3β-(3,4-Dihydroxycinnamoyl)-erythrodiol and 3β-(4-hydroxycinnamoyl)-erythrodiol from Larrea tridentata (original) (raw)

Pentacyclic Triterpenoids from the Aerial Parts of Lantana camara

CHEMICAL & PHARMACEUTICAL BULLETIN, 2003

Lantana camara L. (Verbenaceae) is a hairy shrub, native to tropical America. Different parts of this plant are used for the treatment of various human ailments such as itches, cuts, ulcers, swellings, bilious fever, catarrh, eczema, tetanus, malaria, tumors and rheumatism. 1,2) Phytochemical studies carried out by different groups of workers on different parts of the plant have resulted in the isolation of various terpenoids, steroids and flavonoids. In the course of investigations on the constituents of the aerial parts of L. camara, three new pentacyclic triterpenoids namely camaryolic acid (1), methylcamaralate (2) and camangeloyl acid (3) were isolated. The structures of these constituents were elucidated as 3,25-epoxy-3a -methoxy-22b -[b ,b -dimethylacryloyloxy]urs-12-en-28-oic acid, methyl 22b-acetoxy-3,25-epoxy-3ahydroxy-urs-12-en-28-oate and 3,25-epoxy-3a-hydroxy-22b-[(Z)-2Ј-methyl-2Ј-butenoyloxy]-11-oxoolean-12-en-28-oic acid respectively on the basis of various 2D-NMR techniques including 1 H-1 H correlation spectroscopy (COSY), nuclear overhauser enhancement spectroscopy (NOESY), heteronuclear multiple quantum coherence (HMQC) and heteronuclear multiple bond connectivity (HMBC). In addition six known compounds b-sitosterol 3-O-b-D-glucopyranoside (4), 6) octadecanoic acid (5), 7) docosanoic acid (6), 8) palmitic acid (7), 9) camaric acid (8) 10) and lantanolic acid (9) 11) were isolated from this plant. This is the first report of the isolation of compound 4 from L. camara. Herein, we report the structural assignments of the three new triterpenoids.

ChemInform Abstract: Two New Pentacyclic Triterpenoids from Lantana camara Linn

ChemInform, 2009

Lantana camara LINN. (family: Verbenaceae), commonly known as lantana, is a hairy shrub, native of Tropical America cultivated elsewhere as an ornamental or hedge plant. Different parts of the plant are used for the treatment of various human ailments, such as itches, cuts, ulcers, malaria, influenza, anemia, tumors, swellings, bilious fever, eczema eruptions, rheumatism, stomachache, toothache, scabies, and leprosy and as antiseptic for wounds. Aqueous extract of the leaves showed antihyperglycaemic activity and wound-healing property. Pharmacological investigations indicated that extracts of the shoot of L. camara exhibit antibacterial properties. Lancamarone, a steroid from the leaves, possesses cardiotonic property, whereas lantamine, an alkaloid from the bark of stems and roots, shows strong antipyretic and antispasmodic properties comparable with those of quinine. Phytochemical studies undertaken by several groups on different parts of the plant have resulted in the isolation of various terpenoids, 3,5) steroids, 3) and flavonoids. 3,6) The present studies were undertaken on the chemical constituents of the aerial parts of this plant, which resulted in the isolation and structure elucidation of two new triterpenoids, lantanoic acid (1) and camaranoic acid (2), along with six known triterpenoids, lantic acid, 7) camarinic acid, 8) camangeloyl acid, camarinin, 10) oleanonic acid, 11) and ursonic acid. 12) Two new pentacyclic triterpenoids, namely lantanoic acid (1) and camaranoic acid (2), and six known compounds such as lantic acid, camarinic acid, camangeloyl acid, camarinin, oleanonic acid, and ursonic acid were isolated from the aerial parts of Lantana camara LINN. Structures of the new constituents were elucidated by chemical transformation and spectral studies including 1D ( 1 H-and 13 C-NMR) and 2D ( 1 H-1 H correlation spectroscopy (COSY), nuclear Overhauser effect spectroscopy (NOESY), 1 H-1 H total correlation spectroscopy (TOCSY), J-resolved, 1 H-detected heteronuclear multiple quantum coherence (HMQC), and heteronuclear multiple bond connectivity (HMBC)) NMR spectroscopy.

Noroleanane Triterpenoids from the Aerial Parts ofLantana camara

Helvetica Chimica Acta, 2008

Two novel triterpenoids, lantadienone (1) and camaradienone (2), were isolated from the aerial parts of Lantana camara, along with seven known compounds, lantadene A, lantadene B, b-sitosterol 3-(b-dglucopyranoside), camaric acid, lantanilic acid, lantanolic acid, and camangeloyl acid. Their structures were elucidated as (3b,22b)-3,25-epoxy-3-hydroxy-22-{[(2Z)-2-methyl-1-oxobut-2-enyl]oxy}-28-noroleana-12,17-dien-11-one (1) and (3b)-3,25-epoxy-3-hydroxy-28-noroleana-12,17-dien-11-one (2), respectively, by means of spectral studies. The triterpenoids 1 and 2 represent 28-noroleananes oxidized at C(11) and C(22) or at C(11), reported for the first time.

A NEW TRITERPENOID ISOLATED FROM LANTANA CAMARA

From the whole plant of Lantana camara, a new triterpenoid was isolated. Its structure was elucidated as 317dihydroxy-olean-12-ene on the basis of spectroscopic data. This is the first report from Lantana camara and from the nature.

Latazienone, a new lathyrane-type diterpenoid from Euphorbia latazi Kunth

Natural Product Research, 2005

A new lathyrane-type diterpene 8,15-diacetoxy-7-benzoyloxy-3-(2-methylpropanoyloxy)-4H,9H, 11H-lathyra-5E,12E-dien-14-one (latazienone) has been isolated from the latex of Euphorbia latazi Kunth. The structure of the new diterpene was determined by a combination of 1D-and 2D-NMR techniques.

Two new pentacyclic triterpenoids from Lantana camara Linn.

Lantana camara LINN. (family: Verbenaceae), commonly known as lantana, is a hairy shrub, native of Tropical America cultivated elsewhere as an ornamental or hedge plant. Different parts of the plant are used for the treatment of various human ailments, such as itches, cuts, ulcers, malaria, influenza, anemia, tumors, swellings, bilious fever, eczema eruptions, rheumatism, stomachache, toothache, scabies, and leprosy and as antiseptic for wounds. Aqueous extract of the leaves showed antihyperglycaemic activity and wound-healing property. Pharmacological investigations indicated that extracts of the shoot of L. camara exhibit antibacterial properties. Lancamarone, a steroid from the leaves, possesses cardiotonic property, whereas lantamine, an alkaloid from the bark of stems and roots, shows strong antipyretic and antispasmodic properties comparable with those of quinine. Phytochemical studies undertaken by several groups on different parts of the plant have resulted in the isolation of various terpenoids, 3,5) steroids, 3) and flavonoids. 3,6) The present studies were undertaken on the chemical constituents of the aerial parts of this plant, which resulted in the isolation and structure elucidation of two new triterpenoids, lantanoic acid (1) and camaranoic acid (2), along with six known triterpenoids, lantic acid, 7) camarinic acid, 8) camangeloyl acid, camarinin, 10) oleanonic acid, 11) and ursonic acid. 12) Two new pentacyclic triterpenoids, namely lantanoic acid (1) and camaranoic acid (2), and six known compounds such as lantic acid, camarinic acid, camangeloyl acid, camarinin, oleanonic acid, and ursonic acid were isolated from the aerial parts of Lantana camara LINN. Structures of the new constituents were elucidated by chemical transformation and spectral studies including 1D ( 1 H-and 13 C-NMR) and 2D ( 1 H-1 H correlation spectroscopy (COSY), nuclear Overhauser effect spectroscopy (NOESY), 1 H-1 H total correlation spectroscopy (TOCSY), J-resolved, 1 H-detected heteronuclear multiple quantum coherence (HMQC), and heteronuclear multiple bond connectivity (HMBC)) NMR spectroscopy.

A new 28-noroleanane triterpenoid from the aerial parts of Lantana camara Linn

Natural Product Research, 2010

A new 28-norolean-12,17-diene triterpene lantigdienone (1) oxidised at C-11 and C-22 has been isolated from the aerial parts of Lantana camara, along with two known compounds, camarinin (2) and camangeloyl acid (3). The structure of compound 1 was elucidated as 3,25-epoxy-3-hydroxy-22-[,dimethylacryloyloxy]-11-oxo-28-norolean-12,17-diene, with the help of spectral studies.

Triterpenoids from Phyllanthus acidus (L.) Skeels

Science and Technology Development Journal - Natural Sciences, 2019

The genus Phyllanthus (Phyllanthaceae) includes more than 900 plant species found in tropical and subtropical regions. Many of these species are widely used in folk medicine. The leaves, roots, and stem bark of Phyllanthus acidus (L.) Skeels have been used in Vietnamese folk medicine as an antibacterial, antiviral, analgesic, anti-inflammatory, neuroprotective, hepatoprotective, antifibrotic. From the ethanol extract of the roots of Phyllanthus acidus (L.) Skeels growing in Binh Thuan province, six compounds phyllanthol (1), glochidone (2), lupeol (3), glochidonol (4), 􀀱-lupene (5), and spruceanol (6) were isolated. Their structures were established by extensive spectroscopic analysis as well as comparison with NMR data in the literatures. This is the first time that compounds 4-6 were found in Phyllanthus acidus (L.) Skeels.