotoxic Pregnane Alkaloids from Wrightia javanica

Abstract

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.

Parviflorenes B–F, novel cytotoxic unsymmetrical sesquiterpene-dimers with three backbone skeletons from Curcuma parviflora

“…The EtOAc-soluble fraction of the MeOH extracts, combined with previously obtained EtOAc and n-BuOH-soluble fractions of this plant, were subjected to repeated chromatography on silica gel and Sephadex LH-20, followed by purification with HPLC on ODS to give five new compounds, parviflorenes B-F (2)(3)(4)(5)(6), in addition to parviflorene A (1). Parviflorene B (2) was obtained as yellow prisms, [a] D 24 ZK16 (c 1.4,MeOH), and the molecular formula was established to be C 30 H 32 O 4 by its HRFABMS data (m/z 456.2260, M C , D K4.1 mmu).…”

“…(Zingiberaceae) is widely distributed over a forest area of the northern part of Thailand, 1 and is used as an ornamental plant, and is edible, and also it has been said to be used for detoxification of scorpion bites in certain areas. During our search for bioactive natural products from tropical plants, 2 we investigated the chemical constituents of C. parviflora collected in Thailand, and recently isolated the cytotoxic sesquiterpene-dimer, parviflorene A (1) from this plant. 3 We further investigated this plant and here we describe the isolation and structure elucidation of five new sesquiterpene-dimers, parviflorenes B-F (2)(3)(4)(5)(6) from the underground part of C. parviflora.…”

“…During our search for bioactive natural products from tropical plants, 2 we investigated the chemical constituents of C. parviflora collected in Thailand, and recently isolated the cytotoxic sesquiterpene-dimer, parviflorene A (1) from this plant. 3 We further investigated this plant and here we describe the isolation and structure elucidation of five new sesquiterpene-dimers, parviflorenes B-F (2)(3)(4)(5)(6) from the underground part of C. parviflora. These sesquiterpene-dimers may be classified into three groups with different carbon frameworks: (i) biscadinanes (compounds 1, 2, 4, and 6); (ii) a cadinane-isocadinane adduct (compound 3), and (iii) a biscadinane with an alternate bond connection (compound 5).…”

Isolation of Austroinulin Possessing Cell Cycle Inhibition Activity fromBlumea glomerataand Revision of Its Absolute Configuration

“…Plants belonging to the genus Blumea (Compositae) are aromatic herbs widely distributed in tropical Asian areas and are used in folk medicine. During our search for bioactive natural products from tropical plants [1], we investigated the chemical constituents of leaves of Blumea glomerata (Compositae) collected in Thailand. Here we describe the isolation and identification of a labdane-diterpene, austroinulin (1), and several known flavonoids and sesquiterpenes, and a revision of the absolute configuration of austroinulin (1).…”

Studies of antiviral activity and cytotoxicity ofWrightia tinctoriaandMorinda citrifolia

“…Many compounds of plant origin have been identified that inhibit different stages in the replication cycle of HIV[1–4]. Wrightia tinctoria is an important medicinal plant used in the Indian system of medicine for the treatment of variety of diseases[5] and it to possessed analgesic[6], cytotoxic[7] activities. Morinda citrifolia L (Noni) has been used in folk remedies by Polynesians for over 2000 years and is reported to have a broad range of therapeutic effects[8], including antibacterial, antiviral, antifungal, antitumor, analgesic, hypotensive, antiinflammatory, and immune enhancing effects.…”