Diosphenols from Spirostachys africana

Munkombwe, Namboole Moses; Maswabi, Titus Motswadi; Hughes, N. A.

doi:10.1016/s0031-9422(97)00113-1

Cited by 6 publications

(5 citation statements)

References 4 publications

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“…Compound 6 was isolated and identified as a known dolabrane norditerpenoid, − possessing a diosphenol system in the A ring, which has been found in both diterpenes ,, and triterpenes .…”

Section: Resultsmentioning

confidence: 99%

“…Compound 6 was isolated and identified as a known dolabrane norditerpenoid, [15][16][17] possessing a diosphenol system in the A ring, which has been found in both diterpenes 15,17,18 and triterpenes. 19 This isolate from D. gelonioides exhibited the same 1 H and 13 C NMR and MS data as "ent-16-nor-5R,3-oxodolabr-1,4(18)-dien-2ol-15-oic acid", isolated from Endospermum diadenum Airy Shaw (Euphorbiaceae).…”

Section: Resultsmentioning

confidence: 99%

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Cytotoxic Constituents from the Stem Bark of Dichapetalum gelonioides Collected in the Philippines^,1

et al. 2005

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Fractionation of an ethyl acetate-soluble extract of the stem bark of Dichapetalum gelonioides, collected in the Philippines, using the LNCaP (hormone-dependent human prostate) cell line as a monitor, led to the purification of three dichapetalin-type triterpenoids [dichapetalins A (1), I (2), and J (3)], along with two dolabrane norditerpenoids (6, 7), and the additional triterpenoids zeylanol (8), 28-hydroxyzeylanol (9), and betulinic acid. Since compounds 1-3 exhibited promising selectivity against the SW626 (human ovarian cancer) cell line, a recollection of the plant material was carried out, in order to obtain more of these compounds for additional biological testing. Two further phenylpyranotriterpenoids [dichapetalins K (4) and L (5)] were isolated from the recollected plant material. The structures of the new compounds 2-5 and 9 were determined based on spectroscopic data interpretation, and the relative configuration of 6 was confirmed using X-ray crystallography. Compounds 4-6 and the methyl ester, 6a, exhibited broad cytotoxic activity when tested against a panel of human tumor cell lines. Dichapetalin A (1) was not active when evaluated in an in vivo hollow fiber assay in the dose range 1-6 mg/kg. Dichapetalum Thouars represents the major genus in the family Dichapetalaceae (syn. Chailletiaceae), and comprises 124 species, of which the majority (86 species) are found in Africa, with the others occurring in tropical Asia (19 species) and South America (19 species). 2 Many Dichapetalum species are poisonous to livestock due to the presence of fluorinated compounds such as fluoracetic acids and ω-fluorinated fatty acids. 3-6 The leaves of D. gelonioides have been used to treat amenorrhea in the Philippines. 7 Several phenylpyranotriterpenoids (dichapetalins A-H) have been isolated and structurally characterized from the roots of D. madagascariense Poir. 8-10 The absolute configuration of dichapetalin A was determined by single-crystal X-ray diffraction analysis. 9 While this # Dedicated to Dr. Norman R. Farnsworth of the University of Illinois at Chicago for his pioneering work on bioactive natural products.*Author to whom correspondence should be addressed. Tel.: (614) compound was reported to show potent activity in the brine shrimp lethality bioassay, exceeding that of podophyllotoxin by seven-fold, and also exhibited cytotoxicity for L1210 murine leukemia cells (EC 90 <0.0001 μg/mL), the KB cell line and an unspecified murine bone marrow cell line were not sensitive to this triterpenoid. 8As a part of our program on the discovery of new anticancer agents from plants, an ethyl acetatesoluble extract has been investigated of the stem bark of D. gelonioides (Roxb.) Engl., collected in 1994 on Palawan Island in the Philippines. Only one phytochemical investigation has been reported previously on this species, resulting in the isolation of the triterpenoid, friedelin. 11 Activity-guided fractionation using the LNCaP (hormone-dependent human prostate cancer) cell line led to the isolation of tw...

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“…Compound 6 was isolated and identified as a known dolabrane norditerpenoid, − possessing a diosphenol system in the A ring, which has been found in both diterpenes ,, and triterpenes .…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Cytotoxic Constituents from the Stem Bark of Dichapetalum gelonioides Collected in the Philippines^,1

et al. 2005

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“…A total of 30 carbon signals, including a ketone carbonyl at δ C 200.5 (C-3), a carboxyl carbon at δ C 182.2 (C-28), four olefinic carbons at δ C 145.8 (C-2), 140.4 (C-13), 129.5 (C-1), and 129.0 (C-12), and two oxygenated carbons at δ C 73.5 (C-19) and 65.9 (C-23), were displayed in its 13 C NMR spectrum. The aforementioned NMR data of 1 highly resembled those of fupenzic acid ( 4 ) [ 13 ], a co-occurring ursane-type triterpenoid with an α , β -unsaturated keto-enol moiety (i.e., diosphenol chromophore [ 13 , 35 , 36 ]) in ring A. The only difference between them was that the Me-23 in 4 was hydroxylated in 1 , which was confirmed by the H 3 -24/C-23 and H 2 -23/C-3 correlations ( Figure 2 ) in its HMBC NMR spectrum.…”

Section: Resultsmentioning

confidence: 99%

Highly Oxygenated Triterpenoids and Diterpenoids from Fructus Rubi (Rubus chingii Hu) and Their NF-kappa B Inhibitory Effects

et al. 2021

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During a phytochemical investigation of the unripe fruits of Rubus chingii Hu (i.e., Fructus Rubi, a traditional Chinese medicine named “Fu-Pen-Zi”), a number of highly oxygenated terpenoids were isolated and characterized. These included nine ursane-type (1, 2, and 4–10), five oleanane-type (3, 11–14), and six cucurbitane-type (15–20) triterpenoids, together with five ent-kaurane-type diterpenoids (21–25). Among them, (4R,5R,8R,9R,10R,14S,17S,18S,19R,20R)-2,19α,23-trihydroxy-3-oxo-urs-1,12-dien-28-oic acid (rubusacid A, 1), (2R*,4S*,5R*,8R*,9R*,10R*,14S*,17S*, 18S*,19R*,20R*)-2α,19α,24-trihydroxy-3-oxo-urs-12-en-28-oic acid (rubusacid B, 2), (5R,8R,9R,10R, 14S,17R,18S,19S)-2,19α-dihydroxy-olean-1,12-dien-28-oic acid (rubusacid C, 3), and (3S,5S,8S,9R, 10S,13R,16R)-3α,16α,17-trihydroxy-ent-kaur-2-one (rubusone, 21) were previously undescribed. Their chemical structures and absolute configurations were elucidated on the basis of spectroscopic data and electronic circular dichroism (ECD) analyses. Compounds 1 and 3 are rare naturally occurring pentacyclic triterpenoids featuring a special α,β-unsaturated keto-enol (diosphenol) unit in ring A. Cucurbitacin B (15), cucurbitacin D (16), and 3α,16α,20(R),25-tetrahydroxy-cucurbita-5,23- dien-2,11,22-trione (17) were found to have remarkable inhibitory effects against NF-κB, with IC50 values of 0.08, 0.61, and 1.60 μM, respectively.

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“…84 have now been isolated. 113 The biotransformation of some ent-atiserenes and beyerenes by Rhizopus nigricans has been shown 114 ent-Trachylobanic-18-and -19-oic acids have been obtained 115 from the Malaysian liverwort, Mastigophora diclades. Conditions for the production of scopadulcic acid by leaf tissue cultures derived from Scoparia dulcis, have been examined.…”

Section: Beyerenes Atiserenes and Aphidicolanesmentioning

confidence: 99%

Diterpenoids

Hanson¹

1999

Nat. Prod. Rep.

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Diosphenols from Spirostachys africana

Cited by 6 publications

References 4 publications

Cytotoxic Constituents from the Stem Bark of Dichapetalum gelonioides Collected in the Philippines^,1

Cytotoxic Constituents from the Stem Bark of Dichapetalum gelonioides Collected in the Philippines^,1

Highly Oxygenated Triterpenoids and Diterpenoids from Fructus Rubi (Rubus chingii Hu) and Their NF-kappa B Inhibitory Effects

Diterpenoids

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Diosphenols from Spirostachys africana

Cited by 6 publications

References 4 publications

Cytotoxic Constituents from the Stem Bark of Dichapetalum gelonioides Collected in the Philippines,1

Cytotoxic Constituents from the Stem Bark of Dichapetalum gelonioides Collected in the Philippines,1

Highly Oxygenated Triterpenoids and Diterpenoids from Fructus Rubi (Rubus chingii Hu) and Their NF-kappa B Inhibitory Effects

Diterpenoids

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Cytotoxic Constituents from the Stem Bark of Dichapetalum gelonioides Collected in the Philippines^,1

Cytotoxic Constituents from the Stem Bark of Dichapetalum gelonioides Collected in the Philippines^,1