Organosulfur Compounds Detected in the Genus Aloe Volume 59- Issue 5

Adamu Tizazu* and Abdela Nebi

• Department of Chemistry, College of Natural and Computational Sciences, P.O. Box 32, Mekdela Amba University, Ethiopia

Received: November 29, 2024; Published: December 06, 2024

*Corresponding author: Adamu Tizazu, Department of Chemistry, College of Natural and Computational Sciences, P.O. Box 32, Mekdela Amba University, Tulu Awuliya, Ethiopia

DOI: 10.26717/BJSTR.2024.59.009358

Abstract PDF

An organosulfur compound has at least one carbon-sulfur (C-S) bond. All living things’ bodies contain organosulfur compounds in the form of proteins, peptides, enzymes, amino acids, vitamins, coenzymes, hormones, etc. Numerous plants contain organosulfur compounds, and for centuries, folk and traditional medicines have made use of their bioactive qualities. Almost all of the compounds detected from Aloe plants are organic compounds among which some of them are organosulfur compounds. Five organosulfur compounds have been reported from the genus Aloe. Aloe species have been found to contain thiamine/vitamin B1 (C₁₂H₁₇N₄OS⁺), pluridone (C₁₂H₁₂O3S), methionine (C₅H₁₁NO₂S), cysteine (C₃H₇NO₂S), and 1-(phenylthioxomethyl) piperidine (C₁₂H₁₅NS). The compounds are grouped into various functional groups: sulfide (R-S-R), thiol (R-SH), and thioamide (R=SN). These compounds have potential biological activities that are used in medicine, food, cosmetics, etc. The biological activities of organosulfur compounds are the same as those of Aloe species. This agreement shows that organosulfur compounds have roles in the applications of Aloe species. Therefore, organosulfur compounds from the genus Aloe are strongly recommended to be tested for their potential biological activities and how to extract, isolate, and specifically perform structural characterization.

Keywords: Sulfur; Organosulfur Compounds; Functional Groups; Aloe Genus; Biological Activities

In all organic compounds carbon and hydrogen elements are common elements [1,2]. However, in addition to carbon and hydrogen, elements such as oxygen, nitrogen, sulfur, phosphorus, halogens, etc. present in organic compounds [3,4]. Sulfur is one of the most mentioned elements in organic compounds [5]. Organosulfur compounds (OSCs) have at least one carbon-sulfur (C-S) bond [6]. Organosulfur compounds are subclass of sulfur-containing organic compounds distinguished by their peculiar characteristics and wide range of occurrence [7]. All living things’ bodies contain organosulfur compounds in the form of the protein, peptides, enzymes, amino acids, vitamins, coenzymes, hormones, etc. [8]. Numerous plants contain organosulfur compounds, and for centuries, folk and traditional medicines have made use of their bioactive qualities [9]. Aloe plants are rich in phytochemicals because they can tolerate hot and dry weather conditions. Almost all of the compounds detected from the genus Aloe are organic compounds among which some of them are organosulfur compounds [10,11]. Phytochemicals containing organosulfur are vital for a variety of uses in medicine, food, cosmetics, agriculture, and other fields [12]. Aloe species’ uses are typically described in literature as having synergistic effects rather than a single effect [13-15]. Nevertheless, no research has been conducted on the organosulfur compound found in Aloe species for their potential uses specifically. As a result, the organosulfur compounds found in Aloe genus are the main topic of this review.

Thiamine

One of the organosulfur compounds, thiamine has a five-membered heterocyclic structure with sulfur as the heteroatom in additional to the nitrogen atom [16] (Figure 1). The genus Aloe has been found to contain vitamin B1 (C₁₂H₁₇N₄OS⁺) [13]. Like the other vitamins of B complex, vitamin B1 is a water-soluble vitamin and is also referred to as thiamine or thiamin [17]. Although thiamine cannot be produced by the body, it can be obtained as a dietary supplement and is present in a variety of foods [18]. Thiamine is an essential nutrient that plays a critical role in energy metabolism which is necessary for growth, cellular function, and development. It enables the body to use carbohydrates as energy/fuel [19]. In another way, Aloe species have been reported for their metabolism actions [20,21]. In addition to this, Aloe species have been reported for the cell function and development [22,23]. Therefore, the role of thiamine in the consuming Aloe-based products is observed as synergistic effect in these biological activities of Aloe extracts.

Figure 1

Pluridone

Pluridone (C₁₂H₁₂O₃S) is an organosulfur compound that has sulfide (C-S-C) functional group. Pluridone (Figure 2) was isolated from Aloe pluridens Haw. It is a novel insecticide chemical. In works of literature, the insecticide activities of Aloe species have been reported [24-26]. The matching of insecticide activities of Aloe species and pluridone confirms the presence of pluridone and other bioactive compounds of the genus Aloe for insecticide application whether individually or together.

Figure 2

Methionine

Methionine (C₅H₁₁NO₂S) is an organosulfur compound that has a sulfide skeleton. One of the essential amino acids, methionine (Figure 3) has been reported from Aloe greatheadii var. davyana quantitatively. Moreover, many Aloe species have reported methionine [27-29]. Being essential amino acids, methionine has a variety of applications such as protein biosynthesis, methyl transfer reactions, formation of polyamines, and synthesis of cysteine and other metabolites [30] which are revealed in applications of Aloe species.

Figure 3

Cysteine

In addition to methionine, cysteine (C₃H₇NO₂S) has also been reported from the genus Aloe (Figure 4) [29]. Cysteine is a thiol (C-SH or R-SH) containing amino acid. It has crucial role for synthesizing sulfur- containing biomolecules that control multiple essential cellular activities [31]. Cysteine is applicable for normal growth rate of hair, reduce the effects of aging on the skin, healing burns and protect the skin from radiation injury [32-34]. Cysteine also helps the burning of fat and increase muscle mass [35]. All these applications have been reported from Aloe species extracts [36-38]. This reflects the role of cysteine in the Aloe species indirectly.

Figure 4

1-(Phenylthioxomethyl) Piperidine

The organosulfur compound called 1-(phenylthioxomethyl) piperidine (C₁₂H₁₅NS) (Figure 5) has been detected in Aloe vera [39]. The compound has the amide-like functional group except carbonyl oxygen is replaced by sulfur. Therefore, it is called thioamide (R=SN) [40]. The applications of 1-(phenylthioxomethyl) piperidine have not been reported widely. However, the presence of piperidine, phenyl, and thioxomethyl groups in the compound may be effective to antimicrobial, anti-inflammatory, antioxidant, etc. [41-43]. For these applications, Aloe species have been reported. This shows the role of 1-(phenylthioxomethyl) piperidine together with other compounds [44,45].

Figure 5

Five organosulfur compounds have been reported in the Aloe species. The detected compounds are neither sulfur element nor sulfur inorganic compounds. The Organosulfur compounds detected from the genus Aloe are classified in vitamin (thiamine), amino acids (methionine and cysteine), and other organic compounds (pluridone and 1-(phenylthioxomethyl)piperidine). These compounds are also classified based on the organic chemistry functional groups. According to this classification thiamine, pluridone, and methionine have sulfide (R-S-R) functional group while Cysteine and 1-(phenylthioxomethyl) piperidine have thiol (R-SH) and thiomide (R=SN) functional groups respectively. These compounds have potential biological activities that are used in medicine, food, cosmetics, etc. The biological activities of organosulfur compounds reflect the biological activities of Aloe species. This agreement shows that organosulfur compounds have roles in the applications of Aloe species. Therefore, it is strongly recommended to test organosulfur compounds from the genus Aloe for the potential biological activities and how to extract, isolate, and structural characterization organosulfur compounds specifically

The authors declare that they have no conflict of interest.

Adamu Tizazu: Propose idea, write original draft, data collection, and Chemdraw software; Abdela Nebi: Reviewing, editing, and data collection.

1. Kwok S (2004) The synthesis of organic and inorganic compounds in evolved stars. Nature 430(7003): 985-991.
2. Baráth E (2018) Hydrogen transfer reactions of carbonyls, alkynes, and alkenes with noble metals in the presence of alcohols/ethers and amines as hydrogen donors. Catalysts 8(12): 671.
3. Xia Y, Jiang H, Wu W (2021) Recent Advances in Chemical Modifications of Nitriles. European Journal of Organic Chemistry. 2021(48): 6658-6669.
4. Borah P, Kumar M, Devi P (2020) Types of inorganic pollutants: metals/metalloids, acids, and organic forms. In Inorganic pollutants in water Elsevier, p. 17-31.
5. Amrani A (2014) Organosulfur compounds: molecular and isotopic evolution from biota to oil and gas. Annual Review of Earth and Planetary Sciences 42(1): 733-768.
6. Kutuzov I, Rosenberg YO, Bishop A, Amrani A (2020) The origin of organic sulphur compounds and their impact on the paleoenvironmental record. Hydrocarbons, oils and lipids: Diversity, origin, chemistry and fate, pp. 355-408.
7. Petropoulos S, Di Gioia F, Ntatsi G (2017) Vegetable organosulfur compounds and their health promoting effects. Current pharmaceutical design 23(19): 2850-2875.
8. Goncharov NV, Belinskaia DA, Ukolov AI, Jenkins RO, Avdonin PV (2021) Organosulfur compounds as nutraceuticals. In Nutraceuticals, pp. 911-924.
9. Petropoulos S, Di Gioia F, Ntatsi G (2017) Vegetable organosulfur compounds and their health promoting effects. Current pharmaceutical design 23(19): 2850-2875.
10. Yadeta AT (2024) Chemical structures, biological activities, and medicinal potentials of amine compounds detected from Aloe Frontiers in Chemistry 12: 1363066.
11. Dagne E, Bisrat D, Viljoen A, Van Wyk BE (2000) Chemistry of Aloe Current organic chemistry 4(10): 1055-1078.
12. Asfaw MD, Yadeta AT, Awoke MG (2024) Determination of the Fatty Acid Compositions and Bioactive Properties of Argemone mexicana Seed Oil. Natural Product Communications 19(6): 1934578X241257824.
13. Cock IE (2011) Problems of reproducibility and efficacy of bioassays using crude extracts, with reference to Aloe vera. Pharmacognosy communications 1(1): 52-62.
14. Jangra A, Sharma G, Sihag S, Chhokar V (2022) The dark side of miracle plant-Aloe vera: a review. Molecular Biology Reports. 49(6): 5029-5040.
15. Sánchez Machado DI, López Cervantes J, Sendón R, Sanches Silva A (2017) Aloe vera: Ancient knowledge with new frontiers. Trends in Food Science & Technology 61: 94-102.
16. Francioso A, Baseggio Conrado A, Mosca L, Fontana M (2020) Chemistry and biochemistry of sulfur natural compounds: Key intermediates of metabolism and redox biology. Oxidative Medicine and Cellular Longevity 2020(1): 8294158.
17. Hrubša M, Siatka T, Nejmanová I, Vopršalová M, Kujovská Krčmová L, et al. (2022) Biological properties of vitamins of the B-complex, part 1: Vitamins B1, B2, B3, and B5. Nutrients 14(3): 484.
18. Marrs C, Lonsdale D (2021) Hiding in plain sight: modern thiamine deficiency. Cells 10(10): 2595.
19. Tardy AL, Pouteau E, Marquez D, Yilmaz C, Scholey A (2020) Vitamins and minerals for energy, fatigue and cognition: a narrative review of the biochemical and clinical evidence. Nutrients 12(1): 228.
20. Shakib Z, Shahraki N, Razavi BM, Hosseinzadeh H (2019) Aloe vera as an herbal medicine in the treatment of metabolic syndrome: A review. Phytotherapy Research 33(10): 2649-2660.
21. Govindarajan S, Babu SN, Vijayalakshmi MA, Manohar P, Noor A (2021) Aloe vera carbohydrates regulate glucose metabolism through improved glycogen synthesis and downregulation of hepatic gluconeogenesis in diabetic rats. Journal of Ethnopharmacology 281: 114556.
22. Baruah A, Bordoloi M, Baruah HP (2016) Aloe vera: A multipurpose industrial crop. Industrial Crops and Products 94: 951-963.
23. Moriyama M, Moriyama H, Uda J, Kubo H, Nakajima Y, et al. (2016) Beneficial effects of the genus Aloe on wound healing, cell proliferation, and differentiation of epidermal keratinocytes. PLoS One 11(10): e0164799.
24. Chore JK, Obonyo M, Wachira FN, Mireji PO (2014) Larvicidal activity of selected Aloe species against Aedes aegypti (Diptera: Culiciade). Journal of Insect Science 14(1): 202.
25. Hiremath B (2022) Review on Study of Insecticidal Activity of Cymbopogon citratus, and Aloe vera against Musca domestica. SPAST Express 2(1): 536779.
26. Mallavadhani UV, Prasad BR, Soujanya PL, Rao MB, Ratanlal M (2016) Aloe vera (L.) Burm. f.: A highly useful Indian traditional plant for the management of maize storage pest, Sitophilus oryzae (Coleoptera: Curculionidae). Journal of Biopesticides 9(2): 157-166.
27. Human H, Nicolson SW (2006) Nutritional content of fresh, bee-collected and stored pollen of Aloe greatheadii davyana (Asphodelaceae). Phytochemistry 67(14): 1486-1492.
28. Fan JJ, Li CH, Hu G, Tan CN, Yang FQ, et al. (2019) Comparative analysis of soluble proteins in four medicinal Aloe species by two-dimensional electrophoresis and MALDI-TOF-MS. Journal of AOAC International 102(3): 748-760.
29. Hendrawati TY, Nugrahani RA, Ramadhan AI, Susanty S, Siswahyu A (2019) The effects of vacuum evaporation on amino acid contents in pureed aloe chinensis baker gel using HPLC. InIOP Conference Series: Materials Science and Engineering 543(1): 012014.
30. Stintzing FC, Carle R (2005) Cactus stems (Opuntia spp.): A review on their chemistry, technology, and uses. Molecular nutrition & food research 49(2): 175-194.
31. Atmaca G (2004) Antioxidant effects of sulfur-containing amino acids. Yonsei medical journal 45(5): 776-788.
32. Piste P (2013) Cysteine–master antioxidant. International journal of pharmaceutical, chemical and biological sciences 3(1): 143-149.
33. Kang S, Chung JH, Lee JH, Fisher GJ, Wan YS, et al. (2003) Topical N-acetyl cysteine and genistein prevent ultraviolet-light-induced signaling that leads to photoaging in human skin in vivo. Journal of Investigative Dermatology 120(5): 835-841.
34. Soriano JL, Calpena AC, Souto EB, Clares B (2019) Therapy for prevention and treatment of skin ionizing radiation damage: a review. International Journal of Radiation Biology 95(5): 537-553.
35. Dröge W (2005) Oxidative stress and ageing: is ageing a cysteine deficiency syndrome?. Philosophical Transactions of the Royal Society B: Biological Sciences 360(1464): 2355-2372.
36. Shedoeva A, Leavesley D, Upton Z, Fan C (2019) Wound healing and the use of medicinal plants. Evidence‐Based Complementary and Alternative Medicine 2019(1): 2684108.
37. Svitina H, Swanepoel R, Rossouw J, Netshimbupfe H, Gouws C, et al. (2019) Treatment of skin disorders with Aloe Current pharmaceutical design 25(20): 2208-2240.
38. Varpe BD, Kulkarni AA, Mali AS (2021) Aloe vera compositions used for medicinal applications: a patent review (2013-till 2020). Recent Patents on Food, Nutrition & Agriculture 12(2): 104-111.
39. Bawankar R, Deepti VC, Singh P, Subashkumar R, Vivekanandhan G, et al. (2013) Evaluation of bioactive potential of an Aloe vera sterol extract. Phytotherapy Research 27(6): 864-868.
40. Mahanta N, Szantai Kis DM, Petersson EJ, Mitchell DA (2019) Biosynthesis and chemical applications of thioamides. ACS chemical biology 14(2): 142-163.
41. Majumdar P, Pati A, Patra M, Behera RK, Behera AK (2014) Acid hydrazides, potent reagents for synthesis of oxygen-, nitrogen-, and/or sulfur-containing heterocyclic rings. Chemical reviews 114(5): 2942-2977.
42. Siwek A, Stefańska J, Dzitko K, Ruszczak A (2012) Antifungal effect of 4-arylthiosemicarbazides against Candida Search for molecular basis of antifungal activity of thiosemicarbazide derivatives. Journal of molecular modeling 18: 4159-4170.
43. Rani N, Sharma A, Singh R (2013) Imidazoles as promising scaffolds for antibacterial activity: a review. Mini reviews in medicinal chemistry 13(12): 1812-1835.
44. Benson KF, Newman RA, Jensen GS (2015) Antioxidant, anti-inflammatory, anti-apoptotic, and skin regenerative properties of an Aloe vera-based extract of Nerium oleander leaves (NAE-8®). Clinical, Cosmetic and Investigational Dermatology 6: 239-248.
45. Salehi B, Albayrak S, Antolak H, Kręgiel D, Pawlikowska E, et al. (2018) Aloe genus plants: from farm to food applications and phytopharmacotherapy. International journal of molecular sciences19(9): 2843.