Molecular pharmacology and therapeutic advances of the pentacyclic triterpene lupeol

Sohag, Abdullah Al Mamun; Hossain, Md. Tahmeed; Rahaman, A.; Rahman, Papia; Hasan, Mohammad Shahinul; Das, Ranjita; Khan, Md Kibria; Sikder, Mahmudul Hasan; Alam, Mahboob; Uddin, Jamal; Rahman, Md. Hasanur; Tahjib‐Ul‐Arif, Md.; Islam, Tofazzal; Moon, Il Soo; Hannan, Md. Abdul

doi:10.1016/j.phymed.2022.154012

Cited by 25 publications

(17 citation statements)

References 115 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In addition, lupeol shows potential to decrease neuroinflammation and neurodegeneration, and to protect various tissues and organs. [49][50][51][52][53][54][55] It is also reported to attenuate cataract in rats. 56 Compound 5 was purified as a white powder with molecular ion peak [M + H] + at m/z 143.10 in the positive-ion EI-MS spectrum, and as result of 1 H NMR and 13 C NMR spectrum, it was determined that molecular formula to be C 6 H 6 O 4 .…”

Section: Resultsmentioning

confidence: 99%

Chemical constituents from Betula schmidtii and their free radical scavenging, tyrosinase inhibitory, and neuroprotective activities

Wang

Koh

Lee

et al. 2022

Bulletin Korean Chem Soc

View full text Add to dashboard Cite

The study was performed to identify bioactive constituents from the inner bark of Betula schmidtii. Seven compounds were isolated through silica gel and Sephadex LH‐20 column chromatography, and identified to be betulin (1), betulinic acid (2), β‐sitosterol (3), lupeol (4), kojic acid (5), 1,7‐bis‐(ρ‐hydroxyphenyl)‐(3,4‐dihydroxy)‐hepan‐5‐one (6), and platyphyllenone (7) using EI‐MS, 1D‐, and 2D‐NMR data. Compounds 5, 6, and 7 show antioxidant effect with IC50 values of 18.23 ± 1.08, 29.37 ± 1.42, and 40.14 ± 1.75 μM in DPPH free radical scavenging activity. Compounds 4 and 5 show an antioxidant effect with IC50 values of 28.21 ± 1.80 and 37.74 ± 1.02 μM in DCHF‐DA intracellular ROS generations. Compounds 5, 6, and 7 also exhibited mushroom tyrosinase inhibitory activity with IC50 values of 17.42 ± 1.08, 47.17 ± 1.92, and 26.64 ± 1.40 μM. Compound 1 showed cell viability of 24.50 ± 6.30 and 45.60 ± 3.10% at 10 and 25 μM, while compound 6 showed 11.20 ± 1.40% at 25 μM in glutamate‐induced damaged mouse neuronal cells.

show abstract

Section: Resultsmentioning

confidence: 99%

Chemical constituents from Betula schmidtii and their free radical scavenging, tyrosinase inhibitory, and neuroprotective activities

Wang

Koh

Lee

et al. 2022

Bulletin Korean Chem Soc

View full text Add to dashboard Cite

show abstract

“…These four molecules have the common characteristic of being present in natural foods, such as phytol, which is in the chlorophylls of vegetables, curcumin is in curry, lupeol is in both vegetables and fruit, and heptacosane is in fruits; moreover, they can be assumed to be nutraceutical substances [ 50 , 51 , 52 , 53 ]. The list of therapeutic properties is certainly very long for curcumin and lupeol, whose anti-inflammatory, antioxidant, antimicrobial, antitumor, cardioprotective, antipyretic, analgesic, wound healing, anticonvulsant, antiarthritic, and antidiabetic activities are well known [ 54 , 55 , 56 , 57 ], whereas for phytol and heptacosane, the knowledge of those is limited. Furthermore, it is known that the dysfunction of the intestinal microbiome is associated with both the outcome of chemotherapy and adverse events, in many types of neoplastic tumors as well as in AML [ 58 , 59 ].…”

Section: Four Natural Molecules Active In Aml: Our Experiencementioning

confidence: 99%

“…Heptacosane is one of the major components (8%) of the Centaurea baseri essential oil, Köse et al have previously described its multiple activities, including its cytotoxic properties against MCF-7, PANC-1, A549, and C6 glioma cell lines [ 114 ]. Antitumor properties of the Euphorbia intisy essential oil on AML cells were likewise investigated, and the specific actions of its two major components phytol and heptacosane were evaluated [ 57 ]. In contrast to phytol, heptacosane does not modulate the NF-κB pathway but reduces the expression levels of some of the NF-κB targets.…”

Section: Heptacosanementioning

confidence: 99%

Natural Inhibitors of P-glycoprotein in Acute Myeloid Leukemia

Labbozzetta

Poma

Notarbartolo

2023

IJMS

View full text Add to dashboard Cite

Acute myeloid leukemia (AML) remains an insidious neoplasm due to the percentage of patients who develop resistance to both classic chemotherapy and emerging drugs. Multidrug resistance (MDR) is a complex process determined by multiple mechanisms, and it is often caused by the overexpression of efflux pumps, the most important of which is P-glycoprotein (P-gp). This mini-review aims to examine the advantages of using natural substances as P-gp inhibitors, focusing on four molecules: phytol, curcumin, lupeol, and heptacosane, and their mechanism of action in AML.

show abstract

“…4 Many other triterpenoids are investigated for a plethora of applications, including betulinic acid and lupeol. 5, 6…”

Section: Introductionmentioning

confidence: 99%

“…4 Many other triterpenoids are investigated for a plethora of applications, including betulinic acid and lupeol. 5,6 Triterpenoids are the largest natural product class, with more than 20,000 molecules identified to date, derived from a cascade of reactions that leads to a combinatorial explosion. Briefly, after the cyclization of 2,3-oxidosqualene or squalene to mono-up to pentacyclic triterpenoids, these molecules are modified by cytochrome P450 monooxygenases (CYPs), glycosyl-and acyltransferases in cascades of more than ten enzymatic steps.…”

Section: Introductionmentioning

confidence: 99%

Triterpenoid production with a minimally engineered Saccharomyces cerevisiae chassis

Guo

Jacobsen

Walter

et al. 2022

Preprint

View full text Add to dashboard Cite

Triterpenoids, one of the most diverse classes of natural products, have been used for centuries as active ingredients in essential oils and Chinese medicines and are of interest for many industrial applications ranging from low-calorie sweeteners to cosmetic ingredients and vaccine adjuvants. However, not only can the extraction from plant material be cumbersome due to low concentrations of the specific triterpenoid, but concerns are also increasing regarding the sustainability of wild plant harvest while meeting market demands. The alternative is to produce triterpenoids with engineered microbes. Here, we present a generally applicable strategy for triterpenoid production in the yeast Saccharomyces cerevisiae based on a modified oxidosqualene cyclase Erg7. The modification reduces the flux into the sterol pathway while increasing the precursor supply for triterpenoid production. The minimally engineered strain was exploited for the exemplary production of the lupane triterpenoids betulin, betulin aldehyde, and betulinic acid at a total titer above 6 g/L, the highest reported so far. To further highlight the chassis concept, squalene, oleanane- and dammarane-type triterpenoids were synthesized to titers at a similar gram scale. We propose the developed baker's yeast as a host for the thousands of triterpenoid synthesis pathways from plants, reducing the pressure on the natural resources.

show abstract

Molecular pharmacology and therapeutic advances of the pentacyclic triterpene lupeol

Cited by 25 publications

References 115 publications

Chemical constituents from Betula schmidtii and their free radical scavenging, tyrosinase inhibitory, and neuroprotective activities

Chemical constituents from Betula schmidtii and their free radical scavenging, tyrosinase inhibitory, and neuroprotective activities

Natural Inhibitors of P-glycoprotein in Acute Myeloid Leukemia

Triterpenoid production with a minimally engineered Saccharomyces cerevisiae chassis

Contact Info

Product

Resources

About