Sesqui- and di-terpenoids from the liverwort Jungermannia vulcanicola

Nagashima, Fumihiro; Tanaka, Hironao; Asakawa, Yoshinori

doi:10.1016/0031-9422(95)00890-x

Cited by 16 publications

(17 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Several bicyclic diterpenes containing the 3-methylpent-1-en-3-ol moiety have been isolated from nature;t hey include 5, [24,41] manool, [42,43] ent-manool, [44,45] vitexifolin A, [46] and sclareol. Several bicyclic diterpenes containing the 3-methylpent-1-en-3-ol moiety have been isolated from nature;t hey include 5, [24,41] manool, [42,43] ent-manool, [44,45] vitexifolin A, [46] and sclareol.…”

Section: Discussionmentioning

confidence: 99%

Identification of a New Diterpene Biosynthetic Gene Cluster that Produces O‐Methylkolavelool in Herpetosiphon aurantiacus

et al. 2015

View full text Add to dashboard Cite

Diterpenoids are usually found in plants and fungi, but are rare in bacteria. We have previously reported new diterpenes, named tuberculosinol and isotuberculosinol, which are generated from the Mycobacterium tuberculosis gene products Rv3377c and Rv3378c. No homologous gene was found at that time, but we recently found highly homologous proteins in the Herpetosiphon aurantiacus ATCC 23779 genome. Haur_2145 was a class II diterpene cyclase responsible for the conversion of geranylgeranyl diphosphate into kolavenyl diphosphate. Haur_2146, homologous to Rv3378c, synthesized (+)-kolavelool through the nucleophilic addition of a water molecule to the incipient cation formed after the diphosphate moiety was released. Haur_2147 afforded (+)-O-methylkolavelool from (+)-kolavelool, so this enzyme was an O-methyltransferase. This new diterpene was indeed detected in H. aurantiacus cells. This is the first report of the identification of a (+)-O-methylkolavelool biosynthetic gene cluster.

show abstract

Section: Discussionmentioning

confidence: 99%

Identification of a New Diterpene Biosynthetic Gene Cluster that Produces O‐Methylkolavelool in Herpetosiphon aurantiacus

et al. 2015

View full text Add to dashboard Cite

show abstract

“…Compounds 5-7 were determined as ent-13-epi-manool, 17 kaur-15-en-17-ol, 18 and ent-2b-hydroxymanool, 19 respectively. Compounds 8 and 9 were rocagloic acid derivatives and were determined as 1-O-formylrocagloic acid and 3¢-hydroxyrocagloic acid, respectively, including absolute stereochemistry.…”

Section: Introductionmentioning

confidence: 99%

Constituents of Amoora cucullata with TRAIL resistance-overcoming activity

et al. 2010

View full text Add to dashboard Cite

In search of bioactive natural products for overcoming TRAIL resistance from natural resources, we previously reported a number of active compounds. Bioassay-guided fractionation of mangrove, Amoora cucullata, collected from Sundarbans Mangrove Forest, Bangladesh, led to the isolation of four new compounds (1-4), along with seven known compounds (5-11). Of the isolates, compounds 1, 5, 8, and 9 showed TRAIL resistance-overcoming activity, among which 8 showed the most potent activity and enhanced TRAIL-induced apoptosis in TRAIL-resistant human gastric adenocarcinoma (AGS) cells through the activation of caspase-3/7, enhancing the expression of DR4 and DR5 mRNA in AGS cells. Cell death caused by the combined treatment of 8 and TRAIL was inhibited by human recombinant DR5/Fc and DR4/Fc chimera proteins, indicating that 8 sensitizes TRAIL-resistant AGS cells to TRAIL through the induction of DR4 and DR5.

show abstract

“…These experiments allowed us to perform the first enzymatic synthesis of naturally occurring manool (24), ent-manool (26), and vitexifoin A (28); however, the acyclic terpenes 1, 10, and 11 were not accepted as substrates. These experiments allowed us to perform the first enzymatic synthesis of naturally occurring manool (24), ent-manool (26), and vitexifoin A (28); however, the acyclic terpenes 1, 10, and 11 were not accepted as substrates.…”

Section: Introductionmentioning

confidence: 99%

Substrate specificity of Rv3378c, an enzyme from Mycobacterium tuberculosis, and the inhibitory activity of the bicyclic diterpenoids against macrophagephagocytosis

et al. 2011

View full text Add to dashboard Cite

The Rv3378c gene product from Mycobacterium tuberculosis encodes a diterpene synthase to produce tuberculosinol (3), 13R-isotuberculosinol (4a), and 13S-isotuberculosinol (4b) from tuberculosinyl diphosphate (2). The product distribution ratios are 1 : 1 for 3 to 4 and 1 : 3 for 4a to 4b. The substrate specificity of the Rv3378c-encoded enzyme was examined. The 3 labdadienyl diphosphates, copalyl diphosphate (CDP) (7), ent-CDP (8), and syn-CDP (9), underwent the conversion reaction, with good yields (67-78%). Copalol (23) and manool (24) were produced from 7, ent-copalol (25) and ent-manool (26) from 8, and syn-copalol (27) and vitexifolin A (28) from 9. The ratio of 23 to 24 was 40 : 27, that of 25:26 was 22 : 50, and that of 27:28 was 16 : 62. Analysis on a GC-MS chromatograph equipped with a chiral column revealed that 24, 26, and 28 consisted of a mixture of 13R- (a) and 13S-stereoisomers (b) in the following ratio: ca. 1 : 1 for 24a to 24b, ca. 1 : 5 for 26a to 26b, and ca. 1 : 19 for 28a to 28b. The structures of these products indicate that the reactions of the 3 CDPs proceeded in the same fashion as that of 2. This is the first report on the enzymatic synthesis of natural diterpenes manool, ent-manool, and vitexifolin A. Both Rv3377c and Rv3378c genes are found in virulent Mycobacterium species, but not in avirulent species. We found that 3 and 4 inhibited the phagocytosis of opsonized zymosan particles by human macrophage-like cells. Interestingly, the inhibitory activity was synergistically increased by the coexistence of 3 and 4b. Other labdane-related diterpenes, 13-16 and 23-28, had little or no inhibitory activity. This synergistic inhibition by 3 and 4 may provide further advantage to the impairment of phagocyte function, which might contribute to pathogenicity of M. tuberculosis.

show abstract

Sesqui- and di-terpenoids from the liverwort Jungermannia vulcanicola

Cited by 16 publications

References 7 publications

Identification of a New Diterpene Biosynthetic Gene Cluster that Produces O‐Methylkolavelool in Herpetosiphon aurantiacus

Identification of a New Diterpene Biosynthetic Gene Cluster that Produces O‐Methylkolavelool in Herpetosiphon aurantiacus

Constituents of Amoora cucullata with TRAIL resistance-overcoming activity

Substrate specificity of Rv3378c, an enzyme from Mycobacterium tuberculosis, and the inhibitory activity of the bicyclic diterpenoids against macrophagephagocytosis

Contact Info

Product

Resources

About