Triterpenoid compounds. VI. The constitution of malaleucic acid - II.

Chopra, Geetanjali; Fuller, MW; Thieberg, Kjl; SHAW, DAVID C.; White, DJ; Hall, Sydney; Maslen, E. N.

doi:10.1016/s0040-4039(01)90928-1

Cited by 9 publications

(3 citation statements)

References 6 publications

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“…As reported earlier (Chopra et al, 1963) the structure of methyl melaleueate iodoacetate has confirmed the constitution of melaleucic acid as 3fl-hydroxylup-20(29)-ene-27,28-dioic acid.…”

Section: Generalsupporting

confidence: 81%

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The determination of the crystal structure of methyl melaleucate iodoacetate

Hall¹,

Maslen²

1965

Acta Crystallogr

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The crystal structure of methyl melaleucate iodoacetate (C34H5106I), a derivative of melaleucic acid, was determined from phases calculated by anomalous dispersion methods (Ramachandran & Raman, 1956) and refined by block diagonal least squares to a final R index of 0-079 for 1342 measurab]e reflexions. The unit cell is orthorhombic, space group _P212121 with a = 15-719, b =24-533 and c=8.618 A. 48 of the 51 H atoms were located in a 3-D difference synthesis enabling a close study of the packing and associated steric hindrance in the structure. Abnormally high C-C bond lengths of up to 1.66 A are attributed to strain resulting from this hindrance.

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“…As reported earlier (Chopra et al, 1963) the structure of methyl melaleueate iodoacetate has confirmed the constitution of melaleucic acid as 3fl-hydroxylup-20(29)-ene-27,28-dioic acid.…”

Section: Generalsupporting

confidence: 81%

“…Methyl melaleucate iodoacetate (I) was prepared with the aim of using X-ray diffraction techniques to provide an independent check of the molecular formula and the position of the carboxyl at C(27). Preliminary structure analysis confirming the suggested constitution has already been reported (Chopra et al, 1963). …”

Section: Introductionsupporting

confidence: 68%

The determination of the crystal structure of methyl melaleucate iodoacetate

Hall¹,

Maslen²

1965

Acta Crystallogr

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“…The most potent fraction, the 100% MeOH eluate (0.30% from Zizyphi Semen), was purified by Sephadex LH-20, silica gel, reversed-phase gel, and reversed-phase HPLC to afford a new compound and nine known compounds. The known compounds were identified as betulinic acid (63.26 mg, 0.00316%), betulin (20.08 mg, 0.00100%), alphitolic acid (37.97 mg, 0.00190%), pomolic acid (7.34 mg, 0.00037%), pomolic acid 28-methyl ester (2.02 mg, 0.00010%), pomonic acid (3.50 mg, 0.00018%), ceanothic acid (21.33 mg, 0.00107%), epiceanothic acid (1.73 mg, 0.00009%), and ceanothic acid 28-methyl ester (1.41 mg, 0.00007%) on the basis of their NMR spectra. The new compound showed a molecular formula of C 31 H 48 O 5 as determined by HR FAB MS ( m / z 499.3439 [M − H] − ; calcd for C 31 H 47 O 5 , 499.3423).…”

Section: Methodsmentioning

confidence: 99%

Triterpenoids Isolated from Zizyphus jujuba Inhibit Foam Cell Formation in Macrophages

Fujiwara

Hayashida

Tsurushima

et al. 2011

J. Agric. Food Chem.

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Because foam cell formation in macrophages is believed to play an essential role in the progression of early atherosclerotic lesions in vivo, prevention of foam cell formation is considered to be one of the major targets for the treatment of atherosclerosis. The present study examined the inhibitory effect of 50 crude plant extracts on foam cell formation. Among those crude extracts, Zizyphi Fructus (ZF) and Zizyphi Semen (ZS) extracts significantly inhibited the foam cell formation induced by acetylated LDL. Furthermore, triterpenoids such as oleanonic acid, pomolic acid, and pomonic acid were the major active compounds, and triterpenoids containing a carboxylic acid at C-28 play an important role in the inhibitory effect on foam cell formation in human macrophages. These data suggest that triterpenoids in Zizyphus jujuba , the plant source of ZF and ZS, may therefore be useful for the prevention of atherosclerosis.

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Myrtaceae

Hegnauer

1969

Chemotaxonomie Der Pflanzen

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Triterpenoid compounds. VI. The constitution of malaleucic acid - II.

Cited by 9 publications

References 6 publications

The determination of the crystal structure of methyl melaleucate iodoacetate

The determination of the crystal structure of methyl melaleucate iodoacetate

Triterpenoids Isolated from Zizyphus jujuba Inhibit Foam Cell Formation in Macrophages

Myrtaceae

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