Drimane-type Sesquiterpenoids Research Articles

ChemInform Abstract: Novel and Enantioselective Total Synthesis of Drimane Type Sesquiterpenes.

Two drimane type sesquiterpenoids, (+)-drimane-8,11-diol 1 and (+)-drim-9(11)-en-8-ol 2, have been synthesized in an optically pure form starting from geraniol.

Ugandenial A, a New Drimane-type Sesquiterpenoid from Warburgia ugandensis

One new drimane-type sesquiterpenoid, named ugandenial A (1), was isolated from the ethyl acetate extract of the bark of Warburgia ugandensis (Canellaceae) together with eight known drimane-type sesquiterpenoids: 11α-hydroxycinnamosmolide (2), warburganal (3), polygodial (4), mukaadial (5), dendocarbin A (6), 9α-hydroxycinnamolide (7), dendocarbin L (8) and dendocarbin M (9). Their structures were established by detailed spectroscopic analysis. In addition a keto-enol equilibrium was demonstrated for compound 1 through a detailed NMR analysis run in CD2Cl2 at 190 K. Cytotoxicity of the isolated compounds against KB cells was evaluated.

Drimanes and Other Terpenoids from the FernThelypteris hispidula (Decne.)Reed

The drimane-type sesquiterpenoids (-)-polygodial (1), (-)-isopolygodial (4), drimenin (5), and isodrimenin (6) were isolated from a pungent Argentine collection of the fern Thelypteris hispidula, along with other terpenoids. As the mentioned drimanes have been previously found in liverworts, the present results strongly support the theory that Pteridophytes and Bryophytes share the same line of evolution. Our present investigations indicate that two chemotypes of T. hispidula are widespread in the northwest of Argentina. Plants belonging to the pungent chemotype contain drimanes, while nonpungent plants lack drimanes.

Synthesis of (+)‐Drim‐9(11)‐en‐8α‐ol from Sclareol.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Total Synthesis of Biologically Intriguing Drimane‐type Sesquiterpenoids via Intramolecular Diels—Alder Approaches

AbstractFor Abstract see ChemInform Abstract in Full Text.

Synthesis of (+)-drim-9(11)-en-8 -ol from sclareol

A drimane-type sesquiterpenoid, (+)-drim-9(11)-en-8α-ol, was synthesized from sclareol in four steps. The ozonolysis product of sclareol diacetate reacts with Cu(OAc)2·H2O to give 8α-acetoxy-14,15-bisnorlabdan-13-one. Photolysis of this compound followed by alkaline hydrolysis results in the target compound belonging to the normal steric series. (+)-Drim-9(11)-en-8α-ol acetate is highly unstable and decomposes during chromatography on SiO2.

Total synthesis of (−)-mniopetal F, a novel inhibitor of RNA-directed DNA-polymerases

We have achieved a total synthesis of (−)-mniopetal F, a drimane-type sesquiterpenoid which inhibits the reverse transcriptase activity of the human immunodeficiency virus (HIV)-1. The key step in our enantiospecific synthesis is a stereoselective intramolecular Diels–Alder reaction, in which the π-facial selectivity is controlled by the stereoelectronic effect of a trialkylsilyloxy substituent existing adjacent to the dienophile part.

Albaconol, A Novel Prenylated Resorcinol (=Benzene-1,3-diol) from BasidiomycetesAlbatrellus confluens

The new substance albaconol (1) was isolated along with grifolin (2), emeheterone (3), and the pyrazinol derivative 4 from the fresh fruiting bodies of the basidiomycetes Albatrellus confluens. Structures were established by spectral analysis, including 2D NMR spectroscopy. Albaconol (1) possesses the skeleton of a drimane-type sesquiterpenoid, which is directly connected to a resorcinol (= benzene-1,3-diol) moiety; this prenylated resorcinol represents a new C skeleton.

Drimane-Type Sesquiterpenoids as Chemosystematic Markers of Canellaceae

Polygodial, isopolygodial, mukaadial and polygonone were isolated for the first time from Capsicodendron dinisii. Thus, with respect to drimane-type sesquiterpenoids of the Canellaceae, the close affinity of the South American genus Capsicodendron with the African genus Warburgia rather than the Madagascarian genus Cinnamosma is established.

Phytotoxic sesquiterpenoids from Canella winterana

Nine new drimane-type sesquiterpenoids: 3α-acetoxypolygodial, 3α-acetoxypolygodial 12-dimethyl acetal, 9-deoxymuzigadial 12α-acetal, 9-deoxymuzigadial 12β-acetal, 3β-acetoxypolygodial 12α-acetal, 3β-acetoxypolygodial 12β-acetal, 9-epideoxymuzigadial, 3β-acetoxypolygonal and muzigaal, were isolated from the leaves of Canella winterana, together with six previously known sesquiterpenoids; muzigadial, 3β-acetoxypolygodial, 3β-acetoxycinnamolide, isopolygodial, polygodial 12α-acetal and drimenol. Unambiguous assignments of all 1H and 13C signals of 15 sesquiterpenoids were established by 2D NMR experiments.

Drimane-type sesquiterpenoids from the liverwort Diplophyllum serrulatum

The liverwort, Diplophyllum serrulatum afforded three new drimane-type sesquiterpenoids albicanic acid, albicanal and isoalbicanal, in addition to (+)-albicanol, (−)-drimenol, (+)-trans-γ-monocyclofarnesol, ent-spathulenol and anastreptene. Their structures were established by chemical and spectral means. Albicanol and albicanal were major constitutents of this species. This is the first report of the isolation of (−)-albicanic acid in nature and (+)-trans-γ-monocyclofarnesol from the liverworts.

Drimane-type sesquiterpenoids from Cryptoporus volvatus infected by Paecilomyces varioti

Three simple drimane-type sesquiterpenoids and two drimane sesquiterpenic ethers of isocitric acid were isolated from Cryptoporus volvatus infected by the fungus Paecylomyces varioti. The ether bond of cryptoporic acids obtained from fresh C. volvatus, were cleaved by P. varioti to give simple drimane sesquiterpenoids.

Biosynthesis of cryptoporic acids H and I in Ganoderma neo-japonicum

Since cryptoporic acid I, a drimane-type sesquiterpenoid, possesses a hydroxyl group at C-3, it was of interest to examine whether it is formed by cycl

Cryptoporic acids A-G, drimane-type sesquiterpenoid ethers of isocitric acid from the fungus Cryptoporus volvatus

Seven novel bitter drimane-type sesquiterpenoids with an isocitric acid group named cryptoporic acids (CA) A-G have been isolated from the fungus Cryptoporous volvatus and their absolute stereostructures established by a combination of chemical transformation, NMR spectral data and X-ray crystallographic analysis. Cryptoporic acids strongly inhibited the release of superoxide anion radicals from guinea-pig peritoneal macrophage as well as rabbit polymorphonuclear leucocyte. CA-E showed anti-tumour promoting activity whilst CA-D slightly enhanced tumour promoting and protein kinase C activity. CAs also inhibited elongation of the second coleoptile and germination of rice in husk at 200 ppm.

Novel and enantioselective total synthesis of drimane type sesquiterpenes

Two drimane type sesquiterpenoids, (+)-drimane-8,11-diol 1 and (+)-drim-9(11)-en-8-ol 2, have been synthesized in an optically pure form starting from geraniol.

Drimane-type sesquiterpenoids from the liverwort Makinoa crispata

Three new drimane-type sesquiterpenoids, 7α-chloro-6β-hydroxyconfertifoline, 6β,7α-dihydroxyconfertifoline and 6β,7β-epoxyconfertifoline were isolated from the liverwort Makinoa crispata together with the previously known eudesmane-type sesquiterpene lactone, crispatanolide and a sacculatane-type diterpene dialdehyde, perrottetianal A. The stereostructures of the new compounds were established by 2D NMR and CD spectroscopy and chemical evidence. The present chemical results support Schuster's phylogenic classification of the two orders, Metzgeriales and Jungermanniales.